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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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39 Results

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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.

Cupecoy Beach with white resort buildings, St. Maarten.

FREE All-Inclusive Package Upgrade*+ 1 more offer

14-night Star Collector: Leeward & Windward Caribbean Havens Cruise

St. Maarten (Philipsburg)

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Jan 4, 2026

1 Sailing

Jan 4, 2026

Up to FREE $2,000 Onboard Credit*

7-night Yachtsman's Caribbean Cruise

St. Maarten (Philipsburg)

Sopers Hole

Carambola Beach

St. Pierre

Port Elizabeth (Bequia)

+3 more

Aboard

Seabourn Ovation

From

Philipsburg, St. Maarten, The Netherlands

12 Sailings

Jan 17, 2026 - Mar 20, 2027

12 Sailings

Jan 17, 2026 - Mar 20, 2027

Published prices from

$4,299

per person*

taxes & fees included

FREE All-Inclusive Package Upgrade*+ 1 more offer

7-night Beach Fun & Sun: A Remote Caribbean Getaway Cruise

St. Maarten (Philipsburg)

Aboard

Wind Spirit

From

Philipsburg, St. Maarten, The Netherlands

2 Sailings

Jan 24 - Jan 31, 2026

2 Sailings

Jan 24 - Jan 31, 2026

FREE All-Inclusive Package Upgrade*+ 1 more offer

6-night Beach Fun & Sun: A Remote Caribbean Getaway Cruise

St. Maarten (Philipsburg)

Aboard

Wind Spirit

From

Philipsburg, St. Maarten, The Netherlands

2 Sailings

Feb 14 - Feb 21, 2026

2 Sailings

Feb 14 - Feb 21, 2026

FREE All-Inclusive Package Upgrade*+ 1 more offer

7-night Classic Caribbean Cruise

St. Maarten (Philipsburg)

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

11 Sailings

Dec 7, 2025 - Mar 20, 2027

11 Sailings

Dec 7, 2025 - Mar 20, 2027

FREE Butler Service, Gourmet Dining & More*+ 1 more offer

14-night Eastern and Southern Caribbean Cruise

St. Maarten (Philipsburg)

St. John's

St. Thomas (Charlotte Amalie)

Little Bay

Castries

+9 more

Aboard

Silver Shadow

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Feb 19, 2026

1 Sailing

Feb 19, 2026

FREE Butler Service, Gourmet Dining & More*+ 1 more offer

7-night Eastern and Southern Caribbean Cruise

St. Maarten (Philipsburg)

St. John's

St. Thomas (Charlotte Amalie)

Little Bay

Castries

+2 more

Aboard

Silver Shadow

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Feb 19, 2026

1 Sailing

Feb 19, 2026

Published prices from

$5,800

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.

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 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

7-night Lush & Lovely Islands of the Lesser Antilles Cruise

St. Maarten (Philipsburg)

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Jan 11, 2026

1 Sailing

Jan 11, 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

12-night Star Collector: Ivory Beaches & Sapphire Seas of the Caribbean Cruise

St. Maarten (Philipsburg)

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Dec 2, 2025

1 Sailing

Dec 2, 2025

A captivating half-underwater, half-above-water shot of a person snorkeling in the vibrant turquoise waters of the British Virgin Islands with stunning rock formations and palm trees visible above the waterline.

FREE All-Inclusive Package Upgrade*+ 1 more offer

5-night Barefoot Break in the British Virgin Islands Cruise

St. Maarten (Philipsburg)

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Dec 2, 2025

1 Sailing

Dec 2, 2025

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 Butler Service, Gourmet Dining & More*+ 1 more offer

7-night Caribbean Cruise

St. Maarten (Philipsburg)

Aboard

Silver Shadow

From

Philipsburg, St. Maarten, The Netherlands

2 Sailings

Jan 11 - Feb 26, 2026

2 Sailings

Jan 11 - Feb 26, 2026

Published prices from

$5,500

per person*

taxes & fees included

FREE All-Inclusive Package Upgrade*+ 1 more offer

6-night Beach Fun & Sun: A Remote Caribbean Getaway Cruise

St. Maarten (Philipsburg)

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

4 Sailings

Dec 14, 2025 - Mar 28, 2026

4 Sailings

Dec 14, 2025 - Mar 28, 2026

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 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

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

An aerial view of Road Bay, Anguilla, showing a pristine white sand beach, lush green vegetation, and the stunningly clear turquoise water of the Caribbean Sea.

FREE All-Inclusive Package Upgrade*+ 1 more offer

14-night Star Collector: Caribbean Explorations Cruise

St. Maarten (Philipsburg)

Aboard

Wind Spirit

From

Philipsburg, St. Maarten, The Netherlands

2 Sailings

Jan 31 - Feb 7, 2026

2 Sailings

Jan 31 - Feb 7, 2026

A stunning image of Little Bay in Anguilla, a secluded, beautiful beach with turquoise water surrounded by towering rocky cliffs and lush green vegetation.

FREE Butler Service, Gourmet Dining & More*+ 1 more offer

7-night Eastern & Southern Caribbean Cruise

St. Maarten (Philipsburg)

St. John's

St. Thomas (Charlotte Amalie)

Little Bay

Castries

+2 more

Aboard

Silver Shadow

From

Philipsburg, St. Maarten, The Netherlands

2 Sailings

Jan 4 - Jan 18, 2026

2 Sailings

Jan 4 - Jan 18, 2026

Published prices from

$4,700

per person*

taxes & fees included

A wide-angle view of the bustling harbor of Charlotte Amalie, St. Thomas, with many sailboats and yachts docked in the tranquil blue water, and the town's buildings climbing the lush green hills.

FREE Butler Service, Gourmet Dining & More*+ 1 more offer

14-night Caribbean Cruise

St. Maarten (Philipsburg)

St. John's

St. Thomas (Charlotte Amalie)

Little Bay

Castries

+9 more

Aboard

Silver Shadow

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Jan 11, 2026

1 Sailing

Jan 11, 2026

An aerial view of the colorful waterfront of St. John's, Antigua, with a long pier extending into the calm, blue sea and the town's charming buildings and marina in the background.

Up to FREE $2,000 Onboard Credit*

14-night Gems Of The Caribbean Cruise

St. Maarten (Philipsburg)

Sopers Hole

Carambola Beach

St. Pierre

Port Elizabeth (Bequia)

+7 more

Aboard

Seabourn Ovation

From

Philipsburg, St. Maarten, The Netherlands

2 Sailings

Jan 17 - Feb 21, 2026

2 Sailings

Jan 17 - Feb 21, 2026

Published prices from

$8,699

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 FREE $2,000 Onboard Credit*

14-night Yachtsman's Island Jewels Cruise

St. Maarten (Philipsburg)

Sopers Hole

Carambola Beach

St. Pierre

Port Elizabeth (Bequia)

+7 more

Aboard

Seabourn Ovation

From

Philipsburg, St. Maarten, The Netherlands

2 Sailings

Jan 31 - Mar 7, 2026

2 Sailings

Jan 31 - Mar 7, 2026

Published prices from

$8,899

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 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 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 Package Upgrade*+ 1 more offer

7-night Classic Caribbean Cruise

St. Maarten (Philipsburg)

Aboard

Wind Spirit

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Feb 7, 2026

1 Sailing

Feb 7, 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

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

FREE All-Inclusive Package Upgrade*+ 1 more offer

14-night Star Collector: Caribbean Explorations Cruise

St. Maarten (Philipsburg)

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

19 Sailings

Dec 7, 2025 - Mar 13, 2027

19 Sailings

Dec 7, 2025 - Mar 13, 2027