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4.9/5 ⭐Google 600+ Reviews | A+ Better Business Bureau

Destinations Departure Ports Cruise Lines Deals Land Tours Find Cruises

1-800-377-9383

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29 Results

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Showing results 1 - 24 of 29

Oranjestad, Aruba harbor with boats and colorful Dutch architecture.

FREE All-Inclusive Package Upgrade*+ 1 more offer

18-night Star Collector: Reefs & Rainforests: The Caribbean, Colombia, Panama & Costa Rica via the Panama Canal Cruise

Bridgetown (Barbados)

Aboard

Wind Spirit

From

Bridgetown, Barbados

1 Sailing

Nov 18, 2025

1 Sailing

Nov 18, 2025

FREE All-Inclusive Package Upgrade*+ 1 more offer

25-night Star Collector: Southern Caribbean Thanksgiving Jubilee Cruise

Lisbon

Bridgetown (Barbados)

Aboard

Wind Spirit

From

Lisbon, Portugal

1 Sailing

Nov 4, 2025

1 Sailing

Nov 4, 2025

*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.

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

FREE All-Inclusive Package Upgrade*+ 1 more offer

7-night Windward Islands Surf & Sunsets Cruise

Aboard

Star Seeker

From

San Juan, Puerto Rico

4 Sailings

Jan 30 - Mar 13, 2026

4 Sailings

Jan 30 - Mar 13, 2026

Blue Mosque and historic Istanbul skyline with Bosphorus Strait.

FREE Champagne, Entertainment, Dining & More*

70-night Star Collector: Grand Mediterranean And Latin America Adventure Cruise

Aboard

Star Legend

From

Istanbul, Turkey

1 Sailing

Oct 19, 2026

1 Sailing

Oct 19, 2026

FREE All-Inclusive Package Upgrade*+ 1 more offer

7-night Jewels of the Windward Islands Cruise

Bridgetown (Barbados)

Aboard

Wind Surf

From

Bridgetown, Barbados

1 Sailing

Jan 18, 2026

1 Sailing

Jan 18, 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.

FREE Champagne, Entertainment, Dining & More*

25-night Star Collector: Southern Caribbean Thanksgiving Jubilee Cruise

Lisbon

Bridgetown (Barbados)

Aboard

Wind Star

From

Lisbon, Portugal

1 Sailing

Nov 10, 2026

1 Sailing

Nov 10, 2026

A beautiful panoramic view of Roseau, Dominica, with a colorful town nestled between the deep blue Caribbean Sea and a backdrop of lush green, volcanic mountains.

FREE All-Inclusive Package Upgrade*+ 1 more offer

15-night Star Collector: Merry Christmas & Happy New Years From The Caribbean Cruise

Aboard

Wind Spirit

From

Oranjestad, Aruba, Caribbean

1 Sailing

Dec 20, 2025

1 Sailing

Dec 20, 2025

A sunny view of the colorful waterfront of Willemstad, Curacao, with its iconic pastel-colored Dutch colonial buildings lining the Handelskade street and a ship docked in the port.

FREE Champagne, Entertainment, Dining & More*

15-night Star Collector: Captivating Caribbean Cruise

Bridgetown (Barbados)

Aboard

Star Legend

From

Bridgetown, Barbados

1 Sailing

Nov 27, 2026

1 Sailing

Nov 27, 2026

A close-up of a small, adorable squirrel monkey with a black cap and a light brown body, perched on a tree branch surrounded by lush, yellow-green leaves.

FREE Champagne, Entertainment, Dining & More*

18-night Star Collector: Reefs & Rainforests: The Caribbean, Colombia, Panama & Costa Rica Via The Panama Canal Cruise

Bridgetown (Barbados)

Aboard

Wind Star

From

Bridgetown, Barbados

1 Sailing

Nov 24, 2026

1 Sailing

Nov 24, 2026

An aerial view of Anse Mitan in Martinique, a beautiful Caribbean village with a bustling beach, sailboats moored in the bay, and lush green hills in the distance.

