Princess Cruises to Caribbean

Stunning panoramic view of Caneel Bay in St. John, with its pristine beach and turquoise waters, a highlight of Princess Cruises' Caribbean destinations.

Overview

Cruise to the Caribbean with Princess Cruises for a relaxing and delightful voyage that you won’t soon forget. Delicious cuisine, enriching cultural experiences, and incredible weather are just a few highlights of a trip to the Caribbean islands, whether it be in the Eastern, Southern, or Western Caribbean.

Shop duty-free in St. Thomas for some local treasures, plunder the mysterious caves in Curacao, or frolic in the butterfly farms of Aruba. Or, put your feet up and vegetate on the beaches of Costa Maya or Honduras. Relaxation, eccentricity, and culture are just three reasons to choose a Princess Cruises Caribbean cruise.

Upcoming Princess Cruises to Caribbean

Filter

167 Results

Taxes and fees included in all prices shown

Sort

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

7-night Eastern Caribbean With Turks & Caicos Cruise From Fort Lauderdale, Florida

Aboard

Regal Princess

From

Fort Lauderdale, Florida

2 Sailings

Oct 10 - Oct 17, 2026

2 Sailings

Oct 10 - Oct 17, 2026

A scenic view of Princess Cays, Bahamas, featuring a row of colorful cabanas with thatched roofs, surrounded by swaying palm trees on a white-sand beach.

Up to 40% OFF + up to $300 Instant Savings + FREE 3rd & 4th Guest*

7-night Eastern Caribbean with Turks & Caicos Cruise From Port Canaveral, Florida

Aboard

Caribbean Princess

From

Port Canaveral, Florida

1 Sailing

Oct 11, 2026

1 Sailing

Oct 11, 2026

A classic, two-story colonial building, the Abbey of Our Lady of Exile, with a red roof, a clock tower, and arches in Port of Spain, Trinidad and Tobago, under a cloudy blue sky.

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

14-night Circle Caribbean Cruise From Fort Lauderdale, Florida

Ft. Lauderdale

St. Maarten (Philipsburg)

Aboard

Coral Princess

From

Fort Lauderdale, Florida

2 Sailings

Oct 15, 2026 - Dec 6, 2027

2 Sailings

Oct 15, 2026 - Dec 6, 2027

Published prices from

$1,094

per person*

taxes & fees included

A sunny, tropical beach on Grand Turk Island with multiple hot air balloons flying over the turquoise water and shoreline.

14-night Eastern/Western Caribbean Adventurer Cruise From Fort Lauderdale, Florida

Aboard

Regal Princess

From

Fort Lauderdale, Florida

2 Sailings

Oct 17, 2026 - Mar 20, 2027

2 Sailings

Oct 17, 2026 - Mar 20, 2027

Published prices from

$1,443

per person*

taxes & fees included

A beautiful panoramic shot of the Ottawa skyline and the Parliament Hill buildings, seen from across the Ottawa River, a landmark tourist destination.

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

19-night Maple Explorer Cruisetour #2B From Toronto, Ontario

Aboard

Sapphire Princess

From

Toronto, Ontario

1 Sailing

Oct 18, 2026

1 Sailing

Oct 18, 2026

An aerial view of the Kralendijk waterfront in Bonaire, showcasing the contrast between the deep blue ocean and the shallow turquoise water near the shore, with sailboats anchored offshore.

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

12-night Southern Caribbean Islander Cruise From Port Canaveral, Florida

Aboard

Caribbean Princess

From

Port Canaveral, Florida

1 Sailing

Oct 18, 2026

1 Sailing

Oct 18, 2026

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

4-night Caribbean Getaway Cruise With Grand Turk From Fort Lauderdale, Florida

Ft. Lauderdale

Grand Turk

Aboard

Star Princess

From

Fort Lauderdale, Florida

1 Sailing

Oct 20, 2026

1 Sailing

Oct 20, 2026

A scenic view of the Castle Hill Lighthouse in Newport, Rhode Island, with a white and black stone base, overlooking the deep blue Atlantic Ocean under a clear sky.

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

14-night Canada & Colonial America Cruise From Quebec City, Quebec

Halifax (Nova Scotia)

+6 more

Aboard

Sapphire Princess

From

Quebec City, Quebec

1 Sailing

Oct 23, 2026

1 Sailing

Oct 23, 2026

Tropical beach with lounge chairs in Cozumel.

7-night Western Caribbean With Mexico Cruise From Fort Lauderdale, Florida

Aboard

Regal Princess

From

Fort Lauderdale, Florida

2 Sailings

Oct 24, 2026 - Mar 27, 2027

2 Sailings

Oct 24, 2026 - Mar 27, 2027

Published prices from

$759

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

14-night Eastern/Western Caribbean Adventurer Cruise From Fort Lauderdale, Florida

Aboard

Star Princess

From

Fort Lauderdale, Florida

21 Sailings

Oct 24, 2026 - Mar 20, 2027

21 Sailings

Oct 24, 2026 - Mar 20, 2027

Published prices from

$1,933

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

7-night Western Caribbean Cruise With Mexico From Fort Lauderdale, Florida

Aboard

Star Princess

From

Fort Lauderdale, Florida

11 Sailings

Oct 24, 2026 - Mar 27, 2027

11 Sailings

Oct 24, 2026 - Mar 27, 2027

Published prices from

$849

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

10-night Eastern Caribbean With St. Kitts Cruise From Fort Lauderdale, Florida

St. Maarten (Philipsburg)

+3 more

Aboard

Coral Princess

From

Fort Lauderdale, Florida

3 Sailings

Oct 29 - Nov 18, 2026

3 Sailings

Oct 29 - Nov 18, 2026

Colorful colonial balconies in Cartagena.

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

12-night Panama Canal With Costa Rica & Caribbean Cruise From Fort Lauderdale, Florida

Aboard

Caribbean Princess

From

Fort Lauderdale, Florida

10 Sailings

Oct 30, 2026 - Feb 12, 2028

10 Sailings

Oct 30, 2026 - Feb 12, 2028

Published prices from

$1,314

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

7-night Eastern Caribbean Cruise With Bahamas From Fort Lauderdale, Florida

Aboard

Star Princess

From

Fort Lauderdale, Florida

11 Sailings

Oct 31, 2026 - Mar 20, 2027

11 Sailings

Oct 31, 2026 - Mar 20, 2027

Published prices from

$889

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

8-night Eastern Caribbean With Puerto Rico Cruise From Fort Lauderdale, Florida

Ft. Lauderdale

St. Maarten (Philipsburg)

San Juan

Amber Cove

Grand Turk

Aboard

Regal Princess

From

Fort Lauderdale, Florida

5 Sailings

Oct 31, 2026 - Feb 20, 2027

5 Sailings

Oct 31, 2026 - Feb 20, 2027

Published prices from

$1,129

per person*

taxes & fees included

Yellow kayak on sandy beach in Puerto Vallarta, Mexico.

