Nothing says summer like spending the day sailing. For our fourth installment in the “Spend the day on the water” series we are providing places your family can head our for a sail on the Chesapeake Bay and its tributaries.
Whether you want to learn to sail or just sit back while someone else takes the helm, there are plenty of options for both in the Annapolis area.
“Sailing can help families to get in touch with the Bay,” says Jamie Lane of KidShip Sailing in Annapolis. “It’s a great way for kids to unplug, but it also promotes teamwork and the opportunity to learn a new skill.”
Places to set sail on the Chesapeake
Chesapeake Bay Maritime Museum, St. Michaels
Take a ride on an authentic historic skipjack, the H.M. Krentz, which sails daily from the Chesapeake Bay Maritime Museum in St. Michaels. This 1955 working skipjack has a roomy and comfortable deck perfect for families with children of all ages. Climb aboard for a 2-hour journey around the Chesapeake, Miles and Choptank Rivers with Captain Ed Farley, who is also a commercial oysterman.
“We love having kids on the ship,” says Captain Ed, who encourages young sailors to help steer, dredge for oysters, and explore his treasure trove of artifacts found on past sails. Families can even pack their own food and drink for the journey.
213 N. Talbot St., St. Michaels
South River Boat Rentals, Edgewater
Sail down the South River and past the Thomas Point lighthouse on a sailing adventure with South River Boat Rentals. Choose from 10 different sailboats ranging in size from 24-37 feet. Captain your own boat or hire an instructor for a half-day or a full-day excursion.
Prices vary depending on boat size, starting at $300/half-day rental without instruction
2802 Solomons Island Road, Edgewater
KidShip Sailing School, Annapolis
Enjoy sailing instruction “The Annapolis Way” through the KidShip Sailing School. The 3½-hour course is designed for families of two adults and up to three children and provides hands-on learning on 24-foot Rainbows. Learn water safety, sailing terminology, capsize recovery, sail trim and steering with a tiller.
For more confident sailors, rent your own rainbow from the adjoining Annapolis Sailing School and glide past the Naval Academy or further south towards Tolly Point. Annapolis Sailing School offers full- and half-day sailboat rentals and optional private instruction for families.
Half-day family course, including boat and equipment: $395
KidShip Sailing School
Sailboat Rentals: $160/half day, $250/full day
Advance reservations strongly advised.
Annapolis Sailing School
7001 Bembe Beach Road, Annapolis
Schooner Woodwind, Annapolis
Kick back and relax as you cruise down the Chesapeake on the Schooner Woodwind, a 74-foot wooden schooner that sails from the Annapolis Marriott four times daily in the summer. Help hoist the sails, steer the ship or just enjoy a cocktail or refreshment as your family takes in the scenery from the Bay Bridge to Thomas Point.
Two hour sailing cruises: adults $41-46, children $29
Advance reservations required.
80 Compromise St., Annapolis
Be sure to see the other parts to the series Spend the day on the water: Fishing with the family and Spend the day on the water: Paddling a kayak, canoe or paddleboat and Spend the day on the water: Tubing down a MD river
Updated May 2019