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Yachtsman’s Caribbean

Yachtsman’s Caribbean

At a glance

Duration: 8 Days, 7 Nights

Coverage: Roundtrip Philipsburg, St. Maarten

From: $2,199

Season: January - March, November - December

Activities: Adventure, Culture, History, Wildlife

Book this Trip › or call us toll-free 1-888-815-5428

Wind Star Cruises

Experience the Caribbean’s private yachting scene during this voyage.

Let us take you into hidden coves and tiny harbors no one else can reach as you fully experience the Caribbean’s private yachting scene. Explore the quaint island charm of Soper’s Hole and the inviting beaches of Jost Van Dyke as you overnight in the harbor. Sail to Virgin Gorda, with its assembly of house-sized rocks called The Baths. Savor the high life on St. Barts and relax on this Caribbean cruise.

Popular Highlights

  • Shop and dine in duty-free St. Maarten
  • Local treasures at Soper's Hole Wharf
  • Beachcomb at St. Barts
  • Soak in the natural bathing pools of "The Baths" at Virgin Gorda
  • Sail, swim, and kayak off the Watersports Platform
  • Mingle with the glitterati in St. Barts
  • Enjoy the Island Experience at Prickly Pear Beach

Day-to-Day Itinerary

Day 1 - Philipsburg, St. Maarten

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.

Day 2 - Falmouth, Antigua

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 to midnight to accommodate them all. Watch the stars come out as darkness falls and imagine how residents of Andromeda must envy you.

Day 3 - Falmouth, Antigua

Depart Falmouth, Antigua after lunch and hit the open Caribbean sea.

Day 4 - Soper's Hole, Tortola, B.V.I. - Jost Van Dyke Great Harbour, B.V.I

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 sunset Sail Away and cruise that glides along Sir Francis Drake Channel and on through “The Narrows.”

For an island comprised of a mere eight square miles, it’s amazing how much there is to do on Jost Van Dyke. An overnight stay gives you ample time to 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 yacht aglow in the harbor.

Day 5 - Jost Van Dyke Great Harbour, B.V.I - Virgin Gorda, Prickly Pear Beach, B.V.I.

A beautiful coral reef wavers just beneath you as your yacht makes the break into exclusive North Sound. You can imagine the reaction of the locals watching from The Bitter End Yacht Club as your ship comes around the corner under full canvas. At the other end of the island lies the curious assembly of house-sized boulders called “The Baths,” which form huge underground pools and caverns that you’re free to explore.

Day 6 - Virgin Gorda, Prickly Pear Beach, B.V.I.

A beautiful coral reef wavers just beneath you as your yacht makes the break into exclusive North Sound. You can imagine the reaction of the locals watching from The Bitter End Yacht Club as your ship comes around the corner under full canvas. At the other end of the island lies the curious assembly of house-sized boulders called “The Baths,” which form huge underground pools and caverns that you’re free to explore.

Day 7 - Gustavia, St. Barthelemy

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.

Day 8 - Philipsburg, St. Maarten

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.

Dates & Rates

Dates Ship B BX A AX TX Suite Bridge Suite
Nov 18, 2017 Wind Surf $1,499 $1,599 $1,699 $1,899 $2,099 $2,599 $3,499
Dec 16, 2017 Wind Surf $1,499 $1,599 $1,699 $1,899 $2,099 $2,599 $3,499
Dec 30, 2017 Wind Surf $2,699 $2,899 $3,099 $3,399 $3,699 $4,899 $6,499
Jan 13, 2018 Wind Surf $1,699 $1,799 $1,899 $2,099 $2,299 $2,999 $3,999
Jan 27, 2018 Wind Surf $1,699 $1,799 $1,899 $2,099 $2,299 $2,999 $3,999
Feb 10, 2018 Wind Surf $1,999 $2,199 $2,299 $2,499 $2,799 $3,599 $4,999
Feb 24, 2018 Wind Surf $1,999 $2,199 $2,299 $2,499 $2,799 $3,599 $4,799
Mar 10, 2018 Wind Surf $1,999 $2,199 $2,299 $2,499 $2,799 $3,599 $4,799
Mar 24, 2018 Wind Surf $1,999 $2,199 $2,299 $2,499 $2,799 $3,599 $4,799

Map

Yachtsman’s Caribbean

Ships

Wind Surf

Wind Surf Hosting only 310 privileged guests, the gleaming decks and sparkling sails of the Wind Surf invite you to discover a world of gracious indulgence. From sumptuous staterooms and suites to the cozy sophistication of the Yacht Club living room and library, every detail is designed for contemporary luxury. Treat your palate to the nouveau French cuisine of Stella Bistro. Work out in the state-of-the-art top deck Fitness Room with a sweeping sea view. Relax in the whirlpools or swimming pool. Or bask like royalty in the beautiful WindSpa. With an international crew of 191, your wish is our command. View ship details...

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