Best Sailing Destinations in the US

Sailing is a perfect antidote to the stresses of living in today’s modern world.

Sailing in Newport Harbor, R.I. Dreamstime/TNS

By Noreen Kompanik TravelPulse

It is widely believed that Mark Twain said: “Twenty years from now, you will be more disappointed by the things you didn’t do than those you did. So, throw off the bowlines. Sail away from the safe harbor. Catch the wind in your sails. Explore. Dream. Discover.”

There’s just something special about sailing, whether it’s the open water, the sunshine on your face, the wind in your hair, or the total sense of freedom, relaxation, and centering. Sailing is a perfect antidote to the stresses of living in today’s modern world.

Whether you decide to be part of a crew manning the sails or just come along for the ride, we are so fortunate to have so many incredible destinations here in the United States for sailing, whether it be a tranquil lake or ocean waves.

Newport, R.I.

Often referred to as the “sailing capital of the world,” Newport, Rhode Island, offers a deep maritime history, ideal sailing conditions, and an important role in international competitive sailing. The coastal town hosted the America’s Cup from 1930 to 1983 and continues to attract sailors from around the globe to its annual sailing events.

Newport has been a longtime training hub for Olympic and professional sailors, and there’s nothing like moving under the impressive Newport Bridge, the longest suspension span in New England.

Chesapeake Bay, Annapolis, Md.

In Annapolis, Maryland, sailing is a major part of the city’s identity. Annapolis is also the location of the United States Naval Academy, where future naval officers are trained in the art. Located where the Severn River meets the Chesapeake Bay, the area offers easy access to both open water and protected coves, making it a sailor’s haven.

The bay’s deep, navigable waters make it ideal for recreational and competitive sailing, and the destination hosts numerous sailing and regatta events and boat shows throughout the year.

Charleston, S.C.

This southern belle consistently ranks as one of the top places in the United States for sailing, offering incredibly picturesque views. With its historic charm, great sailing conditions, and a vibrant maritime culture, it’s only natural that sailors want to be out on the water.

Charleston, South Carolina, has some top-notch marinas, yacht clubs, sailing schools, and charters, and the College of Charleston sailing team is nationally ranked. My favorite time to sail is at day’s end. The view includes an impressive combination of historic skyline, calm harbor waters, and glowing sunsets over the Charleston Peninsula, creating an unforgettable experience.

Charleston Harbor, in Charleston, S.C., is dotted with historic sites, including Fort Sumter, where the first shots of the Civil War were fired. Dreamstime/TNS

Florida Keys, Fla.

The Florida Keys are home to the only barrier coral reef in North America and the third-largest in the world. Sailing here is a tropical dream. The Keys’ multihued waters, warm trade winds, and laid-back island culture make for a paradise. And you don’t have to venture farther into the Caribbean with a passport to get to it.

Stretching more than 129 miles from Key Largo to Key West, the island chain with more than 800 keys offers countless places to sail, anchor, dock, and explore. Constant trade winds, shallow warm waters (especially on the Gulf of America side), and easy access to snorkeling, diving, and fishing right off the boat make the Florida Keys a popular sailing destination.

Santa Barbara, Calif.

Known for its mild weather, rich maritime history, picturesque coastline, and vibrant sailing community, Santa Barbara, California, is a haven for sailors of all levels. Affectionately known as “The American Riviera,” this jewel of the California coast’s mild winds, calm seas, and near constant sunshine make for picture-perfect sailing conditions.

Those into competitive sailing can join in the adventure on Wet Wednesday races at the Santa Barbara Yacht Club, a beloved tradition in the sailing community. The region also hosts several regattas and sailing festivals throughout the year.

Finger Lakes, N.Y.

This region consists of 11 glacial lakes and one Great Lake (Ontario), making it a superb destination for the sailing fan. Visitors can choose from a number of sailing companies or use private charters such as Sail True Love out of Watkins Glen, New York, and Sail Seneca from Geneva, New York.

The lakes are long and narrow, creating consistent and moderate wind channels that funnel down the length of the lake, making for reliable sailing conditions. Many of the Finger Lakes are deep and clear and good for keelboats. This helps sailors avoid hazards such as submerged rocks and sudden shoals. And it’s hard to beat the views, with waters surrounded by hills, vineyards, and charming small towns.

San Diego

The United States’ finest city, as it’s often called, is home to almost year-round picture-perfect weather, reliable winds, and a stunningly picturesque and protected sheltered bay with easy access to the open Pacific Ocean.

San Diego has a long naval and maritime history, which means that sailors will get great views of not only the city, the Embarcadero, and Coronado Island from the water, but also a myriad of U.S. Navy ships. It’s also a great chance to view gray whales, blue whales, dolphins, and a slew of various seabirds.

With its vibrant racing and cruising community and notable yacht clubs, this Southern California gem is a true sailor’s city.

San Juan Islands, Wash.

Located in the Pacific Northwest, the San Juan Islands, with more than 170 islands and reefs, are a hidden gem for sailors seeking peaceful tranquility while surrounded by stunning landscapes and quiet coves. Yet they are still considered one of the top sailing destinations in the region.

Situated in the rain shadow of the Olympic Mountains, the islands offer calmer seas and less wind and rain than the outer coast, ensuring smoother, safer sailing. Sailors regularly spot seals, sea lions, porpoises, bald eagles, and orcas, especially around San Juan Island.

San Francisco

Unless you’re a skilled sailor or racer, an individual sail might be a challenge here because of the bay’s strong winds and currents. However, there are plenty of opportunities to get out on the water via a guided catamaran.

Seeing the City by the Bay’s skyline via water is a rewarding experience, as is sailing beneath one of the world’s most recognizable bridges and past the haunting site of the abandoned Alcatraz Island. You’ll encounter calm waters turning gusty, choppy, and tide-driven, but it’s all part of the fun. The city hosts world-class regattas, including the America’s Cup and SailGP events.

US Virgin Islands

Sailing the cerulean waters of the U.S. Virgin Islands provides an exhilarating, authentic Caribbean experience without a passport. It’s best to hire a boat captain for the day or take a catamaran sail, as you would need a passport to enter British Virgin Island waters.

The three islands making up the U.S. Virgin Island chain are only a few miles apart, allowing for easy navigation and line-of-sight sailing. Warm water temperatures and steady trade winds offer nearly perfect sail conditions, and the crystalline waters with their colorful, stunning coral reefs and tropical fish make for amazing snorkeling or diving conditions.

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