Menu
Call
No Avoya Fees on Cruises or Tours. Click Here!

Windstar Cruises to Caribbean

Showing 26-50 of 132 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.
Help Me Plan
7-night caribbean cruise
$4,753
Windstar Cruises – Star Pride
4.5 (95)
Departs Dec 27, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$7,016
Windstar Cruises – Star Pride
4.5 (95)
Departs Dec 27, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$2,483
Windstar Cruises – Wind Surf
4.7 (148)
Departs Jan 02, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$5,736
Windstar Cruises – Wind Surf
4.7 (148)
Departs Jan 02, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$3,776
Windstar Cruises – Star Pride
4.5 (95)
Departs Jan 03, 2027 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$6,856
Windstar Cruises – Star Pride
4.5 (95)
Departs Jan 03, 2027 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$2,537
Windstar Cruises – Wind Surf
4.7 (148)
Departs Jan 09, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$5,816
Windstar Cruises – Wind Surf
4.7 (148)
Departs Jan 09, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$3,178
Windstar Cruises – Star Pride
4.5 (95)
Departs Jan 10, 2027 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$3,358
Windstar Cruises – Wind Surf
4.7 (148)
Departs Jan 16, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$5,976
Windstar Cruises – Wind Surf
4.7 (148)
Departs Jan 16, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$3,727
Windstar Cruises – Wind Surf
4.7 (148)
Departs Jan 23, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$6,136
Windstar Cruises – Wind Surf
4.7 (148)
Departs Jan 23, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$2,763
Windstar Cruises – Wind Surf
4.7 (148)
Departs Jan 30, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$6,136
Windstar Cruises – Wind Surf
4.7 (148)
Departs Jan 30, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$3,342
Windstar Cruises – Wind Surf
4.7 (148)
Departs Feb 06, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$6,136
Windstar Cruises – Wind Surf
4.7 (148)
Departs Feb 06, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$3,533
Windstar Cruises – Wind Surf
4.7 (148)
Departs Feb 13, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$6,056
Windstar Cruises – Wind Surf
4.7 (148)
Departs Feb 13, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$3,062
Windstar Cruises – Wind Surf
4.7 (148)
Departs Feb 20, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$5,976
Windstar Cruises – Wind Surf
4.7 (148)
Departs Feb 20, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
8-night caribbean cruise
$3,220
Windstar Cruises – Star Legend
4.5 (86)
Departs Feb 22, 2027 from Oranjestad, Aruba
7-night caribbean cruise
$2,798
Windstar Cruises – Wind Surf
4.7 (148)
Departs Feb 27, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$5,816
Windstar Cruises – Wind Surf
4.7 (148)
Departs Feb 27, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$2,467
Windstar Cruises – Wind Surf
4.7 (148)
Departs Mar 06, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
Don't Miss the Latest Deals!
Talk to a Vacation Planner
Avoya Travel Logo Mark
Why Choose Avoya?
U.S. / Canada:
1-888-447-8459

International: +1-760-305-5070
Avoya Travel.
CST: 2085569-40
Fla. Seller of Travel Ref. No. ST36781
© Avoya Travel®. All Rights Reserved.
Avoya Travel Logo