Get

$75-$4,500

Instant avoya cash

No, Thank You.

*Terms & conditions apply.

Your privacy is important to us. Privacy Policy

Get $75–$4,500 in Avoya Cash and save on your vacation — act now and save big. Get $75-$4,500 Avoya Cash CLAIM YOUR AVOYA CASH NOW!

Speak To A Vacation Planner Now

1-888-447-8459

Call

Speak To A Vacation Planner Now

1-888-447-8459

Call

Search
Cruises
Tours
Resorts
Destinations
Deals
Blog
Get Started

Speak To A Vacation Planner

1-888-447-8459

Get $75–$4,500 in Avoya Cash and save on your vacation — act now and save big. Get $75-$4,500 Avoya Cash CLAIM YOUR AVOYA CASH NOW!

Home

cruises

windstar cruises

cruises to caribbean

Windstar Cruises to Caribbean

Showing 101-105 of 105 results

Sort By

Avoya Top Picks

Avoya Top Picks
Price (Lowest)
Price (Highest)
Date (Earliest)
Date (Latest)
No elements found. Consider changing the search query.
List is empty.

Clear filters

Date Range

Sun

Mon

Tue

Wed

Thur

Fri

Sat

Sun

Mon

Tue

Wed

Thur

Fri

Sat

May 2025

June 2025

July 2025

August 2025

Departure Port

Boston, Massachusetts
Bridgetown, Barbados
Cozumel, Mexico
Miami, Florida
Oranjestad, Aruba
Saint Maarten (Phillipsburg), Netherlands Antilles
San Juan, Puerto Rico
No elements found. Consider changing the search query.
List is empty.

Arrival Port

Bridgetown, Barbados
Juneau, Alaska
Lisbon, Portugal
Oranjestad, Aruba
Puerto Caldera (Puntarenas), Costa Rica
Puerto Vallarta, Mexico
Saint Maarten (Phillipsburg), Netherlands Antilles
San Juan, Puerto Rico
No elements found. Consider changing the search query.
List is empty.

Cruise Ship

Windstar Cruises

Star Pride

Star Seeker

Wind Spirit

Wind Star

Wind Surf

Trip Length

3–6 Nights

7-9 Nights

10-14 Nights

15+ Nights

Cabin Type

inside or better

oceanview or better

balcony or better

suite

Clear Filters

7-night caribbean cruise

$2,599

Windstar Cruises – Star Pride

4.5 (93)

5 Star

65%

4 Star

26%

3 Star

2 Star

1 Star

Date:

Jan 03, 2027 View Other Dates

Ports:

San Juan → Saint George's → Saint Vincent And Grenadines (Bequia) → Saint Vincent And Grenadines (Mayreau) → Isle De Saintes → Saint Martin (Marigot) → San Juan

Departs Jan 03, 2027 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

Oceanview From

$2,599

Top Picks Rank: 8

14-night caribbean cruise

$4,099

Windstar Cruises – Star Pride

4.5 (93)

5 Star

65%

4 Star

26%

3 Star

2 Star

1 Star

Date:

Jan 03, 2027 View Other Dates

Ports:

San Juan → Saint George's → Saint Vincent And Grenadines (Bequia) → Saint Vincent And Grenadines (Mayreau) → Isle De Saintes → Saint Martin (Marigot) → Saint John → Saint Kitts And Nevis (Basse Terre) → Saint Barthelemy (Gustavia) → Saint Maarten (Phillipsburg) → Jost Van Dyke → Virgin Gorda → San Juan

Departs Jan 03, 2027 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

Oceanview From

$4,099

Top Picks Rank: 8

7-night caribbean cruise

$2,599

Windstar Cruises – Star Pride

4.5 (93)

5 Star

65%

4 Star

26%

3 Star

2 Star

1 Star

Date:

Jan 10, 2027 View Other Dates

Ports:

San Juan → Saint John → Saint Kitts And Nevis (Basse Terre) → Saint Barthelemy (Gustavia) → Saint Maarten (Phillipsburg) → Jost Van Dyke → Virgin Gorda → San Juan

Departs Jan 10, 2027 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

Oceanview From

$2,599

Top Picks Rank: 8

8-night caribbean cruise

$5,749

Windstar Cruises – Star Seeker

Date:

Jan 15, 2026

Ports:

Miami → Puerto Plata → Samana → Jost Van Dyke → Virgin Gorda → Soper's Hole → San Juan

Departs Jan 15, 2026 from Miami, Florida

Oceanview From

$5,749

Top Picks Rank: -1

6-night caribbean cruise

$2,699

Windstar Cruises – Wind Spirit

4.8 (98)

5 Star

86%

4 Star

3 Star

2 Star

1 Star

Date:

Jan 24, 2026

Ports:

Saint Maarten (Phillipsburg) → San Jose → Road Bay → Soper's Hole → Virgin Gorda → Jost Van Dyke → Saint Barthelemy (Gustavia) → Saint Maarten (Phillipsburg)

Departs Jan 24, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles

Up to 2 deals including an Avoya Exclusive

Oceanview From

$2,699

Top Picks Rank: -1

Showing 25 of 105 results

Don't Miss the Latest Deals!

Save favorite vacations & searches
Early access to promotions
Exclusive deals, discounts & prices
Plus more!

Talk to a Vacation Planner

Call at 1-888-447-8459 1-888-447-8459
or click here to submit a form and we will connect you with an Independent Vacation Planner that specializes in the type of travel you are interested in.

Why Choose Avoya?

From powerful online search, to specialized vacation planning services, and exclusive deals and extras - discover what makes Avoya Travel a different, better type of travel company.

About Avoya Travel

About
Privacy Policy
Don't Sell My Personal Information
About Our Ads
Website Terms of Use
Pricing Terms
Careers
Join The Avoya Network

U.S. / Canada: 1-888-877-7042
UK: 0-800-098-8475
Australia: 1-800-651-320
International: 001-760-305-5070