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

16-night Panama Canal - Ocean To Ocean Cruise From Fort Lauderdale, Florida

Ft. Lauderdale

Oranjestad

Panama Canal

Fuerte Amador (Panama City)

Puntarenas

+5 more

Aboard

Sapphire Princess

From

Fort Lauderdale, Florida

1 Sailing

Nov 6, 2026

1 Sailing

Nov 6, 2026

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

12-night Southern Caribbean Islander Cruise From New York City, New York

New York City

St. Maarten (Philipsburg)

Aboard

Majestic Princess

From

New York City, New York

1 Sailing

Nov 7, 2026

1 Sailing

Nov 7, 2026

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

14-night Southern/Eastern Caribbean Adventurer Cruise From Fort Lauderdale, Florida

Grand Cayman (George Town)

+3 more

Aboard

Regal Princess

From

Fort Lauderdale, Florida

10 Sailings

Nov 8, 2026 - Mar 6, 2027

10 Sailings

Nov 8, 2026 - Mar 6, 2027

Published prices from

$2,337

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

6-night Eastern Caribbean With Turks & Caicos Cruise From Fort Lauderdale, Florida

Aboard

Regal Princess

From

Fort Lauderdale, Florida

10 Sailings

Nov 8, 2026 - Mar 14, 2027

10 Sailings

Nov 8, 2026 - Mar 14, 2027

Published prices from

$649

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

8-night Southern Caribbean With Abc Islands Cruise From Fort Lauderdale, Florida

Ft. Lauderdale

Grand Cayman (George Town)

Ocho Rios

Oranjestad

Aboard

Regal Princess

From

Fort Lauderdale, Florida

4 Sailings

Nov 14, 2026 - Feb 6, 2027

4 Sailings

Nov 14, 2026 - Feb 6, 2027

A breathtaking underwater view of a coral reef with multiple schools of fish swimming over the colorful and diverse marine ecosystem near Roatan Island, Honduras.

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

14-night Eastern/Western Caribbean Adventurer Cruise From Fort Lauderdale, Florida

Aboard

Sun Princess

From

Fort Lauderdale, Florida

23 Sailings

Nov 15, 2026 - Feb 5, 2028

23 Sailings

Nov 15, 2026 - Feb 5, 2028

Published prices from

$1,413

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

7-night Western Caribbean Cruise With Mexico From Fort Lauderdale, Florida

Aboard

Sun Princess

From

Fort Lauderdale, Florida

9 Sailings

Nov 15, 2026 - Mar 21, 2027

9 Sailings

Nov 15, 2026 - Mar 21, 2027

Published prices from

$679

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

18-night Brazilian Adventure Cruise From Fort Lauderdale, Florida

Ft. Lauderdale

St. Maarten (Philipsburg)

Castries

Bridgetown (Barbados)

Fortaleza

+4 more

Aboard

Majestic Princess

From

Fort Lauderdale, Florida

1 Sailing

Nov 19, 2026

1 Sailing

Nov 19, 2026

Cupecoy Beach with white resort buildings, St. Maarten.

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

33-night Brazilian & Cape Horn Grand Adventure Cruise From Fort Lauderdale, Florida

Ft. Lauderdale

St. Maarten (Philipsburg)

Castries

Bridgetown (Barbados)

Fortaleza

+12 more

Aboard

Majestic Princess

From

Fort Lauderdale, Florida

1 Sailing

Nov 19, 2026

1 Sailing

Nov 19, 2026

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

9-night Eastern Caribbean Cruise With St. Thomas From Port Canaveral, Florida

St. Maarten (Philipsburg)

+2 more

Aboard

Sky Princess

From

Port Canaveral, Florida

1 Sailing

Nov 20, 2026

1 Sailing

Nov 20, 2026

A secluded cove with white sand and turquoise water on Half Moon Cay, Bahamas, surrounded by jagged, rocky cliffs and a serene blue ocean under a partly cloudy sky.

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

7-night Eastern Caribbean Cruise With Puerto Rico From Fort Lauderdale, Florida

Aboard

Sun Princess

From

Fort Lauderdale, Florida

9 Sailings

Nov 22, 2026 - Mar 14, 2027

9 Sailings

Nov 22, 2026 - Mar 14, 2027

Published prices from

$869

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

14-night Caribbean Eastern Adventurer Cruise From Fort Lauderdale, Florida

St. Maarten (Philipsburg)

+3 more

Aboard

Regal Princess

From

Fort Lauderdale, Florida

8 Sailings

Nov 22, 2026 - Feb 20, 2027

8 Sailings

Nov 22, 2026 - Feb 20, 2027

Published prices from

$1,401

per person*

taxes & fees included

A sunny, idyllic beach scene in Amber Cove, Dominican Republic, with a small boat and paddle resting under a palm tree beside the turquoise ocean and a clear blue sky.

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

5-night Caribbean Getaway With Grand Turk Cruise From Fort Lauderdale, Florida

Ft. Lauderdale

Grand Turk

Amber Cove

Aboard

Island Princess

From

Fort Lauderdale, Florida

1 Sailing

Nov 25, 2026

1 Sailing

Nov 25, 2026

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

8-night Eastern Caribbean Cruise With Puerto Rico From Port Canaveral, Florida

Aboard

Sky Princess

From

Port Canaveral, Florida

7 Sailings

Nov 29, 2026 - Feb 21, 2027

7 Sailings

Nov 29, 2026 - Feb 21, 2027

Published prices from

$1,109

per person*

taxes & fees included

A panoramic view of the coastal city of Roseau in Dominica, with its colorful buildings nestled between the Caribbean Sea and lush, mountainous terrain under a beautiful sky.

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

12-night Southern Caribbean With Aruba Cruise From Fort Lauderdale, Florida

Bridgetown (Barbados)

+3 more

Aboard

Island Princess

From

Fort Lauderdale, Florida

1 Sailing

Nov 30, 2026

1 Sailing

Nov 30, 2026

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

16-night Panama Canal Cruise - Ocean To Ocean From Los Angeles, California

Aboard

Crown Princess

From

Los Angeles, California

1 Sailing

Dec 3, 2026

1 Sailing

Dec 3, 2026

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

14-night Circle Caribbean Cruise From Fort Lauderdale, Florida

Ft. Lauderdale

St. Maarten (Philipsburg)

Aboard

Enchanted Princess

From

Fort Lauderdale, Florida

1 Sailing

Dec 3, 2026

1 Sailing

Dec 3, 2026

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

6-night Eastern Caribbean Cruise With Turks & Caicos From Port Canaveral, Florida

Aboard

Sky Princess

From

Port Canaveral, Florida

7 Sailings

Dec 7, 2026 - Mar 1, 2027

7 Sailings

Dec 7, 2026 - Mar 1, 2027

Published prices from

$922

per person*

taxes & fees included

Puntarenas, Costa Rica tropical landscape with palm trees and mountains.

