Windstar

Windstar Cruises from San Juan, Puerto Rico

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

Upcoming Windstar Cruises from San Juan, Puerto Rico

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A high-angle view of the bustling harbor of Marigot, St. Martin, with boats and yachts docked along the coast and colorful buildings nestled against the green hills.
FREE Champagne, Entertainment, Dining & More*
Windstar

14-night Star Collector: Lovely Leewards Cruise

Aboard

Star Pride

From

San Juan, Puerto Rico

A high-angle view of the bustling harbor of Marigot, St. Martin, with boats and yachts docked along the coast and colorful buildings nestled against the green hills.
FREE Champagne, Entertainment, Dining & More*
Windstar

7-night San Juan & The Virgin Islands Cruise

Aboard

Star Pride

From

San Juan, Puerto Rico

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.
FREE Champagne, Entertainment, Dining & More*
Windstar

13-night Star Collector: Beaches & Bastions Of The BVI And Spanish Caribbean Cruise

Aboard

Star Pride

From

San Juan, Puerto Rico

Immaculate Conception Cathedral in Colon.
FREE Champagne, Entertainment, Dining & More*
Windstar

20-night Star Collector: Central America & The Caribbean: Cloudforest Coastlines, Canal Locks & Calypso Concerts Cruise

Aboard

Star Pride

From

San Juan, Puerto Rico

A tranquil beach on Isla Parida, with gentle waves lapping against the sandy shore and a lush green rainforest lining the coast.
FREE Champagne, Entertainment, Dining & More*
Windstar

13-night Star Collector: Coffee, Canal & Callaloo: Central America, Colombia & The Caribbean Cruise

Aboard

Star Pride

From

San Juan, Puerto Rico

Colorful colonial balconies in Cartagena.
FREE Champagne, Entertainment, Dining & More*
Windstar

6-night The Spanish Main: Rise Of The New World Cruise

Aboard

Star Pride

From

San Juan, Puerto Rico

A panoramic view of Gustavia, Saint Barthélemy, featuring a bay filled with luxury yachts and sailboats, framed by lush, green hillsides dotted with houses.
FREE Champagne, Entertainment, Dining & More*
Windstar

14-night Star Collector: Lovely Leewards Cruise

Aboard

Star Seeker

From

San Juan, Puerto Rico

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.
FREE Champagne, Entertainment, Dining & More*
Windstar

7-night San Juan & The Virgin Islands Cruise

Aboard

Star Seeker

From

San Juan, Puerto Rico

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.
FREE Champagne, Entertainment, Dining & More*
Windstar

7-night Windward Islands Surf & Sunsets Cruise

Aboard

Star Seeker

From

San Juan, Puerto Rico

A scenic view of Forte de São João Baptista, a fortress built on a rocky islet in the Berlengas Archipelago, connected by a stone causeway over turquoise water.
FREE Champagne, Entertainment, Dining & More*
Windstar

7-night 2026 President’s Mystery Cruise

Aboard

Star Seeker

From

San Juan, Puerto Rico

A scenic view of a pristine beach on the San Blas Islands, Panama, with a line of tall palm trees casting shadows on the white sand and clear turquoise water.
FREE Champagne, Entertainment, Dining & More*
Windstar

49-night Star Collector: Grand Caribbean & Americas Explorer Cruise

Aboard

Star Seeker

From

San Juan, Puerto Rico

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.
FREE Champagne, Entertainment, Dining & More*
Windstar

10-night Gems Of The Leeward Islands Cruise

Aboard

Star Seeker

From

San Juan, Puerto Rico

Colorful colonial balconies in Cartagena.
FREE Champagne, Entertainment, Dining & More*
Windstar

17-night Star Collector: Seeking The Antilles Cruise

Aboard

Star Seeker

From

San Juan, Puerto Rico

A panoramic view of Gustavia, Saint Barthélemy, featuring a bay filled with luxury yachts and sailboats, framed by lush, green hillsides dotted with houses.
FREE Champagne, Entertainment, Dining & More*
Windstar

24-night Star Collector: Historic Caribbean: Legendary Islands, Colombia And Panama Cruise

Aboard

Star Seeker

From

San Juan, Puerto Rico

An aerial view of the bustling city of Balboa, Panama, with a scenic coastal road alongside a marina and tall modern skyscrapers in the background.
FREE Champagne, Entertainment, Dining & More*
Windstar

22-night Star Collector Cruise: Central American Explorations Via The Panama Canal

Aboard

Star Seeker

From

San Juan, Puerto Rico

A scenic view of a pristine beach on the San Blas Islands, Panama, with a line of tall palm trees casting shadows on the white sand and clear turquoise water.
FREE Champagne, Entertainment, Dining & More*
Windstar

14-night Star Collector: Rainforest Refuges Of Panama & Costa Rica Via The Panama Canal Cruise

Aboard

Star Seeker

From

San Juan, Puerto Rico

Colorful colonial balconies in Cartagena.
FREE Champagne, Entertainment, Dining & More*
Windstar

7-night New World Caribbean Trio Cruise

Aboard

Star Seeker

From

San Juan, Puerto Rico

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.
FREE Champagne, Entertainment, Dining & More*
Windstar

11-night Gems Of The Leeward Islands Cruise

Aboard

Star Pride

From

San Juan, Puerto Rico

A picturesque view of a small town nestled at the base of a lush, green mountain on Iles des Saintes, Guadeloupe, with boats moored in the deep blue water and fluffy clouds in the sky.
FREE Champagne, Entertainment, Dining & More*
Windstar

7-night Windward Islands Surf & Sunsets Cruise

Aboard

Star Pride

From

San Juan, Puerto Rico

*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.

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