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

Up to $500 FREE Onboard Credit*+ 2 more offers

Windstar

7-night Windward Islands Surf & Sunsets Cruise From San Juan, Puerto Rico

Iles des Saintes

Aboard

Star Pride

From

San Juan, Puerto Rico

9 Sailings

Nov 8, 2026 - Mar 27, 2028

9 Sailings

Nov 8, 2026 - Mar 27, 2028

Published prices from

$2,411

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.

Up to $500 FREE Onboard Credit*+ 2 more offers

Windstar

14-night Star Collector: Lovely Leewards Cruise From San Juan, Puerto Rico

St. Maarten (Philipsburg)

Aboard

Star Pride

From

San Juan, Puerto Rico

14 Sailings

Nov 8, 2026 - Mar 20, 2028

14 Sailings

Nov 8, 2026 - Mar 20, 2028

Published prices from

$4,586

per person*

taxes & fees included

An aerial view of Carambola Beach Resort in St. Croix, with red-roofed buildings nestled among lush green tropical trees along the turquoise Caribbean Sea.

Up to $500 FREE Onboard Credit*+ 2 more offers

16-night Leeward Island Holiday Cruise From Miami, Florida

Carambola Beach

Aboard

Seabourn Quest

From

Miami, Florida

1 Sailing

Dec 20, 2026

1 Sailing

Dec 20, 2026

Published prices from

$10,998

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 $500 FREE Onboard Credit*+ 1 more offer

Windstar

21-night Star Collector Cruise: Windward Islands, Spanish Cities & Costa Rica From San Juan, Puerto Rico

Iles des Saintes

Aboard

Star Pride

From

San Juan, Puerto Rico

1 Sailing

Nov 22, 2027

1 Sailing

Nov 22, 2027

Published prices from

$7,204

per person*

taxes & fees included

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.

Up to $500 FREE Onboard Credit*+ 1 more offer

Windstar

14-night Star Collector Cruise: Caribbean Islands & Colombian Coast Discovery From San Juan, Puerto Rico

Iles des Saintes

Aboard

Star Pride

From

San Juan, Puerto Rico

1 Sailing

Nov 22, 2027

1 Sailing

Nov 22, 2027

Published prices from

$4,614

per person*

taxes & fees included

A breathtaking panoramic view of Cruz Bay, St. John, showcasing a vibrant coastal town with white-sand beaches, clear turquoise waters, and numerous boats in the harbor.

Up to $500 FREE Onboard Credit*+ 1 more offer

Windstar

14-night Star Collector Cruise: Lovely Leewards From San Juan, Puerto Rico

Iles des Saintes

Aboard

Star Legend

From

San Juan, Puerto Rico

9 Sailings

Dec 20, 2027 - Feb 14, 2028

9 Sailings

Dec 20, 2027 - Feb 14, 2028

Published prices from

$4,586

per person*

taxes & fees included

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.

Up to $500 FREE Onboard Credit*+ 1 more offer

Windstar

7-night Windward Islands Surf & Sunsets Cruise From San Juan, Puerto Rico

Iles des Saintes

Aboard

Star Legend

From

San Juan, Puerto Rico

5 Sailings

Dec 27, 2027 - Feb 21, 2028

5 Sailings

Dec 27, 2027 - Feb 21, 2028

Published prices from

$2,411

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.

Up to $500 FREE Onboard Credit*+ 1 more offer

Windstar

22-night Star Collector Cruise: Caribbean Charms To Iberian Shores From San Juan, Puerto Rico

Iles des Saintes

Aboard

Star Legend

From

San Juan, Puerto Rico

1 Sailing

Feb 21, 2028

1 Sailing

Feb 21, 2028

Published prices from

$2,451

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.

Up to $500 FREE Onboard Credit*+ 1 more offer

Windstar

21-night Star Collector Cruise: Caribbean Collection: ABC, BVI & The Windwards From Oranjestad, Aruba, Caribbean

Aboard

Star Pride

From

Oranjestad, Aruba, Caribbean

1 Sailing

Mar 6, 2028

1 Sailing

Mar 6, 2028

Published prices from

$7,246

per person*

taxes & fees included

A scenic landscape view of Admiralty Bay in Bequia, St. Vincent and the Grenadines, with dozens of sailboats moored on the vibrant turquoise water, surrounded by lush green hills.

Up to $500 FREE Onboard Credit*+ 1 more offer

Windstar

14-night Star Collector Cruise: Windward Islands, ABC Islands & The Virgin Islands From Oranjestad, Aruba, Caribbean

Aboard

Star Pride

From

Oranjestad, Aruba, Caribbean

1 Sailing

Mar 6, 2028

1 Sailing

Mar 6, 2028

Published prices from

$4,920

per person*

taxes & fees included

A scenic landscape view of Admiralty Bay in Bequia, St. Vincent and the Grenadines, with dozens of sailboats moored on the vibrant turquoise water, surrounded by lush green hills.

Up to $500 FREE Onboard Credit*+ 1 more offer

Windstar

23-night Star Collector Cruise: Tropical Horizons To Historic Amsterdam From San Juan, Puerto Rico

Iles des Saintes

Aboard

Star Pride

From

San Juan, Puerto Rico

1 Sailing

Mar 27, 2028

1 Sailing

Mar 27, 2028

Published prices from

$4,719

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.