Living in California, it’s easy to overlook the Caribbean as a destination for sun, adventure and glorious beaches.  But you won’t do that again after enjoying a WindStar cruise through the Caribbean.  My friend and I boarded our five-masted sailing yacht, the Wind Surf carrying just 270 guests, after an easy flight into St. Maarten. We were greeted with champagne and hors d’oeuvres, eager to embark on our “Yachtsman’s Caribbean” itinerary through the British Virgin Islands.

Our first port of call was Falmouth Harbour on Antigua. We had signed up for a shore excursion, Ziplining through the Canopy, which turned out to be an exhilarating start to our vacation. We zoomed over 12 ziplines (feeling quite safe the entire time thanks to their team of expert guides), followed by an obstacle course through the lush treetops. Probably the best excursion I have ever taken!

What better way to relax from that excitement than toes in the sand.


The second day, we enjoyed a full day at sea starting with a stretching class then yoga in the morning, followed by a galley tour and a cooking demo, Spiced Chocolate Mousse. Our captain announced mid-day that we were under power of only the sails…and we were soon accompanied by a small pod of Minke whales who surfed alongside of us for about an hour. After that thrill, drinks with new friends and it was time to watch our second dramatic sunset.


WindStar has an open-bridge policy for those of us fascinated by all things nautical. We enjoyed chatting with the captain and first officer to learn more about our route, about instrumentation, the workings of the sails. We even watched as one of the crew used a sextant to confirm our course at sunset using just two stars and the horizon.

We came ashore next morning at Soper’s Hole on the tip of Tortola, a tiny village awash in pinks and turquoise and oranges with gingerbread-trimmed shops. WS Sopers Hole.jpg

This was where we discovered our first “Painkiller,” a rum and coconut drink famous in the British Virgin Islands. We snorkeled among sea caves and along a reef with sea turtles, rays, barracuda and an abundance of fish in every pattern. That afternoon, back on the Wind Surf, we played with the water toys at the back of the ship’s Sports Marina—kayaks and stand-up paddleboards, rafts and a huge water trampoline–until close to sunset.

Tiny Jost Van Dyke is where we came ashore in the evening to a moonlit port and spent hours dancing at Foxy’s Bar, again Painkillers in hand. Next morning we crested a hill and looked down upon the most vibrant turquoise water I have ever seen. WS White Bay

This was White Bay, a secluded beach where we spent the afternoon snorkeling, just our guests and a few catamarans and sailboats.


Not another cruise ship in sight for days. Capped off by a visit to the famous Soggy Dollar Bar for more Painkillers, we set sail that night for Virgin Gorda. And what a surprise Virgin Gorda was.

First stop was Devil’s Bay, a small, turquoise cove nestled among huge, dramatic granite boulders.

WS Virgin Gorda

After snorkeling, we went pseudo-spelunking through a vast field of those looming rocks, clambering over them, under them, around them, splashing in hidden shadowy pools—never seen anything like it in the Caribbean before.

WS Baths3.jpg

WS Baths2.jpg

We ended up at secluded Fischer’s Cove where our fabulous WindStar crew had set up a sprawling Beach BBQ for us. We feasted and danced, snorkeled and waterskied and kayaked all afternoon.

Final stop was gorgeous St. Bart’s, a playground of mega-yachts, high-end shopping and beaches and a fascinating place to people-watch.


What makes WindStar cruises so unique is the perfect balance of small ships (150 – 300 guests), luxurious staterooms and lounges, fine dining (from local specialties to classic French cuisine), stellar excursions, attentive service…and those intimate, uncrowded ports of call. The perfect combination for your next cruise to the Caribbean, the Mediterranean, French Polynesia, Asia, even Iceland. You’ll never go back to a big ship again!



About Alamo World Travel

What's your dream vacation? Whether the perfect vacation fills your days and nights with adventure, brings your family together or whisks you off to romance, we can build you a dream vacation filled with the sights, the sounds and the tastes you crave. Luxury travel specialists for 36 years, Alamo World Travel & Tours has been crafting authentic and unforgettable vacations that inspire, that create memories…and that give you the best stories to tell! Give us a call or stop by our office in Alamo Commons and let us whet your appetite for your next adventure. We'll ask the questions you might not even know to ask. And to help you start planning, we have gathered information here on most of the sailings and tours that are currently available.
This entry was posted in Beach, Caribbean, Cruise, kayak, Snorkel, snorkeling, Uncategorized, Windstar and tagged , , , , , , , . Bookmark the permalink.


  1. Rick nesbitt says:

    Great article from one of those friends you met while whale watching at the back of the ship. Can’t wait for our next Windstar cruise. Cheers. Rick and Karen

    Liked by 1 person

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