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31 Results

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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
Seabourn logo

14-night Exotic Caribbean In Depth Cruise From Bridgetown, Barbados

Bridgetown (Barbados)
Castries
Little Bay
St. John's
Carambola Beach
+7 more

Aboard

Seabourn Ovation

From

Bridgetown, Barbados

7 Sailings

Nov 28, 2026 - Mar 13, 2027

7 Sailings

Nov 28, 2026 - Mar 13, 2027

Published prices from

$6,199

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.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

21-night Star Collector: Hearty Ports & Rum Punches - A Transatlantic Crossing Cruise From Lisbon, Portugal

Lisbon
St. John's
St. Maarten (Philipsburg)
Falmouth Harbour
Gustavia
+5 more

Aboard

Wind Surf

From

Lisbon, Portugal

1 Sailing

Dec 5, 2026

1 Sailing

Dec 5, 2026

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 $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Seabourn logo

7-night Yachtsman's Caribbean Cruise From Philipsburg, St. Maarten, The Netherlands

St. Maarten (Philipsburg)
Sopers Hole
Carambola Beach
Trois Isles
Port Elizabeth (Bequia)
+3 more

Aboard

Seabourn Ovation

From

Philipsburg, St. Maarten, The Netherlands

13 Sailings

Dec 5, 2026 - Mar 18, 2028

13 Sailings

Dec 5, 2026 - Mar 18, 2028

Published prices from

$3,299

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.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Seabourn logo

14-night Yachtsman's Caribbean In Depth Cruise From Philipsburg, St. Maarten, The Netherlands

St. Maarten (Philipsburg)
Sopers Hole
Carambola Beach
Trois Isles
Port Elizabeth (Bequia)
+7 more

Aboard

Seabourn Ovation

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Dec 5, 2026

1 Sailing

Dec 5, 2026

Published prices from

$5,899

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.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

14-night Star Collector: Caribbean Explorations Cruise From Philipsburg, St. Maarten, The Netherlands

St. Maarten (Philipsburg)
Falmouth Harbour
Gustavia
Road Bay
Sopers Hole
+7 more

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

13 Sailings

Dec 19, 2026 - Mar 13, 2027

13 Sailings

Dec 19, 2026 - Mar 13, 2027

Published prices from

$5,210

per person*

taxes & fees included

Cupecoy Beach with white resort buildings, St. Maarten.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

7-night Beach Fun & Sun: A Remote Caribbean Getaway Cruise From Philipsburg, St. Maarten, The Netherlands

St. Maarten (Philipsburg)
Falmouth Harbour
Gustavia
Road Bay
Sopers Hole
+2 more

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

7 Sailings

Dec 19, 2026 - Mar 13, 2027

7 Sailings

Dec 19, 2026 - Mar 13, 2027

Published prices from

$2,726

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 $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Silversea logo

14-night Caribbean Cruise From San Juan, Puerto Rico

San Juan
Jost Van Dyke
Little Bay
Castries
Canouan Island
+7 more

Aboard

Silver Shadow

From

San Juan, Puerto Rico

1 Sailing

Dec 20, 2026

1 Sailing

Dec 20, 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.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Silversea logo

7-night Caribbean Cruise From San Juan, Puerto Rico

San Juan
Jost Van Dyke
Little Bay
Castries
Canouan Island
+2 more

Aboard

Silver Shadow

From

San Juan, Puerto Rico

3 Sailings

Dec 20, 2026 - Feb 26, 2027

3 Sailings

Dec 20, 2026 - Feb 26, 2027

Published prices from

$4,900

per person*

taxes & fees included

A captivating half-underwater, half-above-water shot of a person snorkeling in the vibrant turquoise waters of the British Virgin Islands with stunning rock formations and palm trees visible above the waterline.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Seabourn logo

14-night Caribbean Gems In Depth Cruise From Philipsburg, St. Maarten, The Netherlands

St. Maarten (Philipsburg)
Sopers Hole
Carambola Beach
Trois Isles
Port Elizabeth (Bequia)
+7 more

Aboard

Seabourn Ovation

From

Philipsburg, St. Maarten, The Netherlands

3 Sailings

Jan 16 - Mar 6, 2027

3 Sailings

Jan 16 - Mar 6, 2027

Published prices from

$9,899

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.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Seabourn logo

19-night Yachtsman's Caribbean & Atlantic Passage Cruise From Philipsburg, St. Maarten, The Netherlands

