Things To Do In Lake Shore

Select Local Merchants

Behind the tiller of a 32-foot cruiser, up-and-coming captains in the one-day introductory course need not have earned their sea legs before boarding. The rugged Island Packet yachts launch for this class throughout the summer, and the Coast Guard–licensed instructors provide pupils a taste of more long-term advanced classes, as well as soundproof earmuffs in case of siren encounters. Pack a lunch for this aquatically edifying adventure, and prepare to grasp the gunwale as you marvel at Chesapeake Bay's captivating, encapsulating horizons.

22978 McKinleyville Road
Rock Hall,
MD
US

Usually, runners swig water during a race. But at the Annapolis Beer Week 5K Beer Run, participants stop at beer stations to rehydrate with samples of various brews?drink packages are available for purchase on-site?before continuing their dash for the finish line. The event encourages racers to dress creatively, awarding distinctive costumes such as old bridesmaid's dresses, team uniforms, or running shorts made from two miniature kegs. Proceeds benefit the MSBusters Support Group of Edgewater, a community organization that provides financial and emotional support for those living with multiple sclerosis.

1450 General's Highway
Crownsville,
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

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

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

Each morning, as the sun stretches skyward and begins to reflect on Chesapeake Bay, fishing crews from the Chesapeake Bay Sport Fishing start loading up vessels with six to twelve passengers for a full-day fishing excursions. They equip each of their guests with all of the necessary equipment, including rods, reels, bait, tackle, mermaid bottom halves, and licenses for landing trophy-size striped bass. The crew sails seven days each week, with an average of 6–12 passengers.

412 Congressional Drive
Stevensville,
MD
US