8-night caribbean cruise
Inside From
$2,867
Windstar Cruises – Star Pride
4.595 Reviews
Departs Oct 20, 2026 from Boston, Massachusetts
Up to 2 deals including an Avoya ExclusiveView Expanded Details
Windstar Cruises to Caribbean
Showing 1-25 of 128 results
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.
Up to 2 deals including an Avoya Exclusive
11-night caribbean cruise
Oceanview From
$3,908
Windstar Cruises – Star Pride
4.595 Reviews
Departs Oct 28, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya ExclusiveView Expanded Details
7-night caribbean cruise
Oceanview From
$2,411
Windstar Cruises – Star Pride
4.595 Reviews
Departs Nov 08, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya ExclusiveView Expanded Details
14-night caribbean cruise
Oceanview From
$4,434
Windstar Cruises – Star Pride
4.595 Reviews
Departs Nov 08, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya ExclusiveView Expanded Details
7-night caribbean cruise
Oceanview From
$2,443
Windstar Cruises – Star Pride
4.595 Reviews
Departs Nov 15, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya ExclusiveView Expanded Details
14-night caribbean cruise
Oceanview From
$4,434
Windstar Cruises – Star Pride
4.595 Reviews
Departs Nov 15, 2026 from San Juan, Puerto Rico
Up to 1 deal
View Expanded Details
7-night caribbean cruise
Oceanview From
$2,411
Windstar Cruises – Star Pride
4.595 Reviews
Departs Nov 22, 2026 from San Juan, Puerto Rico
Up to 1 deal
View Expanded Details
14-night caribbean cruise
Oceanview From
$4,574
Windstar Cruises – Star Pride
4.595 Reviews
Departs Nov 22, 2026 from San Juan, Puerto Rico
Up to 1 deal
View Expanded Details
11-night caribbean cruise
Oceanview From
$4,761
Windstar Cruises – Wind Star
4.689 Reviews
Departs Nov 24, 2026 from Bridgetown, Barbados
Up to 1 deal
View Expanded Details
7-night caribbean cruise
Oceanview From
$2,419
Windstar Cruises – Star Legend
4.586 Reviews
Departs Nov 27, 2026 from Bridgetown, Barbados
Up to 3 deals including Avoya ExclusivesView Expanded Details
15-night caribbean cruise
Oceanview From
$4,709
Windstar Cruises – Star Legend
4.586 Reviews
Departs Nov 27, 2026 from Bridgetown, Barbados
Up to 2 deals including an Avoya ExclusiveView Expanded Details
7-night caribbean cruise
Oceanview From
$2,548
Windstar Cruises – Star Pride
4.595 Reviews
Departs Nov 29, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya ExclusiveView Expanded Details
14-night caribbean cruise
Oceanview From
$5,204
Windstar Cruises – Star Pride
4.595 Reviews
Departs Nov 29, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya ExclusiveView Expanded Details
8-night caribbean cruise
Oceanview From
$2,740
Windstar Cruises – Star Legend
4.586 Reviews
Departs Dec 04, 2026 from Bridgetown, Barbados
Up to 2 deals including an Avoya ExclusiveView Expanded Details
16-night caribbean cruise
Oceanview From
$5,182
Windstar Cruises – Star Legend
4.586 Reviews
Departs Dec 04, 2026 from Bridgetown, Barbados
Up to 2 deals including an Avoya ExclusiveView Expanded Details
7-night caribbean cruise
Oceanview From
$3,111
Windstar Cruises – Star Pride
4.595 Reviews
Departs Dec 06, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya ExclusiveView Expanded Details
14-night caribbean cruise
Oceanview From
$6,044
Windstar Cruises – Star Pride
4.595 Reviews
Departs Dec 06, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya ExclusiveView Expanded Details
7-night caribbean cruise
Oceanview From
$3,493
Windstar Cruises – Star Pride
4.595 Reviews
Departs Dec 13, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya ExclusiveView Expanded Details
14-night caribbean cruise
Oceanview From
$6,744
Windstar Cruises – Star Pride
4.595 Reviews
Departs Dec 13, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya ExclusiveView Expanded Details
7-night caribbean cruise
Oceanview From
$3,708
Windstar Cruises – Wind Surf
4.7148 Reviews
Departs Dec 19, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya ExclusiveView Expanded Details
14-night caribbean cruise
Oceanview From
$8,030
Windstar Cruises – Wind Surf
4.7148 Reviews
Departs Dec 19, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya ExclusiveView Expanded Details
7-night caribbean cruise
Inside From
$3,916
Windstar Cruises – Star Pride
4.595 Reviews
Departs Dec 20, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya ExclusiveView Expanded Details
14-night caribbean cruise
Oceanview From
$6,744
Windstar Cruises – Star Pride
4.595 Reviews
Departs Dec 20, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya ExclusiveView Expanded Details
7-night caribbean cruise
Oceanview From
$4,742
Windstar Cruises – Wind Surf
4.7148 Reviews
Departs Dec 26, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya ExclusiveView Expanded Details
14-night caribbean cruise
Oceanview From
$7,960
Windstar Cruises – Wind Surf
4.7148 Reviews
Departs Dec 26, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya ExclusiveView Expanded Details
AmaWaterways American Cruise Lines Atlas Ocean Voyages Aurora Expeditions Avalon Waterways Azamara Cruises Carnival Cruises Celebrity Cruises Celebrity River Cruises Celestyal Cruises Crystal Cruises Cunard Disney Cruises Explora Journeys Holland America HX Cruises Margaritaville at Sea MSC Cruises Norwegian Cruise Line Oceania Cruises Paul Gauguin Cruises Ponant Explorations Princess Cruises Regent Cruises Riviera Travel Royal Caribbean Scenic River Cruises Seabourn Silversea Swan Hellenic Tauck River Cruises Viking Ocean Cruises Viking River Cruises Virgin Voyages Windstar Cruises
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 a Personal Travel Advisor 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.