7-night caribbean cruise

$3,051

Windstar Cruises – Wind Surf

4.7 (148)

Date:

Dec 07, 2025

Ports:

Departs Dec 07, 2025 from Saint Maarten (Phillipsburg), Netherlands Antilles

Up to 2 deals including an Avoya Exclusive

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Oceanview From

$3,051

14-night caribbean cruise

$9,719

Windstar Cruises – Wind Surf

4.7 (148)

Date:

Dec 07, 2025

Ports:

Departs Dec 07, 2025 from Saint Maarten (Phillipsburg), Netherlands Antilles

Up to 2 deals including an Avoya Exclusive

View Details

Inside From

$9,719

7-night caribbean cruise

$5,467

Windstar Cruises – Wind Surf

4.7 (148)

Date:

Dec 14, 2025 View Other Dates

Ports:

Departs Dec 14, 2025 from Saint Maarten (Phillipsburg), Netherlands Antilles

Up to 2 deals including an Avoya Exclusive

View Details

Inside From

$5,467

7-night caribbean cruise

$3,967

Windstar Cruises – Wind Surf

4.7 (148)

Date:

Dec 28, 2025 View Other Dates

Ports:

Departs Dec 28, 2025 from Saint Maarten (Phillipsburg), Netherlands Antilles

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$3,967

7-night caribbean cruise

$6,210

Windstar Cruises – Wind Surf

4.7 (148)

Date:

Jan 04, 2026 View Other Dates

Ports:

Departs Jan 04, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles

Up to 2 deals including an Avoya Exclusive

View Details

Inside From

$6,210

14-night caribbean cruise

$12,047

Windstar Cruises – Wind Surf

4.7 (148)

Date:

Jan 04, 2026

Ports:

Departs Jan 04, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles

Up to 2 deals including an Avoya Exclusive

View Details

Suite From

$12,047

7-night caribbean cruise

$6,436

Windstar Cruises – Wind Surf

4.7 (148)

Date:

Jan 11, 2026

Ports:

Departs Jan 11, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles

Up to 2 deals including an Avoya Exclusive

View Details

Suite From

$6,436

14-night caribbean cruise

$14,759

Windstar Cruises – Wind Surf

4.7 (148)

Date:

Jan 11, 2026

Ports:

Departs Jan 11, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles

Up to 2 deals including an Avoya Exclusive

View Details

Suite From

$14,759

8-night caribbean cruise

$6,796

Windstar Cruises – Star Seeker

Date:

Jan 15, 2026

Ports:

Miami → Puerto Plata → Samana → Jost Van Dyke → Virgin Gorda → Sopers Hole → San Juan

Departs Jan 15, 2026 from Miami, Florida

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$6,796

7-night caribbean cruise

$7,622

Windstar Cruises – Wind Surf

4.7 (148)

Date:

Jan 18, 2026

Ports:

Departs Jan 18, 2026 from Bridgetown, Barbados

Up to 2 deals including an Avoya Exclusive

View Details

Suite From

$7,622

7-night caribbean cruise

$3,624

Windstar Cruises – Wind Surf

4.7 (148)

Date:

Jan 25, 2026

Ports:

Departs Jan 25, 2026 from Bridgetown, Barbados

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$3,624

15-night caribbean cruise

$6,766

Windstar Cruises – Wind Surf

4.7 (148)

Date:

Jan 25, 2026

Ports:

Departs Jan 25, 2026 from Bridgetown, Barbados

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$6,766

7-night caribbean cruise

$5,127

Windstar Cruises – Star Seeker

Date:

Jan 30, 2026 View Other Dates

Ports:

Departs Jan 30, 2026 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$5,127

7-night caribbean cruise

$5,227

Windstar Cruises – Star Seeker

Date:

Feb 13, 2026 View Other Dates

Ports:

Departs Feb 13, 2026 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$5,227

11-night caribbean cruise

$4,463

Windstar Cruises – Wind Surf

4.7 (148)

Date:

Feb 17, 2026

Ports:

Departs Feb 17, 2026 from Cozumel, Mexico

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$4,463

18-night caribbean cruise

$6,915

Windstar Cruises – Wind Surf

4.7 (148)

Date:

Feb 17, 2026

Ports:

Departs Feb 17, 2026 from Cozumel, Mexico

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$6,915

7-night caribbean cruise

$6,492

Windstar Cruises – Star Seeker

Date:

Feb 20, 2026

Ports:

Departs Feb 20, 2026 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

View Details

Balcony From

$6,492

7-night caribbean cruise

$5,136

Windstar Cruises – Star Seeker

Date:

Feb 27, 2026

Ports:

Departs Feb 27, 2026 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$5,136

14-night caribbean cruise

$9,999

Windstar Cruises – Star Seeker

Date:

Feb 27, 2026

Ports:

Departs Feb 27, 2026 from San Juan, Puerto Rico

Up to 1 deal

View Details

Oceanview From

$9,999

7-night caribbean cruise

$3,651

Windstar Cruises – Wind Surf

4.7 (148)

Date:

Feb 28, 2026

Ports:

Departs Feb 28, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$3,651

7-night caribbean cruise

$3,920

Windstar Cruises – Wind Spirit

4.8 (100)

Date:

Feb 28, 2026

Ports:

Departs Feb 28, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$3,920

14-night caribbean cruise

$6,619

Windstar Cruises – Wind Surf

4.7 (148)

Date:

Feb 28, 2026

Ports:

Departs Feb 28, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$6,619

7-night caribbean cruise

$5,362

Windstar Cruises – Star Seeker

Date:

Mar 06, 2026

Ports:

Departs Mar 06, 2026 from San Juan, Puerto Rico

Up to 1 deal

View Details

Oceanview From

$5,362

14-night caribbean cruise

$9,796

Windstar Cruises – Star Seeker

Date:

Mar 06, 2026

Ports:

Departs Mar 06, 2026 from San Juan, Puerto Rico

View Details

Oceanview From

$9,796

7-night caribbean cruise

$3,467

Windstar Cruises – Wind Surf

4.7 (148)

Date:

Mar 07, 2026

Ports:

Departs Mar 07, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$3,467