The World’s Best Destinations for Sailing

Whether for recreation or for sport, sailing is one of the great joys of traveling. If these two activities also happen to fall at the top of your favorite hobbies, it makes perfect sense to combine them. After all, there are important (and enticing) elements that sailing and traveling share, such as movement, exploration, gorgeous scenery, and a sense of freedom. 

Seafarers with all levels of expertise will find accommodating waterways around the world, though it’s impossible to cover them all. For instance, places like Tanzania, Kuwait (where the first sailboat is said to have originated in 5000 B.C.), Indonesia, the South Pacific, and, heck, even Denver all hold their own in the nautical world. That being said, here are some of the best destinations to cast off your bowlines. And good news for North Americans -- many of these spots are easily accessible from Canada, Mexico, and the U.S. 

So, if you’re borrowing a sailboat from your all-inclusive resort, chartering a windjammer from a full-service marina, or taking your own vessel across the ocean, here are our top destinations in which to set sail.

Caribbean

_dChris/Flickr

_dChris/Flickr

With glistening waters, white-sand beaches, hidden coves, innumerable snorkeling and diving possibilities, and authentic onshore island culture, the Caribbean (in the absence of tropical storms and hurricanes) is a sailor’s delight. Though each island has its own unique appeal, some have advantages over others. Especially notable for sailing enthusiasts are the Grenadines, a chain of 32 picturesque islands sprinkled across the West Indies where you’ll find ideal sailing conditions and a lack of crowds. 

To the north is St. Lucia, nicknamed the Jewel of the Windwards, which offers superb sailing conditions combined with stunning Piton mountain views, picturesque harbors, dense rainforests, and easy access to Mustique and the nearby islands of Tobago Cays.

Also popular with sailors are the British Virgin Islands -- 40 islands dotted across the turquoise Caribbean Sea, with pristine white sands, chic resorts, fine restaurants and shops, and hundreds of anchorages. It also has an abundance of natural beauty, especially with several protected national parks, as well as an average year-round temperature of nearly 79 degrees, which is great for frequent dips.

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Chesapeake Bay

Cyndy Sims Parr/Flickr

Cyndy Sims Parr/Flickr

Technically an estuary (in fact, the largest in the U.S.), spanning tens of thousands of square miles, Chesapeake Bay offers sailors a vast range of opportunities, from calm inlets to competitive sailing regattas in open water. It’s no surprise that Annapolis is considered the sailing capital of the U.S.; set sail from here and you can easily spend a week exploring the bay’s rich maritime history and picture-perfect towns, such as historic St. Michaels. St. Michaels is arguably one of the most beautiful towns on the bay, with marinas, anchorages, the Chesapeake Bay Maritime Museum, and a great selection of restaurants and bars. If nature and solitude is more your speed, check out the 2,800-acre wildlife refuge on Wye Island, which is teeming with bald eagles and great blue herons, as well as the largest old growth forest on the eastern shore.

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Croatia (and Montenegro)

Kamil Porembinski/Flickr

Kamil Porembinski/Flickr

This stunning Balkan nation on the Adriatic Sea, sometimes referred to as the “new Riviera,” has increasingly become a must-see destination for all types of travelers over the last few decades. There is no better way to experience it than to set sail, especially since Croatia offers access to more than 1,000 miles of rolling green coastline and nearly 2,000 islands. There are a lot of beaches and national parks to explore, as well as traditional fishing villages, charming towns, and hikes to waterfalls and UNESCO World Heritage sites.

For even more dramatic coastlines, consider sailing south to Montenegro. There are several overnight anchorages here, and the main attraction of the country is the winding Bay of Kotor, which boasts well-preserved medieval towns and access to ancient monasteries. Like Croatia, Montenegro is one of the most popular sailing destinations in the world, so expect company.

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Florida Keys

gabe popa/Flickr

gabe popa/Flickr

Stretching 125 miles from Biscayne National Park in the northeast to Key West to the southwest, the Florida Keys offer some of the best opportunities for sailing. With the subtropical marine wilderness of Florida Bay, the Gulf of Mexico and the remote reaches of the Everglades, this area is home to numerous birds and abundant marine life. Turquoise waters, warm temperatures, and prevailing easterly winds provide exceptional sailing, while the Atlantic side offers open water sailing and, in calm weather, excellent snorkeling in the outer reefs and Dry Tortugas National Park. Stay near Key West for big marinas, memorable sunsets, restaurants, and nightlife, or take an extended cruise from one end of the island chain to the other, which some say is as good as the Bahamas. 

For a longer trip, start or finish in Fort Lauderdale, which boasts 300 miles of waterways and more than 40,000 resident boats. Not only does Fort Lauderdale border the Atlantic, but it’s crisscrossed by the Intracoastal Waterway as well as a number of rivers, lakes, and canals, giving it the nickname “Venice of America.”