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

16-night Panama Canal Cruise - Ocean To Ocean Holiday From Fort Lauderdale, Florida

Ft. Lauderdale

Oranjestad

Panama Canal

Fuerte Amador (Panama City)

Puntarenas

+5 more

Aboard

Island Princess

From

Fort Lauderdale, Florida

1 Sailing

Dec 12, 2026

1 Sailing

Dec 12, 2026

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

10-night Eastern Caribbean With St. Kitts Holiday Cruise From Fort Lauderdale, Florida

St. Maarten (Philipsburg)

+3 more

Aboard

Enchanted Princess

From

Fort Lauderdale, Florida

2 Sailings

Dec 17 - Dec 27, 2026

2 Sailings

Dec 17 - Dec 27, 2026

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

12-night Panama Canal With Costa Rica & Caribbean Holiday Cruise From Fort Lauderdale, Florida

Aboard

Caribbean Princess

From

Fort Lauderdale, Florida

3 Sailings

Dec 17, 2026 - Dec 23, 2027

3 Sailings

Dec 17, 2026 - Dec 23, 2027

Published prices from

$1,974

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

10-night Eastern Caribbean With Puerto Rico Holiday Cruise From Fort Lauderdale, Florida

Ft. Lauderdale

Half Moon Cay

San Juan

St. Maarten (Philipsburg)

Aboard

Coral Princess

From

Fort Lauderdale, Florida

1 Sailing

Dec 19, 2026

1 Sailing

Dec 19, 2026

A wide-angle view of the bustling harbor of Charlotte Amalie, St. Thomas, with many sailboats and yachts docked in the tranquil blue water, and the town's buildings climbing the lush green hills.

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

8-night Southern Caribbean Islander Holiday Cruise From Fort Lauderdale, Florida

St. Thomas (Charlotte Amalie)

+2 more

Aboard

Crown Princess

From

Fort Lauderdale, Florida

1 Sailing

Dec 19, 2026

1 Sailing

Dec 19, 2026

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

14-night Eastern/Western Caribbean Adventurer Holiday Cruise From Fort Lauderdale, Florida

Aboard

Star Princess

From

Fort Lauderdale, Florida

1 Sailing

Dec 19, 2026

1 Sailing

Dec 19, 2026

A beautiful sailboat rests in the shallow, clear turquoise waters off the coast of Belize City, with lush palm trees and colorful buildings lining the shore.

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

7-night Western Caribbean With Mexico Holiday Cruise From Fort Lauderdale, Florida

Aboard

Star Princess

From

Fort Lauderdale, Florida

1 Sailing

Dec 19, 2026

1 Sailing

Dec 19, 2026

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

14-night Eastern/Western Caribbean Adventurer Holiday Cruise From Fort Lauderdale, Florida

Aboard

Sun Princess

From

Fort Lauderdale, Florida

1 Sailing

Dec 20, 2026

1 Sailing

Dec 20, 2026

A panoramic view of Fort-de-France, Martinique, showing a bustling bay filled with boats and yachts, with colorful houses nestled on the surrounding green hillsides and the deep blue Caribbean Sea beyond.

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

11-night Southern Caribbean With Martinique Holiday Cruise From Fort Lauderdale, Florida

Ft. Lauderdale

St. Thomas (Charlotte Amalie)

Basseterre

Fort de France

Bridgetown (Barbados)

+3 more

Aboard

Coral Princess

From

Fort Lauderdale, Florida

1 Sailing

Dec 26, 2026

1 Sailing

Dec 26, 2026

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

7-night Western Caribbean Cruise With Mexico Holiday From Fort Lauderdale, Florida

Aboard

Sun Princess

From

Fort Lauderdale, Florida

1 Sailing

Dec 27, 2026

1 Sailing

Dec 27, 2026

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

14-night Southern Caribbean Adventurer Cruise From San Juan, Puerto Rico

San Juan

St. Thomas (Charlotte Amalie)

St. Maarten (Philipsburg)

St. John's

Castries

+5 more

Aboard

Crown Princess

From

San Juan, Puerto Rico

12 Sailings

Dec 27, 2026 - Mar 14, 2027

12 Sailings

Dec 27, 2026 - Mar 14, 2027

Published prices from

$1,457

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

7-night Southern Caribbean Cruise With Barbados From San Juan, Puerto Rico

San Juan

St. Thomas (Charlotte Amalie)

St. Maarten (Philipsburg)

St. John's

Castries

+2 more

Aboard

Crown Princess

From

San Juan, Puerto Rico

13 Sailings

Dec 27, 2026 - Mar 21, 2027

13 Sailings

Dec 27, 2026 - Mar 21, 2027

Published prices from

$667

per person*

taxes & fees included

A cruise ship navigating through the Gatun Locks of the Panama Canal, an important navigational route and popular tourist destination.

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

16-night Panama Canal Cruise - Ocean To Ocean Holiday From Los Angeles, California

Aboard

Island Princess

From

Los Angeles, California

1 Sailing

Dec 28, 2026

1 Sailing

Dec 28, 2026

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

5-night Eastern Caribbean With St. Kitts Cruise From San Juan, Puerto Rico

San Juan

St. Thomas (Charlotte Amalie)

Basseterre

Dominica

St. George's

Aboard

Crown Princess

From

San Juan, Puerto Rico

1 Sailing

Jan 3, 2027

1 Sailing

Jan 3, 2027

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

10-night Eastern Caribbean With St. Kitts Cruise From Fort Lauderdale, Florida

Aboard

Enchanted Princess

From

Fort Lauderdale, Florida

10 Sailings

Jan 6 - Apr 6, 2027

10 Sailings

Jan 6 - Apr 6, 2027

Published prices from

$1,040

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

7-night Southern Caribbean With St. Lucia Cruise From Bridgetown, Barbados

Bridgetown (Barbados)

San Juan

St. Thomas (Charlotte Amalie)

St. Maarten (Philipsburg)

St. John's

+2 more

Aboard

Crown Princess

From

Bridgetown, Barbados

6 Sailings

Jan 8 - Mar 19, 2027

6 Sailings

Jan 8 - Mar 19, 2027

A golden sunset over the beach in Huatulco, Mexico, with footprints in the sand leading towards the shimmering ocean and a warm glow over the water.

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

16-night Panama Canal Cruise - Ocean To Ocean From Fort Lauderdale, Florida

Ft. Lauderdale

Oranjestad

Panama Canal

Fuerte Amador (Panama City)

Puntarenas

+5 more

Aboard

Island Princess

From

Fort Lauderdale, Florida

4 Sailings

Jan 13 - Apr 19, 2027

4 Sailings

Jan 13 - Apr 19, 2027

Published prices from

$1,764

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

16-night Panama Canal Cruise - Ocean To Ocean From San Diego, California

Aboard

Island Princess

From

San Diego, California

1 Sailing

Jan 29, 2027

1 Sailing

Jan 29, 2027

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

7-night Southern Caribbean With Puerto Rico Cruise From Bridgetown, Barbados

Bridgetown (Barbados)

San Juan

St. Thomas (Charlotte Amalie)

Pointe A Pitre

Dominica

+2 more

Aboard

Crown Princess

From

Bridgetown, Barbados

5 Sailings

Jan 29 - Mar 12, 2027

5 Sailings

Jan 29 - Mar 12, 2027

Published prices from

$1,489

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

7-night Eastern Caribbean With Turks & Caicos Cruise From Fort Lauderdale, Florida

Aboard

Caribbean Princess

From

Fort Lauderdale, Florida

1 Sailing

Feb 27, 2027

1 Sailing

Feb 27, 2027

Published prices from

$611

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

16-night Panama Canal Cruise - Ocean To Ocean From Los Angeles, California

Aboard

Island Princess

From

Los Angeles, California

2 Sailings

Mar 2 - Apr 3, 2027

2 Sailings

Mar 2 - Apr 3, 2027

Published prices from

$1,809

per person*

taxes & fees included

A scenic coastal view in Curaçao featuring houses with orange roofs on a cliffside overlooking a rocky beach with beautiful turquoise Caribbean water.

