Watching sailing from a distance can be like watching an insect’s funeral procession: white specks slowly moving across a blue background. But if you get out on the water, a boat race comes to life. Deckhands sprint across the decks, sails powerfully unfurl, and hulls crash into towering waves. During Antigua Sailing Week, Ondeck Ocean Racing can give you the sailing equivalent of courtside seats at a professional basketball game. The company’s Chase the Race experience puts six passengers aboard a Farr 65 racing boat with a pro crew that’s not out to win but works hard enough to keep you close to the action. Antigua has been the last stop on the Caribbean winter regatta circuit for nearly 50 years. I’d always thought it was the after- party scene that made Sailing Week most appealing, but actually riding the waves made me want to give up my landlubber status. The Ondeck adventure also included a hands-on sailing lesson that covered the physics of wind and the mechanics of hoisting a sail without straining your back. I eagerly clambered around the decks to yank ropes and take the wheel as often as I could. Salt spray hitting my face, wind power palpable in my hands, I was hooked. Ondeck offers short recreational sailing trips and pro training—and I’m seriously thinking of enrolling. Rooms from $635. Photo courtesy of Carlisle Bay. This appeared in the November/December 2012 issue.
- Highlights7
- Wanderlists0
- Features0
- Q&A13
- Locals1

Oceanic View
Antigua is one of the hidden gems of the Caribbean! The Island embodies a slower pace that helps you recharge your batteries and forget about all your cares back in your real life. I was only able to spend 4 days there but came back very rejuvenated!
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Bird Island
Taking a nature tour of Antigua opens up a new side to the Island. The last stop on the tour was Bird Island which offered beautiful views of Turtle Grass spotted lagoons and warm tropical breezes.
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Jolly Harbour
We just arrived in Antigua for our wedding and honeymoon. The view from our room overlooks Jolly Harbor and is breathtaking. I think this is going to be one amazing week.
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Antigua
Learn to sail in Antigua and St. Martin. Sam is an amazing coach and offers adventures to gain mileage, explore the off the beaten path islands that are only reachable by boat and also provides adventures for singles. I ended up on a beginner certification course which was a learning experience that I will never forget. Honestly, this trip was totally worth every penny.
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Shirley Heights
Stunning views while savoring a Rum Punch
Pigeon beach
Amazing beach. Watch out for sand fleas though!!!


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