Find Your Cruise Vacation

Roundtrip

7-Night Caribbean Cruise

$2,599

Windstar Cruises – Wind Spirit

98 Reviews

Date:

Feb 01, 2025

Ports:

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

Departs Feb 01, 2025 from Bridgetown, Barbados

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 08, 2025

Ports:

Bridgetown → Basseterre → Les Saintes → Roseau → Anse Mitan → Pigeon Island

Departs Feb 08, 2025 from Bridgetown, Barbados

Up to 2 deals and Avoya Exclusives

From

$2,599

Roundtrip

7-Night Caribbean Cruise

$2,599

Windstar Cruises – Wind Surf

142 Reviews

Date:

Feb 08, 2025

Ports:

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

Departs Feb 08, 2025 from Philipsburg, Sint Maarten

Up to 2 deals and Avoya Exclusives

From

$2,599

Roundtrip

7-Night Caribbean Cruise

$2,399

Windstar Cruises – Wind Surf

142 Reviews

Date:

Feb 15, 2025

Ports:

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

Departs Feb 15, 2025 from Philipsburg, Sint Maarten

Up to 2 deals and Avoya Exclusives

From

$2,399

Roundtrip

7-Night Caribbean Cruise

$2,499

Windstar Cruises – Wind Spirit

98 Reviews

Date:

Feb 15, 2025

Ports:

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

Departs Feb 15, 2025 from Bridgetown, Barbados

Up to 2 deals and Avoya Exclusives

From

$2,499

Roundtrip

7-Night Caribbean Cruise

$2,399

Windstar Cruises – Wind Surf

142 Reviews

Date:

Feb 22, 2025

Ports:

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

Departs Feb 22, 2025 from Philipsburg, Sint Maarten

Up to 2 deals and Avoya Exclusives

From

$2,399

7-Night Caribbean Cruise

$2,499

Windstar Cruises – Star Pride

89 Reviews

Date:

Feb 22, 2025

Ports:

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

Departs Feb 22, 2025 from Bridgetown, Barbados

Up to 2 deals and Avoya Exclusives

From

$2,499

Roundtrip

7-Night Caribbean Cruise

$2,199

Windstar Cruises – Wind Surf

142 Reviews

Date:

Mar 01, 2025

Ports:

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

Departs Mar 01, 2025 from Philipsburg, Sint Maarten

Up to 2 deals and Avoya Exclusives

From

$2,199

Roundtrip

7-Night Caribbean Cruise

$2,199

Windstar Cruises – Wind Surf

142 Reviews

Date:

Mar 08, 2025

Ports:

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

Departs Mar 08, 2025 from Philipsburg, Sint Maarten

Up to 2 deals and Avoya Exclusives

From

$2,199

11-Night Caribbean Cruise

$3,299

Windstar Cruises – Wind Star

88 Reviews

Date:

Mar 15, 2025

Ports:

Colón → Cartagena → Santa Marta → Oranjestad → Willemstad → St. George's → Mayreau → Bridgetown

Departs Mar 15, 2025 from Colon, Panama

Up to 2 deals and Avoya Exclusives

From

$3,299

Roundtrip

7-Night Caribbean Cruise

$2,599

Windstar Cruises – Wind Surf

142 Reviews

Date:

Mar 15, 2025

Ports:

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

Departs Mar 15, 2025 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:

Mar 22, 2025

Ports:

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

Departs Mar 22, 2025 from Philipsburg, Sint Maarten

Up to 2 deals and Avoya Exclusives

From

$2,299

Roundtrip

7-Night Caribbean Cruise

$2,199

Windstar Cruises – Star Pride

89 Reviews

Date:

Mar 29, 2025

Ports:

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

Departs Mar 29, 2025 from Bridgetown, Barbados

Up to 2 deals and Avoya Exclusives

From

$2,199

Roundtrip

7-Night Caribbean Cruise

$2,799

Windstar Cruises – Star Pride

89 Reviews

Date:

Oct 26, 2025

Ports:

San Juan → Basseterre → Gustavia → St. Maarten → Jost Van Dyke → Virgin Gorda / Prickly Pear

Departs Oct 26, 2025 from San Juan, Puerto Rico

Up to 1 deal

From

$2,799

Roundtrip

7-Night Caribbean Cruise

$2,799

Windstar Cruises – Star Pride

89 Reviews

Date:

Nov 02, 2025

Ports:

San Juan → Basseterre → Gustavia → St. Maarten → Jost Van Dyke → Virgin Gorda / Prickly Pear

Departs Nov 02, 2025 from San Juan, Puerto Rico

Up to 1 deal

From

$2,799

Roundtrip

7-Night Caribbean Cruise

$2,899

Windstar Cruises – Star Pride

89 Reviews

Date:

Nov 09, 2025

Ports:

San Juan → St. George's → Bequia → Pigeon Island → Les Saintes → Marigot

Departs Nov 09, 2025 from San Juan, Puerto Rico

Up to 1 deal

From

$2,899

Roundtrip

7-Night Caribbean Cruise

$2,799

Windstar Cruises – Star Pride

89 Reviews

Date:

Nov 16, 2025

Ports:

San Juan → Basseterre → Gustavia → St. Maarten → Jost Van Dyke → Virgin Gorda / Prickly Pear

Departs Nov 16, 2025 from San Juan, Puerto Rico

Up to 1 deal

From

$2,799

11-Night Caribbean Cruise

$3,499

Windstar Cruises – Wind Spirit

98 Reviews

Date:

Nov 18, 2025

Ports:

Bridgetown → Bequia → Mayreau → St. George's → Kralendijk → Willemstad → Oranjestad → Cartagena → Colón

Departs Nov 18, 2025 from Bridgetown, Barbados

Up to 2 deals and Avoya Exclusives

From

$3,499

Roundtrip

7-Night Caribbean Cruise

$2,899

Windstar Cruises – Star Pride

89 Reviews

Date:

Nov 23, 2025

Ports:

San Juan → St. George's → Bequia → Pigeon Island → Les Saintes → Marigot

Departs Nov 23, 2025 from San Juan, Puerto Rico

Up to 1 deal

From

$2,899

Roundtrip

7-Night Caribbean Cruise

$2,799

Windstar Cruises – Star Pride

89 Reviews

Date:

Nov 30, 2025

Ports:

San Juan → Gustavia → Basseterre → St. Maarten → Jost Van Dyke → Virgin Gorda / Prickly Pear

Departs Nov 30, 2025 from San Juan, Puerto Rico

Up to 1 deal

From

$2,799

Roundtrip

7-Night Caribbean Cruise

$2,299

Windstar Cruises – Wind Surf

142 Reviews

Date:

Dec 07, 2025

Ports:

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

Departs Dec 07, 2025 from Philipsburg, Sint Maarten

Up to 2 deals and Avoya Exclusives

From

$2,299

Roundtrip

7-Night Caribbean Cruise

$2,399

Windstar Cruises – Wind Surf

142 Reviews

Date:

Dec 14, 2025

Ports:

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

Departs Dec 14, 2025 from Philipsburg, Sint Maarten

Up to 2 deals and Avoya Exclusives

From

$2,399

Roundtrip

7-Night Caribbean Cruise

$2,699

Windstar Cruises – Wind Surf

142 Reviews

Date:

Dec 21, 2025

Ports:

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

Departs Dec 21, 2025 from Philipsburg, Sint Maarten

Up to 2 deals and Avoya Exclusives

From

$2,699

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