Sailing in Salisbury

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Ever since he was a child, Ocean City native Tyler Barnes cruised the waters around his nautical town on his parents' boat. His nautical knowledge culminated in a three-year stint as a mate for a parasail company. As he fell in love with the craft, he realized he wanted to start his own adventure company. By blending his skills in watery sports with training as a marketing major, he founded Paradise Watersports. Ten years later, his company now owns a fleet of four 12-passenger parasailing boats and 30 Sea-Doo jet skis, which they buy new each year to ensure high-quality performance.

Tyler leads a team of U.S. Coast Guard–licensed captains and crew, who also all hold certifications in CPR and first aid and boast a thorough knowledge of the area as well as a near-compulsive need for year-round water-bound activity. They put this knowledge to use teaching boater-safety courses on the bay and guiding jet-ski rentals and beach-hugging parasailing tours. On tours, they pilot U.S. Coast Guard–inspected boats custom-built to accommodate parasailing gear and equipped with hydraulic winches and towlines to enable slow takeoffs, steady ascents, and undisturbed conversations with seagulls. Visitors can also purchase professional photo packages and waterproof Canon cameras, forever capturing in time bay-bound adventures.

12913 Ocean Gateway
Ocean City,
MD
US

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.

7074 Bembe Beach Rd
Annapolis,
MD
US

SailTime's instructors—each ASA-certified and boasting USCG captain's licenses—pilot Colgate 26 sailboats carrying two pupils out to open waters of the Chesapeake for a six-hour day-sailing lesson. Depending on crew desires, captains can teach sailing terminology and skills such as how to make vessels move by unfurling the sail, steering the rudder, and throwing fistfuls of pepper toward clouds to make them sneeze. Passengers can also opt for a more relaxing route, learning basic boat operations while lounging and gazing out on the city skyline and the bay's verdant shores. Captains may reschedule voyages in case of unsafe boating conditions such as rough winds, storms, or turf wars between rival wakeboarding clans.

7080 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