St. Maarten (Philipsburg)
Sopers Hole
Carambola Beach
Trois Isles
Port Elizabeth (Bequia)
+7 more

Aboard

Seabourn Ovation

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Mar 20, 2027

1 Sailing

Mar 20, 2027

Published prices from

$11,199

per person*

taxes & fees included

The picturesque fishing village of Deshaies, Guadeloupe, with its colorful waterfront and red-roofed church nestled on a tranquil bay.
Up to $500 FREE Onboard Credit*
TCW EXCLUSIVE
Windstar

23-night Star Collector Cruise: Hearty Ports & Rum Punches - A Transatlantic Crossing From Lisbon, Portugal

Lisbon
Funchal (Madeira)
Jost Van Dyke
St. Maarten (Philipsburg)
Gustavia
+6 more

Aboard

Wind Surf

From

Lisbon, Portugal

1 Sailing

Nov 5, 2027

1 Sailing

Nov 5, 2027

Published prices from

$4,911

per person*

taxes & fees included

Cupecoy Beach with white resort buildings, St. Maarten.
Up to $500 FREE Onboard Credit*
TCW EXCLUSIVE
Windstar

8-night Beach Fun & Sun Cruise: A Remote Caribbean Getaway From Philipsburg, St. Maarten, The Netherlands

St. Maarten (Philipsburg)
Gustavia
St. John's
Deshaies
Road Bay
+3 more

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

2 Sailings

Nov 20 - Dec 19, 2027

2 Sailings

Nov 20 - Dec 19, 2027

Published prices from

$3,096

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.
Up to $500 FREE Onboard Credit*
TCW EXCLUSIVE
Windstar

15-night Star Collector Cruise: Caribbean Explorations From Philipsburg, St. Maarten, The Netherlands

St. Maarten (Philipsburg)
Gustavia
St. John's
Deshaies
Road Bay
+8 more

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

3 Sailings

Nov 20 - Dec 19, 2027

3 Sailings

Nov 20 - Dec 19, 2027

Published prices from

$4,665

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*+ 2 more offers
TCW EXCLUSIVE
Seabourn logo

14-night Caribbean Yacht Explorer Cruise From Bridgetown, Barbados

Bridgetown (Barbados)
Castries
Little Bay
St. John's
Carambola Beach
+7 more

Aboard

Seabourn Ovation

From

Bridgetown, Barbados

6 Sailings

Nov 27, 2027 - Mar 11, 2028

6 Sailings

Nov 27, 2027 - Mar 11, 2028

Published prices from

$8,299

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.
Up to $500 FREE Onboard Credit*
TCW EXCLUSIVE
Windstar

14-night Star Collector Cruise: Caribbean Explorations From Philipsburg, St. Maarten, The Netherlands

St. Maarten (Philipsburg)
Charlestown
Roseau
Mayreau
Iles des Saintes
+7 more

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

11 Sailings

Nov 28, 2027 - Mar 5, 2028

11 Sailings

Nov 28, 2027 - Mar 5, 2028

Published prices from

$3,950

per person*

taxes & fees included

A panoramic view of Fort-de-France, Martinique, showing a bustling bay filled with boats and yachts, with colorful houses nestled on the surrounding green hillsides and the deep blue Caribbean Sea beyond.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Silversea logo

26-night Transatlantic Cruise From Lisbon, Portugal

Lisbon
Gibraltar
St. Maarten (Philipsburg)
San Juan
Miami
+6 more

Aboard

Silver Nova

From

Lisbon, Portugal

1 Sailing

Dec 3, 2027

1 Sailing

Dec 3, 2027

A panoramic view of Gustavia, Saint Barthélemy, featuring a bay filled with luxury yachts and sailboats, framed by lush, green hillsides dotted with houses.
Up to $500 FREE Onboard Credit*+ 1 more offer
TCW EXCLUSIVE
Windstar

7-night Beach Fun & Sun: A Remote Caribbean Getaway From Philipsburg, St. Maarten, The Netherlands

St. Maarten (Philipsburg)
Falmouth Harbour
Road Bay
Sopers Hole
Jost Van Dyke
+2 more

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Dec 5, 2027

1 Sailing

Dec 5, 2027

Published prices from

$2,516

per person*

taxes & fees included

The picturesque fishing village of Deshaies, Guadeloupe, with its colorful waterfront and red-roofed church nestled on a tranquil bay.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Silversea logo

