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At Annapolis Sailing School, the instructors prefer hands-on teaching to traditional textbook methods. They’ve developed this approach ever since their first lesson in 1959, when the school opened. Many lessons later, the staff continues to introduce novice sailors to the sea aboard their fleet of vessels, which includes a rainbow sailboat and a cruiser. From the get-go, students are encouraged to man the jib and barter with Poseidon over the choicest sailing routes. In addition to these private and group sailing lessons, the staff also rents out sailboats and offers a certification program that adheres to the American Sailing Association’s program.

7001 Bembe Beach Rd
Annapolis,
MD
US

Annapolis Bay Charters is the oldest, largest and most respected boat charter company on the East Coast. We have sailboats from 34' to 54' both monohulls and catamarans. Each boat is meticulously maintained and set up for your total enjoyment, skippers and cooks available for extra safety and luxury!

7076 Bembe Beach Rd
Annapolis,
MD
US

The J/Boats sailing vessels at J World Annapolis serve as floating classrooms for students of all skill levels as they improve their sailing techniques under the tutelage of expert coaches. Budding buccaneers can make smooth forays into the sport via one of the school’s many Learn to Sail courses, which range from three-hour group lessons to five-day comprehensives. Up to four students of similar experience levels control the ship from the time they unmoor until they return, rotating through the different onboard positions while the instructor keeps a close eye on safety, expounds upon sailing theory, and warns the team of upcoming whale mouths. From there, intrepid sailors can choose from a variety of courses geared toward continuous improvement, culminating in the advanced racing course for expert speedsters.

213 Eastern Ave
Annapolis,
MD
US

Chesapeake Bay is 200 miles long, but that’s not the only reason it’s the United States’ largest estuary. The Bay also serpentines off into hundreds of rivers and creeks, accessible with South River Boat Rentals’ vessels. Seafarers explore the estuary’s fringes in the powerboats and sailboats, cruising past historic sites, such as Jamestown and Tangier Island. Alternatively, fishing parties set sail for piscatorial hot spots, casting from the boats’ decks. To teach newbies the ropes before they hit the water, the company’s team hosts sessions on boating basics, from steering to stopping at fish crossings.

2822 Solomons Island Rd
Edgewater,
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

Located on the campus of the Baltimore Museum of Industry in the Inner Harbor, the Downtown Sailing Center gives budding seafarers an opportunity to whiz down aquaroads without the cost of boat ownership or maintenance. Each crew membership offers Wednesday-evening and bi-monthly Sunday sail sessions. Members will also be invited to attend the monthly social activitity. Enjoy the fall season’s prime sailing conditions with today's side deal, which offer steady breezes coupled with warm sunshine and a diminished chance of encountering traffic jams.

1425 Key Hwy
Baltimore,
MD
US