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22 Results

Taxes and fees included in all prices shown

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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

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

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

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 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

2 Sailings

Dec 20, 2027 - Dec 21, 2028

2 Sailings

Dec 20, 2027 - Dec 21, 2028

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

Rocky beach and palm trees in Barbados.
Up to 45% OFF + up to $450 Instant Savings + FREE 3rd & 4th Guest*
Princess Cruises logo

16-night Circle Caribbean Cruise From Fort Lauderdale, Florida

Ft. Lauderdale
St. Thomas (Charlotte Amalie)
St. Maarten (Philipsburg)
Basseterre
St. John's
+6 more

Aboard

Island Princess

From

Fort Lauderdale, Florida

2 Sailings

Mar 18 - Apr 3, 2028

2 Sailings

Mar 18 - Apr 3, 2028

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.
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
+6 more

Aboard

Caribbean Princess

From

San Juan, Puerto Rico

6 Sailings

Nov 26, 2028 - Jan 28, 2029

6 Sailings

Nov 26, 2028 - Jan 28, 2029

Published prices from

$1,629

per person*

taxes & fees included

Rocky beach and palm trees in Barbados.
Princess Cruises logo

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

Bridgetown (Barbados)
San Juan
St. Thomas (Charlotte Amalie)
Basseterre
Fort de France
+2 more

Aboard

Caribbean Princess

From

Bridgetown, Barbados

3 Sailings

Dec 1, 2028 - Jan 26, 2029

3 Sailings

Dec 1, 2028 - Jan 26, 2029

Published prices from

$854

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.
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
Fort de France
St. George's
+2 more

Aboard

Caribbean Princess

From

San Juan, Puerto Rico

2 Sailings

Dec 3, 2028 - Jan 7, 2029

2 Sailings

Dec 3, 2028 - Jan 7, 2029

Published prices from

$858

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.
Princess Cruises logo

11-night Southern Caribbean With ABC Islands Holiday Cruise From San Juan, Puerto Rico

San Juan
St. Thomas (Charlotte Amalie)
Basseterre
Fort de France
St. George's
+5 more

Aboard

Caribbean Princess

From

San Juan, Puerto Rico

1 Sailing

Dec 17, 2028

1 Sailing

Dec 17, 2028

Published prices from

$1,994

per person*

taxes & fees included

A scenic coastal view in CuraƧao featuring houses with orange roofs on a cliffside overlooking a rocky beach with beautiful turquoise Caribbean water.
Princess Cruises logo

10-night Southern Caribbean With Aruba Cruise From Bridgetown, Barbados

Bridgetown (Barbados)
Oranjestad
Curacao
San Juan
St. Thomas (Charlotte Amalie)
+4 more

Aboard

Caribbean Princess

From

Bridgetown, Barbados

1 Sailing

Jan 2, 2029

1 Sailing

Jan 2, 2029

Published prices from

$1,334

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.
Princess Cruises logo

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

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

Aboard

Caribbean Princess

From

Bridgetown, Barbados

2 Sailings

Jan 19 - Feb 2, 2029

2 Sailings

Jan 19 - Feb 2, 2029

Published prices from

$974

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.
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

Caribbean Princess

From

San Juan, Puerto Rico

2 Sailings

Jan 21 - Feb 4, 2029

2 Sailings

Jan 21 - Feb 4, 2029

Published prices from

$954

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.