Windstar's small ships draw you closer to each destination so you can see the world from a fresh perspective. Revel in quiet moments away from the crowds and immerse yourself in the local cultures of each and every destination. Explore beautiful places like the Mediterranean, the Middle East, the Caribbean and so much more.
Take advantage of low cruise fares and sail for as low as $115 per day with fares starting at just $1,099 plus get exclusive shipboard from us!
Choose your sailing below or call our experts at 1 (877) 734-6858 to start planning your future Windstar cruise now!
Submit the form below or call us at 1 (877) 734-6858
Includes free extras and bonus savings available only from CruiseInsider.
| Itinerary | Cruise Line | Cruise Ship | Departing | From Price |
|---|---|---|---|---|
| 5-night Barefoot Break in the British Virgin Islands Roundtrip St. Maarten | Cruise Line Windstar Cruises | Cruise Ship Wind Surf | Departs 12/2/25 | From $1,899 |
| 7-night San Juan and the Virgin Islands Cruise Roundtrip San Juan | Cruise Line Windstar Cruises | Cruise Ship Star Pride | Departs 11/16/24 | From $2,499 |
| 6-night San Juan and the Virgin Islands Cruise Roundtrip San Juan | Cruise Line Windstar Cruises | Cruise Ship Star Pride | Departs 11/3/24 | From $2,499 |
| 7-night Windward Ways and Tobago Cays Cruise Bridgetown (Barbados) to Oranjestad, Aruba | Cruise Line Windstar Cruises | Cruise Ship Star Pride | Departs 12/14/24 | From $2,499 |
| 7-night Winter Antilles Escape Cruise San Juan to Bridgetown (Barbados) | Cruise Line Windstar Cruises | Cruise Ship Star Pride | Departs 12/7/24 | From $2,499 |
Shipboard credit amenity only available on select sailings and amount varies by sailing and category booked. May not be combinable with certain fares, promotions and/or amenities. Other restrictions may apply. Contact us for details. Fares/rates are per person, based on double occupancy for select sail and travel dates; are capacity controlled and subject to availability at time booking and may be pulled without notice. We reserve the right to correct errors. Information and pricing is subject to change without notice. While we do our very best to ensure that information and pricing appearing in this website is complete and accurate, we cannot be responsible for incomplete and inaccurate representations, which may or may not be under our control. In the event of a pricing error, misrepresentation or omission, we reserve the right to adjust the pricing or make any other corrections.