Experience Our Nautical Fleet in St. Michaels, Maryland

The breadth and beauty of the fleet at Inn at Perry Cabin is a matter of pride and careful cultivation. From the timelessness of the 1902 Stanley Norman Skipjack, one of the last working skipjacks remaining on the Chesapeake Bay, to sleek Alerion sailing yachts, a classic Friendship 40, and the custom Hinckley Talaria 55 flybridge motor yacht, every vessel has been chosen for its character and its ability to show guests what this stretch of the Eastern Shore looks like from the water. The fleet serves every type of guest. Solo travelers and couples can join captained group sailings alongside others on the Miles River. Families and private groups can book exclusive two-hour, half-day, or full-day private charters on sailing or motor vessels. And for those who want something beyond a standard cruise, guided excursions range from oyster dredging aboard the Stanley Norman to a 4-hour Chesapeake voyage past the Bay Bridge to Annapolis. There is something here for every first-time visitor and every guest who has been coming back to St. Michaels for years.

What sets the Inn at Perry Cabin fleet apart is not just the quality of the vessels. It is the range of experiences only possible because of where the Inn sits. Depart from the Inn's private dock and you are on the Miles River in minutes, with the open Chesapeake Bay reachable by water without a car, a transfer, or a second reservation. The Skipjack Legacy Voyage takes guests aboard the 1902 Stanley Norman for a narrated historical sailing along the Miles River, connecting them to the oystering tradition that defined this region for generations. The Rum Running on the Skipjack experience pairs that same historic vessel with a curated Lyon Rum tasting on Wednesday evenings in summer, timed to coincide with the weekly sailboat races on the Miles River. The Explore the Chesapeake excursion boards the 55-foot Hinckley Five Star for a 4-hour voyage navigating past Kent Narrows, beneath the Chesapeake Bay Bridge, and into downtown Annapolis for a tour by water. Each of these experiences is bookable through the Inn's Guest Services team and is available to both overnight guests and day visitors seasonally.

Most resort sailing experiences require a trip to the marina. At Inn at Perry Cabin, the dock is part of the property. All charters and excursions depart from the Inn's private waterfront dock on the Miles River, giving guests direct access to the water from the moment they arrive. The Inn is located at 308 Watkins Lane in St. Michaels, Maryland, approximately 90 minutes from Washington D.C. and Baltimore. It holds a Forbes Four-Star rating and is a member of Historic Hotels of America, recognized for a nautical and cultural history that stretches back to 1815. Whether you are planning a romantic getaway, a family trip to the Eastern Shore, or a corporate retreat with something genuinely different on the agenda, the fleet at Inn at Perry Cabin gives every stay a reason to get out on the water.