

11-night Stars of the Greater Antilles Cruise
Aboard
Wind Surf
From
Cozumel, Mexico
1 Sailing
Feb 17, 2026
1 Sailing
Feb 17, 2026
Published prices from
$5,313
per person*
taxes & fees included


62 Results
Taxes and fees included in all prices shown
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Aboard
Wind Surf
From
Cozumel, Mexico
1 Sailing
Feb 17, 2026
1 Sailing
Feb 17, 2026
Published prices from
per person*
taxes & fees included


Aboard
Wind Surf
From
Cozumel, Mexico
1 Sailing
Feb 17, 2026
1 Sailing
Feb 17, 2026


Aboard
Star Seeker
From
San Juan, Puerto Rico
2 Sailings
Feb 20 - Mar 6, 2026
2 Sailings
Feb 20 - Mar 6, 2026
Published prices from
per person*
taxes & fees included


Aboard
Star Seeker
From
San Juan, Puerto Rico
3 Sailings
Feb 20 - Mar 6, 2026
3 Sailings
Feb 20 - Mar 6, 2026
Published prices from
per person*
taxes & fees included


Aboard
Wind Spirit
From
Philipsburg, St. Maarten, The Netherlands
1 Sailing
Feb 21, 2026
1 Sailing
Feb 21, 2026
Published prices from
per person*
taxes & fees included


Aboard
Wind Spirit
From
Philipsburg, St. Maarten, The Netherlands
1 Sailing
Feb 21, 2026
1 Sailing
Feb 21, 2026


Aboard
Wind Spirit
From
Philipsburg, St. Maarten, The Netherlands
1 Sailing
Feb 21, 2026
1 Sailing
Feb 21, 2026
Published prices from
per person*
taxes & fees included


Aboard
Wind Spirit
From
Philipsburg, St. Maarten, The Netherlands
1 Sailing
Feb 21, 2026
1 Sailing
Feb 21, 2026
Published prices from
per person*
taxes & fees included


Aboard
Star Seeker
From
San Juan, Puerto Rico
2 Sailings
Feb 27 - Mar 13, 2026
2 Sailings
Feb 27 - Mar 13, 2026
Published prices from
per person*
taxes & fees included


Aboard
Wind Surf
From
Philipsburg, St. Maarten, The Netherlands
10 Sailings
Feb 28, 2026 - Nov 28, 2027
10 Sailings
Feb 28, 2026 - Nov 28, 2027
Published prices from
per person*
taxes & fees included


Aboard
Wind Surf
From
Philipsburg, St. Maarten, The Netherlands
16 Sailings
Feb 28, 2026 - Mar 13, 2027
16 Sailings
Feb 28, 2026 - Mar 13, 2027
Published prices from
per person*
taxes & fees included


Aboard
Wind Spirit
From
Philipsburg, St. Maarten, The Netherlands
1 Sailing
Feb 28, 2026
1 Sailing
Feb 28, 2026
Published prices from
per person*
taxes & fees included


Aboard
Wind Spirit
From
Philipsburg, St. Maarten, The Netherlands
1 Sailing
Feb 28, 2026
1 Sailing
Feb 28, 2026
Published prices from
per person*
taxes & fees included


Aboard
Wind Spirit
From
Bridgetown, Barbados
1 Sailing
Mar 7, 2026
1 Sailing
Mar 7, 2026
Published prices from
per person*
taxes & fees included


Aboard
Wind Spirit
From
Bridgetown, Barbados
1 Sailing
Mar 7, 2026
1 Sailing
Mar 7, 2026


Aboard
Wind Surf
From
Philipsburg, St. Maarten, The Netherlands
9 Sailings
Mar 7, 2026 - Mar 13, 2027
9 Sailings
Mar 7, 2026 - Mar 13, 2027
Published prices from
per person*
taxes & fees included


Aboard
Star Pride
From
Colon, Panama
1 Sailing
Mar 9, 2026
1 Sailing
Mar 9, 2026
Published prices from
per person*
taxes & fees included


Aboard
Wind Spirit
From
Bridgetown, Barbados
1 Sailing
Mar 15, 2026
1 Sailing
Mar 15, 2026


Aboard
Star Pride
From
Oranjestad, Aruba, Caribbean
1 Sailing
Mar 15, 2026
1 Sailing
Mar 15, 2026
Published prices from
per person*
taxes & fees included


Aboard
Star Seeker
From
San Juan, Puerto Rico
1 Sailing
Mar 20, 2026
1 Sailing
Mar 20, 2026
Published prices from
per person*
taxes & fees included


Aboard
Wind Spirit
From
Bridgetown, Barbados
1 Sailing
Mar 21, 2026
1 Sailing
Mar 21, 2026


