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

Windstar Cruises to Caribbean

Showing 76-100 of 139 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
$2,930
Windstar Cruises – Star Pride
4.5 (95)
Departs Nov 08, 2027 from San Juan, Puerto Rico
14-night caribbean cruise
$4,593
Windstar Cruises – Star Pride
4.5 (95)
Departs Nov 08, 2027 from San Juan, Puerto Rico
7-night caribbean cruise
$2,862
Windstar Cruises – Star Pride
4.5 (95)
Departs Nov 15, 2027 from San Juan, Puerto Rico
14-night caribbean cruise
$4,593
Windstar Cruises – Star Pride
4.5 (95)
Departs Nov 15, 2027 from San Juan, Puerto Rico
8-night caribbean cruise
$3,067
Windstar Cruises – Wind Surf
4.7 (148)
Departs Nov 20, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
15-night caribbean cruise
$4,719
Windstar Cruises – Wind Surf
4.7 (148)
Departs Nov 20, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
7-night caribbean cruise
$2,930
Windstar Cruises – Star Pride
4.5 (95)
Departs Nov 22, 2027 from San Juan, Puerto Rico
7-night caribbean cruise
$2,851
Windstar Cruises – Wind Surf
4.7 (148)
Departs Nov 28, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
14-night caribbean cruise
$4,519
Windstar Cruises – Wind Surf
4.7 (148)
Departs Nov 28, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
7-night caribbean cruise
$2,835
Windstar Cruises – Star Pride
4.5 (95)
Departs Nov 29, 2027 from San Juan, Puerto Rico
14-night caribbean cruise
$4,993
Windstar Cruises – Star Pride
4.5 (95)
Departs Nov 29, 2027 from San Juan, Puerto Rico
7-night caribbean cruise
$2,867
Windstar Cruises – Wind Surf
4.7 (148)
Departs Dec 05, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
14-night caribbean cruise
$4,519
Windstar Cruises – Wind Surf
4.7 (148)
Departs Dec 05, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
7-night caribbean cruise
$2,851
Windstar Cruises – Wind Surf
4.7 (148)
Departs Dec 12, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
15-night caribbean cruise
$4,919
Windstar Cruises – Wind Surf
4.7 (148)
Departs Dec 12, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
8-night caribbean cruise
$3,267
Windstar Cruises – Wind Surf
4.7 (148)
Departs Dec 19, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
15-night caribbean cruise
$5,219
Windstar Cruises – Wind Surf
4.7 (148)
Departs Dec 19, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
7-night caribbean cruise
$3,262
Windstar Cruises – Star Legend
4.5 (86)
Departs Dec 20, 2027 from San Juan, Puerto Rico
14-night caribbean cruise
$5,193
Windstar Cruises – Star Legend
4.5 (86)
Departs Dec 20, 2027 from San Juan, Puerto Rico
7-night caribbean cruise
$3,230
Windstar Cruises – Star Legend
4.5 (86)
Departs Dec 27, 2027 from San Juan, Puerto Rico
7-night caribbean cruise
$3,251
Windstar Cruises – Wind Surf
4.7 (148)
Departs Dec 27, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
13-night caribbean cruise
$4,819
Windstar Cruises – Wind Surf
4.7 (148)
Departs Dec 27, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
14-night caribbean cruise
$4,993
Windstar Cruises – Star Legend
4.5 (86)
Departs Dec 27, 2027 from San Juan, Puerto Rico
6-night caribbean cruise
$2,767
Windstar Cruises – Wind Surf
4.7 (148)
Departs Jan 03, 2028 from Saint Maarten (Phillipsburg), Netherlands Antilles
7-night caribbean cruise
$3,062
Windstar Cruises – Star Legend
4.5 (86)
Departs Jan 03, 2028 from San Juan, Puerto Rico
Don't Miss the Latest Deals!
Talk to a Vacation Planner
Avoya Travel Logo Mark
Why Choose Avoya?
U.S. / Canada: 1-888-877-7042
UK: 0-800-098-8475
Australia: 1-800-651-320
International: 001-760-305-5070
Avoya Travel. Beyond The Web.®
CST: 2085569-40
Fla. Seller of Travel Ref. No. ST36781
© Avoya Travel®. All Rights Reserved.
Avoya Travel Logo