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Destinations Departure Ports Cruise Lines Deals Land Tours Find Cruises

1-800-377-9383

Call

61 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

14-night Caribbean East/West Adventurer Holiday Cruise

Ft. Lauderdale

Grand Cayman (George Town)

Aboard

Sun Princess

From

Fort Lauderdale, Florida

5 Sailings

Nov 23 - Dec 28, 2025

5 Sailings

Nov 23 - Dec 28, 2025

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

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

6 Sailings

Nov 30, 2025 - Feb 22, 2026

6 Sailings

Nov 30, 2025 - Feb 22, 2026

Published prices from

$4,624

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 4 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

Cupecoy Beach with white resort buildings, St. Maarten.

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

14-night Eastern Caribbean Adventurer Cruise

Port Canaveral

St. Thomas (Charlotte Amalie)

St. Maarten (Philipsburg)

San Juan

Grand Turk

+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

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

Up to $500 FREE Onboard Credit*+ 4 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

$2,720

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 4 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

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

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

$5,193

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*+ 4 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

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*+ 4 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

$1,451

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*+ 4 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

$4,958

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

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

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

TCW EXCLUSIVE

20-night Caribbean Explorer Holiday Cruise

Ft. Lauderdale

Princess Cays®

Grand Turk

St. Maarten (Philipsburg)

Basseterre

+7 more

Aboard

Enchanted Princess

From

Fort Lauderdale, Florida

2 Sailings

Dec 17 - Dec 27, 2025

2 Sailings

Dec 17 - Dec 27, 2025

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

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

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

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

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*+ 4 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

$3,989

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

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*+ 4 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

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

2 Sailings

Feb 15 - Mar 7, 2026

2 Sailings

Feb 15 - Mar 7, 2026

Published prices from

$2,879

per person*

taxes & fees included

Exclusive Events, Experiences & More with Captain's Circle*+ 3 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

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*+ 4 more offers

TCW EXCLUSIVE

14-night Eastern/Western Caribbean Adventurer Holiday Cruise

Aboard

Star Princess

From

Fort Lauderdale, Florida

5 Sailings

Nov 22, 2025 - Dec 19, 2026

5 Sailings

Nov 22, 2025 - Dec 19, 2026