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.
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.