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

Windstar Cruises to Caribbean

Showing 1-25 of 138 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
11-night caribbean cruise
$3,902
Windstar Cruises – Wind Surf
4.7 (148)
Departs Feb 17, 2026 from Cozumel, Mexico
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$3,867
Windstar Cruises – Wind Surf
4.7 (148)
Departs Mar 07, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$5,733
Windstar Cruises – Star Seeker
Departs Mar 13, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$3,767
Windstar Cruises – Wind Surf
4.7 (148)
Departs Mar 14, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$6,819
Windstar Cruises – Wind Surf
4.7 (148)
Departs Mar 14, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$2,399
Windstar Cruises – Star Pride
4.5 (95)
Departs Mar 15, 2026 from Oranjestad, Aruba
Up to 3 deals including an Avoya Exclusive
6-night caribbean cruise
$4,216
Windstar Cruises – Wind Spirit
4.8 (100)
Departs Mar 15, 2026 from Bridgetown, Barbados
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$3,851
Windstar Cruises – Wind Surf
4.7 (148)
Departs Mar 21, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$12,419
Windstar Cruises – Wind Surf
4.7 (148)
Departs Mar 21, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
10-night caribbean cruise
$6,757
Windstar Cruises – Star Seeker
Departs Mar 27, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
17-night caribbean cruise
$10,084
Windstar Cruises – Star Seeker
Departs Mar 27, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$3,267
Windstar Cruises – Wind Surf
4.7 (148)
Departs Mar 28, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
21-night caribbean cruise
$6,344
Windstar Cruises – Wind Surf
4.7 (148)
Departs Mar 28, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$4,426
Windstar Cruises – Star Seeker
Departs Apr 06, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
8-night caribbean cruise
$2,926
Windstar Cruises – Star Pride
4.5 (95)
Departs Oct 20, 2026 from Boston, Massachusetts
Up to 2 deals including an Avoya Exclusive
11-night caribbean cruise
$4,257
Windstar Cruises – Star Pride
4.5 (95)
Departs Oct 28, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$3,330
Windstar Cruises – Star Pride
4.5 (95)
Departs Nov 08, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$5,793
Windstar Cruises – Star Pride
4.5 (95)
Departs Nov 08, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$3,462
Windstar Cruises – Star Pride
4.5 (95)
Departs Nov 15, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$5,793
Windstar Cruises – Star Pride
4.5 (95)
Departs Nov 15, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$3,330
Windstar Cruises – Star Pride
4.5 (95)
Departs Nov 22, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$5,193
Windstar Cruises – Star Pride
4.5 (95)
Departs Nov 22, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
11-night caribbean cruise
$6,030
Windstar Cruises – Wind Star
4.6 (89)
Departs Nov 24, 2026 from Bridgetown, Barbados
Up to 2 deals including an Avoya Exclusive
18-night caribbean cruise
$15,500
Windstar Cruises – Wind Star
4.6 (89)
Departs Nov 24, 2026 from Bridgetown, Barbados
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$3,138
Windstar Cruises – Star Legend
4.5 (86)
Departs Nov 27, 2026 from Bridgetown, Barbados
Up to 2 deals including an Avoya Exclusive
  1. 1
  2. 2
  3. 3
  4. 4
  5. 5
  6. …6
  7. Next
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