Sailing isn’t just another way to get around—it grants you access to places, communities, and experiences that other travelers often miss.
Sailors are the masters of their travel time: They can go (almost) anywhere in the world on a whim and always receive a warmer reception than that afforded to mere tourists. Like a fraternal club that doesn’t advertise, they rendezvous at those select locales known for great sailing weather and a welcoming attitude toward visiting boats. Once at anchor, sailors have access to everything else a new port has to offer, including cosmopolitan nightlife, tropical beaches, or national wildernesses. Whether you’re a seasoned sailor or a landlubber looking to charter a boat and dip your toes into the lifestyle, you’ll want to head to one of these seven islands. Not only are they beloved by the sailing community, but they also have plenty of non-nautical charms that’ll have you returning time and time again.
1. Azores, Portugal
For 500 years the Azores have been the first land sailors touch after long west-to-east routes across the Atlantic as they near the Iberian Peninsula. It’s traditional for captain and crew of each arriving boat to pass through sailing’s most legendary meeting spot, Peter’s Café Sport, which opened in 1918. Crew members looking to exchange their labor for one-way passage lurk in the café, while leisure visitors sit back and soak up the atmosphere. The islands are known for their dramatic landscapes and peaceful fishing villages, but come as a sailor rather than a fly-in tourist to experience a truly welcoming, fraternal atmosphere on this island run by sailors for sailors.
Five hundred miles off the east coast of Madagascar, Réunion rises out of the Indian Ocean like a steep-sided salad bowl. Twin volcanoes, Piton de la Fournaise and Piton des Neiges, poke holes 8,600 and 10,000 feet into the sky, respectively. Hiking trails lace the wilderness around them, and the slopes attract climbers, cavers, and canyoneers. Tickets from JFK or LAX often run $2,000 or more to this remote tropical island filled with rain forests and surrounded by coral reefs, and the trip takes more than 24 hours of plane-hopping. Instead, pilot your own boat into the arms of a large sailing community and enjoy the best harbor facilities in the Indian Ocean, according to Noonsite, an online sailors’ database of routes and destinations.
Every even-numbered year, more than 150 privately owned sailboats depart Newport, Rhode Island, for a 635-mile race to Bermuda as part of the most famous amateur yacht race in the world, the Bermuda Race. Competition is relaxed, and honor goes to any who compete regardless of a win, so ready your boat (or talk your way onto somebody else’s) for the 51st event, running on June 15. The camaraderie and instant community alone are enough to make anyone fall in love with sailing. Once you’re docked in Bermuda, be sure to weave past the harbors’ forests of steel boat masts to the 20-square-mile island’s interior, and check out a few of the more than 90 remaining British forts, the earliest of which was built in 1612.
The most famous waters in Western history also happen to be in the sunniest part of Greece. The people of Rhodes have hoisted sail into the winds since before Homer recounted their meddling in the Trojan War 3,000 years ago. Closer to the Turkish coast than to the Greek mainland, it’s home to the oldest inhabited medieval town in Europe, the Old Town in the city of Rhodes. The island’s rocky coastlines, suited to the medieval fortifications bricked into them, make for a break of scenery from typical, flat stretches of white sand in the Mediterranean, although the natural harbors make for beautiful beaches, too. With mild Mediterranean winds and currents, Rhodes is famous for its pleasant sailing conditions, making this the perfect place to brush up on your captaining.
5. Santa Catalina Island, California
Because of its jagged coastline, limited number of natural harbors, and hazardous wind conditions, sailors are less inclined to frequent the Pacific Coast of the United States than they are the Atlantic and Gulf Coasts. But Santa Catalina, a desert island 20 miles off the coast of Los Angeles, is a haven for boat life in the region. It’s also a paragon of raw nature: The Catalina Island Conservancy protects 85 percent of the island’s 75 square miles. Bison roam wild on land and whales swim in the natural harbors. Avalon, the only town, keeps car traffic to a minimum by restricting each household to only one ultra-small vehicle—think classic VW Beetle or golf cart.
The cactus-strewn desert island of Aruba is the last Caribbean stop for many private boats heading through the Panama Canal and out to the Pacific Ocean. It sits outside the hurricane belt that sweeps up so much of the region, which makes it a perfect refuge for off-season sailors. (Hurricane season runs from June to November.) Dutch-flavored capital Oranjestad is a cosmopolitan city of rainbow-hued colonial buildings and is known to punch above its weight with trendy after-hours nightlife. You’re as likely to hear English, Spanish, and French spoken by locals as you are the official Dutch and Papiamento creole; from Aruba’s more tropical southern shore, you can easily see Venezuela, just 15 miles away.
7. Key West, Florida
Too often overlooked by sailors eager to enter the Caribbean’s foreign waters, laid-back Key West is exactly the scenic backdrop of tropical beaches and turquoise sailing waters U.S. residents seek in other countries. If Key West weren’t within our borders, it would rank a lot higher on sailing itineraries. Sailors who crave foreign shores can easily skip over to The Bahamas at daybreak and arrive by lunch, but the mellow Keys have all the sugar sand and palm trees you could want.