16 Results
Taxes and fees included in all prices shown
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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 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
Star Pride
From
San Juan, Puerto Rico
14 Sailings
Nov 8, 2026 - Mar 20, 2028
14 Sailings
Nov 8, 2026 - Mar 20, 2028
Published prices from
per person*
taxes & fees included
Aboard
Star Pride
From
San Juan, Puerto Rico
9 Sailings
Nov 8, 2026 - Mar 27, 2028
9 Sailings
Nov 8, 2026 - Mar 27, 2028
Published prices from
per person*
taxes & fees included
Aboard
Star Pride
From
San Juan, Puerto Rico
9 Sailings
Nov 15, 2026 - Mar 20, 2028
9 Sailings
Nov 15, 2026 - Mar 20, 2028
Published prices from
per person*
taxes & fees included
Aboard
Wind Surf
From
Lisbon, Portugal
1 Sailing
Dec 5, 2026
1 Sailing
Dec 5, 2026
Aboard
Wind Surf
From
Philipsburg, St. Maarten, The Netherlands
7 Sailings
Dec 19, 2026 - Mar 13, 2027
7 Sailings
Dec 19, 2026 - Mar 13, 2027
Published prices from
per person*
taxes & fees included
Aboard
Wind Surf
From
Philipsburg, St. Maarten, The Netherlands
13 Sailings
Dec 19, 2026 - Mar 13, 2027
13 Sailings
Dec 19, 2026 - Mar 13, 2027
Published prices from
per person*
taxes & fees included
Aboard
Wind Surf
From
Philipsburg, St. Maarten, The Netherlands
8 Sailings
Dec 26, 2026 - Nov 28, 2027
8 Sailings
Dec 26, 2026 - Nov 28, 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
Aboard
Star Pride
From
Montreal, Quebec
1 Sailing
Oct 11, 2027
1 Sailing
Oct 11, 2027
Published prices from
per person*
taxes & fees included
Aboard
Star Pride
From
Boston, Massachusetts
1 Sailing
Oct 22, 2027
1 Sailing
Oct 22, 2027
Published prices from
per person*
taxes & fees included
Aboard
Star Pride
From
San Juan, Puerto Rico
1 Sailing
Nov 29, 2027
1 Sailing
Nov 29, 2027
Aboard
Star Pride
From
San Juan, Puerto Rico
1 Sailing
Nov 29, 2027
1 Sailing
Nov 29, 2027
Aboard
Wind Surf
From
Philipsburg, St. Maarten, The Netherlands
1 Sailing
Dec 5, 2027
1 Sailing
Dec 5, 2027
*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.
Ports
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Overview
A Windstar cruise to the Eastern Caribbean offers a truly intimate and luxurious escape to some of the most stunning islands in the world. Aboard their elegant yachts, guests can enjoy a personalized cruising experience that feels more like sailing on a private vessel. The small ship size is a key advantage, allowing access to exclusive anchorages and smaller ports that larger cruise ships simply cannot reach.
The itineraries are thoughtfully designed to reveal the best of the region, from the chic shores of St. Barts to the lush, volcanic landscapes of Dominica. Windstar's focus on "destination immersion" means more time in port, often with late-night stays, giving guests ample opportunity to explore the vibrant culture, savor local cuisine, and experience the unique charm of each island at a leisurely pace.
