Name: 7-Night Caribbean Cruise
Brand: Windstar Cruises
Price: 4262 USD
Availability: InStock
Rating: 4.52 (95 reviews)

Meet Natalie Thompson, one of Avoya's trusted travel advisors.

Our team has helped more than 2.5 million travelers save time, save money, and book their perfect vacation.

Choose your adventure and let us handle the rest.

Your dedicated Personal Travel Advisor is here to help you plan the vacation of your dreams. From finding the best price to answering every question, we are with you every step of the way at no extra cost.

Help Me Plan

7-night caribbean cruise

$4,262

Windstar Cruises – Star Pride

4.5 (95)

Date:

Dec 27, 2026 View Other Dates

Ports:

Departs Dec 27, 2026 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$4,262

14-night caribbean cruise

$7,393

Windstar Cruises – Star Pride

4.5 (95)

Date:

Dec 27, 2026 View Other Dates

Ports:

Departs Dec 27, 2026 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$7,393

7-night caribbean cruise

$3,267

Windstar Cruises – Wind Surf

4.7 (148)

Date:

Jan 02, 2027 View Other Dates

Ports:

Departs Jan 02, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$3,267

7-night caribbean cruise

$4,030

Windstar Cruises – Star Pride

4.5 (95)

Date:

Jan 03, 2027 View Other Dates

Ports:

Departs Jan 03, 2027 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$4,030

14-night caribbean cruise

$7,293

Windstar Cruises – Star Pride

4.5 (95)

Date:

Jan 03, 2027 View Other Dates

Ports:

Departs Jan 03, 2027 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$7,293

14-night caribbean cruise

$6,019

Windstar Cruises – Wind Surf

4.7 (148)

Date:

Jan 09, 2027

Ports:

Departs Jan 09, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$6,019

7-night caribbean cruise

$4,062

Windstar Cruises – Star Pride

4.5 (95)

Date:

Jan 10, 2027 View Other Dates

Ports:

Departs Jan 10, 2027 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$4,062

7-night caribbean cruise

$3,667

Windstar Cruises – Wind Surf

4.7 (148)

Date:

Jan 16, 2027 View Other Dates

Ports:

Departs Jan 16, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$3,667

14-night caribbean cruise

$6,019

Windstar Cruises – Wind Surf

4.7 (148)

Date:

Jan 16, 2027 View Other Dates

Ports:

Departs Jan 16, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$6,019

7-night caribbean cruise

$3,451

Windstar Cruises – Wind Surf

4.7 (148)

Date:

Jan 23, 2027 View Other Dates

Ports:

Departs Jan 23, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$3,451

14-night caribbean cruise

$5,919

Windstar Cruises – Wind Surf

4.7 (148)

Date:

Jan 23, 2027

Ports:

Departs Jan 23, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$5,919

7-night caribbean cruise

$3,467

Windstar Cruises – Wind Surf

4.7 (148)

Date:

Jan 30, 2027 View Other Dates

Ports:

Departs Jan 30, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$3,467

14-night caribbean cruise

$5,919

Windstar Cruises – Wind Surf

4.7 (148)

Date:

Jan 30, 2027 View Other Dates

Ports:

Departs Jan 30, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$5,919

14-night caribbean cruise

$5,919

Windstar Cruises – Wind Surf

4.7 (148)

Date:

Feb 06, 2027 View Other Dates

Ports:

Departs Feb 06, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$5,919

7-night caribbean cruise

$3,467

Windstar Cruises – Wind Surf

4.7 (148)

Date:

Feb 13, 2027 View Other Dates

Ports:

Departs Feb 13, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$3,467

14-night caribbean cruise

$5,719

Windstar Cruises – Wind Surf

4.7 (148)

Date:

Feb 20, 2027

Ports:

Departs Feb 20, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$5,719

7-night caribbean cruise

$3,367

Windstar Cruises – Wind Surf

4.7 (148)

Date:

Feb 27, 2027

Ports:

Departs Feb 27, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$3,367

7-night caribbean cruise

$3,151

Windstar Cruises – Wind Surf

4.7 (148)

Date:

Mar 06, 2027 View Other Dates

Ports:

Departs Mar 06, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$3,151

7-night caribbean cruise

$3,367

Windstar Cruises – Wind Surf

4.7 (148)

Date:

Mar 13, 2027 View Other Dates

Ports:

Departs Mar 13, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$3,367

14-night caribbean cruise

$5,619

Windstar Cruises – Wind Surf

4.7 (148)

Date:

Mar 13, 2027 View Other Dates

Ports:

Departs Mar 13, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$5,619

7-night caribbean cruise

$3,251

Windstar Cruises – Wind Surf

4.7 (148)

Date:

Mar 20, 2027 View Other Dates

Ports:

Departs Mar 20, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$3,251

7-night caribbean cruise

$2,862

Windstar Cruises – Star Pride

4.5 (95)

Date:

Nov 01, 2027 View Other Dates

Ports:

Departs Nov 01, 2027 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$2,862

7-night caribbean cruise

$2,930

Windstar Cruises – Star Pride

4.5 (95)

Date:

Nov 08, 2027 View Other Dates

Ports:

Departs Nov 08, 2027 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$2,930

14-night caribbean cruise

$4,593

Windstar Cruises – Star Pride

4.5 (95)

Date:

Nov 08, 2027

Ports:

Departs Nov 08, 2027 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$4,593

7-night caribbean cruise

$2,862

Windstar Cruises – Star Pride

4.5 (95)

Date:

Nov 15, 2027 View Other Dates

Ports:

Departs Nov 15, 2027 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$2,862

Windstar Cruises to Caribbean