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

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

14-night Leeward Island Jewels Cruise From Miami, Florida

Carambola Beach

Aboard

Seabourn Quest

From

Miami, Florida

2 Sailings

Nov 22 - Dec 6, 2026

2 Sailings

Nov 22 - Dec 6, 2026

Published prices from

$6,499

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

Windstar

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

St. Maarten (Philipsburg)

Falmouth Harbour

Aboard

Wind Surf

From

Lisbon, Portugal

1 Sailing

Dec 5, 2026

1 Sailing

Dec 5, 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.

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

$5,216

per person*

taxes & fees included

Cupecoy Beach with white resort buildings, St. Maarten.

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

Windstar

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

St. Maarten (Philipsburg)

Falmouth Harbour

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

$3,183

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 $500 FREE Onboard Credit*+ 3 more offers

16-night Leeward Island Holiday Cruise From Miami, Florida

Carambola Beach

Aboard

Seabourn Quest

From

Miami, Florida

1 Sailing

Dec 20, 2026

1 Sailing

Dec 20, 2026

Published prices from

$10,999

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*

Windstar

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

Funchal (Madeira)

St. Maarten (Philipsburg)

Aboard

Wind Surf

From

Lisbon, Portugal

1 Sailing

Nov 5, 2027

1 Sailing

Nov 5, 2027

Published prices from

$4,602

per person*

taxes & fees included

Cupecoy Beach with white resort buildings, St. Maarten.

Up to $500 FREE Onboard Credit*

Windstar

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

St. Maarten (Philipsburg)

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

$3,148

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

$4,572

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

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

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

14-night Windward & Leeward Islands Cruise From Miami, Florida

Carambola Beach

Aboard

Seabourn Quest

From

Miami, Florida

1 Sailing

Dec 4, 2027

1 Sailing

Dec 4, 2027

Published prices from

$7,299

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.

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

Windstar

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

St. Maarten (Philipsburg)

Falmouth Harbour

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Dec 5, 2027

1 Sailing

Dec 5, 2027

Published prices from

$2,448

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*+ 2 more offers

17-night Hidden Yacht Harbor Holiday Cruise From Bridgetown, Barbados

Bridgetown (Barbados)

Aboard

Seabourn Ovation

From

Bridgetown, Barbados

1 Sailing

Dec 11, 2027

1 Sailing

Dec 11, 2027

Published prices from

$8,799

per person*

taxes & fees included

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

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

10-night Southern Caribbean & St. Barts Holiday Cruise From Miami, Florida

Carambola Beach

Aboard

Seabourn Quest

From

Miami, Florida

1 Sailing

Dec 18, 2027

1 Sailing

Dec 18, 2027

Published prices from

$5,499

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 $500 FREE Onboard Credit*+ 2 more offers

10-night Caribbean Yacht Harbor Holiday Cruise From Bridgetown, Barbados

Bridgetown (Barbados)

Port Elizabeth (Bequia)

Aboard

Seabourn Ovation

From

Bridgetown, Barbados

1 Sailing

Dec 18, 2027

1 Sailing

Dec 18, 2027

Published prices from

$5,799

per person*

taxes & fees included

Rocky beach and palm trees in Barbados.

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

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

Bridgetown (Barbados)

Port Elizabeth (Bequia)

Aboard

Seabourn Ovation

From

Bridgetown, Barbados

1 Sailing

Dec 18, 2027

1 Sailing

Dec 18, 2027

Published prices from

$12,354

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

$3,852

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 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

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

St. Maarten (Philipsburg)

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Jan 3, 2028

1 Sailing

Jan 3, 2028

Published prices from

$2,108

per person*

taxes & fees included

Cupecoy Beach with white resort buildings, St. Maarten.

Up to $500 FREE Onboard Credit*

Windstar

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

St. Maarten (Philipsburg)

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

$2,273

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*

Windstar

22-night Star Collector Cruise: Hearty Ports & Rum Punches - A Transatlantic Crossing From Philipsburg, St. Maarten, The Netherlands

St. Maarten (Philipsburg)

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Mar 12, 2028

1 Sailing

Mar 12, 2028

Published prices from

$4,210

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.