You’ll have to go pretty far to find better sailing conditions or a more pleasant Caribbean destination than Antigua. The tradewinds here typically blow out of the east at 15 knots, and the island’s high coastline provides a spectacular backdrop. On shore you’ll find great restaurants, sailor-friendly bars, quaint villages and an abundance of great anchorages.

“The four main places that I recommend are Green Island on the east coast, Carlisle Bay on the south, Deep Bay on the West and Great Bird Island on the North,” says Sylvain Caburet, Sunsail’s Antigua base manager. (Antigua is also home to charter bases for The Moorings and Horizon Yacht Charters.)

According to Caburet, nature lovers should pay special attention to Great Bird Island, while those seeking a more active nightlife should visit Jolley Harbor or Dickinson Bay. For history buffs, a stop in English Harbor and Nelson’s Dockyard National Park provides a look at the world’s only working Georgian-era dockyard. A trip to the once heavily fortified Shirley Heights offers insight into how the British defended this prized harbor.

Spend enough time in Antigua and you realize that the island offers something for everybody. Adventure lovers, for example, should enjoy the Antiguan Rainforest Canopy Tour. Zip lines whisk visitors through the island’s rainforest canopy on a 21-stage tour that’s sure to elicit big grins. Another popular attraction is Sting Ray City. Once some chum is offered, 50 or 60 wild stingrays quickly arrive, eager for a free meal. The rays are accustomed to human interactions and allow themselves to be touched and occasionally held.

Antigua’s less-sheltered coast can be subject to long-period open-ocean swells and sailing here requires a bit more know-how than, say, the BVI. “We’ve got a lot more open water, more open conditions. We’re about the same level as St. Vincent or St. Maarten,” Caburet says, adding that Sunsail requires Antigua charterers to have a Level II certification. For charterers, though, this translates to two things: more engaging conditions and far less competition for moorings or anchorage space. “Here, if you find four or five boats, it’s crowded,” Caburet says with a laugh.

A perfect example is Green Island on the island’s southeast side. This popular destination offers fantastic swimming and one of the most spectacular anchorages imaginable. During a recent visit there I encountered no more than one or two other boats, yet local sailors refer to Green Island as “crowded.”

“Antigua has a very indented coastline so you’ve got a lot of places you can pull into and anchor,” agrees OnDeck’s Peter Anthony, adding that one of his favorite snorkeling spots is Cades Reef, along the southwest corner of the island. (OnDeck has a permanent base in Antigua, and while the company caters more toward racers, some of the less racy boats are also available for charter.)

Another great destination, according to Anthony, is Antigua’s east coast, although he warns that sailing inside the reef requires a shoal-draft boat because of the many underwater hazards.

The best time to sail in Antigua is between January and May. In fact, most charter bases close from roughly August to October. But Antigua has plenty to offer summer charters, albeit with less breeze and hotter temperatures. In August, the island hosts its annual Mango Festival, where visitors can sample locally grown mangoes and Antigua’s legendary “Black Gold” pineapples. But if you ask for bananas, the locals may give you a quizzical look. Here they’re called “Green Figs.”

Call it a quirky Antiguan thing, but it begs a question for sailors: Do “green figs” conjure the same bad luck at sea as bananas?