Aboard
Wind Spirit
From
Bridgetown, Barbados
1 Sailing
Mar 21, 2026
1 Sailing
Mar 21, 2026


Aboard
Star Pride
From
Bridgetown, Barbados
1 Sailing
Mar 22, 2026
1 Sailing
Mar 22, 2026
Published prices from
per person*
taxes & fees included


Aboard
Star Seeker
From
San Juan, Puerto Rico
1 Sailing
Mar 27, 2026
1 Sailing
Mar 27, 2026
Published prices from
per person*
taxes & fees included


Aboard
Star Seeker
From
San Juan, Puerto Rico
1 Sailing
Mar 27, 2026
1 Sailing
Mar 27, 2026
Published prices from
per person*
taxes & fees included


Aboard
Star Seeker
From
San Juan, Puerto Rico
1 Sailing
Mar 27, 2026
1 Sailing
Mar 27, 2026
Published prices from
per person*
taxes & fees included


Aboard
Star Seeker
From
San Juan, Puerto Rico
1 Sailing
Mar 27, 2026
1 Sailing
Mar 27, 2026
Published prices from
per person*
taxes & fees included


Aboard
Wind Spirit
From
Bridgetown, Barbados
1 Sailing
Mar 28, 2026
1 Sailing
Mar 28, 2026
Published prices from
per person*
taxes & fees included


Aboard
Wind Spirit
From
Bridgetown, Barbados
1 Sailing
Mar 28, 2026
1 Sailing
Mar 28, 2026


Aboard
Wind Surf
From
Philipsburg, St. Maarten, The Netherlands
1 Sailing
Mar 28, 2026
1 Sailing
Mar 28, 2026
Published prices from
per person*
taxes & fees included


Aboard
Wind Surf
From
Philipsburg, St. Maarten, The Netherlands
1 Sailing
Mar 28, 2026
1 Sailing
Mar 28, 2026
Published prices from
per person*
taxes & fees included


Aboard
Wind Surf
From
Philipsburg, St. Maarten, The Netherlands
1 Sailing
Apr 4, 2026
1 Sailing
Apr 4, 2026
Published prices from
per person*
taxes & fees included


Aboard
Wind Surf
From
Philipsburg, St. Maarten, The Netherlands
1 Sailing
Apr 4, 2026
1 Sailing
Apr 4, 2026
Published prices from
per person*
taxes & fees included


Aboard
Star Seeker
From
San Juan, Puerto Rico
1 Sailing
Apr 6, 2026
1 Sailing
Apr 6, 2026
Published prices from
per person*
taxes & fees included


Aboard
Star Seeker
From
San Juan, Puerto Rico
1 Sailing
Apr 6, 2026
1 Sailing
Apr 6, 2026
Published prices from
per person*
taxes & fees included


Aboard
Star Seeker
From
San Juan, Puerto Rico
1 Sailing
Apr 6, 2026
1 Sailing
Apr 6, 2026
Published prices from
per person*
taxes & fees included


Aboard
Star Pride
From
Boston, Massachusetts
1 Sailing
Sep 14, 2026
1 Sailing
Sep 14, 2026
Published prices from
per person*
taxes & fees included


Aboard
Star Pride
From
Montreal, Quebec
1 Sailing
Sep 25, 2026
1 Sailing
Sep 25, 2026
Published prices from
per person*
taxes & fees included


Aboard
Star Pride
From
Montreal, Quebec
1 Sailing
Sep 25, 2026
1 Sailing
Sep 25, 2026
Published prices from
per person*
taxes & fees included


Aboard
Star Pride
From
Montreal, Quebec
1 Sailing
Oct 9, 2026
1 Sailing
Oct 9, 2026
Published prices from
per person*
taxes & fees included


Aboard
Star Legend
From
Istanbul, Turkey
1 Sailing
Oct 19, 2026
1 Sailing
Oct 19, 2026


Aboard
Star Pride
From
Boston, Massachusetts
1 Sailing
Oct 20, 2026
1 Sailing
Oct 20, 2026
Published prices from
per person*
taxes & fees included


Aboard
Star Pride
From
San Juan, Puerto Rico
1 Sailing
Oct 28, 2026
1 Sailing
Oct 28, 2026
Published prices from
per person*
taxes & fees included


Aboard
Wind Star
From
Barcelona, Spain
1 Sailing
Oct 31, 2026
1 Sailing
Oct 31, 2026
Published prices from
per person*
taxes & fees included


