Sailing in Severna Park

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Under the steady hand of Coast Guard-licensed captain Larry Vazzano, the Wharf Rat slices through the blue waters of Chesapeake Bay. The intimate vessel's sails harness the breeze, turning this way and that above the heads of passengers to find the best angle to the wind. Its decks bustle with activity of guests helping prepare sails or taking the helm as well as relaxed onlookers enjoying the unique view. Meanwhile, viewed from the cockpit dining table, the sun reaches its zenith and glitters off the peaks of waves, or dips slowly behind the forested shoreline, dyeing the whole world in orange, red, and purple.

Captain Larry loves this experience––the Atlantic Sailing Experience, as he calls it––so much that he's shared it with over 600 guests. In addition to his nautical know-how, he shows off his prowess at the grill for brunch and dinner, churning out tasty barbecue and vegetable sides from his own garden. Of course, he doesn't just sail and eat. He also charters his ship for exciting sailboat races and the occasional voyage to the end of the Earth.

1343 Old Water Oak Point Road
Pasadena,
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

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

Let's Go Cruising blows encouraging winds into the sails of aspiring first mates with expert instruction, yacht rentals, and luxury charters in Chesapeake Bay. Break free from lackluster land and the constant fear of rockslides by plunging into luxury-cruise accommodations in one of Let's Go Cruising fully equipped luxury yachts, decked out with opulent amenities such as flat-screen TVs, kitchens, and a wealth of sunlight-welcoming windows. A skilled skipper is assigned to each trip, ensuring the entire crew has a safe and stress-free trip. Each yacht can comfortably take in as many as 11 guests, making it an ideal choice for families, co-ed softball teams, or a band of swim-exhausted seals. Charterers have the added benefit of determining the trip itinerary, sailing routes, and destinations. To spice up destination ideas, check out Let's Go Cruising's three-day itineraries or apply a Wasabi brain tonic.

300 2nd Street
Annapolis,
MD
US