Luxury Eastern Caribbean Cruises

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

Aboard

Seabourn Ovation

From

Bridgetown, Barbados

1 Sailing

Jan 3, 2026

1 Sailing

Jan 3, 2026

7-night Treasures Of Aruba, Bonaire & Curacao Cruise

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

Aboard

Seabourn Ovation

From

Bridgetown, Barbados

2 Sailings

Jan 3, 2026 - Jan 2, 2027

2 Sailings

Jan 3, 2026 - Jan 2, 2027

Published prices from

$3,824

per person*

taxes & fees included

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.

35-night Eastern Caribbean Cruise

London (Southampton)

Funchal (Madeira)

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

St. George's

+9 more

Aboard

Queen Victoria

From

Southampton (London), England

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.

10-night Sublime Southern Caribbean Cruise

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

Aboard

Wind Spirit

From

Bridgetown, Barbados

1 Sailing

Jan 4, 2026

1 Sailing

Jan 4, 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.

7-night Eastern & Southern Caribbean Cruise

St. John's

Little Bay

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

+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

$7,400

per person*

taxes & fees included

Cupecoy Beach with white resort buildings, St. Maarten.

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

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

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Jan 4, 2026

1 Sailing

Jan 4, 2026

An idyllic white-sand beach with turquoise water and palm trees on Jost Van Dyke, with a lush green hill in the background.

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

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

2 Sailings

Jan 4 - Mar 28, 2026

2 Sailings

Jan 4 - Mar 28, 2026

Published prices from

$4,267

per person*

taxes & fees included

Tropical beach with lounge chairs in Cozumel.

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

24-night Yucatan & Leeward Seafarer Voyage

Santo Tomas de Castilla

+12 more

Aboard

Allura

From

Miami, Florida

1 Sailing

Jan 4, 2026

1 Sailing

Jan 4, 2026

Published prices from

$9,499

per person*

taxes & fees included

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.

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

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

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Jan 4, 2026

1 Sailing

Jan 4, 2026

55-night Star Collector: A Grand Caribbean Adventure Cruise

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

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.

21-night Star Collector: A Lesser Antilles Odyssey Cruise

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Jan 4, 2026

1 Sailing

Jan 4, 2026

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

12-night Azure Caribbean Voyage

Aboard

Nautica

From

Miami, Florida

1 Sailing

Jan 5, 2026

1 Sailing

Jan 5, 2026

Published prices from

$3,649

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.

11-night Caribbean Cruise

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

Aboard

Silver Spirit

From

Bridgetown, Barbados

3 Sailings

Jan 5, 2026 - Feb 29, 2028

3 Sailings

Jan 5, 2026 - Feb 29, 2028

Published prices from

$6,400

per person*

taxes & fees included

A stunning panoramic view of Road Town on Tortola, British Virgin Islands, showing the harbor filled with boats and a small town surrounded by lush green hills overlooking the Caribbean Sea.

21-night Caribbean Cruise

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

Aboard

Silver Spirit

From

Bridgetown, Barbados

2 Sailings

Jan 5 - Feb 2, 2026

2 Sailings

Jan 5 - Feb 2, 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.

11-night Eastern Caribbean Voyage

St. John (U.S.V.I.)

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

Charlestown

+6 more

Aboard

Azamara Quest

From

Miami, Florida

1 Sailing

Jan 6, 2026

1 Sailing

Jan 6, 2026

A white colonial-style cathedral with a bell tower and wooden doors is visible under a clear blue sky, likely in Santa Marta, Colombia.

79-night Circle South America Grand Voyage

St. John (U.S.V.I.)

Charlestown

+40 more

Aboard

Azamara Quest

From

Miami, Florida

1 Sailing

Jan 6, 2026

1 Sailing

Jan 6, 2026

A scenic view of Devil's Island, a small tropical island in French Guiana, completely covered by a dense forest of palm trees.

60-night Circle South America - 2026 World Voyage Segment

Gustavia

Roseau

Devil's Island

+31 more

Aboard

Vista

From

Miami, Florida

1 Sailing

Jan 6, 2026

1 Sailing

Jan 6, 2026

Published prices from

$17,699

per person*

taxes & fees included

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

18-night Vibrant Voyage To Rio - 2026 World Voyage Segment

Gustavia

Roseau

Devil's Island

+6 more

Aboard

Vista

From

Miami, Florida

1 Sailing

Jan 6, 2026

1 Sailing

Jan 6, 2026

Published prices from

$6,399

per person*

taxes & fees included

180-night Around the World Voyage

Gustavia

Roseau

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

Devil's Island

+97 more

Aboard

Vista

From

Miami, Florida

1 Sailing

Jan 6, 2026

1 Sailing

Jan 6, 2026

Published prices from

$58,099

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

2 Sailings

Jan 6 - Jan 27, 2026

2 Sailings

Jan 6 - Jan 27, 2026

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

25 Sailings

Jan 8, 2026 - Feb 16, 2028

25 Sailings

Jan 8, 2026 - Feb 16, 2028

Published prices from

$3,699

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.

12-night Eastern Caribbean Cruise

St. John's

+3 more

Aboard

Queen Elizabeth

From

Miami, Florida

8 Sailings

Jan 8 - Nov 26, 2026

8 Sailings

Jan 8 - Nov 26, 2026

Published prices from

$1,399

per person*

taxes & fees included

Oranjestad, Aruba harbor with boats and colorful Dutch architecture.

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

19-night Caribbean Tour De Force Voyage

Aboard

Insignia

From

Miami, Florida

1 Sailing

Jan 8, 2026

1 Sailing

Jan 8, 2026

Published prices from

$5,749

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

St. John's

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

+7 more

Aboard

Queen Elizabeth

From

Miami, Florida

13 Sailings

Jan 8 - Nov 26, 2026

13 Sailings

Jan 8 - Nov 26, 2026

Published prices from

$2,409

per person*

taxes & fees included

7-night Classic Caribbean Yacht Harbors Cruise