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

FREE All-Inclusive Upgrade + FREE Hotel Stay + up to $2,000 Onboard Credit*+ 1 more offer

Windstar

7-night San Juan & The Virgin Islands Cruise

St. Maarten (Philipsburg)

Aboard

Star Seeker

From

San Juan, Puerto Rico

4 Sailings

Jan 23 - Mar 6, 2026

4 Sailings

Jan 23 - Mar 6, 2026

Published prices from

$5,362

per person*

taxes & fees included

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 All-Inclusive Upgrade + FREE Hotel Stay + up to $2,000 Onboard Credit*+ 1 more offer

Windstar

14-night Star Collector: Lovely Leewards Cruise

St. Maarten (Philipsburg)

Aboard

Star Seeker

From

San Juan, Puerto Rico

7 Sailings

Jan 23 - Mar 6, 2026

7 Sailings

Jan 23 - Mar 6, 2026

Published prices from

$9,796

per person*

taxes & fees included

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

FREE All-Inclusive Upgrade + FREE Hotel Stay + up to $2,000 Onboard Credit*+ 1 more offer

Windstar

7-night Windward Islands Surf & Sunsets Cruise

Iles des Saintes

Aboard

Star Seeker

From

San Juan, Puerto Rico

4 Sailings

Jan 30 - Mar 13, 2026

4 Sailings

Jan 30 - Mar 13, 2026

Published prices from

$5,033

per person*

taxes & fees included

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 All-Inclusive Upgrade + FREE Hotel Stay + up to $2,000 Onboard Credit*+ 1 more offer

Windstar

7-night 2026 President’s Mystery Cruise

Aboard

Star Seeker

From

San Juan, Puerto Rico

1 Sailing

Mar 20, 2026

1 Sailing

Mar 20, 2026

Published prices from

$8,362

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.

FREE All-Inclusive Upgrade + FREE Hotel Stay + up to $2,000 Onboard Credit*+ 1 more offer

Windstar

10-night Gems Of The Leeward Islands Cruise

Iles des Saintes

Aboard

Star Seeker

From

San Juan, Puerto Rico

1 Sailing

Mar 27, 2026

1 Sailing

Mar 27, 2026

Published prices from

$5,857

per person*

taxes & fees included

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 All-Inclusive Upgrade + FREE Hotel Stay + up to $2,000 Onboard Credit*+ 1 more offer

Windstar

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

Iles des Saintes

Aboard

Star Seeker

From

San Juan, Puerto Rico

1 Sailing

Mar 27, 2026

1 Sailing

Mar 27, 2026

Published prices from

$24,243

per person*

taxes & fees included

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 All-Inclusive Upgrade + FREE Hotel Stay + up to $2,000 Onboard Credit*+ 1 more offer

Windstar

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

Iles des Saintes

Aboard

Star Seeker

From

San Juan, Puerto Rico

1 Sailing

Mar 27, 2026

1 Sailing

Mar 27, 2026

Published prices from

$13,038

per person*

taxes & fees included

Colorful colonial balconies in Cartagena.

FREE All-Inclusive Upgrade + FREE Hotel Stay + up to $2,000 Onboard Credit*+ 1 more offer

Windstar

17-night Star Collector: Seeking The Antilles Cruise

Iles des Saintes

Aboard

Star Seeker

From

San Juan, Puerto Rico

1 Sailing

Mar 27, 2026

1 Sailing

Mar 27, 2026

Published prices from

$8,584

per person*

taxes & fees included

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 All-Inclusive Upgrade + FREE Hotel Stay + up to $2,000 Onboard Credit*+ 1 more offer

Windstar

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

Catalina Island/Casa de Campo

Cartagena (Colombia)

San Blas Islands

Aboard

Star Seeker

From

San Juan, Puerto Rico

1 Sailing

Apr 6, 2026

1 Sailing

Apr 6, 2026

Published prices from

$11,605

per person*

taxes & fees included

Colorful colonial balconies in Cartagena.

FREE All-Inclusive Upgrade + FREE Hotel Stay + up to $2,000 Onboard Credit*+ 1 more offer

Windstar

7-night New World Caribbean Trio Cruise

Catalina Island/Casa de Campo

Cartagena (Colombia)

San Blas Islands

Aboard

Star Seeker

From

San Juan, Puerto Rico

1 Sailing

Apr 6, 2026

1 Sailing

Apr 6, 2026

Published prices from

$3,726

per person*

taxes & fees included

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 All-Inclusive Upgrade + FREE Hotel Stay + up to $2,000 Onboard Credit*+ 1 more offer

Windstar

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

Catalina Island/Casa de Campo

Cartagena (Colombia)

San Blas Islands

Aboard

Star Seeker

From

San Juan, Puerto Rico

1 Sailing

Apr 6, 2026

1 Sailing

Apr 6, 2026

Published prices from

$7,980

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.

FREE All-Inclusive Upgrade + FREE Hotel Stay + up to $2,000 Onboard Credit*+ 1 more offer

Windstar

11-night Gems Of The Leeward Islands Cruise

Falmouth Harbour

Aboard

Star Pride

From

San Juan, Puerto Rico

1 Sailing

Oct 28, 2026

1 Sailing

Oct 28, 2026

Published prices from

$3,757

per person*

taxes & fees included

An idyllic white-sand beach with turquoise water and palm trees on Jost Van Dyke, with a lush green hill in the background.

FREE All-Inclusive Upgrade + FREE Hotel Stay + up to $2,000 Onboard Credit*+ 1 more offer

Windstar

14-night Star Collector: Lovely Leewards Cruise

St. Maarten (Philipsburg)

Aboard

Star Pride

From

San Juan, Puerto Rico

9 Sailings

Nov 8, 2026 - Jan 3, 2027

9 Sailings

Nov 8, 2026 - Jan 3, 2027

Published prices from

$4,393

per person*

taxes & fees included

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 All-Inclusive Upgrade + FREE Hotel Stay + up to $2,000 Onboard Credit*+ 1 more offer

Windstar

7-night Windward Islands Surf & Sunsets Cruise

Iles des Saintes

Aboard

Star Pride

From

San Juan, Puerto Rico

5 Sailings

Nov 8, 2026 - Jan 3, 2027

5 Sailings

Nov 8, 2026 - Jan 3, 2027

Published prices from

$2,730

per person*

taxes & fees included

A snorkeler swims in the turquoise waters of the Baths National Park on Virgin Gorda, surrounded by massive granite boulders and palm trees.

FREE All-Inclusive Upgrade + FREE Hotel Stay + up to $2,000 Onboard Credit*+ 1 more offer

Windstar

7-night San Juan & The Virgin Islands Cruise

St. Maarten (Philipsburg)

Aboard

Star Pride

From

San Juan, Puerto Rico

5 Sailings

Nov 15, 2026 - Jan 10, 2027

5 Sailings

Nov 15, 2026 - Jan 10, 2027

Published prices from

$2,762

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.