Our Fleet
Meet Our Fleet in St. Michaels, Maryland
A Nautical Heritage Rooted in the Chesapeake Bay Since 1819
Founded in 1819 by Navy man, seafarer, and hometown hero Samuel Hambleton, the nautical heritage of Perry Cabin runs deep, a fact that is reflected in every vessel of our esteemed fleet. Hambleton's connection to the water was not incidental. He was a decorated officer of the United States Navy and a key figure in the Battle of Lake Erie, and the property he built on the Miles River carried that maritime spirit from its very first days. More than two centuries later, that spirit is alive in a fleet of sailing yachts, motor vessels, and a historic 1902 skipjack, all available for private charters, group sailings, and guided excursions on the Chesapeake Bay.
All vessels depart from Inn at Perry Cabin's private dock on the Miles River in St. Michaels, Maryland, roughly 90 minutes from Washington D.C. and Baltimore.
Reserve your experience through the Concierge Team by calling 443.258.2228 or emailing [email protected].
Private Charters
Personalized Luxury Excursions on the Miles River and Chesapeake Bay
A private charter at Inn at Perry Cabin means the vessel is yours. No shared deck, no other guests, no fixed route unless you want one. Just you, your group, a seasoned captain, and the full expanse of the Miles River and Chesapeake Bay ahead of you.
Group Sailing Charters
Sail the Miles River with Good Company
Perfect for solo travellers, couples, and small groups looking to get out on the Chesapeake Bay without booking an entire vessel to themselves, these captained group charters offer a genuine sailing experience aboard some of the most beautifully maintained vessels on the Eastern Shore of Maryland.