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

8-night Southern Caribbean With ABC Islands Cruise From Fort Lauderdale, Florida

Aboard

Regal Princess

From

Fort Lauderdale, Florida

1 Sailing

Mar 6, 2027

1 Sailing

Mar 6, 2027

Published prices from

$2,199

per person*

taxes & fees included

An aerial view of the historic Tower of Hercules, a UNESCO World Heritage site and the oldest Roman lighthouse, situated on a grassy peninsula overlooking the Atlantic Ocean in La Coruna, Spain.

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

22-night Moroccan & Iberian Grand Adventure Cruise From Port Canaveral, Florida

Port Canaveral

Bermuda

Ponta Delgada (Azores)

Casablanca

La Coruna

+5 more

Aboard

Sky Princess

From

Port Canaveral, Florida

1 Sailing

Mar 7, 2027

1 Sailing

Mar 7, 2027

Published prices from

$3,997

per person*

taxes & fees included

Peaceful sunrise over a sandy Florida beach with sea oats in Port Canaveral.

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

15-night Moroccan Passage Cruise From Port Canaveral, Florida

Port Canaveral

Bermuda

Ponta Delgada (Azores)

Casablanca

La Coruna

+2 more

Aboard

Sky Princess

From

Port Canaveral, Florida

1 Sailing

Mar 7, 2027

1 Sailing

Mar 7, 2027

Published prices from

$1,402

per person*

taxes & fees included

Oranjestad, Aruba harbor with boats and colorful Dutch architecture.

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

9-night Southern Caribbean With Aruba Cruise From Fort Lauderdale, Florida

Aboard

Caribbean Princess

From

Fort Lauderdale, Florida

3 Sailings

Mar 19, 2027 - Feb 3, 2028

3 Sailings

Mar 19, 2027 - Feb 3, 2028

Published prices from

$765

per person*

taxes & fees included

Up to 40% OFF + up to $300 Instant Savings + FREE 3rd & 4th Guest*

7-night Eastern Caribbean With Puerto Rico Cruise From Fort Lauderdale, Florida

Aboard

Regal Princess

From

Fort Lauderdale, Florida

2 Sailings

Mar 20 - Apr 3, 2027

2 Sailings

Mar 20 - Apr 3, 2027

Published prices from

$749

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

9-night Southern Caribbean With Aruba Cruise From Bridgetown, Barbados

Bridgetown (Barbados)

San Juan

St. Maarten (Philipsburg)

Oranjestad

Curacao

+2 more

Aboard

Crown Princess

From

Bridgetown, Barbados

1 Sailing

Mar 26, 2027

1 Sailing

Mar 26, 2027

Published prices from

$2,284

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

12-night Southern Caribbean With Panama Cruise From Fort Lauderdale, Florida

Aboard

Caribbean Princess

From

Fort Lauderdale, Florida

3 Sailings

Mar 28, 2027 - Jan 13, 2028

3 Sailings

Mar 28, 2027 - Jan 13, 2028

Published prices from

$1,016

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

7-night Southern Caribbean Islander Cruise From San Juan, Puerto Rico

San Juan

St. Maarten (Philipsburg)

Oranjestad

Curacao

Ft. Lauderdale

Aboard

Crown Princess

From

San Juan, Puerto Rico

1 Sailing

Mar 28, 2027

1 Sailing

Mar 28, 2027

Published prices from

$749

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

16-night Panama Canal Cruise - Ocean To Ocean From Fort Lauderdale, Florida

Ft. Lauderdale

Oranjestad

Panama Canal

Fuerte Amador (Panama City)

Mazatlan

+3 more

Aboard

Star Princess

From

Fort Lauderdale, Florida

1 Sailing

Apr 3, 2027

1 Sailing

Apr 3, 2027

Published prices from

$1,829

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

12-night Southern Caribbean With Aruba Cruise From Fort Lauderdale, Florida

Bridgetown (Barbados)

+3 more

Aboard

Caribbean Princess

From

Fort Lauderdale, Florida

1 Sailing

Apr 9, 2027

1 Sailing

Apr 9, 2027

Published prices from

$1,310

per person*

taxes & fees included

Up to 40% OFF + up to $300 Instant Savings + FREE 3rd & 4th Guest*

7-night Eastern Caribbean With Puerto Rico Cruise From Fort Lauderdale, Florida

Ft. Lauderdale

Half Moon Cay

San Juan

St. Maarten (Philipsburg)

Aboard

Regal Princess

From

Fort Lauderdale, Florida

1 Sailing

Apr 10, 2027

1 Sailing

Apr 10, 2027

Published prices from

$960

per person*

taxes & fees included

A beautiful view of the bustling harbor in Ajaccio, Corsica, with colorful historic buildings lining the port and numerous yachts docked in the marina.

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

25-night Western Mediterranean & Adriatic Grand Adventure Cruise From Fort Lauderdale, Florida

Ft. Lauderdale

Bermuda

Ponta Delgada (Azores)

Gibraltar

Cartagena (Spain)

+10 more

Aboard

Enchanted Princess

From

Fort Lauderdale, Florida

1 Sailing

Apr 16, 2027

1 Sailing

Apr 16, 2027

Published prices from

$4,209

per person*

taxes & fees included

A beautiful daytime view of the iconic windmills of Mykonos, Greece, with their white-washed walls and thatched roofs against a vivid blue sky.

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

46-night Mediterranean & Greek Isles Grand Adventure Cruise From Fort Lauderdale, Florida

Ft. Lauderdale

Bermuda

Ponta Delgada (Azores)

Gibraltar

Cartagena (Spain)

+22 more

Aboard

Enchanted Princess

From

Fort Lauderdale, Florida

1 Sailing

Apr 16, 2027

1 Sailing

Apr 16, 2027

Published prices from

$8,833

per person*

taxes & fees included

Split, Croatia harbor with Diocletian's Palace at dusk.

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

36-night Mediterranean & Aegean Grand Adventure Cruise From Fort Lauderdale, Florida

Ft. Lauderdale

Bermuda

Ponta Delgada (Azores)

Gibraltar

Cartagena (Spain)

+16 more

Aboard

Enchanted Princess

From

Fort Lauderdale, Florida

1 Sailing

Apr 16, 2027

1 Sailing

Apr 16, 2027

Published prices from

$5,994

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

15-night Western Mediterranean Passage Cruise From Fort Lauderdale, Florida

Ft. Lauderdale

Bermuda

Ponta Delgada (Azores)

Gibraltar

Cartagena (Spain)

+3 more

Aboard

Enchanted Princess

From

Fort Lauderdale, Florida

2 Sailings

Apr 16, 2027 - Mar 2, 2028

2 Sailings

Apr 16, 2027 - Mar 2, 2028

Published prices from

$1,360

per person*

taxes & fees included

Up to 40% OFF + up to $300 Instant Savings + FREE 3rd & 4th Guest*

23-night Panama Canal & Pacific Coast Cruise From Fort Lauderdale, Florida

Ft. Lauderdale

Oranjestad

Panama Canal

Fuerte Amador (Panama City)

Puntarenas

+10 more

Aboard

Island Princess

From

Fort Lauderdale, Florida

1 Sailing

Apr 19, 2027

1 Sailing

Apr 19, 2027

Published prices from

$2,323

per person*

taxes & fees included

Colorful buildings and boats in Nyhavn, Copenhagen.

