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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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62 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.

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

TCW EXCLUSIVE

14-night Eastern/Western Caribbean Adventurer Cruise

Aboard

Star Princess

From

Fort Lauderdale, Florida

34 Sailings

Nov 29, 2025 - Mar 20, 2027

34 Sailings

Nov 29, 2025 - Mar 20, 2027

Published prices from

$2,438

per person*

taxes & fees included

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

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

14-night Eastern Caribbean Adventurer Cruise

Port Canaveral

Grand Turk

San Juan

St. Maarten (Philipsburg)

St. Thomas (Charlotte Amalie)

+3 more

Aboard

Sky Princess

From

Port Canaveral, Florida

5 Sailings

Nov 30, 2025 - Feb 22, 2026

5 Sailings

Nov 30, 2025 - Feb 22, 2026

Published prices from

$2,723

per person*

taxes & fees included

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

TCW EXCLUSIVE

14-night Caribbean East/West Adventurer Cruise

Ft. Lauderdale

Princess Cays®

San Juan

St. Thomas (Charlotte Amalie)

Costa Maya

+3 more

Aboard

Sun Princess

From

Fort Lauderdale, Florida

9 Sailings

Nov 30, 2025 - Feb 22, 2026

9 Sailings

Nov 30, 2025 - Feb 22, 2026

Published prices from

$2,468

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

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

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

6-night Eastern Caribbean With Turks & Caicos Cruise

Aboard

Sky Princess

From

Port Canaveral, Florida

4 Sailings

Dec 8, 2025 - Feb 16, 2026

4 Sailings

Dec 8, 2025 - Feb 16, 2026

Published prices from

$1,109

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

Ft. Lauderdale

Princess Cays®

San Juan

St. Maarten (Philipsburg)

Aboard

Sun Princess

From

Fort Lauderdale, Florida

1 Sailing

Dec 28, 2025

1 Sailing

Dec 28, 2025

Published prices from

$2,724

per person*

taxes & fees included

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

TCW EXCLUSIVE

7-night Eastern Caribbean Cruise With Puerto Rico

Ft. Lauderdale

Princess Cays®

San Juan

St. Thomas (Charlotte Amalie)

Aboard

Sun Princess

From

Fort Lauderdale, Florida

7 Sailings

Nov 16, 2025 - Feb 22, 2026

7 Sailings

Nov 16, 2025 - Feb 22, 2026

Published prices from

$1,264

per person*

taxes & fees included

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

TCW EXCLUSIVE

10-night Southern Caribbean With Martinique Cruise

Ft. Lauderdale

Princess Cays®

St. Thomas (Charlotte Amalie)

Dominica

Castries

+3 more

Aboard

Enchanted Princess

From

Fort Lauderdale, Florida

4 Sailings

Jan 16 - Mar 17, 2026

4 Sailings

Jan 16 - Mar 17, 2026

Published prices from

$1,169

per person*

taxes & fees included

A stunning aerial view of the turquoise waters and white-sand beaches around Paradise Island in Nassau, Bahamas, with the Atlantis resort visible in the distance.

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

14-night Eastern Caribbean Adventurer Holiday Cruise

Aboard

Sky Princess

From

Port Canaveral, Florida

2 Sailings

Dec 22 - Dec 28, 2025

2 Sailings

Dec 22 - Dec 28, 2025

Published prices from

$3,028

per person*

taxes & fees included

A stunning panoramic view of Road Town on Tortola, British Virgin Islands, showing the harbor filled with boats and a small town surrounded by lush green hills overlooking the Caribbean Sea.

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

TCW EXCLUSIVE

10-night Eastern Caribbean With Tortola Cruise

Ft. Lauderdale

Princess Cays®

St. Thomas (Charlotte Amalie)

St. Maarten (Philipsburg)

St. John's

+3 more

Aboard

Caribbean Princess

From

Fort Lauderdale, Florida

2 Sailings

Nov 7, 2025 - Apr 8, 2026

2 Sailings

Nov 7, 2025 - Apr 8, 2026

Published prices from

$1,329

per person*

taxes & fees included

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

20-night Caribbean Explorer Holiday Cruise

Ft. Lauderdale

Princess Cays®

St. Thomas (Charlotte Amalie)

St. Maarten (Philipsburg)

St. John's

+6 more

Aboard

Enchanted Princess

From

Fort Lauderdale, Florida

3 Sailings

Nov 13 - Dec 27, 2025

3 Sailings

Nov 13 - Dec 27, 2025

Published prices from

$4,998

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.

