Yachtsman’s Caribbean on Wind Surf

Wind Surf’s Captain John Clark shares highlights of this amazing itinerary showcasing Windstar’s ability to sail into exclusive ports and enjoy the Caribbean uniquely.

Wind Surf’s Captain John Clark

Wind Surf is the largest sailing vessel in the world and the longest vessel to have ever been into North Sound, Virgin Gorda.  When I proposed this many years ago the company and our local agents were in doubt as to whether the yacht would fit in through the gap in the reef or not. Even though Wind Surf, with only 312 guests, is the length of cruise vessels four times its size (I was Captain on the ’Island Escape’ which was exactly the same length, carrying 1,700 guests over 13 decks), the nature of Wind Surf’s fine-lined sailing keel and draft of only 17 feet means that we can fit snugly into the smallest of harbors with ease.

Well, this is Wind Surf’s third call now to North Sound, and I’ve been Captain on each occasion. It has to be one of the most spectacular places in the Caribbean and the most satisfying from a professional mariner’s point of view. To clearly see the coral reef slip by within feet of our hull as we make the break into the Sound is very exciting. I can only imagine what it looks like to the residents and visitors at the Bitter End Yacht Club as we come around the corner of the sound, under full canvas!

Wind Surf at Virgin Gorda

So, this location has to be one of my all-time favorites, not only are we a snug fit, from the anchorage we offer three locations to our guests, by running a tender service to the Bitter End Yacht Club, Prickly Pear Beach and Gun Creek. The smallest of locations with plenty to do. I can also tell you from personal experience that the water sports we offer both from the marina and from the beach is second to none! And then there is Windstar’s beach barbecue, our own private beach for the day!

Water sports from Wind Surf’s Watersports platform

The itinerary includes an evening trip to Foxy’s, on Jost Van Dyke, one of the most heralded bars of the Caribbean, and what better than having a drink on a beach at night with your yacht framing the harbor and blocking the skyline, lit up in lights.

Les Saintes, just south of Guadeloupe, the southernmost stop on the itinerary, has to be the most picture-perfect locations in the Caribbean. If you dreamt of the most idyllic Caribbean bay, this would be the one in your dream.

The first stop on the route is Soper’s Hole, Tortola. We used to visit Roadtown, Tortola; however, larger ships stop there and due to the its commercialism and crowds we opted for Soper’s Hole on another part of the island. It is an idyllic protected small harbor with a warm history of pirates and adventure and we land our guests right onto the board walk of a quaint marina known as Pusser’s Landing. Soper’s Hole is known as the one time home of Blackbeard and it’s rumored that his ghost lives on here (searching for the head that was chopped off once he was caught!), as do many of his descendants live here and on the surrounding Islands. The departure from Soper’s Hole includes a sunset sail away and cruise through the southern end of the Sir Francis Drake Channel and out through “the Narrows.”

The final call of the week is St. Barts where the rich and famous hang out, smart expensive yachts are in abundance and a stroll through this marina town will most likely include a sight of a celebrity. It  should definitely include a visit to the infamous ‘Cheeseburger in Paradise,’ made famous by Jimmy Buffet. The final moment of the itinerary is a midnight sail away from St. Barts where we set the sails and head off under sail power alone, without even starting the engines.

Yachtsman’s Caribbean Voyages

John Clark
Wind Surf

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10 years ago

We are so excited to be joining Captain Clark on Christmas Eve for this exciting cruise. As 5 time Windstar returning guests, we have brought along our entire family ( 6 members) to help us celebrate this Holiday season. John and Michelle Freise. Surprise AZ. Cabin 329.

Reply to  Johnfreise
10 years ago

We can’t wait to welcome you back onboard! We would love to hear all about your voyage once you return – find us on or!

Anne Arnold
10 years ago

Hi, John!  So, now we found you!  Jerry and I are boarding the Wind Spirit on Dec 31…disappointed to find you are at another helm!  We shall miss you!  We loved the two week back to back with you last Holiday and will never forget New Year’s Eve last December 31, and the approach to St. Barts!  Have a wonderful Christmas and a Happy New Year!  All the Best from Jerry and Anne!

Reply to  Anne Arnold
10 years ago

Thanks so much, Jerry and Anne! We know John will be delighted to see this!

Joel Miller
9 years ago

Would love to sail again with John. Is he on the Star or only on the the Surf?
Looking at the Panama Canal in Nov.

Reply to  Joel Miller
9 years ago

Hi Joel, unfortunately Captain John Clark recently left Windstar to work closer to his home and family. We’re glad you were able to sail with him and we’re sure you’ll enjoy your next trip just as much! Hope to see you in November!

9 years ago

Cruised on the Island Star and the Island Escape , and was very impressed with Captain John Clark and his Crew. Fantasic man with a great manner for both adults and children. Hope to have the pleasure of cruising on one of his ships again.

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