Beach Fun & Sun: A Remote Caribbean Getaway
Dec 19, 2026 — Dec 26, 2026
Starting from
PHILIPSBURG, ST. MAARTEN → PHILIPSBURG, ST. MAARTEN
7 Nights on Wind Surf
Bask on remote beaches resplendent in natural beauty during this relaxing and uncrowded getaway to secluded Caribbean destinations Windstar specializes in. Board a private speedboat bound for Little Bay, Anguilla’s smallest and most private beach, then snorkel among flitting grunts, wrasses and snappers. Guide your own rigid inflatable boat (RIB) through Sir Francis Drake Waterway bays and isles around Jost Van Dyke. Sink in solitude to the silent depths where an 1867 steamship rests, an iconic Tortola dive site that doubled as an underwater movie set. Embark from our yacht’s onboard Marina Platform on your own self-directed snorkeling and kayaking adventures. Find the warm sunset twilight during an overnight port stay at Virgin Gorda. Windstar invites you to join us for our private Signature Beach Party, a fun in the sun affair, full of the rhythm and joy of the Caribbean.





Popular Highlights
Relax on the sands of Norman Island, inspiration for Robert Louis Stevenson’s Treasure Island.
Find your perfect spot on the beach while you sample some of the most delicious rum punch found in the Caribbean at Road Bay.
Stroll Pusser’s Landing, the charming boardwalk of Soper’s Hole, on your way to a secluded beach.
Overnight in Virgin Gorda with plenty of time to see lovely beaches like The Baths, Spring Bay and Savannah Bay.
Snorkel among the sea sponges and angelfish in Jost Van Dyke’s Sandy Spit.
Discover the culinary delights of both the Signature Beach Party and the Signature Onboard Barbecue.
Staterooms
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Available Dates
| Date | Yacht | Starting from | Actions |
|---|---|---|---|
| Jan 2 (Sat) – Jan 9 (Sat), 2027January 2 (Sat) – January 9 (Sat), 2027 | Wind Surf | $5,134 | |
| Jan 16 (Sat) – Jan 23 (Sat), 2027January 16 (Sat) – January 23 (Sat), 2027 | Wind Surf | $5,334 | |
| Jan 30 (Sat) – Feb 6 (Sat), 2027January 30 (Sat) – February 6 (Sat), 2027 | Wind Surf | $5,334 | |
| Feb 13 (Sat) – Feb 20 (Sat), 2027February 13 (Sat) – February 20 (Sat), 2027 | Wind Surf | $5,334 | |
| Feb 27 (Sat) – Mar 6 (Sat), 2027February 27 (Sat) – March 6 (Sat), 2027 | Wind Surf | $5,334 | |
| Mar 13 (Sat) – Mar 20 (Sat), 2027March 13 (Sat) – March 20 (Sat), 2027 | Wind Surf | $5,334 |