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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*+ 2 more offers

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

St. Maarten (Philipsburg)

Carambola Beach

Port Elizabeth (Bequia)

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

$3,799

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*+ 2 more offers

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

St. Maarten (Philipsburg)

Carambola Beach

Port Elizabeth (Bequia)

Aboard

Seabourn Ovation

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Dec 5, 2026

1 Sailing

Dec 5, 2026

Published prices from

$6,199

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

Windstar

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

St. Maarten (Philipsburg)

Falmouth Harbour

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

$5,188

per person*

taxes & fees included

A breathtaking panoramic view of Charlotte Amalie harbor in St. Thomas, with a cruise ship anchored in the bay, surrounded by rolling green hills and a colorful sunset.

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

Windstar

7-night Classic Caribbean Cruise From Philipsburg, St. Maarten, The Netherlands

St. Maarten (Philipsburg)

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

15 Sailings

Dec 26, 2026 - Mar 5, 2028

15 Sailings

Dec 26, 2026 - Mar 5, 2028

Published prices from

$2,362

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*+ 2 more offers

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

St. Maarten (Philipsburg)

Carambola Beach

Port Elizabeth (Bequia)

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

$7,899

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

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

St. Maarten (Philipsburg)

Carambola Beach

Port Elizabeth (Bequia)

Aboard

Seabourn Ovation

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Mar 20, 2027

1 Sailing

Mar 20, 2027

Published prices from

$10,699

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*

Windstar

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

St. Maarten (Philipsburg)

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

$4,392

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*

Windstar

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

St. Maarten (Philipsburg)

Iles des Saintes

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

$3,872

per person*

taxes & fees included

Cupecoy Beach with white resort buildings, St. Maarten.

Up to $500 FREE Onboard Credit*

Windstar

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

St. Maarten (Philipsburg)

Iles des Saintes

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

$3,712

per person*

taxes & fees included

Cupecoy Beach with white resort buildings, St. Maarten.

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

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

St. Maarten (Philipsburg)

Falmouth Harbour

Carambola Beach

Aboard

Seabourn Ovation

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Dec 28, 2027

1 Sailing

Dec 28, 2027

Published prices from

$6,399

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

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

St. Maarten (Philipsburg)

Carambola Beach

Port Elizabeth (Bequia)

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

$8,199

per person*

taxes & fees included

Rocky beach and palm trees in Barbados.

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

19-night Yacht Harbors & Atlantic Crossing Cruise From Philipsburg, St. Maarten, The Netherlands

St. Maarten (Philipsburg)

Carambola Beach

Port Elizabeth (Bequia)

Aboard

Seabourn Ovation

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Mar 18, 2028

1 Sailing

Mar 18, 2028

Published prices from

$9,899

per person*

taxes & fees included

*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.