Luxury Eastern Caribbean Cruises

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+2 more

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

$6,062

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.

14-night Star Collector: Lovely Leewards Cruise

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+5 more

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

$11,296

per person*

taxes & fees included

Cupecoy Beach with white resort buildings, St. Maarten.

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

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Aboard

Wind Spirit

From

Philipsburg, St. Maarten, The Netherlands

2 Sailings

Jan 24 - Jan 31, 2026

2 Sailings

Jan 24 - Jan 31, 2026

Published prices from

$4,360

per person*

taxes & fees included

7-night Classic Caribbean Yacht Harbors Cruise

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Aboard

Seabourn Ovation

From

Bridgetown, Barbados

11 Sailings

Jan 24, 2026 - Mar 13, 2027

11 Sailings

Jan 24, 2026 - Mar 13, 2027

Published prices from

$4,079

per person*

taxes & fees included

14-night Exotic Caribbean Isles Cruise

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Aboard

Seabourn Ovation

From

Bridgetown, Barbados

4 Sailings

Jan 24 - Mar 21, 2026

4 Sailings

Jan 24 - Mar 21, 2026

Published prices from

$7,874

per person*

taxes & fees included

15-night Star Collector: Windward Islands & Spanish New World Cruise

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

Aboard

Wind Surf

From

Bridgetown, Barbados

1 Sailing

Jan 25, 2026

1 Sailing

Jan 25, 2026

Published prices from

$7,766

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.

7-night Caribbean Cruise

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

Aboard

Silver Spirit

From

Bridgetown, Barbados

4 Sailings

Jan 26, 2026 - Mar 11, 2028

4 Sailings

Jan 26, 2026 - Mar 11, 2028

Published prices from

$4,300

per person*

taxes & fees included

FREE Wi-Fi, Dining, Spa Access & More*+ 1 more offer

10-night Eastern Caribbean Cruise

Aboard

Silver Ray

From

Fort Lauderdale, Florida

1 Sailing

Jan 27, 2026

1 Sailing

Jan 27, 2026

Published prices from

$9,500

per person*

taxes & fees included

10-night West Indies Explorer Cruise

Up to $500 FREE Onboard Credit*+ 3 more offers

+4 more

Aboard

Viking Sea

From

San Juan, Puerto Rico

23 Sailings

Jan 28, 2026 - Feb 16, 2028

23 Sailings

Jan 28, 2026 - Feb 16, 2028

Published prices from

$3,699

per person*

taxes & fees included

12-night Eastern Caribbean Cruise

Up to $500 FREE Onboard Credit*+ 3 more offers

+3 more

Aboard

Queen Elizabeth

From

Miami, Florida

7 Sailings

Jan 29 - Nov 26, 2026

7 Sailings

Jan 29 - Nov 26, 2026

Published prices from

$1,399

per person*

taxes & fees included

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.

21-night Caribbean Cruise

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+8 more

Aboard

Queen Elizabeth

From

Miami, Florida

11 Sailings

Jan 29 - Nov 26, 2026

11 Sailings

Jan 29 - Nov 26, 2026

Published prices from

$2,409

per person*

taxes & fees included

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

Published prices from

$5,733

per person*

taxes & fees included

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 Upgrade + FREE Hotel Stay + up to $2,300 Onboard Credit*+ 1 more offer

14-night Star Collector: Caribbean Explorations Cruise

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Aboard

Wind Spirit

From

Philipsburg, St. Maarten, The Netherlands

2 Sailings

Jan 31 - Feb 7, 2026

2 Sailings

Jan 31 - Feb 7, 2026

14-night Yachtsman's Island Jewels Cruise

Save up to 30% on Last Minute Sailings*+ 1 more offer

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

$9,289

per person*

taxes & fees included

7-night Yachtsman's Caribbean Cruise

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

Sopers Hole

Carambola Beach

St. Pierre

Port Elizabeth (Bequia)

+3 more

Aboard

Seabourn Ovation

From

Philipsburg, St. Maarten, The Netherlands

11 Sailings

Jan 31, 2026 - Mar 20, 2027

11 Sailings

Jan 31, 2026 - Mar 20, 2027

Published prices from

$4,079

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.

10-night Caribbean Cruise

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

Aboard

Silver Spirit

From

Bridgetown, Barbados

1 Sailing

Feb 2, 2026

1 Sailing

Feb 2, 2026

21-night Caribbean Cruise

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

Aboard

Silver Spirit

From

Bridgetown, Barbados

1 Sailing

Feb 2, 2026

1 Sailing

Feb 2, 2026

16-night Caribbean Cruise

Aboard

Silver Shadow

From

Cartagena, Colombia

1 Sailing

Feb 3, 2026

1 Sailing

Feb 3, 2026

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

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

10-night Leeward & Windward Gems Voyage

Aboard

Nautica

From

Miami, Florida

1 Sailing

Feb 6, 2026

1 Sailing

Feb 6, 2026

Published prices from

$2,999

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.

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11-night Eastern Caribbean Cruise

Aboard

Silver Ray

From

Fort Lauderdale, Florida

1 Sailing

Feb 6, 2026

1 Sailing

Feb 6, 2026

Published prices from

$11,000

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.

7-night Classic Caribbean Cruise

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Aboard

Wind Spirit

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Feb 7, 2026

1 Sailing

Feb 7, 2026

Published prices from

$4,917

per person*

taxes & fees included

A long, green steel-arched bridge with multiple supports, the Laviolette Bridge, spanning the wide St. Lawrence River near Trois-Rivières, with a grassy riverbank in the foreground.

7-night Caribbean Gems Cruise

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Aboard

Seabourn Ovation

From

Bridgetown, Barbados

4 Sailings

Feb 7, 2026 - Feb 6, 2027

4 Sailings

Feb 7, 2026 - Feb 6, 2027

Published prices from

$3,824

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.

14-night Yachtsman's Island Jewels Cruise

Up to $500 FREE Onboard Credit*+ 3 more offers

Aboard

Seabourn Ovation

From

Bridgetown, Barbados

1 Sailing

Feb 7, 2026

1 Sailing

Feb 7, 2026

A close-up aerial view of the dramatic limestone bluff, known as the "Bluff," a landmark on Cayman Brac island, with waves crashing against its vertical face.

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

19-night Star Collector: Caribbean Cultures: Latin America & the Greater Antilles Cruise

Aboard

Wind Surf

From

Colon, Panama

1 Sailing

Feb 9, 2026

1 Sailing

Feb 9, 2026

Published prices from

$8,108

per person*

taxes & fees included

Miami skyline at dusk, showcasing vibrant colors and reflections shimmering in the water below.