Sailing in Annapolis

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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 Road
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.

7082 Bembe Beach Road
Annapolis,
MD
US

Established: 2009

Handicap Accessible: No

Staff Size: 1 person

Parking: Parking lot

Reservations/Appointments: Required

Most popular offering: Half-Day and Sunset Sailing

Pro Tip: Bring sunscreen, hats, and a smile

Q&A with Tony Ireland, Captain

What inspired you to start or run this business?

Before starting Classic Sail Charters, I volunteered with a community sailing organization that exposed people to sailing who had never sailed before. Most of the participants in the program realized the special calm joy that comes after casting off lines and raising sail. Gliding quietly through the water under sail seems to wash the stress away, and it was apparent in their eyes and faces. After 25 years working in corporate offices, I decided this was for me.

What?s your favorite part about your job?

Helping people get away from it, and watching the faces light up.

Is there anything else you want to add that we didn't cover?

Sailing yachts is a sporty activity that requires some mental concentration, as well as some physical strength. When the wind is up and the boat pitches and rolls a bit, it is not the best or safest activity for children under 7, nor is it much fun for the parents.

What is the best reaction you?ve ever gotten from a customer?

"Thank you, that was wonderful."

105 Eastern Ave
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

Each morning seven days a week, as the sun stretches skyward and begins to reflect on Chesapeake Bay, crews from Chesapeake Bay Sport Fishing prep one of their three vessels?Jessie Girl, Net Profits, or Gotcha?for another day of fishing trips around one of America's most famous bodies of water. During their scenic outings, these seasoned captains equip groups with fishing gear and sail past famous landmarks including Annapolis Harbor, the Chesapeake Bay Bridge, and picturesquely historic lighthouses. At the end of the trip, the crew offers fish cleaning services so anglers can take home their catches. Guests can also book vessels for parties, adding some nautical flavor to birthdays, anniversaries, or celebrations of a new high score in Burger Time.

412 Congressional Dr.
Stevensville,
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