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26 Results

Taxes and fees included in all prices shown

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Peaceful sunrise over a sandy Florida beach with sea oats in Port Canaveral.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Carnival Cruise Line Logo

14-night Carnival Journeys Cruise - Southern Caribbean From Port Canaveral, Florida

Port Canaveral
St. Thomas (Charlotte Amalie)
St. John's
Dominica
Bridgetown (Barbados)
+5 more

Aboard

Carnival Venezia

From

Port Canaveral, Florida

3 Sailings

Nov 29, 2026 - Feb 21, 2027

3 Sailings

Nov 29, 2026 - Feb 21, 2027

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

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 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*+ 2 more offers
TCW EXCLUSIVE
Carnival Cruise Line Logo

11-night Journeys - Southern Caribbean Cruise From Miami, Florida

Miami
St. Thomas (Charlotte Amalie)
Dominica
St. George's
Bridgetown (Barbados)
+3 more

Aboard

Carnival Conquest

From

Miami, Florida

3 Sailings

Jan 11 - Nov 29, 2027

3 Sailings

Jan 11 - Nov 29, 2027

Published prices from

$1,295

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

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

Bridgetown (Barbados)
San Juan
St. Thomas (Charlotte Amalie)
Pointe A Pitre
Dominica
+2 more

Aboard

Crown Princess

From

Bridgetown, Barbados

5 Sailings

Jan 29 - Mar 12, 2027

5 Sailings

Jan 29 - Mar 12, 2027

Rocky beach and palm trees in Barbados.
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
Fort de France
Bridgetown (Barbados)
+3 more

Aboard

Caribbean Princess

From

Fort Lauderdale, Florida

1 Sailing

Apr 9, 2027

1 Sailing

Apr 9, 2027

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

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

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

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

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

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

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

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

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

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 Barbados Holiday Cruise From Fort Lauderdale, Florida

Ft. Lauderdale
Basseterre
Dominica
Bridgetown (Barbados)
Pointe A Pitre
+4 more

Aboard

Enchanted Princess

From

Fort Lauderdale, Florida

1 Sailing

Dec 24, 2027

1 Sailing

Dec 24, 2027

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 Tortola Holiday Cruise From San Juan, Puerto Rico

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

Aboard

Emerald Princess

From

San Juan, Puerto Rico

1 Sailing

Dec 26, 2027

1 Sailing

Dec 26, 2027

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

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

Bridgetown (Barbados)
Castries
San Juan
St. Thomas (Charlotte Amalie)
Basseterre
+3 more

Aboard

Emerald Princess

From

Bridgetown, Barbados

1 Sailing

Jan 20, 2028

1 Sailing

Jan 20, 2028

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. Kitts Cruise From San Juan, Puerto Rico

San Juan
St. Thomas (Charlotte Amalie)
Basseterre
Dominica
St. George's
+2 more

Aboard

Emerald Princess

From

San Juan, Puerto Rico

1 Sailing

Jan 23, 2028

1 Sailing

Jan 23, 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*+ 1 more offer
TCW EXCLUSIVE
Carnival Cruise Line Logo

14-night Journeys - Caribbean Carnaval Cruise From Port Canaveral, Florida

Port Canaveral
St. Maarten (Philipsburg)
St. John's
Castries
St. George's
+5 more

Aboard

Carnival Firenze

From

Port Canaveral, Florida

1 Sailing

Feb 20, 2028

1 Sailing

Feb 20, 2028

Published prices from

$1,276

per person*

taxes & fees included

    • Showing results 1 - 24 of 26

*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.