SAILING
Sailboats and the Chesapeake Bay are a classic combination. There’s nothing quite like being beneath billowing sails as you explore our waterways. Talbot County’s fleet of sailboats offers you a chance to slow down and soak in our stunning scenery. If you’re inclined, many boats will encourage you to hoist a sail or take the wheel. Should you find the experience irresistible, there happens to be no better place to take sailing lessons than right here.
Hilda M. Willing Skipjack Tours
Two-hour sailing tours aboard a 1905 historic Chesapeake Bay skipjack.
Inn at Perry Cabin by Belmond
Whether setting off on a tranquil chartered cruise or learning new skills on an in-depth sailing course, our fleet of luxury sailing vessels are sure to make a splash. For enquiries contact our Boating Concierge by calling 410-745-2200 or emailing ipc.waterfront@belmond.com
Lady Patty Classic Yacht Charters
A 1935-built offshore sailing yacht that sails daily; offering drink service including craft beer, wine and fresh-squeezed lime juice margaritas.
Selina II
Upscale and exclusive tours for just six guests aboard the vintage 41-foot 1926 sailing yacht Selina II, with two-hour day sails and romantic sunset champagne cruises from the St. Michaels Harbour Inn & Marina.
Skipjack H.M. Krentz
Relaxing and educational sailing aboard historic skipjack; offering two-hour sails and all-day charters. Bring your own food and beverages.
Skipjack Rebecca T. Ruark
Two-hour sails and group charters aboard the oldest working skipjack on the Chesapeake; enjoy nautical tales and ecology stories as told by a fifth-generation waterman.