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

27-night Scandinavia & Baltic Grand Adventure Cruise From Fort Lauderdale, Florida

Ft. Lauderdale

Bermuda

Ponta Delgada (Azores)

London (Dover)

Kristiansand

+12 more

Aboard

Caribbean Princess

From

Fort Lauderdale, Florida

1 Sailing

Apr 21, 2027

1 Sailing

Apr 21, 2027

Published prices from

$3,560

per person*

taxes & fees included

A beautiful Norwegian landscape with traditional red and white wooden houses on the water's edge, nestled against a rocky, forested hillside under a clear blue sky.

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

15-night Northern Europe Passage Cruise From Fort Lauderdale, Florida

Ft. Lauderdale

Bermuda

Ponta Delgada (Azores)

London (Dover)

Kristiansand

+2 more

Aboard

Caribbean Princess

From

Fort Lauderdale, Florida

1 Sailing

Apr 21, 2027

1 Sailing

Apr 21, 2027

Published prices from

$1,170

per person*

taxes & fees included

Statue of Liberty and Manhattan skyline.

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

23-night Panama Canal & Pacific Coast Cruise From Vancouver, British Columbia

Aboard

Coral Princess

From

Vancouver, British Columbia

1 Sailing

Sep 22, 2027

1 Sailing

Sep 22, 2027

Published prices from

$3,059

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

18-night Panama Canal - Ocean To Ocean Cruise From Los Angeles, California

Aboard

Coral Princess

From

Los Angeles, California

1 Sailing

Sep 27, 2027

1 Sailing

Sep 27, 2027

Published prices from

$2,100

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

23-night Panama Canal & Pacific Coast Cruise From Vancouver, British Columbia

Aboard

Star Princess

From

Vancouver, British Columbia

1 Sailing

Oct 3, 2027

1 Sailing

Oct 3, 2027

Published prices from

$2,868

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

20-night Panama Canal & Pacific Coast Cruise From Vancouver, British Columbia

Aboard

Island Princess

From

Vancouver, British Columbia

1 Sailing

Oct 6, 2027

1 Sailing

Oct 6, 2027

Published prices from

$2,708

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

16-night Panama Canal - Ocean To Ocean Cruise From Los Angeles, California

Los Angeles

Cabo San Lucas

Mazatlan

Fuerte Amador (Panama City)

Panama Canal

+3 more

Aboard

Star Princess

From

Los Angeles, California

1 Sailing

Oct 10, 2027

1 Sailing

Oct 10, 2027

Published prices from

$2,019

per person*

taxes & fees included

A wide-angle landscape shot of the three iconic volcanoes, Agua, Fuego, and Acatenango, in Guatemala, rising above the clouds during a vibrant sunrise, a scenic view near Puerto Quetzal.

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

16-night Panama Canal - Ocean To Ocean Cruise From Los Angeles, California

Aboard

Island Princess

From

Los Angeles, California

3 Sailings

Oct 13, 2027 - Mar 2, 2028

3 Sailings

Oct 13, 2027 - Mar 2, 2028

Published prices from

$1,824

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

16-night Panama Canal - Ocean To Ocean Cruise From Los Angeles, California

Aboard

Emerald Princess

From

Los Angeles, California

1 Sailing

Oct 24, 2027

1 Sailing

Oct 24, 2027

Published prices from

$1,575

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

5-night Caribbean Getaway With Grand Turk Cruise From Port Canaveral, Florida

Port Canaveral

Princess Cays®

Grand Turk

Aboard

Star Princess

From

Port Canaveral, Florida

2 Sailings

Oct 26, 2027 - Mar 14, 2028

2 Sailings

Oct 26, 2027 - Mar 14, 2028

Published prices from

$629

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

7-night Eastern Caribbean With St. Kitts Cruise From Fort Lauderdale, Florida

Aboard

Island Princess

From

Fort Lauderdale, Florida

1 Sailing

Oct 29, 2027

1 Sailing

Oct 29, 2027

Published prices from

$689

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

7-night Eastern Caribbean With Puerto Rico Cruise From Port Canaveral, Florida

Aboard

Star Princess

From

Port Canaveral, Florida

12 Sailings

Oct 31, 2027 - Feb 27, 2028

12 Sailings

Oct 31, 2027 - Feb 27, 2028

Published prices from

$734

per person*

taxes & fees included

A vibrant panoramic view of Castries, St. Lucia, with colorful buildings nestled along the harbor and lush green hills in the background under a blue sky with white clouds.

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

10-night Southern Caribbean With St. Lucia Cruise From Fort Lauderdale, Florida

Aboard

Island Princess

From

Fort Lauderdale, Florida

1 Sailing

Nov 5, 2027

1 Sailing

Nov 5, 2027

Published prices from

$1,409

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

14-night Southern Caribbean Islander Cruise From New York City, New York

New York City

St. Thomas (Charlotte Amalie)

Aboard

Regal Princess

From

New York City, New York

1 Sailing

Nov 6, 2027

1 Sailing

Nov 6, 2027

Published prices from

$1,224

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

5-night Caribbean Getaway With Grand Turk Cruise From Fort Lauderdale, Florida

Ft. Lauderdale

Grand Turk

Amber Cove

Aboard

Emerald Princess

From

Fort Lauderdale, Florida

2 Sailings

Nov 9, 2027 - Apr 2, 2028

2 Sailings

Nov 9, 2027 - Apr 2, 2028

Published prices from

$579

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

4-night Eastern Caribbean Getaway With Bahamas Cruise From Fort Lauderdale, Florida

Ft. Lauderdale

Princess Cays®

Half Moon Cay

Aboard

Sky Princess

From

Fort Lauderdale, Florida

1 Sailing

Nov 10, 2027

1 Sailing

Nov 10, 2027

Published prices from

$564

per person*

taxes & fees included

St. Peter's Basilica, Rome cityscape at sunset.

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

23-night Mediterranean, Canary Islands & Moroccan Grand Adventure Cruise From Civitavecchia, Rome, Italy

Aboard

Enchanted Princess

From

Civitavecchia, Rome, Italy

1 Sailing

Nov 13, 2027

1 Sailing

Nov 13, 2027

Published prices from

$2,550

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

7-night Eastern Caribbean With St. Kitts Cruise From Fort Lauderdale, Florida

Aboard

Sky Princess

From

Fort Lauderdale, Florida

5 Sailings

Nov 14, 2027 - Feb 27, 2028

5 Sailings

Nov 14, 2027 - Feb 27, 2028

Published prices from

$656

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

14-night Southern Caribbean Adventurer Holiday Cruise From Fort Lauderdale, Florida

Aboard

Emerald Princess

From

Fort Lauderdale, Florida

1 Sailing

Nov 14, 2027

1 Sailing

Nov 14, 2027

Published prices from

$1,523

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

7-night Southern Caribbean With Curacao Cruise From Fort Lauderdale, Florida

Aboard

Emerald Princess

From

Fort Lauderdale, Florida

1 Sailing

Nov 14, 2027

1 Sailing

Nov 14, 2027

Published prices from

$699

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

9-night Eastern Caribbean With St. Thomas Cruise From Port Canaveral, Florida

St. Maarten (Philipsburg)

+2 more

Aboard

Star Princess

From

Port Canaveral, Florida

3 Sailings

Nov 14, 2027 - Mar 29, 2028

3 Sailings

Nov 14, 2027 - Mar 29, 2028

Published prices from

$1,064

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

14-night Circle Caribbean Holiday Cruise From Fort Lauderdale, Florida

Ft. Lauderdale

St. Maarten (Philipsburg)

Aboard

Island Princess

From

Fort Lauderdale, Florida

1 Sailing

Nov 15, 2027

1 Sailing

Nov 15, 2027

Published prices from

$1,614

per person*

taxes & fees included

Miami skyline at dusk, showcasing vibrant colors and reflections shimmering in the water below.

