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This deal was published November 23, 2021 and sold out November 30, 2021. See current deals
The Caribbean

$1499 – Sail the Caribbean on a Yacht This Winter

Windstar Cruises -- No Change Fee
Casey Gasinowski
Deal Expert
Sail to secluded Caribbean beaches this winter aboard a newly transformed, intimate yacht.

Why We Love This Deal

Change without Fee

Windstar Cruises allows you to cancel cruise bookings up to 48 hours prior to departure for a 100% Future Cruise Credit without risk or penalty for voyages departing through March 31, 2022. Learn more

As part of Windstar Cruises’ "Book Your Bucket List" sale, you can save big (up to $1200 per person) on dreamy Caribbean sailings, while receiving exclusive onboard credit. We're putting one of these luxe, all-suite voyages on our Christmas list. 

What's included:

  • Sail aboard the 312-guest Star Legend in an oceanview suite for 7 nights
  • All meals and dining at specialty restaurants, plus 24-hour room service
  • Non-alcoholic drinks
  • Complimentary water-sport and snorkeling gear
  • $100 onboard credit per guest (can be applied to shore excursions, spa treatments, alcohol and more)

Per-person pricing:

  • $1499 ... Dec. 11, 2021; Jan. 8, 15, 22 or 29, 2022
  • $1899 ... Feb. 5, 2022
  • $1999 ... Feb. 12, 19 or 26, 2022
  • $2199 ... March 12, 2022
  • $2299 ... March 5, 2022

Make it all-inclusive: Purchase Windstar's all-inclusive package for $79 per person, per night, which provides unlimited Wi-Fi; unlimited beer, wine, and cocktails; and all gratuities.

Itinerary: Sail roundtrip for 7 nights from St. Maarten. The St. Maarten & the Virgin Islands itinerary visits St. Barts, Guadeloupe, St. Lucia, Bequia and Grenada. The Windward Islands Surf & Sunsets itinerary visits Jost Van Dyke, Virgin Gorda, Tortola, Montserrat, St. Kitts and St. Barts. Pair both voyages together for the 14-night Lovely Leewards itinerary to visit all ports and enjoy free laundry.

Ship details: Guests will cruise aboard Star Legend, one of Windstar’s All-Suite Star Plus Class 312-guest yachts that is currently completing a $250-million renovation. Star Legend is a richly appointed vessel featuring redesigned oceanview suites, new restaurants and an elevated pool. The vessel delivers yacht travel in an unpretentious and comfortable ambiance, as well as fewer crowds and more space. Savor Spanish-themed culinary delights at the ship's new restaurant designed by 10-time Michelin starred Chef Anthony Sasso, as well as delicious outdoor barbecue from global grilling authority Steven Raichlen.

Relax and revitalize with a spa treatment in the new World Spa by Windstar or enjoy a variety of water toys on the watersports platform. Shore excursions include visits to off-the-beaten path beaches as well as a signature beach party with a barbecue and music. Windstar's new Beyond Ordinary Care Program provides extra peace of mind with onboard health and safety practices such as enhanced sanitation protocols, extra medical staff, HEPA filters with UV-C irradiation and more.

Customize your trip: This is part of a larger sale, featuring discounted Tahiti, Mediterranean and Mexico cruises with Windstar Cruises. 

Book by Nov. 30.

* All fares mentioned are per person, in US dollars; based on double occupancy in lowest category and includes non-discountable amounts. Shipboard credit offered is $100 per guest ($200 per stateroom/suite). All-inclusive fares include the Captain’s Exclusive Package, unlimited Wi-Fi and service gratuities of $14.50 USD per day and beverage gratuities of 15%. All-inclusive fares must be booked at least five days prior to departure, applies to cruise days only and does not apply to pre- or post-cruise hotels or tours. Taxes, fees and port expenses are additional and published at Offer is valid on new bookings only for select departures and subject to availability. Consult your Windstar representative for promotional offer or discount combinability. Bookings are non-transferable; no name changes can be made nor can this offer be applied retroactively. Cancellation fees may apply, please see website for details. Certain restrictions apply. Fuel surcharges may be imposed or increased over time. Offer is capacity-controlled and may be withdrawn or modified at Windstar's discretion at any time. Information contained herein is accurate at the time of publication and subject to change without notice. All terms and conditions stated on the Windstar website apply. Cruise is provided subject to the terms and conditions of the Passage Contract. Ships' registry: Bahamas. This offer expires November 30, 2021.

Change without Fee: Windstar Cruises allows you to cancel cruise bookings up to 48 hours prior to departure for a 100% Future Cruise Credit without risk or penalty for voyages departing through March 31, 2022. For further assistance, call 844-655-0397.


Sold out

at 11:59 PM CT on Nov 30

When You Can Go

December 2021 - March 2022


Up to $1200 vs. regular rates

How to Book

Continue to Windstar Cruises -- No Change Fee

See below for additional itinerary details, but please call to book.

Book this deal by phone

Call Windstar Cruises -- No Change Fee at 844-655-0397.

The reservation center is open the following hours:

  • Monday-Wednesday: 6 a.m. - 6 p.m. PT
  • Thursday (Thanksgiving): closed
  • Friday-Saturday: 7 a.m. - 3:30 p.m. PT
  • Sunday: closed

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