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Roundtrip

7-Night Caribbean Cruise

$2,499

Windstar Cruises – Wind Spirit

98 Reviews

Date:

Jan 24, 2026

Ports:

Philipsburg → Soper's Hole → Jost Van Dyke → 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:

Philipsburg → Soper's Hole → Jost Van Dyke → 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:

Philipsburg → 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:

Philipsburg → Soper's Hole → Jost Van Dyke → 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:

Cozumel → Grand Cayman → Cayman Brac → Santo Domingo → La Romana → Jost Van Dyke → Philipsburg

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:

Philipsburg → Soper's Hole → Jost Van Dyke → 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:

Philipsburg → 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:

Philipsburg → 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:

Philipsburg → Falmouth Harbour → Road Bay → Soper's Hole → Jost Van Dyke → 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:

Philipsburg → Falmouth Harbour → Road Bay → Soper's Hole → Jost Van Dyke → 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 → 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:

Philipsburg → 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:

Philipsburg → Falmouth Harbour → Road Bay → Soper's Hole → Jost Van Dyke → Gustavia

Departs Mar 28, 2026 from Philipsburg, Sint Maarten

Up to 2 deals and Avoya Exclusives

From

$2,399

Roundtrip

8-Night Caribbean Cruise

$1,435

Celebrity Cruises – Celebrity Beyond

54 Reviews

Date:

Sep 21, 2024 View Other Dates

Ports:

Fort Lauderdale → Oranjestad → Kralendijk → Willemstad

Departs Sep 21, 2024 from Fort Lauderdale, Florida

Up to 4 deals and Avoya Exclusives

Avoya Exclusive Rate

From

$1,435

Roundtrip

10-Night Caribbean Cruise

$1,716

Celebrity Cruises – Celebrity Eclipse

286 Reviews

Date:

Oct 28, 2024 View Other Dates

Ports:

Fort Lauderdale → Tortola → Saint Johns → Bridgetown → Saint Lucia (Castries) → Saint Kitts And Nevis (Basse Terre)

Departs Oct 28, 2024 from Fort Lauderdale, Florida

Up to 4 deals and Avoya Exclusives

Avoya Exclusive Rate

From

$1,716

Roundtrip

7-Night Caribbean Cruise

$1,847

Royal Caribbean – Icon of the Seas

3 Reviews

Date:

Aug 24, 2024 View Other Dates

Ports:

Miami → Saint Maarten (Phillipsburg) → Saint Thomas → Perfect Day At Cococay

Departs Aug 24, 2024 from Miami, Florida

Up to 3 deals and Avoya Exclusives

From

$1,847

Roundtrip

7-Night Caribbean Cruise

$1,677

Royal Caribbean – Icon of the Seas

3 Reviews

Date:

Sep 07, 2024 View Other Dates

Ports:

Miami → Saint Kitts And Nevis (Basse Terre) → Saint Thomas → Perfect Day At Cococay

Departs Sep 07, 2024 from Miami, Florida

Up to 3 deals and Avoya Exclusives

From

$1,677

Roundtrip

7-Night Caribbean Cruise

$679

Royal Caribbean – Freedom of the Seas

361 Reviews

Date:

Sep 08, 2024

Ports:

Fort Lauderdale → Grand Cayman → Falmouth → Nassau → Perfect Day At Cococay

Departs Sep 08, 2024 from Fort Lauderdale, Florida

Up to 2 deals and Avoya Exclusives

Avoya Exclusive Rate

From

$679

Roundtrip

7-Night Caribbean Cruise

$612

1% Off

Royal Caribbean – Rhapsody of the Seas

118 Reviews

Date:

Sep 22, 2024 View Other Dates

Ports:

San Juan → Saint Croix → Saint Thomas → Saint Maarten (Phillipsburg) → Saint Lucia (Castries) → Bridgetown

Departs Sep 22, 2024 from San Juan, Puerto Rico

Up to 2 deals and Avoya Exclusives

Avoya Exclusive Rate

From

$612

1% Off

Compare At

$619

Roundtrip

7-Night Caribbean Cruise

$445

11% Off

Royal Caribbean – Enchantment of the Seas

176 Reviews

Date:

Sep 28, 2024 View Other Dates

Ports:

Tampa → Cozumel → Roatan → Belize City → Costa Maya

Departs Sep 28, 2024 from Tampa, Florida

Up to 2 deals and Avoya Exclusives

Avoya Exclusive Rate

From

$445

11% Off

Compare At

$498

Roundtrip

7-Night Caribbean Cruise

$535

23% Off

Royal Caribbean – Freedom of the Seas

361 Reviews

Date:

Sep 29, 2024 View Other Dates

Ports:

Fort Lauderdale → Perfect Day At Cococay → San Juan → Saint Thomas

Departs Sep 29, 2024 from Fort Lauderdale, Florida

Up to 2 deals and Avoya Exclusives

Avoya Exclusive Rate

From

$535

23% Off

Compare At

$699