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29 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

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

18-night Brazilian Adventure Cruise From Fort Lauderdale, Florida

Ft. Lauderdale
St. Maarten (Philipsburg)
Castries
Bridgetown (Barbados)
Fortaleza
+4 more

Aboard

Majestic Princess

From

Fort Lauderdale, Florida

1 Sailing

Nov 19, 2026

1 Sailing

Nov 19, 2026

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

33-night Brazilian & Cape Horn Grand Adventure Cruise From Fort Lauderdale, Florida

Ft. Lauderdale
St. Maarten (Philipsburg)
Castries
Bridgetown (Barbados)
Fortaleza
+12 more

Aboard

Majestic Princess

From

Fort Lauderdale, Florida

1 Sailing

Nov 19, 2026

1 Sailing

Nov 19, 2026

A panoramic view of the coastal city of Roseau in Dominica, with its colorful buildings nestled between the Caribbean Sea and lush, mountainous terrain under a beautiful sky.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Princess Cruises logo

12-night Southern Caribbean With Aruba Cruise From Fort Lauderdale, Florida

Ft. Lauderdale
Oranjestad
Curacao
Castries
Bridgetown (Barbados)
+3 more

Aboard

Island Princess

From

Fort Lauderdale, Florida

1 Sailing

Nov 30, 2026

1 Sailing

Nov 30, 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

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

Published prices from

$1,457

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

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

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

$667

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

7-night Southern Caribbean With St. Lucia Cruise From Bridgetown, Barbados

Bridgetown (Barbados)
San Juan
St. Thomas (Charlotte Amalie)
St. Maarten (Philipsburg)
St. John's
+2 more

Aboard

Crown Princess

From

Bridgetown, Barbados

6 Sailings

Jan 8 - Mar 19, 2027

6 Sailings

Jan 8 - Mar 19, 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

Published prices from

$1,439

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

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

Published prices from

$1,224

per person*

taxes & fees included

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 Holiday Cruise From Fort Lauderdale, Florida

Ft. Lauderdale
Falmouth (Jamaica)
Oranjestad
Curacao
San Juan
+6 more

Aboard

Emerald Princess

From

Fort Lauderdale, Florida

1 Sailing

Nov 14, 2027

1 Sailing

Nov 14, 2027

Published prices from

$1,533

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

1 Sailing

Nov 15, 2027

1 Sailing

Nov 15, 2027

Published prices from

$1,654

per person*

taxes & fees included

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

5-night Southern Caribbean With St. Lucia Holiday Cruise From San Juan, Puerto Rico

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

Aboard

Emerald Princess

From

San Juan, Puerto Rico

1 Sailing

Nov 21, 2027

1 Sailing

Nov 21, 2027

Published prices from

$618

per person*

taxes & fees included

A panoramic view of the coastal city of Roseau in Dominica, with its colorful buildings nestled between the Caribbean Sea and lush, mountainous terrain under a beautiful sky.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Princess Cruises logo

7-night Southern Caribbean With Barbados And St. Lucia Holiday Cruise From San Juan, Puerto Rico

San Juan
St. Thomas (Charlotte Amalie)
St. Maarten (Philipsburg)
Dominica
Castries
+2 more

Aboard

Emerald Princess

From

San Juan, Puerto Rico

1 Sailing

Nov 21, 2027

1 Sailing

Nov 21, 2027

Published prices from

$889

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

Published prices from

$1,658

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

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

Published prices from

$1,294

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

7-night Southern Caribbean With St. Lucia Cruise From Bridgetown, Barbados

Bridgetown (Barbados)
San Juan
St. Thomas (Charlotte Amalie)
St. Maarten (Philipsburg)
St. John's
+2 more

Aboard

Emerald Princess

From

Bridgetown, Barbados

6 Sailings

Dec 3, 2027 - Mar 10, 2028

6 Sailings

Dec 3, 2027 - Mar 10, 2028

Published prices from

$1,604

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

7-night Southern Caribbean With Barbados And St. Lucia Cruise From San Juan, Puerto Rico

San Juan
St. Thomas (Charlotte Amalie)
St. Maarten (Philipsburg)
St. John's
Castries
+2 more

Aboard

Emerald Princess

From

San Juan, Puerto Rico

8 Sailings

Dec 5, 2027 - Mar 12, 2028

8 Sailings

Dec 5, 2027 - Mar 12, 2028

Published prices from

$879

per person*

taxes & fees included

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

Published prices from

$1,324

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

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

Published prices from

$1,793

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 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

Published prices from

$1,089

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

14-night Circle Caribbean Holiday 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 20, 2027

1 Sailing

Dec 20, 2027

Published prices from

$1,624

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

14-night Southern Caribbean With Martinique Holiday Cruise From Port Canaveral, Florida

Port Canaveral
Princess Cays®
Roadtown
St. Maarten (Philipsburg)
Fort de France
+6 more

Aboard

Star Princess

From

Port Canaveral, Florida

1 Sailing

Dec 22, 2027

1 Sailing

Dec 22, 2027

Published prices from

$1,884

per person*

taxes & fees included

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

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

Ft. Lauderdale
Amber Cove
San Juan
Basseterre
Castries
+4 more

Aboard

Sun Princess

From

Fort Lauderdale, Florida

1 Sailing

Dec 28, 2027

1 Sailing

Dec 28, 2027

Published prices from

$1,384

per person*

taxes & fees included

    • Showing results 1 - 24 of 29

*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.