FREE All-Inclusive Package Upgrade*+ 1 more offer

21-night Star Collector: A Lesser Antilles Odyssey Cruise

St. Maarten (Philipsburg)

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Jan 4, 2026

1 Sailing

Jan 4, 2026

FREE All-Inclusive Package Upgrade*+ 1 more offer

28-night Star Collector: The Best Of The Windward & Leeward Isles Cruise

St. Maarten (Philipsburg)

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Jan 4, 2026

1 Sailing

Jan 4, 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*

11-night Colombian & Southern Caribbean Coastlines Cruise

Bridgetown (Barbados)

Aboard

Wind Star

From

Bridgetown, Barbados

1 Sailing

Nov 24, 2026

1 Sailing

Nov 24, 2026

FREE All-Inclusive Package Upgrade*+ 1 more offer

55-night Star Collector: A Grand Caribbean Adventure Cruise

St. Maarten (Philipsburg)

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Jan 4, 2026

1 Sailing

Jan 4, 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 All-Inclusive Package Upgrade*+ 1 more offer

14-night Star Collector: Antilles Adventures Cruise

St. Maarten (Philipsburg)

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Jan 11, 2026

1 Sailing

Jan 11, 2026

A view of Pigeon Island National Landmark, St. Lucia, showing a lush, green peninsula jutting out into the ocean with waves crashing on the rocks.

FREE All-Inclusive Package Upgrade*+ 1 more offer

14-night Star Collector: Captivating Caribbean Cruise

Bridgetown (Barbados)

Aboard

Wind Surf

From

Bridgetown, Barbados

1 Sailing

Jan 18, 2026

1 Sailing

Jan 18, 2026

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.

FREE All-Inclusive Package Upgrade*+ 1 more offer

10-night Blue Waters Of The Leeward Islands Cruise

St. Maarten (Philipsburg)

Aboard

Wind Spirit

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Jan 14, 2026

1 Sailing

Jan 14, 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

14-night Star Collector: Lovely Leewards Cruise

St. Maarten (Philipsburg)

+5 more

Aboard

Star Seeker

From

San Juan, Puerto Rico

7 Sailings

Jan 23 - Mar 6, 2026

7 Sailings

Jan 23 - Mar 6, 2026

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 Package Upgrade*+ 1 more offer

17-night Star Collector: Hidden Gems of the Caribbean Cruise

St. Maarten (Philipsburg)

Aboard

Wind Spirit

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Jan 14, 2026

1 Sailing

Jan 14, 2026

FREE All-Inclusive Package Upgrade*+ 1 more offer

28-night Star Collector: Grand Caribbean & Panamanian Adventure Cruise

St. Maarten (Philipsburg)

Aboard

Wind Spirit

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Feb 21, 2026

1 Sailing

Feb 21, 2026

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 Package Upgrade*+ 1 more offer

14-night Star Collector: Lovely Leewards Cruise

St. Maarten (Philipsburg)

+8 more

Aboard

Star Pride

From

San Juan, Puerto Rico

13 Sailings

Nov 2, 2025 - Jan 3, 2027

13 Sailings

Nov 2, 2025 - Jan 3, 2027

FREE All-Inclusive Package Upgrade*+ 1 more offer

8-night An ABC Christmas Cruise

Aboard

Wind Spirit

From

Oranjestad, Aruba, Caribbean

1 Sailing

Dec 20, 2025

1 Sailing

Dec 20, 2025

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*

7-night Windward Islands Surf & Sunsets Cruise

Aboard

Star Pride

From

San Juan, Puerto Rico

5 Sailings

Nov 8, 2026 - Jan 3, 2027

5 Sailings

Nov 8, 2026 - Jan 3, 2027

FREE All-Inclusive Package Upgrade*+ 1 more offer

11-night Columbian & Southern Caribbean Coastlines Cruise

Bridgetown (Barbados)

Aboard

Wind Spirit

From

Bridgetown, Barbados

1 Sailing

Nov 18, 2025

1 Sailing

Nov 18, 2025

FREE All-Inclusive Package Upgrade*+ 1 more offer

14-night Star Collector: Captivating Caribbean Cruise

Bridgetown (Barbados)

Aboard

Wind Spirit

From

Bridgetown, Barbados

1 Sailing

Mar 7, 2026

1 Sailing

Mar 7, 2026

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.

FREE All-Inclusive Package Upgrade*+ 1 more offer

7-night Windward Island Delights Cruise

Bridgetown (Barbados)

Aboard

Wind Spirit

From

Bridgetown, Barbados

1 Sailing

Mar 15, 2026

1 Sailing

Mar 15, 2026