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*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.

Colorful colonial balconies in Cartagena.

FREE All-Inclusive Package Upgrade*+ 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

Colorful colonial balconies in Cartagena.

FREE All-Inclusive Package Upgrade*+ 1 more offer

Windstar

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

Cartagena (Colombia)

San Blas Islands

Aboard

Star Pride

From

San Juan, Puerto Rico

1 Sailing

Dec 7, 2025

1 Sailing

Dec 7, 2025

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

FREE All-Inclusive Package Upgrade*+ 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

Immaculate Conception Cathedral in Colon.

FREE All-Inclusive Package Upgrade*+ 1 more offer

Windstar

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

St. Maarten (Philipsburg)

Aboard

Star Pride

From

San Juan, Puerto Rico

1 Sailing

Nov 30, 2025

1 Sailing

Nov 30, 2025

Colorful colonial balconies in Cartagena.

FREE Champagne, Entertainment, Dining & More*

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

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

FREE All-Inclusive Package Upgrade*+ 1 more offer

Windstar

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

St. Maarten (Philipsburg)

Aboard

Star Pride

From

San Juan, Puerto Rico

1 Sailing

Nov 30, 2025

1 Sailing

Nov 30, 2025

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

FREE All-Inclusive Package Upgrade*+ 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

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

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

A tranquil beach on Isla Parida, with gentle waves lapping against the sandy shore and a lush green rainforest lining the coast.

FREE All-Inclusive Package Upgrade*+ 1 more offer

Windstar

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

Cartagena (Colombia)

San Blas Islands

Aboard

Star Pride

From

San Juan, Puerto Rico

1 Sailing

Dec 7, 2025

1 Sailing

Dec 7, 2025

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 All-Inclusive Package Upgrade*+ 1 more offer

Windstar

7-night San Juan & The Virgin Islands Cruise

Iles des Saintes

Aboard

Star Pride

From

San Juan, Puerto Rico

9 Sailings

Nov 9, 2025 - Jan 10, 2027

9 Sailings

Nov 9, 2025 - Jan 10, 2027

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 All-Inclusive Package Upgrade*+ 1 more offer

Windstar

14-night Star Collector: Lovely Leewards Cruise

Iles des Saintes

Aboard

Star Pride

From

San Juan, Puerto Rico

12 Sailings

Nov 9, 2025 - Jan 3, 2027

12 Sailings

Nov 9, 2025 - Jan 3, 2027

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 Package Upgrade*+ 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

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 Package Upgrade*+ 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

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 Package Upgrade*+ 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

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

Falmouth Harbour

Aboard

Star Pride

From

San Juan, Puerto Rico

1 Sailing

Oct 28, 2026

1 Sailing

Oct 28, 2026

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

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

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

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

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 Package Upgrade*+ 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

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 Package Upgrade*+ 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