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55 Results

Taxes and fees included in all prices shown

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

12-night Southern Caribbean Islander Cruise From New York City, New York

New York City
St. Maarten (Philipsburg)
Basseterre
Castries
Curacao
+3 more

Aboard

Majestic Princess

From

New York City, New York

1 Sailing

Nov 7, 2026

1 Sailing

Nov 7, 2026

Boats on a canal in Fort Lauderdale.
Princess Cruises logo

10-night Eastern Caribbean With St. Kitts Cruise From Fort Lauderdale, Florida

Ft. Lauderdale
St. John's
St. Maarten (Philipsburg)
Dominica
Basseterre
+2 more

Aboard

Coral Princess

From

Fort Lauderdale, Florida

2 Sailings

Nov 8 - Nov 18, 2026

2 Sailings

Nov 8 - Nov 18, 2026

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

14-night Circle Caribbean Cruise From Fort Lauderdale, Florida

Ft. Lauderdale
St. Maarten (Philipsburg)
Basseterre
Fort de France
Dominica
+5 more

Aboard

Enchanted Princess

From

Fort Lauderdale, Florida

1 Sailing

Dec 3, 2026

1 Sailing

Dec 3, 2026

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

10-night Eastern Caribbean With St. Kitts Holiday Cruise From Fort Lauderdale, Florida

Ft. Lauderdale
Half Moon Cay
Amber Cove
San Juan
St. Maarten (Philipsburg)
+3 more

Aboard

Enchanted Princess

From

Fort Lauderdale, Florida

2 Sailings

Dec 17 - Dec 27, 2026

2 Sailings

Dec 17 - Dec 27, 2026

A panoramic view of Fort-de-France, Martinique, showing a bustling bay filled with boats and yachts, with colorful houses nestled on the surrounding green hillsides and the deep blue Caribbean Sea beyond.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Princess Cruises logo

11-night Southern Caribbean With Martinique Holiday Cruise From Fort Lauderdale, Florida

Ft. Lauderdale
St. Thomas (Charlotte Amalie)
Basseterre
Fort de France
Bridgetown (Barbados)
+3 more

Aboard

Coral Princess

From

Fort Lauderdale, Florida

1 Sailing

Dec 26, 2026

1 Sailing

Dec 26, 2026

Rocky beach and palm trees in Barbados.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Princess Cruises logo

14-night Southern Caribbean Adventurer Cruise From San Juan, Puerto Rico

San Juan
St. Thomas (Charlotte Amalie)
St. Maarten (Philipsburg)
St. John's
Castries
+5 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

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Princess Cruises logo

5-night Eastern Caribbean With St. Kitts Cruise From San Juan, Puerto Rico

San Juan
St. Thomas (Charlotte Amalie)
Basseterre
Dominica
St. George's

Aboard

Crown Princess

From

San Juan, Puerto Rico

1 Sailing

Jan 3, 2027

1 Sailing

Jan 3, 2027

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

10-night Eastern Caribbean With St. Kitts Cruise From Fort Lauderdale, Florida

Ft. Lauderdale
Princess Cays®
Amber Cove
San Juan
St. John's
+3 more

Aboard

Enchanted Princess

From

Fort Lauderdale, Florida

10 Sailings

Jan 6 - Apr 6, 2027

10 Sailings

Jan 6 - Apr 6, 2027

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

7-night Eastern Caribbean With St. Kitts Cruise From Fort Lauderdale, Florida

Ft. Lauderdale
Amber Cove
San Juan
Basseterre

Aboard

Island Princess

From

Fort Lauderdale, Florida

1 Sailing

Oct 29, 2027

1 Sailing

Oct 29, 2027

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 St. Lucia Cruise From Fort Lauderdale, Florida

Ft. Lauderdale
Amber Cove
San Juan
Basseterre
Castries
+3 more

Aboard

Island Princess

From

Fort Lauderdale, Florida

1 Sailing

Nov 5, 2027

1 Sailing

Nov 5, 2027

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

14-night Southern Caribbean Islander Cruise From New York City, New York

New York City
St. Thomas (Charlotte Amalie)
Basseterre
St. John's
Castries
+5 more

Aboard

Regal Princess

From

New York City, New York

1 Sailing

Nov 6, 2027

1 Sailing

Nov 6, 2027

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

7-night Eastern Caribbean With St. Kitts Cruise From Fort Lauderdale, Florida

Ft. Lauderdale
Amber Cove
San Juan
Basseterre

Aboard

Sky Princess

From

Fort Lauderdale, Florida

10 Sailings

Nov 14, 2027 - Feb 25, 2029

10 Sailings

Nov 14, 2027 - Feb 25, 2029

Published prices from

$800

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

14-night Circle Caribbean Holiday Cruise From Fort Lauderdale, Florida

Ft. Lauderdale
St. Maarten (Philipsburg)
Basseterre
Dominica
Castries
+5 more

Aboard

Island Princess

From

Fort Lauderdale, Florida

2 Sailings

Nov 15, 2027 - Dec 19, 2028

2 Sailings

Nov 15, 2027 - Dec 19, 2028

Published prices from

$2,314

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
Princess Cruises logo

14-night Southern Caribbean Adventurer Cruise From San Juan, Puerto Rico

San Juan
St. Thomas (Charlotte Amalie)
St. Maarten (Philipsburg)
Dominica
Castries
+5 more

Aboard

Emerald Princess

From

San Juan, Puerto Rico

14 Sailings

Nov 21, 2027 - Mar 12, 2028

14 Sailings

Nov 21, 2027 - Mar 12, 2028

Rocky beach and palm trees in Barbados.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Princess Cruises logo