11-night Caribbean Cruise From Miami, Florida

Miami
Sopers Hole
Basseterre
Deshaies
Fort de France
+2 more

Aboard

Silver Nova

From

Miami, Florida

7 Sailings

Dec 18, 2027 - Feb 22, 2028

7 Sailings

Dec 18, 2027 - Feb 22, 2028

Published prices from

$6,650

per person*

taxes & fees included

Rocky beach and palm trees in Barbados.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Seabourn logo

21-night Bonaire, Curacao & Southern Caribbean Holiday Cruise From Bridgetown, Barbados

Bridgetown (Barbados)
St. George's
Port Elizabeth (Bequia)
St. Pierre
Terre-de-Haut
+11 more

Aboard

Seabourn Ovation

From

Bridgetown, Barbados

1 Sailing

Dec 18, 2027

1 Sailing

Dec 18, 2027

Published prices from

$14,299

per person*

taxes & fees included

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Silversea logo

12-night Caribbean Cruise From Miami, Florida

Miami
Great Exuma
Samaná
San Juan
St. John (U.S.V.I.)
+4 more

Aboard

Silver Shadow

From

Miami, Florida

1 Sailing

Dec 24, 2027

1 Sailing

Dec 24, 2027

Published prices from

$6,050

per person*

taxes & fees included

Cupecoy Beach with white resort buildings, St. Maarten.
Up to $500 FREE Onboard Credit*
TCW EXCLUSIVE
Windstar

13-night Star Collector Cruise: Caribbean Explorations From Philipsburg, St. Maarten, The Netherlands

St. Maarten (Philipsburg)
Charlestown
Roseau
Mayreau
Iles des Saintes
+6 more

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

2 Sailings

Dec 27, 2027 - Jan 3, 2028

2 Sailings

Dec 27, 2027 - Jan 3, 2028

Published prices from

$3,880

per person*

taxes & fees included

Cupecoy Beach with white resort buildings, St. Maarten.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Seabourn logo

11-night Yachtsman's Holiday In Aruba, Bonaire & Curacao Cruise From Philipsburg, St. Maarten, The Netherlands

St. Maarten (Philipsburg)
Sopers Hole
Road Bay
Falmouth Harbour
Carambola Beach
+6 more

Aboard

Seabourn Ovation

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Dec 28, 2027

1 Sailing

Dec 28, 2027

Published prices from

$7,699

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.
Up to $500 FREE Onboard Credit*
TCW EXCLUSIVE
Windstar

6-night Beach Fun & Sun Cruise: A Remote Caribbean Getaway From Philipsburg, St. Maarten, The Netherlands

St. Maarten (Philipsburg)
Road Bay
Gustavia
Jost Van Dyke
Virgin Gorda

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Jan 3, 2028

1 Sailing

Jan 3, 2028

Published prices from

$2,176

per person*

taxes & fees included

Cupecoy Beach with white resort buildings, St. Maarten.
Up to $500 FREE Onboard Credit*
TCW EXCLUSIVE
Windstar

7-night Beach Fun & Sun Cruise: A Remote Caribbean Getaway From Philipsburg, St. Maarten, The Netherlands

St. Maarten (Philipsburg)
St. John's
Road Bay
Sopers Hole
Jost Van Dyke
+2 more

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

5 Sailings

Jan 16 - Mar 12, 2028

5 Sailings

Jan 16 - Mar 12, 2028

Published prices from

$2,341

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.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Seabourn logo

14-night Caribbean Yacht Harbors In Depth Cruise From Philipsburg, St. Maarten, The Netherlands

St. Maarten (Philipsburg)
Sopers Hole
Carambola Beach
Trois Isles
Port Elizabeth (Bequia)
+7 more

Aboard

Seabourn Ovation

From

Philipsburg, St. Maarten, The Netherlands

3 Sailings

Feb 5 - Mar 4, 2028

3 Sailings

Feb 5 - Mar 4, 2028

Published prices from

$9,299

per person*

taxes & fees included

    • Showing results 1 - 24 of 31

*Rates and offers are per person, in US Dollars, based on double occupancy, capacity controlled, subject to availability and confirmation, and may change without notice. Government taxes and fees are included. Rates and offers are available for select dates and categories only. Additional restrictions may apply. Call 1-800-377-9383 for full terms and conditions.