Sailing in Fairfield

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Even as a flight attendant and marketing salesperson, Belinda Magruder never forgot her younger years as a crewmember aboard international sailing charters. The freedom of clinging to the wind as the boat raced across open waters continued to call to her, and one day she got an opportunity to go back. After a chance ad for a marketing position led Belinda to work for Getaway Sailing, she eventually took over the company. Since then, Belinda has filled Getaway Sailing's school with American Sailing Association–certified instructors, many of whom were raised on the bay and grew up manning the rigging of their families' ships. Some of the school's captains hold merchant mariner's licenses and boast year-round experience in running freighters via tugboat or beating Poseidon in weekend poker games.

A fleet of 17 boats at lengths of up to 35 feet conveys passengers through classes covering navigation and cruising, as well as certification courses and team-building trips. With the water gently patting hulls, boats cut through the sunshine and across the Inner Harbor or to the Francis Scott Key Bridge on day charters, or take longer trips to farther-flung stretches of aquamarine around Rockhall, Oxford, and St. Michaels. Evening races let larger boats jockey competitively with snails snapping a staccato rhythm against the darkening sky, and harbor sails put small groups out with a skipper, leaving them free to bar-hop or heckle passing schools of fish. Getaway Sailing's instructors immerse their students in the insular sailing world and have drawn members from as far as Hershey, including patrons who have volunteered to help staff the school's booth at boating trade shows.

2700 Lighthouse Pt E
Baltimore,
MD
US

Under the steady hand of Coast Guard-licensed captain Larry Vazzano, the Wharf Rat slices through the blue waters of Chesapeake Bay. The intimate vessel's sails harness the breeze, turning this way and that above the heads of passengers to find the best angle to the wind. Its decks bustle with activity of guests helping prepare sails or taking the helm as well as relaxed onlookers enjoying the unique view. Meanwhile, viewed from the cockpit dining table, the sun reaches its zenith and glitters off the peaks of waves, or dips slowly behind the forested shoreline, dyeing the whole world in orange, red, and purple.

Captain Larry loves this experience––the Atlantic Sailing Experience, as he calls it––so much that he's shared it with over 600 guests. In addition to his nautical know-how, he shows off his prowess at the grill for brunch and dinner, churning out tasty barbecue and vegetable sides from his own garden. Of course, he doesn't just sail and eat. He also charters his ship for exciting sailboat races and the occasional voyage to the end of the Earth.

1343 Old Water Oak Point Road
Pasadena,
MD
US

On the tree-lined shores of Sue Creek, the adventurous can ride stand-up paddleboards to explore the creek's calm waters. From the Baltimore Boating Center, the seafaring staff pairs its clients on boards suited to their skill levels. Paddlers launch from a newly constructed floating pier, meaning no one will have to mount their boards from a low-flying helicopter.

2015 Turkey Point Rd.
Middle River,
MD
US

Each morning, as the sun stretches skyward and begins to reflect on Chesapeake Bay, crews from the Chesapeake Bay Tours prep their vessels for another day of trips around one of America's most famous bodies of water. During their scenic outings, these seasoned captains lead groups past famous landmarks including Annapolis Harbor, the Chesapeake Bay Bridge, and picturesquely historic lighthouses. In addition to tour and cruises, guests can also book vessels for parties, adding some nautical flavor to birthdays, anniversaries, or celebrations of a new high score in Burger Time.

1904 Beeches Glory Path
Annapolis,
MD
US

Chesapeake Bay is home to legendary beautiful waters, diverse flora and fauna, and Paddlefest, an annual paddle-sports event organized by the team at Ultimate Watersports. Held on the Gunpowder River, which flows into the bay, the festival shows off the industry's latest toys, allowing attendees to try out brand-new kayaks and paddleboards on the sparkling fresh water. For the rest of the season, Ultimate Watersports brings its know-how to the shores with kayak tours, paddleboard lessons, and sailing trips that have remained a bay fixture for more than 26 years. Waterfront enthusiasts seek out the company's reliably well-maintained and up-to-date watercraft to do everything from gain a windsurfing certification to practice heckling standup paddleboard comics. Additionally, seasonal kids' camps help youngsters to stay active while gaining an appreciation for watersports and the splendor of the outdoors.

7200 Graces Quarters Rd
Middle River,
MD
US

If Annapolis Community Boating had it's way, everyone could go out and explore the water on a boat, even if they couldn't afford to own boats of their own. That's why its team of volunteers and instructors?along with a fleet of 35 vessels?open up maritime activities to anyone in the neighborhood. It uses this fleet to run a variety of boating programs including youth summer camps and sailing lessons to teach people how to navigate on their own in the great outdoors without needing directions from local walruses. Weekend rentals, on the other hand, let you venture out wherever your imagination can take you on a kayak, canoe, or paddle board.

P.O. Box 4367
Annapolis,
MD
US