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

Windstar Cruises to Caribbean

Showing 51-73 of 73 results
Roundtrip
7-Night Caribbean Cruise
$3,299
Windstar Cruises – Star Seeker
Departs Feb 13, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
Roundtrip
14-Night Caribbean Cruise
$5,399
Windstar Cruises – Star Seeker
Departs Feb 13, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
18-Night Caribbean Cruise
$5,399
Windstar Cruises – Wind Surf
145 Reviews
Departs Feb 17, 2026 from Cozumel, Mexico
Up to 2 deals including an Avoya Exclusive
Roundtrip
7-Night Caribbean Cruise
$3,099
Windstar Cruises – Star Seeker
Departs Feb 20, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
Roundtrip
14-Night Caribbean Cruise
$5,199
Windstar Cruises – Star Seeker
Departs Feb 20, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
Roundtrip
7-Night Caribbean Cruise
$3,099
Windstar Cruises – Star Seeker
Departs Feb 27, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
Roundtrip
14-Night Caribbean Cruise
$7,299
Windstar Cruises – Star Seeker
Departs Feb 27, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
Roundtrip
7-Night Caribbean Cruise
$2,499
Windstar Cruises – Wind Surf
145 Reviews
Departs Feb 28, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
7-Night Caribbean Cruise
$2,499
Windstar Cruises – Wind Spirit
98 Reviews
Departs Feb 28, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
Roundtrip
7-Night Caribbean Cruise
$4,299
Windstar Cruises – Star Seeker
Departs Mar 06, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
Roundtrip
14-Night Caribbean Cruise
$7,199
Windstar Cruises – Star Seeker
Departs Mar 06, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
Roundtrip
7-Night Caribbean Cruise
$2,699
Windstar Cruises – Wind Spirit
98 Reviews
Departs Mar 07, 2026 from Bridgetown, Barbados
Up to 2 deals including an Avoya Exclusive
Roundtrip
7-Night Caribbean Cruise
$2,999
Windstar Cruises – Star Seeker
Departs Mar 13, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
Roundtrip
14-Night Caribbean Cruise
$3,699
Windstar Cruises – Wind Surf
145 Reviews
Departs Mar 21, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
Roundtrip
10-Night Caribbean Cruise
$3,999
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
$5,599
Windstar Cruises – Star Seeker
Departs Mar 27, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
24-Night Caribbean Cruise
$8,099
Windstar Cruises – Star Seeker
Departs Mar 27, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
49-Night Caribbean Cruise
$17,299
Windstar Cruises – Star Seeker
Departs Mar 27, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
Roundtrip
7-Night Caribbean Cruise
$2,399
Windstar Cruises – Wind Surf
145 Reviews
Departs Mar 28, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
7-Night Caribbean Cruise
$3,199
Windstar Cruises – Star Seeker
Departs Apr 06, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
14-Night Caribbean Cruise
$5,599
Windstar Cruises – Star Seeker
Departs Apr 06, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
22-Night Caribbean Cruise
$8,499
Windstar Cruises – Star Seeker
Departs Apr 06, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
1-Night Caribbean Cruise
$299
Windstar Cruises – Star Seeker
Departs May 06, 2026 from Seattle, Washington
Up to 2 deals including an Avoya Exclusive
  1. Prev
  2. 1
  3. 2
  4. 3
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®
CST: 2085569-40
Fla. Seller of Travel Ref. No. ST36781
© Avoya Travel®. All Rights Reserved.
Avoya Travel Logo
Call