Luxury Eastern Caribbean Cruises

Upcoming Luxury Eastern Caribbean Cruises

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

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

TCW EXCLUSIVE

16-night Spotlight With Southern Living Cruise

Aboard

Seven Seas Mariner

From

Miami, Florida

1 Sailing

Jun 13, 2026

1 Sailing

Jun 13, 2026

A colorful view of Ketchikan, Alaska, with fishing boats and a busy marina in the foreground and brightly painted houses on a hill, backed by a lush green forest.

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

TCW EXCLUSIVE

40-night Alaska, Panama Canal & Caribbean Cruise

Aboard

Queen Elizabeth

From

Seattle, Washington

1 Sailing

Sep 17, 2026

1 Sailing

Sep 17, 2026

Published prices from

$3,770

per person*

taxes & fees included

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

Up to $1,000 Onboard Credit + FREE 2. Category Veranda Suite Upgrade*

60-night Labrador Coast, Caribbean, South America & Scotia Arc Cruise

Aboard

Seabourn Venture

From

Reykjavik, Iceland

1 Sailing

Sep 20, 2026

1 Sailing

Sep 20, 2026

Published prices from

$47,698

per person*

taxes & fees included

A wide-angle landscape of icebergs floating in the Kangerlussuaq Fjord in Greenland, with one massive, uniquely shaped iceberg dominating the scene under a dramatic sky.

Up to $1,000 Onboard Credit + FREE 2. Category Veranda Suite Upgrade*

39-night Wild Labrador Coast, Caribbean & South America Cruise

Aboard

Seabourn Venture

From

Reykjavik, Iceland

1 Sailing

Sep 20, 2026

1 Sailing

Sep 20, 2026

Published prices from

$31,098

per person*

taxes & fees included

An aerial view of Carambola Beach Resort in St. Croix, with red-roofed buildings nestled among lush green tropical trees along the turquoise Caribbean Sea.

Up to $1,000 Onboard Credit + FREE 2. Category Veranda Suite Upgrade*

23-night Wild Labrador Coast & Southern Caribbean Cruise

Aboard

Seabourn Venture

From

Reykjavik, Iceland

2 Sailings

Sep 20, 2026 - Sep 16, 2027

2 Sailings

Sep 20, 2026 - Sep 16, 2027

Published prices from

$21,798

per person*

taxes & fees included

A scenic sunset over the iconic rock formations of Land's End, including El Arco, a major landmark of Cabo San Lucas, Mexico.

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

TCW EXCLUSIVE

33-night Panama Canal & Caribbean Cruise

Fuerte Amador (Panama City)

+11 more

Aboard

Queen Elizabeth

From

Seattle, Washington

1 Sailing

Sep 24, 2026

1 Sailing

Sep 24, 2026

Published prices from

$3,268

per person*

taxes & fees included

A vibrant beach scene in Búzios, Brazil, with people swimming and relaxing under white umbrellas on the sand, next to lush green hills and a small white building.

Up to $1,000 Onboard Credit + FREE 2. Category Veranda Suite Upgrade*

45-night Caribbean, South America & Scotia Arc Expedition Cruise

Halifax (Nova Scotia)

Carambola Beach

Little Bay

Rodney Bay

Bridgetown (Barbados)

+17 more

Aboard

Seabourn Venture

From

Halifax, Nova Scotia

1 Sailing

Oct 5, 2026

1 Sailing

Oct 5, 2026

Published prices from

$31,098

per person*

taxes & fees included

A classic, two-story colonial building, the Abbey of Our Lady of Exile, with a red roof, a clock tower, and arches in Port of Spain, Trinidad and Tobago, under a cloudy blue sky.

Up to $1,000 Onboard Credit + FREE 2. Category Veranda Suite Upgrade*

24-night Southern Caribbean Yacht Harbors & Coast Of Brazil Cruise

Halifax (Nova Scotia)

Carambola Beach

Little Bay

Rodney Bay

Bridgetown (Barbados)

+10 more

Aboard

Seabourn Venture

From

Halifax, Nova Scotia

1 Sailing

Oct 5, 2026

1 Sailing

Oct 5, 2026

Published prices from

$14,399

per person*

taxes & fees included

Up to $1,000 Onboard Credit + FREE 2. Category Veranda Suite Upgrade*

8-night Southern Caribbean Yacht Harbors Cruise

Halifax (Nova Scotia)

Carambola Beach

Little Bay

Rodney Bay

Bridgetown (Barbados)

