Lady’s Guide to Learning to Sail in Antigua

Today I want to bring you my guide to how to learn to sail in Antigua. This Caribbean island is the perfect place to go sailing, and Sailing Week in Antigua is a great time to do it.

Sail in Antigua

“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.

Sailing Week 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.

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.

Dating back decades, it’s the oldest regatta in the Caribbean.

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 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. It’s one of the most unique things to do in Antigua.

Learning to Sail in Antigua

After a day at the regatta, 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 a Hobie Cat.

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’s sheltered from the strong winds on the sea. It’s a great place to learn how to sail in Antigua without fear of immediately capsizing.

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’ll remember how to sail, but once he cedes control of the boat, I find my skills aren’t completely lost.

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 who’ve never sailed before pick it up quickly.

Antigua Hotel

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 St James’s Club Resort & Villas to see.

Set over 100 acres, it has several beaches, lots of swimming pools, a handful of restaurants and bars, and a spa.

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.

Back in my room at St James’s Club Resort & Villas—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.

Jolly Harbour, Antigua

My driver, Cleo, 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 my group a taste of the local corn on the cob. Fresh from the grill, it’s a delicious pre-dinner snack and a fun local treat.

Antigua Sailing

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’ll take an individual spot on a racing yacht in the regatta.

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.

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