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4.9/5 ⭐Google 600+ Reviews | A+ Better Business Bureau

Destinations Departure Ports Cruise Lines Deals Land Tours Find Cruises

1-800-377-9383

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22 Results

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*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.

Oranjestad, Aruba harbor with boats and colorful Dutch architecture.

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

TCW EXCLUSIVE

12-night Caribbean Islander Cruise

New York City

St. Maarten (Philipsburg)

Aboard

Enchanted Princess

From

New York, New York

1 Sailing

Nov 1, 2025

1 Sailing

Nov 1, 2025

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

TCW EXCLUSIVE

14-night Caribbean East/West Adventurer Holiday Cruise

Aboard

Majestic Princess

From

Fort Lauderdale, Florida

11 Sailings

Nov 2, 2025 - Feb 22, 2026

11 Sailings

Nov 2, 2025 - Feb 22, 2026

Published prices from

$3,352

per person*

taxes & fees included

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

TCW EXCLUSIVE

8-night Southern Caribbean With ABC Islands Cruise

Ft. Lauderdale

Curacao

Oranjestad

Aboard

Majestic Princess

From

Fort Lauderdale, Florida

4 Sailings

Nov 8, 2025 - Feb 28, 2026

4 Sailings

Nov 8, 2025 - Feb 28, 2026

Published prices from

$1,744

per person*

taxes & fees included

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

TCW EXCLUSIVE

12-night Panama Canal With Costa Rica & Caribbean Holiday Cruise

Aboard

Caribbean Princess

From

Fort Lauderdale, Florida

4 Sailings

Nov 17, 2025 - Dec 29, 2026

4 Sailings

Nov 17, 2025 - Dec 29, 2026

Published prices from

$1,979

per person*

taxes & fees included

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

TCW EXCLUSIVE

8-night Southern Caribbean with Abc Islands Cruise

Aboard

Regal Princess

From

Fort Lauderdale, Florida

1 Sailing

Apr 3, 2026

1 Sailing

Apr 3, 2026

Published prices from

$2,004

per person*

taxes & fees included

Statue of Liberty and Manhattan skyline.

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

TCW EXCLUSIVE

12-night Southern Caribbean Islander Cruise

New York City

St. Maarten (Philipsburg)

Aboard

Majestic Princess

From

New York, New York

1 Sailing

Nov 7, 2026

1 Sailing

Nov 7, 2026

Published prices from

$2,299

per person*

taxes & fees included

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

TCW EXCLUSIVE

12-night Panama Canal With Costa Rica & Caribbean Cruise

Ft. Lauderdale

Grand Cayman (George Town)

Aboard

Caribbean Princess

From

Fort Lauderdale, Florida

10 Sailings

Nov 29, 2025 - Feb 15, 2027

10 Sailings

Nov 29, 2025 - Feb 15, 2027

Published prices from

$1,640

per person*

taxes & fees included

Exclusive Events, Experiences & More with Captain's Circle*+ 2 more offers

12-night Southern Caribbean Islander Cruise

Aboard

Caribbean Princess

From

Port Canaveral, Florida

1 Sailing

Oct 18, 2026

1 Sailing

Oct 18, 2026

Published prices from

$1,789

per person*

taxes & fees included

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

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

TCW EXCLUSIVE

8-night Southern Caribbean Islander Holiday Cruise

Aboard

Crown Princess

From

Fort Lauderdale, Florida

1 Sailing

Dec 19, 2026

1 Sailing

Dec 19, 2026

Published prices from

$1,509

per person*

taxes & fees included

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

TCW EXCLUSIVE

12- night Southern Caribbean with Panama

Ft. Lauderdale

Grand Cayman (George Town)

Aboard

Caribbean Princess

From

Fort Lauderdale, Florida

1 Sailing

Feb 21, 2026

1 Sailing

Feb 21, 2026

Published prices from

$2,079

per person*

taxes & fees included

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

Exclusive Events, Experiences & More with Captain's Circle*+ 2 more offers

27-night Panama Canal and Caribbean Adventurer Cruise

San Juan

St. Thomas (Charlotte Amalie)