7-night Southern Caribbean With Tortola Holiday Cruise From Bridgetown, Barbados

Bridgetown (Barbados)
San Juan
Roadtown
Basseterre
Dominica
+2 more

Aboard

Emerald Princess

From

Bridgetown, Barbados

2 Sailings

Nov 26 - Dec 24, 2027

2 Sailings

Nov 26 - Dec 24, 2027

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

14-night Eastern/Western Caribbean Adventurer Cruise From Fort Lauderdale, Florida

Ft. Lauderdale
Half Moon Cay
Falmouth (Jamaica)
Grand Cayman (George Town)
Cozumel
+4 more

Aboard

Sky Princess

From

Fort Lauderdale, Florida

14 Sailings

Nov 28, 2027 - Feb 18, 2029

14 Sailings

Nov 28, 2027 - Feb 18, 2029

Published prices from

$1,649

per person*

taxes & fees included

An aerial view of the colorful waterfront of St. George's, Grenada, with the town's buildings nestled on a hillside and a long, rocky breakwater extending into the calm, turquoise water.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Princess Cruises logo

7-night Southern Caribbean With Barbados And Tortola Cruise From San Juan, Puerto Rico

San Juan
Roadtown
Basseterre
Dominica
St. George's
+2 more

Aboard

Emerald Princess

From

San Juan, Puerto Rico

7 Sailings

Nov 28, 2027 - Mar 19, 2028

7 Sailings

Nov 28, 2027 - Mar 19, 2028

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

14-night Circle Caribbean Cruise From Fort Lauderdale, Florida

Ft. Lauderdale
St. Maarten (Philipsburg)
Basseterre
Dominica
Bridgetown (Barbados)
+5 more

Aboard

Island Princess

From

Fort Lauderdale, Florida

1 Sailing

Nov 29, 2027

1 Sailing

Nov 29, 2027

A panoramic view of Fort-de-France, Martinique, showing a bustling bay filled with boats and yachts, with colorful houses nestled on the surrounding green hillsides and the deep blue Caribbean Sea beyond.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Princess Cruises logo

9-night Southern Caribbean With Martinique Cruise From Fort Lauderdale, Florida

Ft. Lauderdale
Amber Cove
San Juan
Basseterre
Fort de France
+2 more

Aboard

Enchanted Princess

From

Fort Lauderdale, Florida

1 Sailing

Dec 5, 2027

1 Sailing

Dec 5, 2027

An aerial view of the colorful waterfront of St. George's, Grenada, with the town's buildings nestled on a hillside and a long, rocky breakwater extending into the calm, turquoise water.
Up to 45% OFF + up to $450 Instant Savings + FREE 3rd & 4th Guest*
Princess Cruises logo

14-night Circle Caribbean Cruise From Fort Lauderdale, Florida

Ft. Lauderdale
St. Maarten (Philipsburg)
Basseterre
Dominica
Castries
+5 more

Aboard

Coral Princess

From

Fort Lauderdale, Florida

1 Sailing

Dec 6, 2027

1 Sailing

Dec 6, 2027

A panoramic view of Fort-de-France, Martinique, showing a bustling bay filled with boats and yachts, with colorful houses nestled on the surrounding green hillsides and the deep blue Caribbean Sea beyond.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Princess Cruises logo

7-night Southern Caribbean With Tortola Cruise From Bridgetown, Barbados

Bridgetown (Barbados)
San Juan
Roadtown
Basseterre
Fort de France
+2 more

Aboard

Emerald Princess

From

Bridgetown, Barbados

6 Sailings

Dec 10, 2027 - Mar 17, 2028

6 Sailings

Dec 10, 2027 - Mar 17, 2028

Peaceful sunrise over a sandy Florida beach with sea oats in Port Canaveral.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Princess Cruises logo

10-night Southern Caribbean With St. Lucia Cruise From Port Canaveral, Florida

Port Canaveral
San Juan
Basseterre
Castries
St. Maarten (Philipsburg)
+2 more

Aboard

Star Princess

From

Port Canaveral, Florida

2 Sailings

Dec 12, 2027 - Mar 19, 2028

2 Sailings

Dec 12, 2027 - Mar 19, 2028

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

14-night Southern Caribbean Adventurer Holiday Cruise From San Juan, Puerto Rico

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

Aboard

Emerald Princess

From

San Juan, Puerto Rico

3 Sailings

Dec 12 - Dec 26, 2027

3 Sailings

Dec 12 - Dec 26, 2027

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 St. Lucia Cruise From Fort Lauderdale, Florida

Ft. Lauderdale
Amber Cove
San Juan
Basseterre
St. John's
+3 more

Aboard

Enchanted Princess

From

Fort Lauderdale, Florida

3 Sailings

Dec 14, 2027 - Feb 5, 2028

3 Sailings

Dec 14, 2027 - Feb 5, 2028

A panoramic view of Fort-de-France, Martinique, showing a bustling bay filled with boats and yachts, with colorful houses nestled on the surrounding green hillsides and the deep blue Caribbean Sea beyond.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Princess Cruises logo

10-night Southern Caribbean With Martinique Holiday Cruise From Fort Lauderdale, Florida

Ft. Lauderdale
Amber Cove
San Juan
Basseterre
Fort de France
+3 more

Aboard

Sun Princess

From

Fort Lauderdale, Florida

1 Sailing

Dec 18, 2027

1 Sailing

Dec 18, 2027

    • Showing results 1 - 24 of 55

*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.