Sailing the Chesapeake Bay from St. Michaels, Maryland
The Eastern Shore, as Experienced Only by Sea
Some places are best discovered from the water. At Inn at Perry Cabin, the Chesapeake Bay and Miles River are not just a backdrop; they are the experience itself. Our fleet of sailing and motor vessels offers one of the most distinct ways to explore Maryland's Eastern Shore, whether you are stepping aboard for a private sunset charter, a guided excursion to Annapolis, or a hands-on voyage aboard a working piece of American maritime history. Set sail on the 1902 Stanley Norman Skipjack, one of the last of its kind on the Chesapeake Bay, or choose from our collection of beautifully maintained sailing yachts and motoring vessels, each captained by an experienced crew and ready to take you somewhere memorable. Group sailings, private charters, oyster dredging experiences, rum-tasting voyages, and multi-hour Bay excursions all depart from the Inn's private dock on the Miles River in St. Michaels, Maryland. Whether you are a seasoned sailor or setting foot on a boat for the first time, there is a sailing or boating experience here designed for you.
Our Fleet: Sailing Yachts and Motor Vessels on the Miles River
The breadth and beauty of our fleet is a matter of pride and careful cultivation. From the timelessness of the historic 1902 Stanley Norman Skipjack to sleek Alerion sailing yachts, a Friendship 40, and the custom Hinckley Talaria 55 motor yacht, every vessel in the fleet has been chosen for its character, performance, and ability to make time on the water feel like something more than a boat ride. All sailing and motoring charters depart directly from Inn at Perry Cabin's private dock on the Miles River. No marina transfers, no extra logistics. Just you, the water, and the Eastern Shore stretching out in every direction.
Guided Excursions and Sailing Adventures on the Chesapeake
Beyond the standard charter, our excursions take guests deeper into what makes this stretch of the Chesapeake Bay so singular. Cruise aboard the Hinckley Five Star to Annapolis and explore the city by water. Dredge for oysters the way Chesapeake watermen have for over a century. Join a Lyon Rum tasting voyage on the Stanley Norman while catching front-row views of the Wednesday night sailboat races on the Miles River. Or set out to Wye Island by kayak or paddle board, guided by our crew. These are not amenities checked off a resort list. They are genuinely rare experiences that happen to begin at your hotel dock.
The Stanley Norman Skipjack: A Living Piece of Chesapeake Bay History
Step aboard the Stanley Norman and you are stepping into 1902. Built by boat builder Otis Lloyd of Salisbury, Maryland, and listed on the National Register of Historic Places, the Stanley Norman is one of the last remaining skipjacks that once worked the Chesapeake Bay's oyster reefs. She joined the Inn at Perry Cabin fleet as a teaching vessel, and today she carries guests on Skipjack Legacy Voyages and oyster dredging experiences along the Miles River, the same waters her crew worked more than a hundred years ago. For every ticket sold aboard the Stanley Norman, $10 is donated to 4ocean in support of ocean cleanup and marine conservation.
Group Sailing Charters from St. Michaels, MD
A champagne toast, open water, and the company of people you actually want to spend time with. Group sailing charters at Inn at Perry Cabin are available for solo travelers and couples who want to get on the water alongside others, as well as private groups looking for a shared experience with a difference. Captained two-hour group charters run on the Starbright, Starlight, and Harbor Star, departing from the Inn's dock on the Miles River. Morning, afternoon, and sunset departures are available seasonally from April through October.
Private Sailing and Motor Charters on the Chesapeake Bay
For guests who prefer the water entirely to themselves, private charters are available on every vessel in the fleet, from the intimate Alerion Express 33 to the full-length Hinckley Talaria 55 flybridge motor yacht. Two-hour, half-day, and full-day private charters depart from the Inn's private dock, and food and beverage packages can be arranged through our guest services team. Whether the occasion is a proposal, a family celebration, a corporate outing, or simply a desire for a few undisturbed hours on the Bay, private charters can be tailored to suit.