Aboard

Grand Princess

From

San Juan, Puerto Rico

1 Sailing

Apr 5, 2026

1 Sailing

Apr 5, 2026

Published prices from

$4,373

per person*

taxes & fees included

Exclusive Events, Experiences & More with Captain's Circle*+ 2 more offers

7-night Southern Caribbean Islander Cruise

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

$1,159

per person*

taxes & fees included

Cupecoy Beach with white resort buildings, St. Maarten.

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

TCW EXCLUSIVE

12-night Southern Caribbean With Aruba Cruise

Bridgetown (Barbados)

+3 more

Aboard

Island Princess

From

Fort Lauderdale, Florida

1 Sailing

Nov 30, 2026

1 Sailing

Nov 30, 2026

Published prices from

$2,009

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 4 more offers

TCW EXCLUSIVE

16-night Panama Canal Cruise - Ocean To Ocean

Aboard

Crown Princess

From

Los Angeles, California

1 Sailing

Dec 3, 2026

1 Sailing

Dec 3, 2026

Published prices from

$1,946

per person*

taxes & fees included

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 $500 FREE Onboard Credit*+ 3 more offers

TCW EXCLUSIVE

13-night Southern/Eastern Caribbean Adventurer Cruise

Aboard

Regal Princess

From

Fort Lauderdale, Florida

1 Sailing

Mar 6, 2027

1 Sailing

Mar 6, 2027

Published prices from

$2,459

per person*

taxes & fees included

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.

Exclusive Events, Experiences & More with Captain's Circle*+ 2 more offers

18-night Southern Caribbean Adventurer Cruise

San Juan

St. Maarten (Philipsburg)

Dominica

St. George's

Bridgetown (Barbados)

+10 more

Aboard

Grand Princess

From

San Juan, Puerto Rico

1 Sailing

Mar 29, 2026

1 Sailing

Mar 29, 2026

Published prices from

$2,958

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

14-night Circle Caribbean Cruise

Bridgetown (Barbados)

+5 more

Aboard

Enchanted Princess

From

Fort Lauderdale, Florida

2 Sailings

Dec 3, 2025 - Dec 3, 2026

2 Sailings

Dec 3, 2025 - Dec 3, 2026

Published prices from

$2,206

per person*

taxes & fees included

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

TCW EXCLUSIVE

14-night Caribbean South/East Adventurer Cruise

Aboard

Majestic Princess

From

Fort Lauderdale, Florida

1 Sailing

Jan 11, 2026

1 Sailing

Jan 11, 2026

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

14-night Circle Caribbean Cruise

Ft. Lauderdale

St. Maarten (Philipsburg)

Aboard

Coral Princess

From

Fort Lauderdale, Florida

3 Sailings

Nov 24, 2025 - Oct 15, 2026

3 Sailings

Nov 24, 2025 - Oct 15, 2026

Published prices from

$2,309

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.

Exclusive Events, Experiences & More with Captain's Circle*+ 2 more offers

11-night Southern Caribbean Islander Cruise

San Juan

St. Thomas (Charlotte Amalie)

Aboard

Grand Princess

From

San Juan, Puerto Rico

1 Sailing

Apr 5, 2026

1 Sailing

Apr 5, 2026

Published prices from

$1,834

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

12-night Caribbean Islander Cruise

Aboard

Regal Princess

From

Galveston, Texas

1 Sailing

Mar 22, 2026

1 Sailing

Mar 22, 2026

Published prices from

$1,769

per person*

taxes & fees included

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

TCW EXCLUSIVE

13-night Southern Caribbean Islander Cruise

Aboard

Caribbean Princess

From

Fort Lauderdale, Florida

1 Sailing

Apr 28, 2026

1 Sailing

Apr 28, 2026

Published prices from

$1,929

per person*

taxes & fees included