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

15-night Eastern/Western Caribbean Adventurer Cruise From Miami, Florida

Aboard

Regal Princess

From

Miami, Florida

1 Sailing

Nov 20, 2027

1 Sailing

Nov 20, 2027

Published prices from

$1,633

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

7-night Western Caribbean With Mexico Holiday Cruise From Miami, Florida

Aboard

Regal Princess

From

Miami, Florida

1 Sailing

Nov 20, 2027

1 Sailing

Nov 20, 2027

Published prices from

$729

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

15-night Canary Islands & Moroccan Passage Cruise From Civitavecchia, Rome, Italy

Santa Cruz de Tenerife

+3 more

Aboard

Enchanted Princess

From

Civitavecchia, Rome, Italy

2 Sailings

Nov 20, 2027 - Nov 18, 2028

2 Sailings

Nov 20, 2027 - Nov 18, 2028

Published prices from

$1,451

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

14-night Eastern/Western Caribbean Adventurer Holiday Cruise From Fort Lauderdale, Florida

Aboard

Sky Princess

From

Fort Lauderdale, Florida

2 Sailings

Nov 21 - Dec 19, 2027

2 Sailings

Nov 21 - Dec 19, 2027

Published prices from

$1,792

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

7-night Eastern Caribbean With Puerto Rico Holiday Cruise From Fort Lauderdale, Florida

Aboard

Sky Princess

From

Fort Lauderdale, Florida

1 Sailing

Nov 21, 2027

1 Sailing

Nov 21, 2027

Published prices from

$1,039

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

6-night Eastern Caribbean With Turks & Caicos Holiday Cruise From Fort Lauderdale, Florida

Aboard

Sun Princess

From

Fort Lauderdale, Florida

1 Sailing

Nov 21, 2027

1 Sailing

Nov 21, 2027

Published prices from

$739

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

5-night Southern Caribbean With St. Lucia Holiday Cruise From San Juan, Puerto Rico

San Juan

St. Thomas (Charlotte Amalie)

St. Maarten (Philipsburg)

Dominica

Castries

Aboard

Emerald Princess

From

San Juan, Puerto Rico

1 Sailing

Nov 21, 2027

1 Sailing

Nov 21, 2027

Published prices from

$618

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

7-night Southern Caribbean With Barbados And St. Lucia Holiday Cruise From San Juan, Puerto Rico

San Juan

St. Thomas (Charlotte Amalie)

St. Maarten (Philipsburg)

Dominica

Castries

+2 more

Aboard

Emerald Princess

From

San Juan, Puerto Rico

1 Sailing

Nov 21, 2027

1 Sailing

Nov 21, 2027

Published prices from

$889

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

14-night Southern Caribbean Adventurer Cruise From San Juan, Puerto Rico

San Juan

St. Thomas (Charlotte Amalie)

St. Maarten (Philipsburg)

Dominica

Castries

+5 more

Aboard

Emerald Princess

From

San Juan, Puerto Rico

14 Sailings

Nov 21, 2027 - Mar 12, 2028

14 Sailings

Nov 21, 2027 - Mar 12, 2028

Published prices from

$1,658

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

9-night Southern Caribbean With Abc Islands Holiday Cruise From Fort Lauderdale, Florida

Aboard

Caribbean Princess

From

Fort Lauderdale, Florida

1 Sailing

Nov 23, 2027

1 Sailing

Nov 23, 2027

Published prices from

$830

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

5-night Caribbean Getaway With Grand Turk Holiday Cruise From Port Canaveral, Florida

Port Canaveral

Princess Cays®

Grand Turk

Aboard

Star Princess

From

Port Canaveral, Florida

1 Sailing

Nov 23, 2027

1 Sailing

Nov 23, 2027

Published prices from

$769

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

10-night Southern Caribbean Islander Cruise From New York City, New York

Aboard

Coral Princess

From

New York City, New York

1 Sailing

Nov 26, 2027

1 Sailing

Nov 26, 2027

Published prices from

$1,359

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

7-night Southern Caribbean With Tortola Holiday Cruise From Bridgetown, Barbados

Bridgetown (Barbados)

Aboard

Emerald Princess

From

Bridgetown, Barbados

2 Sailings

Nov 26 - Dec 24, 2027

2 Sailings

Nov 26 - Dec 24, 2027

Published prices from

$1,927

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

7-night Eastern Caribbean With Puerto Rico Cruise From Fort Lauderdale, Florida

Aboard

Sun Princess

From

Fort Lauderdale, Florida

3 Sailings

Nov 27, 2027 - Jan 29, 2028

3 Sailings

Nov 27, 2027 - Jan 29, 2028

Published prices from

$759

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

15-night Eastern Caribbean Adventurer Cruise From Miami, Florida

Miami

Amber Cove

San Juan

St. Maarten (Philipsburg)

Roadtown

+3 more

Aboard

Regal Princess

From

Miami, Florida

1 Sailing

Nov 27, 2027

1 Sailing

Nov 27, 2027

Published prices from

$1,683

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

8-night Eastern Caribbean With Tortola Cruise From Miami, Florida

Miami

Amber Cove

San Juan

St. Maarten (Philipsburg)

Roadtown

Aboard

Regal Princess

From

Miami, Florida

1 Sailing

Nov 27, 2027

1 Sailing

Nov 27, 2027

Published prices from

$979

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

14-night Eastern/Western Caribbean Adventurer Cruise From Fort Lauderdale, Florida

Ft. Lauderdale

Half Moon Cay

Falmouth (Jamaica)

Grand Cayman (George Town)

Cozumel

+4 more

Aboard

Sky Princess

From

Fort Lauderdale, Florida

7 Sailings

Nov 28, 2027 - Feb 20, 2028

7 Sailings

Nov 28, 2027 - Feb 20, 2028

Published prices from

$1,324

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

7-night Western Caribbean With Grand Cayman Cruise From Fort Lauderdale, Florida

Ft. Lauderdale

Half Moon Cay

Falmouth (Jamaica)

Grand Cayman (George Town)

Cozumel

Aboard

Sky Princess

From

Fort Lauderdale, Florida

4 Sailings

Nov 28, 2027 - Feb 20, 2028

4 Sailings

Nov 28, 2027 - Feb 20, 2028

Published prices from

$768

per person*

taxes & fees included

An aerial view of the colorful waterfront of St. George's, Grenada, with the town's buildings nestled on a hillside and a long, rocky breakwater extending into the calm, turquoise water.

