Name: 7-Night Caribbean Cruise
Brand: Windstar Cruises
Price: 2930 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

$2,930

Windstar Cruises – Star Pride

4.5 (95)

Date:

Nov 22, 2027 View Other Dates

Ports:

Departs Nov 22, 2027 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$2,930

14-night caribbean cruise

$4,519

Windstar Cruises – Wind Surf

4.7 (148)

Date:

Nov 28, 2027

Ports:

Departs Nov 28, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$4,519

7-night caribbean cruise

$2,867

Windstar Cruises – Wind Surf

4.7 (148)

Date:

Dec 05, 2027 View Other Dates

Ports:

Departs Dec 05, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$2,867

7-night caribbean cruise

$2,851

Windstar Cruises – Wind Surf

4.7 (148)

Date:

Dec 12, 2027 View Other Dates

Ports:

Departs Dec 12, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$2,851

15-night caribbean cruise

$4,919

Windstar Cruises – Wind Surf

4.7 (148)

Date:

Dec 12, 2027

Ports:

Departs Dec 12, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$4,919

8-night caribbean cruise

$3,267

Windstar Cruises – Wind Surf

4.7 (148)

Date:

Dec 19, 2027

Ports:

Departs Dec 19, 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

$3,251

Windstar Cruises – Wind Surf

4.7 (148)

Date:

Dec 27, 2027 View Other Dates

Ports:

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

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$3,251

13-night caribbean cruise

$4,819

Windstar Cruises – Wind Surf

4.7 (148)

Date:

Dec 27, 2027

Ports:

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

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$4,819

6-night caribbean cruise

$2,767

Windstar Cruises – Wind Surf

4.7 (148)

Date:

Jan 03, 2028

Ports:

Departs Jan 03, 2028 from Saint Maarten (Phillipsburg), Netherlands Antilles

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$2,767

13-night caribbean cruise

$4,619

Windstar Cruises – Wind Surf

4.7 (148)

Date:

Jan 03, 2028

Ports:

Departs Jan 03, 2028 from Saint Maarten (Phillipsburg), Netherlands Antilles

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$4,619

14-night caribbean cruise

$4,893

Windstar Cruises – Star Legend

4.5 (86)

Date:

Jan 03, 2028

Ports:

Departs Jan 03, 2028 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$4,893

7-night caribbean cruise

$3,051

Windstar Cruises – Wind Surf

4.7 (148)

Date:

Jan 09, 2028 View Other Dates

Ports:

Departs Jan 09, 2028 from Saint Maarten (Phillipsburg), Netherlands Antilles

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$3,051

14-night caribbean cruise

$4,819

Windstar Cruises – Wind Surf

4.7 (148)

Date:

Jan 09, 2028 View Other Dates

Ports:

Departs Jan 09, 2028 from Saint Maarten (Phillipsburg), Netherlands Antilles

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$4,819

7-night caribbean cruise

$3,030

Windstar Cruises – Star Legend

4.5 (86)

Date:

Jan 10, 2028 View Other Dates

Ports:

Departs Jan 10, 2028 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$3,030

14-night caribbean cruise

$4,893

Windstar Cruises – Star Legend

4.5 (86)

Date:

Jan 10, 2028 View Other Dates

Ports:

Departs Jan 10, 2028 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$4,893

7-night caribbean cruise

$2,967

Windstar Cruises – Wind Surf

4.7 (148)

Date:

Jan 16, 2028 View Other Dates

Ports:

Departs Jan 16, 2028 from Saint Maarten (Phillipsburg), Netherlands Antilles

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$2,967

14-night caribbean cruise

$4,819

Windstar Cruises – Wind Surf

4.7 (148)

Date:

Jan 16, 2028 View Other Dates

Ports:

Departs Jan 16, 2028 from Saint Maarten (Phillipsburg), Netherlands Antilles

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$4,819

7-night caribbean cruise

$3,062

Windstar Cruises – Star Legend

4.5 (86)

Date:

Jan 17, 2028 View Other Dates

Ports:

Departs Jan 17, 2028 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$3,062

14-night caribbean cruise

$4,893

Windstar Cruises – Star Legend

4.5 (86)

Date:

Jan 17, 2028 View Other Dates

Ports:

Departs Jan 17, 2028 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$4,893

7-night caribbean cruise

$3,051

Windstar Cruises – Wind Surf

4.7 (148)

Date:

Jan 23, 2028 View Other Dates

Ports:

Departs Jan 23, 2028 from Saint Maarten (Phillipsburg), Netherlands Antilles

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$3,051

14-night caribbean cruise

$4,819

Windstar Cruises – Wind Surf

4.7 (148)

Date:

Jan 23, 2028 View Other Dates

Ports:

Departs Jan 23, 2028 from Saint Maarten (Phillipsburg), Netherlands Antilles

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$4,819

7-night caribbean cruise

$3,030

Windstar Cruises – Star Legend

4.5 (86)

Date:

Jan 24, 2028 View Other Dates

Ports:

Departs Jan 24, 2028 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$3,030

14-night caribbean cruise

$4,893

Windstar Cruises – Star Legend

4.5 (86)

Date:

Jan 24, 2028

Ports:

Departs Jan 24, 2028 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$4,893

7-night caribbean cruise

$2,967

Windstar Cruises – Wind Surf

4.7 (148)

Date:

Jan 30, 2028 View Other Dates

Ports:

Departs Jan 30, 2028 from Saint Maarten (Phillipsburg), Netherlands Antilles

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$2,967

14-night caribbean cruise

$4,819

Windstar Cruises – Wind Surf

4.7 (148)

Date:

Jan 30, 2028 View Other Dates

Ports:

Departs Jan 30, 2028 from Saint Maarten (Phillipsburg), Netherlands Antilles

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$4,819

Windstar Cruises to Caribbean