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

Windstar Cruises to Caribbean

Showing 51-75 of 96 results
18-night caribbean cruise
$8,400
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
$2,738
Windstar Cruises – Star Legend
4.5 (86)
Departs Nov 27, 2026 from Bridgetown, Barbados
Up to 2 deals including an Avoya Exclusive
15-night caribbean cruise
$4,658
Windstar Cruises – Star Legend
4.5 (86)
Departs Nov 27, 2026 from Bridgetown, Barbados
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$2,762
Windstar Cruises – Star Pride
4.5 (95)
Departs Nov 29, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$4,393
Windstar Cruises – Star Pride
4.5 (95)
Departs Nov 29, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
8-night caribbean cruise
$3,119
Windstar Cruises – Star Legend
4.5 (86)
Departs Dec 04, 2026 from Bridgetown, Barbados
Up to 2 deals including an Avoya Exclusive
16-night caribbean cruise
$4,661
Windstar Cruises – Star Legend
4.5 (86)
Departs Dec 04, 2026 from Bridgetown, Barbados
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$2,730
Windstar Cruises – Star Pride
4.5 (95)
Departs Dec 06, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$4,393
Windstar Cruises – Star Pride
4.5 (95)
Departs Dec 06, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$2,762
Windstar Cruises – Star Pride
4.5 (95)
Departs Dec 13, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$4,493
Windstar Cruises – Star Pride
4.5 (95)
Departs Dec 13, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$2,967
Windstar Cruises – Wind Surf
4.7 (148)
Departs Dec 19, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$4,519
Windstar Cruises – Wind Surf
4.7 (148)
Departs Dec 19, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$2,930
Windstar Cruises – Star Pride
4.5 (95)
Departs Dec 20, 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 Dec 20, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$2,751
Windstar Cruises – Wind Surf
4.7 (148)
Departs Dec 26, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$4,219
Windstar Cruises – Wind Surf
4.7 (148)
Departs Dec 26, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$3,862
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
$6,193
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
$2,567
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
$4,319
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
$3,330
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
$5,793
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
$2,851
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
$4,519
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
  1. Prev
  2. 1
  3. 2
  4. 3
  5. 4
  6. 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