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Great Lakes

Ray Dumas/Flickr

Ray Dumas/Flickr

The only freshwater contender on this list is a series of naturally beautiful interconnected lakes (Superior, Michigan, Huron, Erie, and Ontario), which make up some of the best places to sail during spring, summer, and fall months (avoid November to April) when the water is warmer and the sunshine is aplenty.  There are too many races to list, but for an example, every year in Lake Michigan, 300 sailboats make their way from Chicago’s Navy Pier to Michigan’s Mackinac Island, a picturesque, car-free paradise that connects to Lake Huron. For a more relaxing journey, sail to charming harbor towns like Saugatuck and Charlevoix on Lake Michigan, Madeline Island on Lake Superior, or Georgian Bay on Lake Huron, which offers over a dozen ports to choose from. The nautical area of Door County Wisconsin also boasts a number of scenic lighthouses. 

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Greek Islands

Roger/Flickr

Roger/Flickr

With an estimated 6,000 islands scattered in the deep-blue Aegean and Ionian Seas, of which only 227 are inhabited, sailing is the best way to experience the Greek islands. There are so many options to choose from and a number of ports to stop in, each offering a different feel. It’s easy to concoct your own island-hopping itinerary -- stop in popular areas like Corfu and Lefkada, or find lesser-known spots punctuated by traditional whitewashed villages and Greek ruins. Did we mention the warm sea breezes and continuous sunshine?

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Newport, Rhode Island

Mike Norton/Flickr

Mike Norton/Flickr

Though Annapolis considers itself to be the sailing capital of the U.S., Newport also claims it’s the sailing capital of the world. Either way, when considering a sailing trip to New England, Newport is the most obvious choice. It’s one of America’s premier yachting centers, dating back to the 19th century when Newport Harbor went from being a maritime trading center to a sailing playground for the rich and famous. Today, this picturesque shoreline town oozes with charm and includes a busy downtown street, America’s Cup Avenue, dedicated to the most coveted sailing race in the world, which was held here for 50 years during the 20th century.

Today, sailing season still begins in early May and ends in late October. There are a number of boat shows and races, including the Newport Regatta, Newport Bermuda Race, and Annapolis to Newport Sailing Race. While in town, don’t miss touring the Newport mansions that were once owned by America’s most influential businessmen -- names like Vanderbilt, Astor, Belmont and Berwind should ring a bell.

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San Juan Islands

Zachary Simonson-Bond/Flickr

Zachary Simonson-Bond/Flickr

Offshore from the college town of Bellingham and near the Canada border, the San Juan Islands in Washington state offer pristine sailing conditions. The Pacific Northwest is already known for gorgeous landscapes, including fragrant green forests of spruces, pines and firs, as well as white-capped mountains (like Mount Baker) that loom in the distance. Plus, it boasts one of the highest concentrations of bald eagles and whale sightings in the country. It should also be known that these 172 named islands and reefs in San Juan County remain quite dry throughout the winter, making sailing possible year-round. 

The four main islands are San Juan Island, Orcas Island, Lopez Island, and Shaw Island, which are the most populous and offer more lodging and activities. Smaller islands include standouts like Lummi Island, which has a world-renowned restaurant called The Willows Inn for the ultimate dinner onshore.

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South of France

Le Pinarello Hotel/Oyster

Le Pinarello Hotel/Oyster

You’d be hard-pressed to find a swankier or more romantic area of the world to sail than the French Riviera, which puts Cannes, Nice, and Saint-Tropez at your fingertips. This stunning Mediterranean coastline along the southeast corner of France is packed with magnificent beaches, rocky inlets, and unspoiled islands. For those who prefer a more down-to-earth locale, sail east towards Marseille for the spectacular Parc National des Calanques, a stretch of high cliffs only interrupted by small idyllic beaches. Other laid-back options include Antibes. Or, sail even further south towards the large island of Corsica, which is located between Sardinia and the Côte d’Azur. Nicknamed the Island of Beauty, sailors can have their pick of great moorings, old cities, and wonderful landscapes in the form of cliffs, mountains, rivers, waterfalls, and sand beaches, and vineyards. To avoid tourists and overcrowded bays, stick to May and September.

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Whitsunday Islands

Petra Bensted/Flickr

Petra Bensted/Flickr

With 74 stunning islands and consistent warm weather, the Whitsunday Islands, located off Airlie Beach on Australia’s east coast, are a sailor’s paradise. The majority of this area belongs to the Great Barrier Reef Marine Park, which is known for its coral gardens, sea turtles, and array of colorful fish. This means that sailing here provides the opportunity to snorkel or dive all day long in the crystal clear turquoise waters. No boat? No problem. Many backpackers who are making their way to Cairns tend to book a two- to three-day sailing Whitsundays tour (there are many options). You can book direct with any of the big companies, though the best way to save money is to reserve with a tourist office or a hostel, as they get a better rate and deals.

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