7-night caribbean cruise
Inside From
$2,656
Windstar Cruises – Star Legend
4.586 Reviews
Departs Dec 27, 2027 from San Juan, Puerto Rico
Up to 2 deals including an Avoya ExclusiveView Expanded Details
Windstar Cruises to Caribbean
Showing 76-100 of 124 results
Up to 2 deals including an Avoya Exclusive
13-night caribbean cruise
Inside From
$3,760
Windstar Cruises – Wind Surf
4.7148 Reviews
Departs Dec 27, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya ExclusiveView Expanded Details
14-night caribbean cruise
Inside From
$4,434
Windstar Cruises – Star Legend
4.586 Reviews
Departs Dec 27, 2027 from San Juan, Puerto Rico
Up to 2 deals including an Avoya ExclusiveView Expanded Details
6-night caribbean cruise
Inside From
$2,108
Windstar Cruises – Wind Surf
4.7148 Reviews
Departs Jan 03, 2028 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya ExclusiveView Expanded Details
7-night caribbean cruise
Inside From
$2,443
Windstar Cruises – Star Legend
4.586 Reviews
Departs Jan 03, 2028 from San Juan, Puerto Rico
Up to 2 deals including an Avoya ExclusiveView Expanded Details
13-night caribbean cruise
Inside From
$3,955
Windstar Cruises – Wind Surf
4.7148 Reviews
Departs Jan 03, 2028 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya ExclusiveView Expanded Details
14-night caribbean cruise
Oceanview From
$4,014
Windstar Cruises – Star Legend
4.586 Reviews
Departs Jan 03, 2028 from San Juan, Puerto Rico
Up to 2 deals including an Avoya ExclusiveView Expanded Details
7-night caribbean cruise
Inside From
$2,432
Windstar Cruises – Wind Surf
4.7148 Reviews
Departs Jan 09, 2028 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya ExclusiveView Expanded Details
14-night caribbean cruise
Oceanview From
$4,250
Windstar Cruises – Wind Surf
4.7148 Reviews
Departs Jan 09, 2028 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya ExclusiveView Expanded Details
7-night caribbean cruise
Inside From
$2,411
Windstar Cruises – Star Legend
4.586 Reviews
Departs Jan 10, 2028 from San Juan, Puerto Rico
Up to 2 deals including an Avoya ExclusiveView Expanded Details
14-night caribbean cruise
Inside From
$4,014
Windstar Cruises – Star Legend
4.586 Reviews
Departs Jan 10, 2028 from San Juan, Puerto Rico
Up to 2 deals including an Avoya ExclusiveView Expanded Details
7-night caribbean cruise
Inside From
$2,448
Windstar Cruises – Wind Surf
4.7148 Reviews
Departs Jan 16, 2028 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya ExclusiveView Expanded Details
14-night caribbean cruise
Inside From
$3,970
Windstar Cruises – Wind Surf
4.7148 Reviews
Departs Jan 16, 2028 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya ExclusiveView Expanded Details
7-night caribbean cruise
Oceanview From
$2,443
Windstar Cruises – Star Legend
4.586 Reviews
Departs Jan 17, 2028 from San Juan, Puerto Rico
Up to 2 deals including an Avoya ExclusiveView Expanded Details
14-night caribbean cruise
Inside From
$4,014
Windstar Cruises – Star Legend
4.586 Reviews
Departs Jan 17, 2028 from San Juan, Puerto Rico
Up to 2 deals including an Avoya ExclusiveView Expanded Details
7-night caribbean cruise
Oceanview From
$2,971
Windstar Cruises – Wind Surf
4.7148 Reviews
Departs Jan 23, 2028 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya ExclusiveView Expanded Details
14-night caribbean cruise
Oceanview From
$3,830
Windstar Cruises – Wind Surf
4.7148 Reviews
Departs Jan 23, 2028 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya ExclusiveView Expanded Details
7-night caribbean cruise
Oceanview From
$2,411
Windstar Cruises – Star Legend
4.586 Reviews
Departs Jan 24, 2028 from San Juan, Puerto Rico
Up to 2 deals including an Avoya ExclusiveView Expanded Details
14-night caribbean cruise
Oceanview From
$4,014
Windstar Cruises – Star Legend
4.586 Reviews
Departs Jan 24, 2028 from San Juan, Puerto Rico
Up to 2 deals including an Avoya ExclusiveView Expanded Details
7-night caribbean cruise
Inside From
$2,273
Windstar Cruises – Wind Surf
4.7148 Reviews
Departs Jan 30, 2028 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya ExclusiveView Expanded Details
14-night caribbean cruise
Oceanview From
$3,970
Windstar Cruises – Wind Surf
4.7148 Reviews
Departs Jan 30, 2028 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya ExclusiveView Expanded Details
7-night caribbean cruise
Oceanview From
$2,443
Windstar Cruises – Star Legend
4.586 Reviews
Departs Jan 31, 2028 from San Juan, Puerto Rico
Up to 2 deals including an Avoya ExclusiveView Expanded Details
14-night caribbean cruise
Oceanview From
$4,014
Windstar Cruises – Star Legend
4.586 Reviews
Departs Jan 31, 2028 from San Juan, Puerto Rico
Up to 2 deals including an Avoya ExclusiveView Expanded Details
7-night caribbean cruise
Oceanview From
$2,537
Windstar Cruises – Wind Surf
4.7148 Reviews
Departs Feb 06, 2028 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya ExclusiveView Expanded Details
14-night caribbean cruise
Oceanview From
$4,320
Windstar Cruises – Wind Surf
4.7148 Reviews
Departs Feb 06, 2028 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.