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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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34 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.

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

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

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

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

14-night Southern Caribbean Adventurer Cruise

San Juan

Bridgetown (Barbados)

Dominica

St. John's

St. Maarten (Philipsburg)

+4 more

Aboard

Grand Princess

From

San Juan, Puerto Rico

21 Sailings

Nov 2, 2025 - Mar 22, 2026

21 Sailings

Nov 2, 2025 - Mar 22, 2026

Published prices from

$2,329

per person*

taxes & fees included

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

TCW EXCLUSIVE

8-night Eastern Caribbean With St. Thomas Cruise

Ft. Lauderdale

Amber Cove

San Juan

St. Maarten (Philipsburg)

St. Thomas (Charlotte Amalie)

Aboard

Majestic Princess

From

Fort Lauderdale, Florida

2 Sailings

Jan 3 - Feb 14, 2026

2 Sailings

Jan 3 - Feb 14, 2026

Published prices from

$1,567

per person*

taxes & fees included

Tropical beach with lounge chairs in Cozumel.

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

TCW EXCLUSIVE

11-night Caribbean East/West Adventurer Cruise

Ft. Lauderdale

Princess Cays®

San Juan

St. Thomas (Charlotte Amalie)

Cozumel

Aboard

Sun Princess

From

Fort Lauderdale, Florida

1 Sailing

Feb 22, 2026

1 Sailing

Feb 22, 2026

Published prices from

$1,953

per person*

taxes & fees included

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

TCW EXCLUSIVE

14-night Eastern/Western Caribbean Adventurer Cruise

Ft. Lauderdale

Princess Cays®

San Juan

St. Thomas (Charlotte Amalie)

Cozumel

+4 more

Aboard

Majestic Princess

From

Fort Lauderdale, Florida

2 Sailings

Mar 8 - Mar 15, 2026

2 Sailings

Mar 8 - Mar 15, 2026

Published prices from

$2,653

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

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

TCW EXCLUSIVE

8-night Eastern Caribbean Cruise With St. Thomas

Ft. Lauderdale

St. Thomas (Charlotte Amalie)

St. Maarten (Philipsburg)

Grand Turk

Aboard

Star Princess

From

Fort Lauderdale, Florida

2 Sailings

Mar 28 - Apr 5, 2026

2 Sailings

Mar 28 - Apr 5, 2026

Published prices from

$2,224

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

Cupecoy Beach with white resort buildings, St. Maarten.

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

8-night Eastern Caribbean With St. Thomas Cruise

Port Canaveral

St. Thomas (Charlotte Amalie)

St. Maarten (Philipsburg)

San Juan

Grand Turk

Aboard

Sky Princess

From

Port Canaveral, Florida

3 Sailings

Dec 14, 2025 - Feb 8, 2026

3 Sailings

Dec 14, 2025 - Feb 8, 2026

Published prices from

$1,694

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

Amber Cove

San Juan

St. Maarten (Philipsburg)

St. Thomas (Charlotte Amalie)

+4 more

Aboard

Majestic Princess

From

Fort Lauderdale, Florida

1 Sailing

Feb 14, 2026

1 Sailing

Feb 14, 2026

Published prices from

$2,842

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

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

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

TCW EXCLUSIVE

12-night Eastern Caribbean Adventurer Cruise

Ft. Lauderdale

Princess Cays®

San Juan

St. Thomas (Charlotte Amalie)

Grand Turk

+2 more

Aboard

Majestic Princess

From

Fort Lauderdale, Florida

1 Sailing

Mar 22, 2026

1 Sailing

Mar 22, 2026

Published prices from

$2,478

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

7-night Eastern Caribbean With St. Thomas Cruise

Ft. Lauderdale

Princess Cays®

San Juan

St. Thomas (Charlotte Amalie)

Aboard

Majestic Princess

From

Fort Lauderdale, Florida

2 Sailings

Mar 8 - Mar 22, 2026

2 Sailings

Mar 8 - Mar 22, 2026

Published prices from

$1,269

per person*

taxes & fees included

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

TCW EXCLUSIVE

8-night Eastern Caribbean With St. Thomas Holiday Cruise

Ft. Lauderdale

Amber Cove

San Juan

St. Maarten (Philipsburg)

St. Thomas (Charlotte Amalie)

Aboard

Majestic Princess

From

Fort Lauderdale, Florida

1 Sailing

Nov 22, 2025

1 Sailing

Nov 22, 2025

Published prices from

$1,604

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

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

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

11-night Eastern Caribbean With St. Thomas Cruise

Ft. Lauderdale

Amber Cove

St. Thomas (Charlotte Amalie)

Basseterre

St. Maarten (Philipsburg)

+3 more

Aboard

Coral Princess

From

Fort Lauderdale, Florida

1 Sailing

Nov 13, 2025

1 Sailing

Nov 13, 2025

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

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

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 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

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

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

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

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

TCW EXCLUSIVE

20-night Caribbean Explorer Cruise

Aboard

Caribbean Princess

From

Fort Lauderdale, Florida

2 Sailings

Mar 29 - Apr 8, 2026

2 Sailings

Mar 29 - Apr 8, 2026

Published prices from

$3,204

per person*

taxes & fees included

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

8-night Eastern Caribbean with St. Thomas Cruise

Port Canaveral

Grand Turk

San Juan

St. Maarten (Philipsburg)

St. Thomas (Charlotte Amalie)

Aboard

Sky Princess

From

Port Canaveral, Florida

2 Sailings

Nov 30, 2025 - Feb 22, 2026

2 Sailings

Nov 30, 2025 - Feb 22, 2026

Published prices from

$1,704

per person*

taxes & fees included