Aboard
Star Pride
From
San Juan, Puerto Rico
9 Sailings
Nov 8, 2026 - Jan 3, 2027
9 Sailings
Nov 8, 2026 - Jan 3, 2027
Published prices from
per person*
taxes & fees included


Aboard
Star Pride
From
San Juan, Puerto Rico
5 Sailings
Nov 8, 2026 - Jan 3, 2027
5 Sailings
Nov 8, 2026 - Jan 3, 2027
Published prices from
per person*
taxes & fees included


Aboard
Wind Star
From
Lisbon, Portugal
1 Sailing
Nov 10, 2026
1 Sailing
Nov 10, 2026
Published prices from
per person*
taxes & fees included


Aboard
Wind Star
From
Lisbon, Portugal
1 Sailing
Nov 10, 2026
1 Sailing
Nov 10, 2026


Aboard
Star Legend
From
Lisbon, Portugal
1 Sailing
Nov 14, 2026
1 Sailing
Nov 14, 2026


Aboard
Star Pride
From
San Juan, Puerto Rico
6 Sailings
Nov 15, 2026 - Nov 15, 2027
6 Sailings
Nov 15, 2026 - Nov 15, 2027
Published prices from
per person*
taxes & fees included


Aboard
Wind Star
From
Bridgetown, Barbados
1 Sailing
Nov 24, 2026
1 Sailing
Nov 24, 2026
Published prices from
per person*
taxes & fees included


Aboard
Wind Star
From
Bridgetown, Barbados
1 Sailing
Nov 24, 2026
1 Sailing
Nov 24, 2026
Published prices from
per person*
taxes & fees included


Aboard
Star Legend
From
Bridgetown, Barbados
1 Sailing
Nov 27, 2026
1 Sailing
Nov 27, 2026
Published prices from
per person*
taxes & fees included


Aboard
Star Legend
From
Bridgetown, Barbados
1 Sailing
Nov 27, 2026
1 Sailing
Nov 27, 2026
Published prices from
per person*
taxes & fees included


Aboard
Star Legend
From
Bridgetown, Barbados
1 Sailing
Dec 4, 2026
1 Sailing
Dec 4, 2026
Published prices from
per person*
taxes & fees included


Aboard
Star Legend
From
Bridgetown, Barbados
1 Sailing
Dec 4, 2026
1 Sailing
Dec 4, 2026
Published prices from
per person*
taxes & fees included


Aboard
Wind Surf
From
Lisbon, Portugal
1 Sailing
Dec 5, 2026
1 Sailing
Dec 5, 2026
Published prices from
per person*
taxes & fees included


Aboard
Wind Surf
From
Lisbon, Portugal
1 Sailing
Dec 5, 2026
1 Sailing
Dec 5, 2026
Published prices from
per person*
taxes & fees included


Aboard
Star Legend
From
Oranjestad, Aruba, Caribbean
1 Sailing
Dec 12, 2026
1 Sailing
Dec 12, 2026
Published prices from
per person*
taxes & fees included


Aboard
Star Legend
From
Oranjestad, Aruba, Caribbean
1 Sailing
Dec 12, 2026
1 Sailing
Dec 12, 2026
Published prices from
per person*
taxes & fees included


Aboard
Star Legend
From
Balboa, Panama
1 Sailing
Feb 16, 2027
1 Sailing
Feb 16, 2027
Published prices from
per person*
taxes & fees included


Aboard
Wind Surf
From
Philipsburg, St. Maarten, The Netherlands
1 Sailing
Mar 27, 2027
1 Sailing
Mar 27, 2027
Published prices from
per person*
taxes & fees included
*Rates and offers are per person, in US Dollars, based on double occupancy, capacity controlled, subject to availability and confirmation, and may change without notice. Government taxes and fees are included. Rates and offers are available for select dates and categories only. Additional restrictions may apply. Call 1-800-377-9383 for full terms and conditions.
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Overview
Windstar Cruises to the Caribbean islands offer a relaxing escape to some of the world’s most beautiful turquoise waters and white beaches. Plus, thanks to Windstar Cruises’ unique small-ship cruising experience, you’ll visit ports that aren’t included in the itineraries of many more traditional cruise lines. These unique ports may include Soper’s Hole, Tortola, BVI; Jost Van Dyke, Great Harbour, BVI; Gustavia, St Barts; Pigeon Island, St. Lucia; or Mayreau and Bequia in St Vincent and the Grenadines.
Less visited islands means less crowded destinations and a more relaxing experience. Windstar Cruises’ guests choose the Caribbean for a variety of reasons, including its vibrant cultures, fascinating history, much sought-after adventure spots, world-renowned beaches and more. No matter what pulls you to the Caribbean, when Windstar Cruises brings you there, the experience is unforgettable.