Ten Great Sailing Trips For This Summer


Maryland Citizens of Newport have been known to dispute Annapolis' moniker as "America's Sailing Capital," Santella says, but the city is undeniably the hub of the mid-Atlantic sailing community. "While it is home for some high-profile races — and the U.S. Naval Academy — a favorite nautical amusement for many Annapolites are the Wednesday night races, sponsored by the Annapolis Yacht Club, where 150 boats or more may compete," he says.


Massachusetts "Quaint Marblehead is custom-made for sailing, with water on three sides and a deep natural harbor," Santella says. "Historically, it was where Bostonians came to moor or race their sailboats." The port is a popular spot for starts and finishes of numerous races. "If there's one week to soak in the ambience of Marblehead, it would be the Marblehead Race Week, held each year at the end of July," he says.


Rhode Island Home to America's Cup races, this historic vacation spot for the well-heeled is a sailor's mecca. "Newport has it all: a deep-water harbor, a large navigable bay, easy access to the ocean and a great funneling sea breeze," Santella says. "Making landfall in Newport via the East Passage with the wind behind you is one of sailing's great moments."

Biscayne Bay

Florida "Biscayne Bay boasts beautiful turquoise waters, extending some 35 miles south from Miami to Key Largo," Santella says. "One highlight of the racing season is the Rolex Miami Olympic Classes Regatta, an Olympic qualifying event that draws 600 of the most talented sailors in the world." Santella suggests heading to Biscayne National Park, where "the 40 islands give a sense of what Florida was once like." 305-230-7275,

Resurrection Bay

Alaska "Alaska has more than 47,300 miles of shoreline, but sailors can get a good sense of the 49th state's sailing opportunities on Resurrection Bay, adjoining the town of Seward," Santella says. "You can sail south and anchor in a fjord in Kenai Fjords National Park and take in the glaciers, cast a line for a fresh coho salmon and watch sea lions, porpoises, orcas and gray, humpback and minke whales swim by." It's not all aquatic wonders you'll spy on this bay. "Moose, grizzly and black bears may also make an appearance on shore to complete your Alaska nature experience," he says.

Channel Islands

California In this archipelago of islands off California's southern coast, no two are alike. "San Miguel is exposed to harsh open-ocean conditions, where 50-mile-per-hour winds are common," Santella says, while calmer Catalina "sees more than 1 million visitors annually, thanks to its 20-odd-mile proximity to Los Angeles." Santella suggests visiting Santa Cruz Island for a break from hoisting sail, with offerings including hiking trails and sea caves.

San Juan Islands

Washington The San Juan Archipelago boasts 700 islands and appeals to the full spectrum of sailors. "There's the scenic beauty of distant snow-capped mountains and pine-studded shorelines, abundant anchorages whichever way the wind is blowing, and the variety of the islands themselves," Santella says. "You can rub elbows with blue-blooded sailors at Roche Harbor, hang out at fun and funky Friday Harbor or get away from it all on secluded Sucia Island. If you're lucky, you'll spy some of the 90 orcas that call the San Juans home in the summer." 888-468-3701,

Lake Michigan

Illinois With a nickname like "The Windy City," it's not surprising Chicago sustains a strong sailing community. "The city skyline is brilliant from the deck of a sailboat, especially as night falls," Santella says. "Sailing fever spikes in late July, when the Chicago to Mackinac race is held. The 333-mile race to a small island just beyond Lake Michigan's boundaries dates back to 1898.


Maine "With more than 3,500 miles of coastline — including hundreds of inviting deep coves and harbors — Maine is a sailor's delight," Santella says. Start your sail in Boothbay, and head north along the coast, he suggests. "Further north is Southwest Harbor and the pristine waters surrounding Acadia National Park; all along the way there's the opportunity to enjoy fresh lobster at dockside eateries."

San Francisco Bay

California "Many local sailors use three words to define San Francisco Bay: intense, exciting and exhilarating," Santella says. "Strong winds, powerful tides and currents and abundant commercial traffic make for challenging navigation. But racers who come out on top here know they've attained a high level of expertise." Views of the cityscape don't hurt, either.