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

7-night Southern Caribbean With Barbados And Tortola Cruise From San Juan, Puerto Rico

Aboard

Emerald Princess

From

San Juan, Puerto Rico

7 Sailings

Nov 28, 2027 - Mar 19, 2028

7 Sailings

Nov 28, 2027 - Mar 19, 2028

Published prices from

$894

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

14-night Circle Caribbean Cruise From Fort Lauderdale, Florida

Ft. Lauderdale

St. Maarten (Philipsburg)

Basseterre

Dominica

Bridgetown (Barbados)

+5 more

Aboard

Island Princess

From

Fort Lauderdale, Florida

1 Sailing

Nov 29, 2027

1 Sailing

Nov 29, 2027

Published prices from

$1,264

per person*

taxes & fees included

An aerial view of the colorful waterfront of St. John's, Antigua, with a long pier extending into the calm, blue sea and the town's charming buildings and marina in the background.

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

7-night Southern Caribbean With St. Lucia Cruise From Bridgetown, Barbados

Bridgetown (Barbados)

San Juan

St. Thomas (Charlotte Amalie)

St. Maarten (Philipsburg)

St. John's

+2 more

Aboard

Emerald Princess

From

Bridgetown, Barbados

6 Sailings

Dec 3, 2027 - Mar 10, 2028

6 Sailings

Dec 3, 2027 - Mar 10, 2028

Published prices from

$1,604

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

7-night Western Caribbean With Mexico Cruise From Fort Lauderdale, Florida

Aboard

Sun Princess

From

Fort Lauderdale, Florida

3 Sailings

Dec 4, 2027 - Feb 5, 2028

3 Sailings

Dec 4, 2027 - Feb 5, 2028

Published prices from

$749

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

14-night Eastern/Western Caribbean Adventurer Cruise From Miami, Florida

Miami

Half Moon Cay

St. Thomas (Charlotte Amalie)

St. Maarten (Philipsburg)

Belize City

+4 more

Aboard

Regal Princess

From

Miami, Florida

10 Sailings

Dec 5, 2027 - Mar 26, 2028

10 Sailings

Dec 5, 2027 - Mar 26, 2028

Published prices from

$1,308

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

7-night Eastern Caribbean With St. Thomas Cruise From Miami, Florida

Miami

Half Moon Cay

St. Thomas (Charlotte Amalie)

St. Maarten (Philipsburg)

Aboard

Regal Princess

From

Miami, Florida

6 Sailings

Dec 5, 2027 - Apr 9, 2028

6 Sailings

Dec 5, 2027 - Apr 9, 2028

Published prices from

$744

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

9-night Southern Caribbean With Martinique Cruise From Fort Lauderdale, Florida

Aboard

Enchanted Princess

From

Fort Lauderdale, Florida

1 Sailing

Dec 5, 2027

1 Sailing

Dec 5, 2027

Published prices from

$979

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

7-night Southern Caribbean With Barbados And St. Lucia Cruise From San Juan, Puerto Rico

San Juan

St. Thomas (Charlotte Amalie)

St. Maarten (Philipsburg)

St. John's

Castries

+2 more

Aboard

Emerald Princess

From

San Juan, Puerto Rico

8 Sailings

Dec 5, 2027 - Mar 12, 2028

8 Sailings

Dec 5, 2027 - Mar 12, 2028

Published prices from

$879

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

7-night Southern Caribbean With Tortola Cruise From Bridgetown, Barbados

Bridgetown (Barbados)

Aboard

Emerald Princess

From

Bridgetown, Barbados

6 Sailings

Dec 10, 2027 - Mar 17, 2028

6 Sailings

Dec 10, 2027 - Mar 17, 2028

Published prices from

$1,699

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

7-night Eastern Caribbean With St. Thomas Cruise From Fort Lauderdale, Florida

Ft. Lauderdale

Half Moon Cay

St. Thomas (Charlotte Amalie)

St. Maarten (Philipsburg)

Aboard

Sun Princess

From

Fort Lauderdale, Florida

3 Sailings

Dec 11, 2027 - Feb 12, 2028

3 Sailings

Dec 11, 2027 - Feb 12, 2028

Published prices from

$739

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

14-night Caribbean East/West Adventurer Cruise From Fort Lauderdale, Florida

Aboard

Sky Princess

From

Fort Lauderdale, Florida

1 Sailing

Dec 12, 2027

1 Sailing

Dec 12, 2027

Published prices from

$1,913

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

7-night Eastern Caribbean With Puerto Rico Cruise From Fort Lauderdale, Florida

Aboard

Sky Princess

From

Fort Lauderdale, Florida

5 Sailings

Dec 12, 2027 - Mar 5, 2028

5 Sailings

Dec 12, 2027 - Mar 5, 2028

Published prices from

$710

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

15-night Eastern/Western Caribbean Adventurer Holiday Cruise From Miami, Florida

Aboard

Regal Princess

From

Miami, Florida

1 Sailing

Dec 12, 2027

1 Sailing

Dec 12, 2027

Published prices from

$1,713

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

7-night Western Caribbean With Mexico Cruise From Miami, Florida

Aboard

Regal Princess

From

Miami, Florida

5 Sailings

Dec 12, 2027 - Mar 26, 2028

5 Sailings

Dec 12, 2027 - Mar 26, 2028

Published prices from

$709

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

10-night Southern Caribbean With St. Lucia Cruise From Port Canaveral, Florida

St. Maarten (Philipsburg)

+2 more

Aboard

Star Princess

From

Port Canaveral, Florida

2 Sailings

Dec 12, 2027 - Mar 19, 2028

2 Sailings

Dec 12, 2027 - Mar 19, 2028

Published prices from

$1,324

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

14-night Southern Caribbean Adventurer Holiday Cruise From San Juan, Puerto Rico

San Juan

St. Thomas (Charlotte Amalie)

St. Maarten (Philipsburg)

St. John's

Castries

+6 more

Aboard

Emerald Princess

From

San Juan, Puerto Rico

3 Sailings

Dec 12 - Dec 26, 2027

3 Sailings

Dec 12 - Dec 26, 2027

Published prices from

$1,793

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

16-night Panama Canal - Ocean To Ocean Holiday Cruise From Fort Lauderdale, Florida

Ft. Lauderdale

Oranjestad

Panama Canal

Fuerte Amador (Panama City)

Puntarenas

+5 more

Aboard

Island Princess

From

Fort Lauderdale, Florida

1 Sailing

Dec 13, 2027

1 Sailing

Dec 13, 2027

Published prices from

$1,549

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

10-night Southern Caribbean With St. Lucia Cruise From Fort Lauderdale, Florida

Aboard

Enchanted Princess

From

Fort Lauderdale, Florida

3 Sailings

Dec 14, 2027 - Feb 5, 2028

3 Sailings

Dec 14, 2027 - Feb 5, 2028

Published prices from

$1,089

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

9-night Southern Caribbean With Abc Islands Cruise From Fort Lauderdale, Florida

Aboard

Caribbean Princess

From

Fort Lauderdale, Florida

2 Sailings

Dec 14, 2027 - Jan 4, 2028

2 Sailings

Dec 14, 2027 - Jan 4, 2028

Published prices from

$794

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

10-night Southern Caribbean With Martinique Holiday Cruise From Fort Lauderdale, Florida

Aboard

Sun Princess

From

Fort Lauderdale, Florida

1 Sailing

Dec 18, 2027

1 Sailing

Dec 18, 2027

Published prices from

$1,459

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

7-night Western Caribbean With Grand Cayman Holiday Cruise From Fort Lauderdale, Florida

