“Sailing is like riding a bicycle,” my instructor says, “you never forget how.” I certainly hope he’s right. After spending my childhood sailing in Santa Cruz, I haven’t touched a tiller in years. But if there’s one place in the world that can inspire me to learn how to sail again, it’s Antigua.

Hobie Cats in Antigua

That’s not least because it’s Sailing Week in Antigua, and everywhere I look, boats fly by on the water. Racing yachts with high-tech fiberglass hulls, sleek ships with colorful spinnakers, and everything in between dots the Caribbean Sea from the shore to the horizon.

Sailing in Antigua

Antigua is up there with Hawaii and Porto Cervo as one of the best places in the world for sailing. A combination of the perfect wind and water conditions draws experts and amateurs alike throughout the season, which culminates in the annual Sailing Week in late April (next year it’s from April 25th to May 1st). Dating back 47 years, it’s the oldest regatta in the Caribbean.

Sailing in Antigua

The previous day I spent the morning in the regatta’s press boat with my host for the trip, the Antigua & Barbuda Tourism Authority. We motored through the heart of the races as the sails zipped past. Eight classes of boats were represented, from the professional to the amateur. I was pleasantly surprised to learn that the regatta is open to anyone, and individuals can sign up for a spot on a boat and sail no matter what their experience level.

Regatta in Antigua

After a day at the races, I’m inspired to be one of those people. I take my instructor’s words to heart, hoping that my long lost sailing skills will manifest themselves in muscle memory as I set foot on the Hobie Cat.

St James's Club Resort in Antigua

I’m sailing at the luxurious St. James’s Club Resort & Villas on the southeast coast of Antigua, which is my home away from home during my stay in the Caribbean. Set on a peninsula, the hotel has a sunny cove that is sheltered from the strong winds on the sea. It’s a great place to learn how to sail without fear of immediately capsizing.

Rowboat in Antigua

I board the boat with my instructor, who points out the various parts of the Hobie Cat and explains the basic concepts of sailing. I’m still skeptical as to whether I will remember how to sail, but once he cedes control of the boat, I find that my skills aren’t completely lost.

Yacht Club in Antigua

After a few turns at the tiller, I start to get the hang of it again, and pretty soon I’m feeling both confident and nostalgic for my childhood. Even the others in my group that have never sailed before pick it up quickly.

St James's Club Resort in Antigua

Back on shore, I feel ready to enter the regatta. But before I do, there’s more of Antigua to see. In fact, there’s more of the resort to see. Set over 100 acres, it has several beaches, lots of swimming pools, a handful of restaurants and bars, and a spa.

Beach at St James's Club in Antigua

It’s the last of these that appeals most. After a day of sailing, I indulge in a massage on an outdoor table overlooking the Caribbean Sea. It’s one of the most idyllic locations I’ve ever been to for a spa treatment, and I feel relaxed before I even lie down.

Spa at St James's Club in Antigua

Back in my room—they’ve put me up in a Royal Suite with a balcony, a lounge area, and the biggest bathroom I’ve ever seen—I get ready to experience more of the island. My driver, Cleo from John Henry taxis, takes me from the resort to Jolly Harbour. On the way, we pass beautiful beaches, dense rainforest, and colorful houses. Cleo even stops by a roadside stand to get us a taste of the local corn on the cob. Fresh from the grill, it’s a delicious pre-dinner snack.

Beach at St James's Club in Antigua

And dinner is quite an event. It takes place aboard the new D•Boat restaurant, a refurbished 1974 oil tanker turned entertainment venue in the waters just off Jolly Harbour. Accessible by a 10-minute boat ride under the stars, D•Boat has outdoor tables for dining and a big bar and stage for weekend parties.

D Boat in Antigua

The menu offers little in the way of local cuisine, and they’re all out of the catch of the day, so I settle for salmon. It’s good, but I would have liked to see some more regional specialties offered. Still, the overall experience is unique, and I’m sure the Friday night DJ events are a lot of fun.

Boats in Antigua

But nothing on the trip has been as much fun as the sailing. It’s what I’m here for, after all, and getting to learn how to sail in Antigua during Sailing Week has been a treat. The prospect of returning to improve my skills is tempting, and maybe one of these years I will take an individual spot on a racing yacht in the regatta.

Beach in Antigua

But remembering how to ride a bike doesn’t mean one can win the Tour de France, and I think it might require a trip or two—or ten—to perfect my skills. That is, if I don’t get distracted by everything else Antigua has to offer in the meantime.

I traveled to Antigua with the Antigua & Barbuda Tourism Authority and stayed at the St James’s Club as a guest of Elite Island Resorts.

12 Comments on Lady in Antigua

  1. Your posts are making me miss the Caribbean! I used to live in a place called Le Marin, which means ‘marina’ in French, so boats are a major part of some of my fondest memories of Martinique. There’s also a sort of sailing week there and it’s one of the most fun/convivial times of the year!

    Will you be going to the French islands?

  2. I’d love to spend a few days in those photos. But if sailing is like riding a bike, it also means you’d better give up learning after you’ve reached a certain age.

  3. What a fabulous write up! We have been to Antigua race week 14 times name as an all ladies crew! Why not come and join us next year and really enjoy the parties with the sailors 🙂 Hope to see you there in 2015!

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