Philipsburg, St. Maarten, The Netherlands Cruise Deals

Cupecoy Beach with white resort buildings, St. Maarten.

Upcoming Philipsburg, St. Maarten, The Netherlands Cruise Deals

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Cupecoy Beach with white resort buildings, St. Maarten.

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

Windstar

14-night Ocean Crossings + Ponta Delgada, Azores Cruise

St. Maarten (Philipsburg)

Ponta Delgada (Azores)

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Apr 4, 2026

1 Sailing

Apr 4, 2026

Published prices from

$3,426

per person*

taxes & fees included

A historic fortress, the Castle of La Calahorra, stands on a hilltop overlooking a town with white-washed houses below, under a blue sky with scattered clouds in Almería, Spain.

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

Windstar

22-night Star Collector: Atlantic Interludes & Iberian Indulgences Cruise

St. Maarten (Philipsburg)

Ponta Delgada (Azores)

Seville (Cadiz)

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Apr 4, 2026

1 Sailing

Apr 4, 2026

Published prices from

$7,588

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

14-night Yachtsman's Caribbean In Depth Cruise

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

$7,299

per person*

taxes & fees included

Cupecoy Beach with white resort buildings, St. Maarten.

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

7-night Yachtsman's Caribbean Cruise

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

$4,299

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

Windstar

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

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

$3,267

per person*

taxes & fees included

A picturesque view of a small town nestled at the base of a lush, green mountain on Iles des Saintes, Guadeloupe, with boats moored in the deep blue water and fluffy clouds in the sky.

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

Windstar

14-night Star Collector: Caribbean Explorations Cruise

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

$5,519

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

Windstar

7-night Classic Caribbean Cruise

St. Maarten (Philipsburg)

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

8 Sailings

Dec 26, 2026 - Nov 28, 2027

8 Sailings

Dec 26, 2026 - Nov 28, 2027

Published prices from

$2,851

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

14-night Caribbean Gems In Depth Cruise

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

$8,899

per person*

taxes & fees included

Cupecoy Beach with white resort buildings, St. Maarten.

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

19-night Yachtsman's Caribbean & Atlantic Passage Cruise

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

$10,199

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*

Windstar

15-night Ocean Crossings Cruise

St. Maarten (Philipsburg)

Funchal (Madeira)

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Mar 27, 2027

1 Sailing

Mar 27, 2027

Published prices from

$4,029

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.