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

6-night Eastern Caribbean With Turks & Caicos Holiday Cruise

Aboard

Sky Princess

From

Port Canaveral, Florida

1 Sailing

Dec 22, 2025

1 Sailing

Dec 22, 2025

Published prices from

$1,816

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

10-night Eastern Caribbean With St. Kitts Cruise

Ft. Lauderdale

Princess Cays®

San Juan

St. Maarten (Philipsburg)

Basseterre

+3 more

Aboard

Enchanted Princess

From

Fort Lauderdale, Florida

12 Sailings

Jan 6, 2026 - Apr 6, 2027

12 Sailings

Jan 6, 2026 - Apr 6, 2027

Published prices from

$1,655

per person*

taxes & fees included

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

8-night Eastern Caribbean with Puerto Rico Holiday Cruise

Aboard

Sky Princess

From

Port Canaveral, Florida

1 Sailing

Dec 28, 2025

1 Sailing

Dec 28, 2025

Published prices from

$2,509

per person*

taxes & fees included

A sunny shot of Mahogany Bay, Roatan, with white sandy beaches, green palm trees, a cruise ship port, and a chairlift.

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

TCW EXCLUSIVE

14-night Caribbean East/West Adventurer Holiday Cruise

Ft. Lauderdale

Princess Cays®

San Juan

St. Thomas (Charlotte Amalie)

Grand Cayman (George Town)

+3 more

Aboard

Sun Princess

From

Fort Lauderdale, Florida

6 Sailings

Nov 16 - Dec 28, 2025

6 Sailings

Nov 16 - Dec 28, 2025

Published prices from

$2,608

per person*

taxes & fees included

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

TCW EXCLUSIVE

7-night Eastern Caribbean With Bahamas Cruise

Aboard

Star Princess

From

Fort Lauderdale, Florida

7 Sailings

Dec 6, 2025 - Mar 14, 2026

7 Sailings

Dec 6, 2025 - Mar 14, 2026

Published prices from

$904

per person*

taxes & fees included

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

TCW EXCLUSIVE

10-night Southern Caribbean With Martinique Holiday Cruise

Aboard

Enchanted Princess

From

Fort Lauderdale, Florida

2 Sailings

Nov 23 - Dec 27, 2025

2 Sailings

Nov 23 - Dec 27, 2025

Published prices from

$1,883

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

3-night Maiden Caribbean With Princess Cays Crusie

Ft. Lauderdale

Princess Cays®

Nassau

Aboard

Star Princess

From

Fort Lauderdale, Florida

1 Sailing

Nov 7, 2025

1 Sailing

Nov 7, 2025

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 Circle Caribbean Cruise

St. Maarten (Philipsburg)

+3 more

Aboard

Caribbean Princess

From

Fort Lauderdale, Florida

4 Sailings

Dec 11, 2025 - Mar 5, 2026

4 Sailings

Dec 11, 2025 - Mar 5, 2026

Published prices from

$1,789

per person*

taxes & fees included

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

TCW EXCLUSIVE

10-night Eastern Caribbean With Tortola Cruise

Ft. Lauderdale

Princess Cays®

St. Thomas (Charlotte Amalie)

St. Maarten (Philipsburg)

St. John's

+3 more

Aboard

Enchanted Princess

From

Fort Lauderdale, Florida

3 Sailings

Nov 13, 2025 - Mar 7, 2026

3 Sailings

Nov 13, 2025 - Mar 7, 2026

Published prices from

$2,339

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

14-night Eastern/Western Caribbean Adventurer Holiday Cruise

Aboard

Star Princess

From

Fort Lauderdale, Florida

6 Sailings

Nov 15, 2025 - Dec 19, 2026

6 Sailings

Nov 15, 2025 - Dec 19, 2026

Published prices from

$3,503

per person*

taxes & fees included

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

6-night Eastern Caribbean Cruise With Turks & Caicos

Aboard

Sky Princess

From

Port Canaveral, Florida

9 Sailings

Jan 19, 2026 - Mar 1, 2027

9 Sailings

Jan 19, 2026 - Mar 1, 2027

Published prices from

$1,045

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

10-night Eastern Caribbean With St. Kitts Holiday Cruise

Ft. Lauderdale

Princess Cays®

Grand Turk

St. Maarten (Philipsburg)

Basseterre

+3 more

Aboard

Enchanted Princess

From

Fort Lauderdale, Florida

3 Sailings

Dec 17, 2025 - Dec 27, 2026

3 Sailings

Dec 17, 2025 - Dec 27, 2026

Published prices from

$2,039

per person*

taxes & fees included

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

TCW EXCLUSIVE

7-night Eastern Caribbean With Bahamas Holiday Cruise

Aboard

Star Princess

From

Fort Lauderdale, Florida

2 Sailings

Nov 22 - Dec 20, 2025

2 Sailings

Nov 22 - Dec 20, 2025

Published prices from

$1,676

per person*

taxes & fees included

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

TCW EXCLUSIVE

20-night Caribbean Explorer Cruise

Ft. Lauderdale

Princess Cays®

San Juan

St. Maarten (Philipsburg)

Basseterre

+6 more

Aboard

Enchanted Princess

From

Fort Lauderdale, Florida

7 Sailings

Jan 6 - Mar 7, 2026

7 Sailings

Jan 6 - Mar 7, 2026

Published prices from

$4,778

per person*

taxes & fees included