Find Your Cruise Vacation

Roundtrip

7-Night Caribbean Cruise

$2,699

Windstar Cruises – Wind Surf

142 Reviews

Date:

Dec 28, 2025

Ports:

St. Maarten → Falmouth Harbour → Road Bay → Soper's Hole → Jost Van Dyke → Virgin Gorda / Prickly Pear → Gustavia

Departs Dec 28, 2025 from Philipsburg, Sint Maarten

Up to 2 deals and Avoya Exclusives

From

$2,699

Roundtrip

7-Night Caribbean Cruise

$2,499

Windstar Cruises – Wind Surf

142 Reviews

Date:

Jan 04, 2026

Ports:

St. Maarten → Falmouth Harbour → Road Bay → Soper's Hole → Jost Van Dyke → Virgin Gorda / Prickly Pear → Gustavia

Departs Jan 04, 2026 from Philipsburg, Sint Maarten

Up to 2 deals and Avoya Exclusives

From

$2,499

7-Night Caribbean Cruise

$2,499

Windstar Cruises – Wind Surf

142 Reviews

Date:

Jan 11, 2026

Ports:

St. Maarten → Basseterre → Little Bay → Gustavia → Deshaies → Roseau → Pigeon Island → Bridgetown

Departs Jan 11, 2026 from Philipsburg, Sint Maarten

Up to 2 deals and Avoya Exclusives

From

$2,499

Roundtrip

10-Night Caribbean Cruise

$3,499

Windstar Cruises – Wind Spirit

98 Reviews

Date:

Jan 14, 2026

Ports:

St. Maarten → Basseterre → Roseau → Castries → Bequia → St. George's → Mayreau → Anse Mitan → Les Saintes → Gustavia

Departs Jan 14, 2026 from Philipsburg, Sint Maarten

Up to 2 deals and Avoya Exclusives

From

$3,499

Roundtrip

7-Night Caribbean Cruise

$2,499

Windstar Cruises – Wind Surf

142 Reviews

Date:

Jan 18, 2026

Ports:

Bridgetown → Anse Mitan → Castries → Pigeon Island → Bequia → Mayreau → St. George's

Departs Jan 18, 2026 from Bridgetown, Barbados

Up to 2 deals and Avoya Exclusives

From

$2,499

Roundtrip

7-Night Caribbean Cruise

$2,499

Windstar Cruises – Wind Spirit

98 Reviews

Date:

Jan 24, 2026

Ports:

St. Maarten → Soper's Hole → Jost Van Dyke → Virgin Gorda / Prickly Pear → Gustavia → Road Bay → Falmouth Harbour

Departs Jan 24, 2026 from Philipsburg, Sint Maarten

Up to 2 deals and Avoya Exclusives

From

$2,499

7-Night Caribbean Cruise

$2,699

Windstar Cruises – Wind Surf

142 Reviews

Date:

Jan 25, 2026

Ports:

Bridgetown → Man-o-war Bay → Mayreau → Soufriere → Kralendijk → Willemstad → Oranjestad

Departs Jan 25, 2026 from Bridgetown, Barbados

Up to 2 deals and Avoya Exclusives

From

$2,699

Roundtrip

7-Night Caribbean Cruise

$2,499

Windstar Cruises – Wind Spirit

98 Reviews

Date:

Jan 31, 2026

Ports:

St. Maarten → Soper's Hole → Jost Van Dyke → Virgin Gorda / Prickly Pear → Gustavia → Road Bay → Falmouth Harbour

Departs Jan 31, 2026 from Philipsburg, Sint Maarten

Up to 2 deals and Avoya Exclusives

From

$2,499

8-Night Caribbean Cruise

$3,199

Windstar Cruises – Wind Surf

142 Reviews

Date:

Feb 01, 2026

Ports:

Oranjestad → Santa Marta → Cartagena → Bocas Del Toro → Colón

Departs Feb 01, 2026 from Oranjestad, Aruba

Up to 2 deals and Avoya Exclusives

From

$3,199

Roundtrip

7-Night Caribbean Cruise

$2,599

Windstar Cruises – Wind Spirit

98 Reviews

Date:

Feb 07, 2026

Ports:

St. Maarten → Charlestown → Roseau → Pigeon Island → Les Saintes → Gustavia → Basseterre

Departs Feb 07, 2026 from Philipsburg, Sint Maarten

Up to 2 deals and Avoya Exclusives

From

$2,599

Roundtrip

7-Night Caribbean Cruise

$2,599

Windstar Cruises – Wind Spirit

98 Reviews

Date:

Feb 14, 2026

Ports:

St. Maarten → Soper's Hole → Jost Van Dyke → Virgin Gorda / Prickly Pear → Gustavia → Road Bay → Falmouth Harbour

Departs Feb 14, 2026 from Philipsburg, Sint Maarten

Up to 2 deals and Avoya Exclusives

From

$2,599

11-Night Caribbean Cruise

$3,799

Windstar Cruises – Wind Surf

142 Reviews

Date:

Feb 17, 2026

Ports:

Departs Feb 17, 2026 from Cozumel, Mexico

Up to 2 deals and Avoya Exclusives

From

$3,799

Roundtrip

7-Night Caribbean Cruise

$2,599

Windstar Cruises – Wind Spirit

98 Reviews

Date:

Feb 21, 2026

Ports:

