Virgin Gorda; St. Barts; St. Maarten; Exumas and more
50% off—Masted sailboat Caribbean winter cruises
Anika Maiberger
Deal Expert
Sip bubbly under billowing sails on an all-inclusive voyage that typically costs double.
Why We Love This Deal
Ride the warm ocean breeze to hidden snorkeling coves and celeb-packed islands. This luxe adventure offers around-the-clock beverages, gourmet dining and personalized service for its 136 guests. With this Travelzoo-exclusive offer, you'll pay half as much as non-members, saving up to $4815.
All sailings include:
- Accommodations in a Superior Stateroom (E), complete with an ocean view
- All meals, including a nightly four-course menu and a five-course signature dinner
- All drinks, including wine, beer, spirits, coffee, tea and soft drinks (premium brands are additional)
- Water sports equipment, including snorkel gear, stand-up paddleboards and towable tubes (weather permitting)
- Zodiac tours for beach landings and photo opportunities around the ship
- Gratuities and port fees
Departures from $3745 per person: Visit the British Virgin Islands, St. Barts and St. John
- Jan. 10 or Jan. 17, 2025 ... 7 nights
- Sail roundtrip San Juan, Puerto Rico
Departures from $4280 per person: Visit Antigua, Nevis, St. Maarten and more
- Jan. 24, 2025 ... 8 nights
- Sail San Juan, Puerto Rico, to Philipsburg, St. Maarten
Departures from $4815 per person: Exumas and Eleuthera, Bahamas and Key West
- March 26, 2025 ... 9 nights
- Sail roundtrip Miami
Upgraded Junior Veranda and Veranda suites are also available, starting at $6499. Suite stays include in-room sparkling wine and daily laundry service.
Book by Oct. 21.
This offer is booked through, and is therefore subject to, the travel or entertainment provider's terms and conditions, including but not limited to refund and cancellation policy. Become a member to see all offer details and learn how to book.