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20 Results

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Offramp
Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.
Exclusive Events, Experiences & More with Captain's Circle*+ 2 more offers
Princess Cruises logo

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

Boats on a canal in Fort Lauderdale.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Princess Cruises logo

11-night Southern Caribbean With Martinique Holiday Cruise

Ft. Lauderdale
St. Thomas (Charlotte Amalie)
St. John's
Fort de France
Dominica
+3 more

Aboard

Coral Princess

From

Fort Lauderdale, Florida

1 Sailing

Dec 26, 2026

1 Sailing

Dec 26, 2026

Published prices from

$2,682

per person*

taxes & fees included

Boats on a canal in Fort Lauderdale.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Princess Cruises logo

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

Boats on a canal in Fort Lauderdale.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Princess Cruises logo

10-night Southern Caribbean With Martinique Cruise

Ft. Lauderdale
Princess Cays®
San Juan
Basseterre
Castries
+3 more

Aboard

Caribbean Princess

From

Fort Lauderdale, Florida

1 Sailing

Mar 29, 2026

1 Sailing

Mar 29, 2026

Published prices from

$1,329

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.

Rocky beach and palm trees in Barbados.
Exclusive Events, Experiences & More with Captain's Circle*+ 2 more offers
Princess Cruises logo

7-night Southern Caribbean Cruise With Barbados

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

$1,161

per person*

taxes & fees included

Cupecoy Beach with white resort buildings, St. Maarten.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Princess Cruises logo

8-night Eastern Caribbean With St. Kitts Holiday Cruise

Ft. Lauderdale
Amber Cove
San Juan
St. John's
St. Maarten (Philipsburg)

Aboard

Majestic Princess

From

Fort Lauderdale, Florida

1 Sailing

Dec 20, 2025

1 Sailing

Dec 20, 2025

Published prices from

$1,637

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
Princess Cruises logo

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

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
Princess Cruises logo

12-night Circle Caribbean Cruise

Ft. Lauderdale
Oranjestad
Kralendijk
Dominica
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

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
Princess Cruises logo

10-night Eastern Caribbean With St. Kitts Cruise

Ft. Lauderdale
Princess Cays®
Amber Cove
San Juan
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

Published prices from

$1,610

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
Princess Cruises logo

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

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
Princess Cruises logo

10-night Southern Caribbean with Martinique Cruise

Ft. Lauderdale
Princess Cays®
St. Thomas (Charlotte Amalie)
Dominica
Castries
+3 more

Aboard

Caribbean Princess

From

Fort Lauderdale, Florida

1 Sailing

Apr 18, 2026

1 Sailing

Apr 18, 2026

Published prices from

$1,767

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
Princess Cruises logo

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 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
Princess Cruises logo

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 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
Princess Cruises logo

20-night Caribbean Explorer Cruise

Ft. Lauderdale
Princess Cays®
San Juan
Basseterre
Castries
+6 more

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

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
Princess Cruises logo

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

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
Princess Cruises logo

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

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

14-night Southern Caribbean Adventurer Cruise

San Juan
St. Thomas (Charlotte Amalie)
St. Maarten (Philipsburg)
St. John's
Castries
+6 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

$3,073

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
Princess Cruises logo

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

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
Princess Cruises logo

10-night Southern Caribbean With Martinique Holiday Cruise

Ft. Lauderdale
Princess Cays®
San Juan
Basseterre
Castries
+3 more

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

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
Princess Cruises logo

12-night Caribbean Islander Cruise

Galveston
Cozumel
Oranjestad
Curacao
St. John's
+3 more

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