Aboard

Seabourn Venture

From

Halifax, Nova Scotia

2 Sailings

Oct 5, 2026 - Oct 1, 2027

2 Sailings

Oct 5, 2026 - Oct 1, 2027

Published prices from

$5,699

per person*

taxes & fees included

FREE All-Inclusive Upgrade*+ 1 more offer

19-night Star Collector: Fall Leaves & Caribbean Breezes Cruise

Aboard

Star Pride

From

Montreal, Quebec

1 Sailing

Oct 9, 2026

1 Sailing

Oct 9, 2026

Published prices from

$9,122

per person*

taxes & fees included

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

TCW EXCLUSIVE

12-night Eastern Caribbean Cruise

Bridgetown (Barbados)

+3 more

Aboard

Queen Elizabeth

From

Miami, Florida

3 Sailings

Oct 15 - Nov 26, 2026

3 Sailings

Oct 15 - 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.

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

TCW EXCLUSIVE

21-night Caribbean Cruise

Bridgetown (Barbados)

+7 more

Aboard

Queen Elizabeth

From

Miami, Florida

5 Sailings

Oct 15 - Nov 26, 2026

5 Sailings

Oct 15 - Nov 26, 2026

Published prices from

$2,259

per person*

taxes & fees included

Plaza Espana in Barcelona, showcasing unique architectural design and vibrant surroundings.

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

TCW EXCLUSIVE

20-night Mediterranean & Atlantic Crossing Cruise

Rome (Civitavecchia)

Florence/Pisa (Livorno)

Aboard

Viking Sea

From

Civitavecchia, Rome, Italy

1 Sailing

Oct 16, 2026

1 Sailing

Oct 16, 2026

Published prices from

$7,698

per person*

taxes & fees included

A stunning autumn landscape in Havre-Saint-Pierre, Quebec, with a lake reflecting a forest of trees in various shades of green, yellow, and orange, with a wooden pier in the foreground.

25-night Canada & Caribbean Isles Voyage

Montreal

Quebec City

Saguenay

Baie-Comeau (Comeau Bay)

Sept-Iles

+16 more

Aboard

Vista

From

Montreal, Quebec

1 Sailing

Oct 17, 2026

1 Sailing

Oct 17, 2026

Published prices from

$12,349

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 $200 Shipboard Credit & More with Azamara Circle*+ 2 more offers

26-night Canada & Caribbean Voyage: Montreal, Quebec & Barbados

Aboard

Azamara Journey

From

Montreal, Quebec

1 Sailing

Oct 19, 2026

1 Sailing

Oct 19, 2026

Published prices from

$8,039

per person*

taxes & fees included

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

TCW EXCLUSIVE

8-night Bermuda Bliss Cruise

Aboard

Star Pride

From

Boston, Massachusetts

1 Sailing

Oct 20, 2026

1 Sailing

Oct 20, 2026

Published prices from

$2,826

per person*

taxes & fees included

A stone lion statue in the foreground with the beautiful city of Perast and the Bay of Kotor in Montenegro in the background, featuring red-roofed buildings and a church steeple by the water.

57-night Old & New World Discovery Voyage

Igoumenitsa (Meteora)

+32 more

Aboard

Insignia

From

Fusina, Venice, Italy

1 Sailing

Oct 23, 2026

1 Sailing

Oct 23, 2026

Published prices from

$18,149

per person*

taxes & fees included

A golden-hour shot of a sandy beach in Portimão, Portugal, with the clear water of the Atlantic Ocean gently washing over the sand and the large, jagged limestone rock formations of the Algarve coast lit by the sun.

32-night Adriatic to Caribbean Isles Voyage

Igoumenitsa (Meteora)

+19 more

Aboard

Insignia

From

Fusina, Venice, Italy

1 Sailing

Oct 23, 2026

1 Sailing

Oct 23, 2026

Published prices from

$8,899

per person*

taxes & fees included

A beautiful panoramic shot from a garden in Funchal, Madeira, Portugal, showcasing meticulously manicured flower beds in geometric patterns with the city and the Atlantic Ocean in the background.

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

TCW EXCLUSIVE

13-night West Indies To Spain Cruise

St. Maarten (Philipsburg)

+2 more

Aboard

Viking Sea

From

Barcelona, Spain

1 Sailing

Oct 23, 2026

1 Sailing

Oct 23, 2026

Published prices from

$3,299

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.

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

25-night Canada & Caribbean Cruise

Montreal

Quebec City

Charlottetown

Halifax (Nova Scotia)

Boston

+11 more

Aboard

Silver Shadow

From

Montreal, Quebec

1 Sailing

Oct 24, 2026

1 Sailing

Oct 24, 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.

