Luxury Southern Caribbean Cruises

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

+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

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

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

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

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

7-night Windward Ways & Tobago Cays Cruise

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Aboard

Wind Surf

From

Bridgetown, Barbados

1 Sailing

Jan 25, 2026

1 Sailing

Jan 25, 2026

Published prices from

$4,424

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 Kralendijk waterfront in Bonaire, showcasing the contrast between the deep blue ocean and the shallow turquoise water near the shore, with sailboats anchored offshore.

9-night Southern Caribbean Cruise

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

Aboard

Silver Shadow

From

Bridgetown, Barbados

1 Sailing

Jan 25, 2026

1 Sailing

Jan 25, 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.

7-night Caribbean Cruise

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

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

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

Exclusive Savings & Events with Oceania Club*

10-night Canal & Caribbean Discovery Voyage

Aboard

Nautica

From

Panama City, Panama

1 Sailing

Jan 27, 2026

1 Sailing

Jan 27, 2026

Published prices from

$3,299

per person*

taxes & fees included

An aerial view of the vast Amazon River in Peru, meandering through a dense, green rainforest with a small floating lodge anchored along its banks.

19-night Amazon To Caribbean Gems Voyage

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

Amazon River

Santarem

Parintins (Amazon River)

Manaus (Amazon River)

+9 more

Aboard

Insignia

From

Bridgetown, Barbados

1 Sailing

Jan 27, 2026

1 Sailing

Jan 27, 2026

Published prices from

$5,499

per person*

taxes & fees included

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

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.

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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

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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

Immaculate Conception Cathedral in Colon.

16-night Star Collector: Natural History Meets Ancient Mystery: Latin America & Beyond Cruise

Aboard

Wind Surf

From

Oranjestad, Aruba, Caribbean

1 Sailing

Feb 1, 2026

1 Sailing

Feb 1, 2026

Published prices from

$7,086

per person*

taxes & fees included

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

8-night In the Wake of the Spanish Armadas Cruise

Aboard

Wind Surf

From

Oranjestad, Aruba, Caribbean

1 Sailing

Feb 1, 2026

1 Sailing

Feb 1, 2026

Published prices from

$4,091

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.

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

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

Oranjestad, Aruba harbor with boats and colorful Dutch architecture.

9-night Southern Caribbean Cruise

Aboard

Silver Shadow

From

Cartagena, Colombia

1 Sailing

Feb 3, 2026

1 Sailing

Feb 3, 2026

Published prices from

$21,200

per person*

taxes & fees included

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

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

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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

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