Princess Cruises from San Juan, Puerto Rico

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.

Upcoming Princess Cruises from San Juan, Puerto Rico

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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 Plus - Drinks, Wi-Fi, Tips Included & More*+ 2 more offers

7-night Southern Caribbean with Barbados Cruise

Aboard

Grand Princess

From

San Juan, Puerto Rico

16 Sailings

Dec 14, 2025 - Mar 29, 2026

16 Sailings

Dec 14, 2025 - Mar 29, 2026

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.

Princess Plus - Drinks, Wi-Fi, Tips Included & More*+ 2 more offers

14-night Southern Caribbean Adventurer Cruise

St. Thomas (Charlotte Amalie)

St. Maarten (Philipsburg)

Aboard

Grand Princess

From

San Juan, Puerto Rico

15 Sailings

Dec 14, 2025 - Mar 22, 2026

15 Sailings

Dec 14, 2025 - Mar 22, 2026

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.

Princess Plus - Drinks, Wi-Fi, Tips Included & More*+ 2 more offers

18-night Southern Caribbean Adventurer Cruise

St. Maarten (Philipsburg)

Bridgetown (Barbados)

Aboard

Grand Princess

From

San Juan, Puerto Rico

1 Sailing

Mar 29, 2026

1 Sailing

Mar 29, 2026

Puntarenas, Costa Rica tropical landscape with palm trees and mountains.

Princess Plus - Drinks, Wi-Fi, Tips Included & More*+ 2 more offers

27-night Panama Canal and Caribbean Adventurer Cruise

St. Thomas (Charlotte Amalie)

Aboard

Grand Princess

From

San Juan, Puerto Rico

1 Sailing

Apr 5, 2026

1 Sailing

Apr 5, 2026

A sunny, idyllic beach scene in Amber Cove, Dominican Republic, with a small boat and paddle resting under a palm tree beside the turquoise ocean and a clear blue sky.

Princess Plus - Drinks, Wi-Fi, Tips Included & More*+ 2 more offers

11-night Southern Caribbean Islander Cruise

St. Thomas (Charlotte Amalie)

Aboard

Grand Princess

From

San Juan, Puerto Rico

1 Sailing

Apr 5, 2026

1 Sailing

Apr 5, 2026

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 Plus - Drinks, Wi-Fi, Tips Included & More*+ 2 more offers

14-night Southern Caribbean Adventurer Cruise

St. Thomas (Charlotte Amalie)

St. Maarten (Philipsburg)

Aboard

Crown Princess

From

San Juan, Puerto Rico

12 Sailings

Dec 27, 2026 - Mar 14, 2027

12 Sailings

Dec 27, 2026 - Mar 14, 2027

Rocky beach and palm trees in Barbados.

Princess Plus - Drinks, Wi-Fi, Tips Included & More*+ 2 more offers

7-night Southern Caribbean Cruise With Barbados

St. Thomas (Charlotte Amalie)

St. Maarten (Philipsburg)

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

Boats on a canal in Fort Lauderdale.

Princess Plus - Drinks, Wi-Fi, Tips Included & More*+ 2 more offers

7-night Southern Caribbean Islander Cruise

St. Maarten (Philipsburg)

Aboard

Crown Princess

From

San Juan, Puerto Rico

1 Sailing

Mar 28, 2027

1 Sailing

Mar 28, 2027

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.

Up to 50% off + up to $400 Instant Savings + 3rd & 4th Guests FREE*

7-night Southern Caribbean With Barbados And St. Lucia Holiday Cruise

St. Thomas (Charlotte Amalie)

St. Maarten (Philipsburg)

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 50% off + up to $400 Instant Savings + 3rd & 4th Guests FREE*

14-night Southern Caribbean Adventurer Cruise

St. Thomas (Charlotte Amalie)

St. Maarten (Philipsburg)

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

$2,329

per person*

taxes & fees included

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.

Up to 50% off + up to $400 Instant Savings + 3rd & 4th Guests FREE*

7-night Southern Caribbean With Barbados And Tortola Cruise

Aboard

Emerald Princess

From

San Juan, Puerto Rico

7 Sailings

Nov 28, 2027 - Mar 19, 2028

7 Sailings

Nov 28, 2027 - Mar 19, 2028

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.

Up to 50% off + up to $400 Instant Savings + 3rd & 4th Guests FREE*

7-night Southern Caribbean With Barbados And St. Lucia Cruise

St. Thomas (Charlotte Amalie)

St. Maarten (Philipsburg)

Aboard

Emerald Princess

From

San Juan, Puerto Rico

8 Sailings

Dec 5, 2027 - Mar 12, 2028

8 Sailings

Dec 5, 2027 - Mar 12, 2028

Rocky beach and palm trees in Barbados.

Up to 50% off + up to $400 Instant Savings + 3rd & 4th Guests FREE*

14-night Southern Caribbean Adventurer Holiday Cruise

St. Thomas (Charlotte Amalie)

St. Maarten (Philipsburg)

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

$2,779

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 50% off + up to $400 Instant Savings + 3rd & 4th Guests FREE*

7-night Southern Caribbean With Barbados And Tortola Holiday Cruise

Aboard

Emerald Princess

From

San Juan, Puerto Rico

1 Sailing

Dec 26, 2027

1 Sailing

Dec 26, 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 50% off + up to $400 Instant Savings + 3rd & 4th Guests FREE*

7-night Southern Caribbean With Barbados And St. Kitts Cruise

St. Thomas (Charlotte Amalie)

Aboard

Emerald Princess

From

San Juan, Puerto Rico

1 Sailing

Jan 23, 2028

1 Sailing

Jan 23, 2028

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.

Up to 50% off + up to $400 Instant Savings + 3rd & 4th Guests FREE*

7-night Southern Caribbean With Abc Islands Cruise

Aboard

Emerald Princess

From

San Juan, Puerto Rico

1 Sailing

Mar 26, 2028

1 Sailing

Mar 26, 2028

*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.