Luxury Caribbean Cruises

Upcoming Luxury Caribbean Cruises

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

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

TCW EXCLUSIVE

12-night Majestic Beaches and Canal Crossing Cruise

Miami

Florida Strait

Grand Cayman (George Town)

Ocho Rios

Kralendijk

+7 more

Aboard

Seven Seas Grandeur

From

Miami, Florida

1 Sailing

Jan 3, 2026

1 Sailing

Jan 3, 2026

A cruise ship navigating through the Gatun Locks of the Panama Canal, an important navigational route and popular tourist destination.

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

TCW EXCLUSIVE

22-night Tropical Escape Across the Canal Cruise

Miami

Florida Strait

Grand Cayman (George Town)

Ocho Rios

Kralendijk

+12 more

Aboard

Seven Seas Grandeur

From

Miami, Florida

1 Sailing

Jan 3, 2026

1 Sailing

Jan 3, 2026

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

TCW EXCLUSIVE

7-night Lush Islands, Lovely Shores Cruise

Aboard

Seven Seas Mariner

From

Miami, Florida

1 Sailing

Jan 3, 2026

1 Sailing

Jan 3, 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.

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

14-night Southern Island Discovery Cruise

Bridgetown (Barbados)

Aboard

Seabourn Ovation

From

Bridgetown, Barbados

1 Sailing

Jan 3, 2026

1 Sailing

Jan 3, 2026

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

7-night Treasures Of Aruba, Bonaire & Curacao Cruise

Bridgetown (Barbados)

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.

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

TCW EXCLUSIVE

35-night Eastern Caribbean Cruise

London (Southampton)

Funchal (Madeira)

Bridgetown (Barbados)

Castries

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.

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

10-night Sublime Southern Caribbean Cruise

Bridgetown (Barbados)

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.

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

$7,400

per person*

taxes & fees included

Cupecoy Beach with white resort buildings, St. Maarten.

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

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

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

St. Maarten (Philipsburg)

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.

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

TCW EXCLUSIVE

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

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

TCW EXCLUSIVE

12-night Maya To Island Heritage Voyage

Santo Tomas de Castilla

+5 more

Aboard

Allura

From

Miami, Florida

1 Sailing

Jan 4, 2026

1 Sailing

Jan 4, 2026

Published prices from

$6,149

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.

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

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

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

TCW EXCLUSIVE

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.

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

11-night Caribbean Cruise

Bridgetown (Barbados)

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.

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

21-night Caribbean Cruise

Bridgetown (Barbados)

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.

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

TCW EXCLUSIVE

11-night Eastern Caribbean Voyage

Miami

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

St. Thomas (Charlotte Amalie)

St. Maarten (Philipsburg)

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.

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

TCW EXCLUSIVE

79-night Circle South America Grand Voyage

Miami

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

St. Thomas (Charlotte Amalie)

St. Maarten (Philipsburg)

Charlestown

+40 more

Aboard

Azamara Quest

From

Miami, Florida

1 Sailing

Jan 6, 2026

1 Sailing

Jan 6, 2026

Illuminated Singapore Marina Bay skyline at night.

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

TCW EXCLUSIVE

100-night 2026 World Cruise Segment: Ft. Lauderdale to Mahe

Aboard

Silver Dawn

From

Fort Lauderdale, Florida

1 Sailing

Jan 6, 2026

1 Sailing

Jan 6, 2026

A stunning shot of a small, natural tunnel in the cliffs of the rugged coastline near Puerto Limon, Costa Rica, with a gnarled tree branch reaching across the top and water flowing through.

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

TCW EXCLUSIVE

48-night 2026 World Cruise Segment: Ft. Lauderdale to Auckland

Aboard

Silver Dawn

From

Fort Lauderdale, Florida

1 Sailing

Jan 6, 2026

1 Sailing

Jan 6, 2026

A vibrant shot of the long pier in Progreso, Mexico, with a large, decorative fish hanging from a wooden frame and the highway bridge visible in the distance over the turquoise sea.

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

TCW EXCLUSIVE

15-night Central America Tapestry Voyage

Fuerte Amador (Panama City)

+5 more

Aboard

Azamara Onward

From

Miami, Florida

1 Sailing

Jan 6, 2026

1 Sailing

Jan 6, 2026

Published prices from

$4,199

per person*

taxes & fees included

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

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

TCW EXCLUSIVE

60-night Circle South America - 2026 World Voyage Segment

Miami

Gustavia

Roseau

Bridgetown (Barbados)

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

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

TCW EXCLUSIVE

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

Miami

Gustavia

Roseau

Bridgetown (Barbados)

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

Luxury Caribbean Cruises

Upcoming Luxury Caribbean Cruises

12-night Majestic Beaches and Canal Crossing Cruise

22-night Tropical Escape Across the Canal Cruise

7-night Lush Islands, Lovely Shores Cruise

14-night Southern Island Discovery Cruise

7-night Treasures Of Aruba, Bonaire & Curacao Cruise

$3,824

35-night Eastern Caribbean Cruise

10-night Sublime Southern Caribbean Cruise

7-night Eastern & Southern Caribbean Cruise

$7,400

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

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

$4,267

24-night Yucatan & Leeward Seafarer Voyage

$9,499

12-night Maya To Island Heritage Voyage

$6,149

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

55-night Star Collector: A Grand Caribbean Adventure Cruise

21-night Star Collector: A Lesser Antilles Odyssey Cruise

12-night Azure Caribbean Voyage

$3,649

11-night Caribbean Cruise

$6,400

21-night Caribbean Cruise

11-night Eastern Caribbean Voyage

79-night Circle South America Grand Voyage

100-night 2026 World Cruise Segment: Ft. Lauderdale to Mahe

48-night 2026 World Cruise Segment: Ft. Lauderdale to Auckland

15-night Central America Tapestry Voyage

$4,199

60-night Circle South America - 2026 World Voyage Segment

$17,699

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

$6,399

More to Explore

12-night Majestic Beaches and Canal Crossing Cruise

22-night Tropical Escape Across the Canal Cruise

7-night Lush Islands, Lovely Shores Cruise

14-night Southern Island Discovery Cruise

7-night Treasures Of Aruba, Bonaire & Curacao Cruise

$3,824

35-night Eastern Caribbean Cruise

10-night Sublime Southern Caribbean Cruise

7-night Eastern & Southern Caribbean Cruise

$7,400

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

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

$4,267

24-night Yucatan & Leeward Seafarer Voyage

$9,499

12-night Maya To Island Heritage Voyage

$6,149

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

55-night Star Collector: A Grand Caribbean Adventure Cruise

21-night Star Collector: A Lesser Antilles Odyssey Cruise

12-night Azure Caribbean Voyage

$3,649

11-night Caribbean Cruise

$6,400

21-night Caribbean Cruise

11-night Eastern Caribbean Voyage

79-night Circle South America Grand Voyage

100-night 2026 World Cruise Segment: Ft. Lauderdale to Mahe

48-night 2026 World Cruise Segment: Ft. Lauderdale to Auckland

15-night Central America Tapestry Voyage

$4,199

60-night Circle South America - 2026 World Voyage Segment

$17,699

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

$6,399