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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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.

Exclusive Events, Experiences & More with Captain's Circle*+ 3 more offers

7-night Southern Caribbean with Barbados Cruise

St. Maarten (Philipsburg)

Bridgetown (Barbados)

Aboard

Grand Princess

From

San Juan, Puerto Rico

20 Sailings

Nov 16, 2025 - Mar 29, 2026

20 Sailings

Nov 16, 2025 - Mar 29, 2026

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

Exclusive Events, Experiences & More with Captain's Circle*+ 3 more offers

14-night Southern Caribbean Adventurer Cruise

St. Maarten (Philipsburg)

Bridgetown (Barbados)

Aboard

Grand Princess

From

San Juan, Puerto Rico

19 Sailings

Nov 16, 2025 - Mar 22, 2026

19 Sailings

Nov 16, 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.

Exclusive Events, Experiences & More with Captain's Circle*+ 3 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.

Exclusive Events, Experiences & More with Captain's Circle*+ 3 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.

Exclusive Events, Experiences & More with Captain's Circle*+ 3 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.

Exclusive Events, Experiences & More with Captain's Circle*+ 3 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.

Exclusive Events, Experiences & More with Captain's Circle*+ 3 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.

Exclusive Events, Experiences & More with Captain's Circle*+ 3 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

*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.