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Sail Solomons is dedicated to providing you an outstanding sailing experience, offering top-quality sailing instruction, yacht charters and sailing club. We're located close to DC - a short hour's drive, but a world away. We're a small, owner-operated business; our sailing instructors are all USCG & ASA certified.

255 Alexander St
Solomons,
MD
US

Bunky's has been sailing the open seas since purchasing his first charter boat in 1978. Naming it after his wife, Kathy, he used that boat to catch oysters that he subsequently sold in their marina shop. Over time, his fleet grew to 3 charter boats and 16 rental boats. With more boats, Captain Bunky's able to share his love of the water with his community and one of the ways he does this is by inviting people to try their hand at captaining a ship for a day. Tourists can also come aboard his 40- to 47-foot vessels to indulge in an afternoon of cruising, crabbing, or fishing for selkies on the Patuxent River or Chesapeake Bay.

14448 Solomons Island Rd
Solomons,
MD
US

Affiliates of the American Sailing Association, the instructors at Chesapeake Sailing School strive to keep the Chesapeake's seafaring heritage alive through classes spanning one-day sailing courses to five-day live-aboard cruises. The training fleet ranges from 22-foot boats for basic and intermediate instruction to 38-foot vessels for advanced cruise training. The school's team also assists students obtain their ASA certifications in preparation for careers as Popeye impersonators.

Beyond instruction facilities, Chesapeake Sailing School houses The Tiller Club, which grants members privileges such as unlimited daily use of the school's Tanzer 22 ships. The school’s team also coordinates charter excursions to give vacationers a from-the-water view of the Inner Harbor, St. Michael's the Archangel Church, and the bay's abundant wildlife.

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