St. Maarten → Soper's Hole → Jost Van Dyke → Virgin Gorda / Prickly Pear → Gustavia → Road Bay → Falmouth Harbour

Departs Feb 21, 2026 from Philipsburg, Sint Maarten

Up to 2 deals and Avoya Exclusives

From

$2,599

Roundtrip

7-Night Caribbean Cruise

$2,299

Windstar Cruises – Wind Surf

142 Reviews

Date:

Feb 28, 2026

Ports:

St. Maarten → Charlestown → Roseau → Pigeon Island → Les Saintes → Gustavia → Basseterre

Departs Feb 28, 2026 from Philipsburg, Sint Maarten

Up to 2 deals and Avoya Exclusives

From

$2,299

7-Night Caribbean Cruise

$2,399

Windstar Cruises – Wind Spirit

98 Reviews

Date:

Feb 28, 2026

Ports:

St. Maarten → Basseterre → Gustavia → Little Bay → Les Saintes → Roseau → Pigeon Island → Bridgetown

Departs Feb 28, 2026 from Philipsburg, Sint Maarten

Up to 2 deals and Avoya Exclusives

From

$2,399

Roundtrip

7-Night Caribbean Cruise

$2,399

Windstar Cruises – Wind Surf

142 Reviews

Date:

Mar 07, 2026

Ports:

St. Maarten → Falmouth Harbour → Road Bay → Soper's Hole → Jost Van Dyke → Virgin Gorda / Prickly Pear → Gustavia

Departs Mar 07, 2026 from Philipsburg, Sint Maarten

Up to 2 deals and Avoya Exclusives

From

$2,399

Roundtrip

7-Night Caribbean Cruise

$2,599

Windstar Cruises – Wind Spirit

98 Reviews

Date:

Mar 07, 2026

Ports:

Bridgetown → Little Bay → Les Saintes → Roseau → Anse Mitan → Pigeon Island

Departs Mar 07, 2026 from Bridgetown, Barbados

Up to 2 deals and Avoya Exclusives

From

$2,599

Roundtrip

7-Night Caribbean Cruise

$2,399

Windstar Cruises – Wind Surf

142 Reviews

Date:

Mar 14, 2026

Ports:

St. Maarten → Falmouth Harbour → Road Bay → Soper's Hole → Jost Van Dyke → Virgin Gorda / Prickly Pear → Gustavia

Departs Mar 14, 2026 from Philipsburg, Sint Maarten

Up to 2 deals and Avoya Exclusives

From

$2,399

Roundtrip

7-Night Caribbean Cruise

$2,599

Windstar Cruises – Wind Spirit

98 Reviews

Date:

Mar 14, 2026

Ports:

Bridgetown → Pigeon Island → Castries → The Pitons → Kingstown → Mayreau → St. George's → Bequia

Departs Mar 14, 2026 from Bridgetown, Barbados

Up to 2 deals and Avoya Exclusives

From

$2,599

Roundtrip

7-Night Caribbean Cruise

$2,299

Windstar Cruises – Wind Surf

142 Reviews

Date:

Mar 21, 2026

Ports:

St. Maarten → Charlestown → Roseau → Pigeon Island → Les Saintes → Gustavia → Basseterre

Departs Mar 21, 2026 from Philipsburg, Sint Maarten

Up to 2 deals and Avoya Exclusives

From

$2,299

Roundtrip

7-Night Caribbean Cruise

$2,599

Windstar Cruises – Wind Spirit

98 Reviews

Date:

Mar 21, 2026

Ports:

Bridgetown → Little Bay → Les Saintes → Roseau → Anse Mitan → Pigeon Island

Departs Mar 21, 2026 from Bridgetown, Barbados

Up to 2 deals and Avoya Exclusives

From

$2,599

Roundtrip

7-Night Caribbean Cruise

$2,399

Windstar Cruises – Wind Surf

142 Reviews

Date:

Mar 28, 2026

Ports:

St. Maarten → Falmouth Harbour → Road Bay → Soper's Hole → Jost Van Dyke → Virgin Gorda / Prickly Pear → Gustavia

Departs Mar 28, 2026 from Philipsburg, Sint Maarten

Up to 2 deals and Avoya Exclusives

From

$2,399

Roundtrip

6-Night Caribbean Cruise

$567

Royal Caribbean – Adventure of the Seas

271 Reviews

Date:

Sep 21, 2024 View Other Dates

Ports:

Port Canaveral → Puerto Plata → Grand Turk → Perfect Day At Cococay

Departs Sep 21, 2024 from Port Canaveral, Florida

Up to 1 deal and Avoya Exclusives

Avoya Exclusive Rate

From

$567

Roundtrip

4-Night Caribbean Cruise

$417

Royal Caribbean – Mariner of the Seas

114 Reviews

Date:

Sep 26, 2024 View Other Dates

Ports:

Galveston → Cozumel

Departs Sep 26, 2024 from Galveston, Texas

Up to 1 deal and Avoya Exclusives

Avoya Exclusive Rate

From

$417

Roundtrip

6-Night Caribbean Cruise

$816

Royal Caribbean – Harmony of the Seas

299 Reviews

Date:

Oct 06, 2024 View Other Dates

Ports:

Galveston → Costa Maya → Roatan → Cozumel

Departs Oct 06, 2024 from Galveston, Texas

Up to 2 deals and Avoya Exclusives

Avoya Exclusive Rate

From

$816