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

TCW EXCLUSIVE

9-night Western Caribbean Cruise

Aboard

Queen Elizabeth

From

Miami, Florida

4 Sailings

Oct 27 - Dec 29, 2026

4 Sailings

Oct 27 - Dec 29, 2026

Published prices from

$1,099

per person*

taxes & fees included

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*

TCW EXCLUSIVE

14-night Caribbean Enchantment Voyage

New York City

St. Thomas (Charlotte Amalie)

Aboard

Vista

From

New York City, New York

1 Sailing

Oct 28, 2026

1 Sailing

Oct 28, 2026

Published prices from

$4,999

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.

FREE All-Inclusive Upgrade*+ 1 more offer

11-night Gems Of The Leeward Islands Cruise

Aboard

Star Pride

From

San Juan, Puerto Rico

1 Sailing

Oct 28, 2026

1 Sailing

Oct 28, 2026

Published prices from

$4,257

per person*

taxes & fees included

A beautiful view from Fort King George in Scarborough, Tobago, with historic cannons overlooking the Caribbean Sea and the town below, framed by lush tropical trees.

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

TCW EXCLUSIVE

16-night Caribbean Voyage: New York, Bermuda & Barbados

New York City

Hamilton

St. Maarten (Philipsburg)

Roadtown

San Juan

+8 more

Aboard

Azamara Journey

From

New York City, New York

1 Sailing

Oct 29, 2026

1 Sailing

Oct 29, 2026

Published prices from

$5,109

per person*

taxes & fees included

A turquoise and white ferry boat cruises through the harbor in Hamilton, Bermuda, with a backdrop of pastel-colored buildings and houses along the waterfront.

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

TCW EXCLUSIVE

9-night Bermuda & Caribbean Voyage: New York, Bermuda & St. Maarten

New York City

Hamilton

St. Maarten (Philipsburg)

Roadtown

San Juan

Aboard

Azamara Journey

From

New York City, New York

1 Sailing

Oct 29, 2026

1 Sailing

Oct 29, 2026

Published prices from

$2,239

per person*

taxes & fees included

Luxury Eastern Caribbean Cruises

Upcoming Luxury Eastern Caribbean Cruises

16-night Spotlight With Southern Living Cruise

40-night Alaska, Panama Canal & Caribbean Cruise

$3,770

60-night Labrador Coast, Caribbean, South America & Scotia Arc Cruise

$47,698

39-night Wild Labrador Coast, Caribbean & South America Cruise

$31,098

23-night Wild Labrador Coast & Southern Caribbean Cruise

$21,798

33-night Panama Canal & Caribbean Cruise

$3,268

45-night Caribbean, South America & Scotia Arc Expedition Cruise

$31,098

24-night Southern Caribbean Yacht Harbors & Coast Of Brazil Cruise

$14,399

8-night Southern Caribbean Yacht Harbors Cruise

$5,699

19-night Star Collector: Fall Leaves & Caribbean Breezes Cruise

$9,122

12-night Eastern Caribbean Cruise

$1,399

21-night Caribbean Cruise

$2,259

20-night Mediterranean & Atlantic Crossing Cruise

$7,698

25-night Canada & Caribbean Isles Voyage

$12,349

26-night Canada & Caribbean Voyage: Montreal, Quebec & Barbados

$8,039

8-night Bermuda Bliss Cruise

$2,826

57-night Old & New World Discovery Voyage

$18,149

32-night Adriatic to Caribbean Isles Voyage

$8,899

13-night West Indies To Spain Cruise

$3,299

25-night Canada & Caribbean Cruise

9-night Western Caribbean Cruise

$1,099

14-night Caribbean Enchantment Voyage

$4,999

11-night Gems Of The Leeward Islands Cruise

$4,257

16-night Caribbean Voyage: New York, Bermuda & Barbados

$5,109

9-night Bermuda & Caribbean Voyage: New York, Bermuda & St. Maarten

$2,239

More to Explore

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16-night Spotlight With Southern Living Cruise

40-night Alaska, Panama Canal & Caribbean Cruise

$3,770

60-night Labrador Coast, Caribbean, South America & Scotia Arc Cruise

$47,698

39-night Wild Labrador Coast, Caribbean & South America Cruise

$31,098

23-night Wild Labrador Coast & Southern Caribbean Cruise

$21,798

33-night Panama Canal & Caribbean Cruise

$3,268

45-night Caribbean, South America & Scotia Arc Expedition Cruise

$31,098

24-night Southern Caribbean Yacht Harbors & Coast Of Brazil Cruise

$14,399

8-night Southern Caribbean Yacht Harbors Cruise

$5,699

19-night Star Collector: Fall Leaves & Caribbean Breezes Cruise

$9,122

12-night Eastern Caribbean Cruise

$1,399

21-night Caribbean Cruise

$2,259