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Beach Fun & Sun: A Remote Caribbean Getaway
Dec 5, 2027 — Dec 12, 2027
Starting from
Early Booking Offer All-In Package
Early Booking Offer SBC
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.
Pastel-colored buildings and shops filled with tempting souvenirs herald your arrival to bustling Philipsburg. Situated near the harbor on the Dutch side of St. Maarten, Philipsburg owes its discovery to Christopher Columbus in 1493. Today, celebrated Front Street is home to a number of local Creole restaurants as well as jewelry stores, stylish boutiques, and lively casinos for visitors seeking an upbeat island experience.
It's said that Antigua has 365 beaches - one for every day of the year. See how many you can discover as our stay in port stretches into the evening to accommodate them all. Watch the stars come out as darkness falls and imagine how residents of Andromeda must envy you.
With its protected shoreline, calm surf, spectacular coral reefs and sugar-soft beaches, Road Bay has become a destination for boaters, with its delightful restaurants, bars, and shops. Anguilla has some of the most beautiful sunsets and delicious rum punch to be found in the Caribbean. It is also home to Cuban tree frogs, red-footed tortoise, green iguanas and five species of bats. Worth checking out is Wallblake House, a heritage plantation house and museum said to be the oldest building on the island and located nearby.
Arrive at the boardwalk of Pusser's Landing and mingle with other yachtsmen in the utterly charming marina at Soper's Hole. Find a deserted stretch of beach to kick back and ponder this tiny port's rich heritage of romance, pirates, and adventure. An evening departure features a once-in-a-lifetime romantic sunset Sail Away.
For an island comprised of a mere eight square miles, it's amazing how much there is to do on Jost Van Dyke. Visit the national park on nearby Diamond Cay, snorkel among swaying sponges and angelfish at Sandy Spit, or pilot your own boat around Sir Francis Drake Waterway. After all that, you'll be ready for an evening drink on the beach - where you can admire your Windstar ship aglow in the harbor.
For an island comprised of a mere eight square miles, it's amazing how much there is to do on Jost Van Dyke. Visit the national park on nearby Diamond Cay, snorkel among swaying sponges and angelfish at Sandy Spit, or pilot your own boat around Sir Francis Drake Waterway. After all that, you'll be ready for an evening drink on the beach - where you can admire your Windstar ship aglow in the harbor.
The beautiful Bank Barrier coral reef wavers just beneath you as your ship makes the break to the bird sanctuary of Prickly Pear Island, so named because it is dotted with prickly pear cacti. Althought uninhabited, it does have a beach bar and water sports facilities. Not far away lies the curious assembly of house-sized boulders called "The Baths," which form huge underground pools and caverns
Affectionately known as St. Barts, the Caribbean's most chic island adds a French flair to Riviera-like beaches and duty-free boutiques. Walk past gingerbread cottages in search of celebrities, shop for designer fashions, or sip the island's signature ti punch as kite surfers fly by.
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Available Dates
| Date | Yacht | Starting from | Actions |
|---|---|---|---|
| Jan 16 (Sun) – Jan 23 (Sun), 2028January 16 (Sun) – January 23 (Sun), 2028 | Wind Surf | ||
| Jan 30 (Sun) – Feb 6 (Sun), 2028January 30 (Sun) – February 6 (Sun), 2028 | Wind Surf | ||
| Feb 13 (Sun) – Feb 20 (Sun), 2028February 13 (Sun) – February 20 (Sun), 2028 | Wind Surf | ||
| Feb 27 (Sun) – Mar 5 (Sun), 2028February 27 (Sun) – March 5 (Sun), 2028 | Wind Surf | ||
| Mar 12 (Sun) – Mar 19 (Sun), 2028March 12 (Sun) – March 19 (Sun), 2028 | Wind Surf |