Name: 14-Night Caribbean Cruise
Brand: Windstar Cruises
Price: 5816 USD
Availability: InStock
Rating: 4.66 (148 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

14-night caribbean cruise

$5,816

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

$5,816

7-night caribbean cruise

$3,113

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

$3,113

14-night caribbean cruise

$5,896

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

$5,896

7-night caribbean cruise

$2,537

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

$2,537

10-night caribbean cruise

$3,026

Windstar Cruises – Star Pride

4.5 (95)

Date:

Oct 22, 2027

Ports:

Boston → Hamilton → Saint George's → Saint Barthelemy (Gustavia) → Virgin Gorda → San Juan

Departs Oct 22, 2027 from Boston, Massachusetts

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$3,026

17-night caribbean cruise

$5,882

Windstar Cruises – Star Pride

4.5 (95)

Date:

Oct 22, 2027

Ports:

Departs Oct 22, 2027 from Boston, Massachusetts

View Details

Oceanview From

$5,882

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

14-night caribbean cruise

$5,336

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

$5,336

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

$5,336

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

$5,336

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

14-night caribbean cruise

$5,336

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

$5,336

8-night caribbean cruise

$2,308

Windstar Cruises – Wind Surf

4.7 (148)

Date:

Nov 20, 2027

Ports:

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

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$2,308

15-night caribbean cruise

$5,336

Windstar Cruises – Wind Surf

4.7 (148)

Date:

Nov 20, 2027

Ports:

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

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$5,336

7-night caribbean cruise

$2,551

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

$2,551

14-night caribbean cruise

$5,364

Windstar Cruises – Star Pride

4.5 (95)

Date:

Nov 22, 2027

Ports:

Departs Nov 22, 2027 from San Juan, Puerto Rico

View Details

Oceanview From

$5,364

21-night caribbean cruise

$8,197

Windstar Cruises – Star Pride

4.5 (95)

Date:

Nov 22, 2027

Ports:

Departs Nov 22, 2027 from San Juan, Puerto Rico

View Details

Oceanview From

$8,197

7-night caribbean cruise

$2,152

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

$2,152

14-night caribbean cruise

$5,176

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

$5,176

7-night caribbean cruise

$2,556

Windstar Cruises – Star Pride

4.5 (95)

Date:

Nov 29, 2027

Ports:

San Juan → Catalina Island → Santo Domingo → Cartagena → San Blas Island → Colon

Departs Nov 29, 2027 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$2,556

14-night caribbean cruise

$5,519

Windstar Cruises – Star Pride

4.5 (95)

Date:

Nov 29, 2027

Ports:

Departs Nov 29, 2027 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$5,519

7-night caribbean cruise

$2,623

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

$2,623

14-night caribbean cruise

$5,176

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

$5,176

7-night caribbean cruise

$2,607

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

$2,607

15-night caribbean cruise

$5,496

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

$5,496

Windstar Cruises to Caribbean