Ft. Lauderdale

Half Moon Cay

Falmouth (Jamaica)

Grand Cayman (George Town)

Cozumel

Aboard

Sky Princess

From

Fort Lauderdale, Florida

1 Sailing

Dec 19, 2027

1 Sailing

Dec 19, 2027

Published prices from

$1,198

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

14-night Eastern Caribbean Adventurer Holiday Cruise From Miami, Florida

Miami

Amber Cove

San Juan

St. Maarten (Philipsburg)

Roadtown

+3 more

Aboard

Regal Princess

From

Miami, Florida

1 Sailing

Dec 19, 2027

1 Sailing

Dec 19, 2027

Published prices from

$2,548

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

8-night Eastern Caribbean With Tortola Holiday Cruise From Miami, Florida

Miami

Amber Cove

San Juan

St. Maarten (Philipsburg)

Roadtown

Aboard

Regal Princess

From

Miami, Florida

1 Sailing

Dec 19, 2027

1 Sailing

Dec 19, 2027

Published prices from

$1,079

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

14-night Circle Caribbean Holiday Cruise From Fort Lauderdale, Florida

Ft. Lauderdale

St. Maarten (Philipsburg)

Aboard

Coral Princess

From

Fort Lauderdale, Florida

1 Sailing

Dec 20, 2027

1 Sailing

Dec 20, 2027

Published prices from

$1,644

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

14-night Southern Caribbean With Martinique Holiday Cruise From Port Canaveral, Florida

Port Canaveral

Princess Cays®

Roadtown

St. Maarten (Philipsburg)

Fort de France

+6 more

Aboard

Star Princess

From

Port Canaveral, Florida

1 Sailing

Dec 22, 2027

1 Sailing

Dec 22, 2027

Published prices from

$1,954

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

11-night Southern Caribbean With Barbados Holiday Cruise From Fort Lauderdale, Florida

Ft. Lauderdale

Basseterre

Dominica

Bridgetown (Barbados)

Pointe A Pitre

+4 more

Aboard

Enchanted Princess

From

Fort Lauderdale, Florida

1 Sailing

Dec 24, 2027

1 Sailing

Dec 24, 2027

Published prices from

$1,704

per person*

taxes & fees included

An aerial panoramic view of a winding road overlooking Frigate Bay and the Caribbean Sea, with rolling green hills, a beach, and the town of Basseterre, St. Kitts.

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

7-night Eastern Caribbean With St. Kitts Holiday Cruise From Fort Lauderdale, Florida

Aboard

Sky Princess

From

Fort Lauderdale, Florida

1 Sailing

Dec 26, 2027

1 Sailing

Dec 26, 2027

Published prices from

$1,293

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

7-night Southern Caribbean With Barbados And Tortola Holiday Cruise From San Juan, Puerto Rico

Aboard

Emerald Princess

From

San Juan, Puerto Rico

1 Sailing

Dec 26, 2027

1 Sailing

Dec 26, 2027

Published prices from

$1,164

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

13-night Eastern/Western Caribbean Adventurer Holiday Cruise From Miami, Florida

Aboard

Regal Princess

From

Miami, Florida

1 Sailing

Dec 27, 2027

1 Sailing

Dec 27, 2027

Published prices from

$2,298

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

6-night Eastern Caribbean With Turks & Caicos Holiday Cruise From Miami, Florida

Aboard

Regal Princess

From

Miami, Florida

1 Sailing

Dec 27, 2027

1 Sailing

Dec 27, 2027

Published prices from

$1,569

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

11-night Southern Caribbean With Barbados Holiday Cruise From Fort Lauderdale, Florida

Aboard

Sun Princess

From

Fort Lauderdale, Florida

1 Sailing

Dec 28, 2027

1 Sailing

Dec 28, 2027

Published prices from

$1,384

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

16-night Panama Canal - Ocean To Ocean Holiday Cruise From Los Angeles, California

Aboard

Island Princess

From

Los Angeles, California

1 Sailing

Dec 29, 2027

1 Sailing

Dec 29, 2027

Published prices from

$1,839

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

7-night Southern Caribbean With St. Lucia Holiday Cruise From Bridgetown, Barbados

Bridgetown (Barbados)

San Juan

St. Thomas (Charlotte Amalie)

St. Maarten (Philipsburg)

St. John's

+2 more

Aboard

Emerald Princess

From

Bridgetown, Barbados

1 Sailing

Dec 31, 2027

1 Sailing

Dec 31, 2027

Published prices from

$2,167

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

11-night Southern Caribbean With Barbados Cruise From Fort Lauderdale, Florida

Ft. Lauderdale

St. Thomas (Charlotte Amalie)

Basseterre

Castries

Bridgetown (Barbados)

+3 more

Aboard

Enchanted Princess

From

Fort Lauderdale, Florida

3 Sailings

Jan 4 - Feb 15, 2028

3 Sailings

Jan 4 - Feb 15, 2028

Published prices from

$1,384

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

4-night Turks & Caicos Getaway Cruise From Port Canaveral, Florida

Port Canaveral

Grand Turk

Aboard

Star Princess

From

Port Canaveral, Florida

1 Sailing

Jan 5, 2028

1 Sailing

Jan 5, 2028

Published prices from

$599

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

14-Eastern Caribbean Adventurer Cruise From Miami, Florida

Aboard

Regal Princess

From

Miami, Florida

5 Sailings

Jan 9 - Apr 2, 2028

5 Sailings

Jan 9 - Apr 2, 2028

Published prices from

$1,338

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

7-night Eastern Caribbean With St. Kitts Cruise From Miami, Florida

Aboard

Regal Princess

From

Miami, Florida

2 Sailings

Jan 9 - Jan 30, 2028

2 Sailings

Jan 9 - Jan 30, 2028

Published prices from

$624

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

16-night Panama Canal - Ocean To Ocean Cruise From Fort Lauderdale, Florida

Ft. Lauderdale

Cartagena (Colombia)

Panama Canal

Fuerte Amador (Panama City)

Puntarenas

+5 more

Aboard

Island Princess

From

Fort Lauderdale, Florida

4 Sailings

Jan 14 - Apr 19, 2028

4 Sailings

Jan 14 - Apr 19, 2028

Published prices from

$1,734

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

6-night Southern Caribbean With Puerto Rico Cruise From Bridgetown, Barbados

Bridgetown (Barbados)

San Juan

St. Thomas (Charlotte Amalie)

St. Maarten (Philipsburg)

St. John's

Aboard

Emerald Princess

From

Bridgetown, Barbados

1 Sailing

Jan 14, 2028

1 Sailing

Jan 14, 2028

Published prices from

$1,766

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

8-night Southern Caribbean With St. Lucia Cruise From Bridgetown, Barbados

Bridgetown (Barbados)

Castries

San Juan

St. Thomas (Charlotte Amalie)

Basseterre

+3 more

Aboard

Emerald Princess

From

Bridgetown, Barbados

1 Sailing

Jan 20, 2028

1 Sailing

Jan 20, 2028

Published prices from

$1,646

per person*

taxes & fees included

*Rates and offers are per person, in US Dollars, based on double occupancy, capacity controlled, subject to availability and confirmation, and may change without notice. Government taxes and fees are included. Rates and offers are available for select dates and categories only. Additional restrictions may apply. Call 1-800-377-9383 for full terms and conditions.