Private Charters on the Chesapeake Bay in St. Michaels, Maryland

A private charter on the Chesapeake Bay is one of those experiences that fits nearly any occasion and elevates every one of them. Couples visiting St. Michaels for a romantic getaway find that a private sunset sailing on the Miles River is the kind of thing that does not need a special occasion to justify it. Guests planning a proposal have the full attention of the water, the sky, and the moment. Families with children who have never been on a sailing yacht find that two hours on the Bay converts even the most reluctant first-timers. Corporate groups and small executive retreats discover that a private motor yacht charter on the Chesapeake has a way of generating more genuine conversation than any conference room agenda. And guests who simply want to mark a birthday, anniversary, or celebration with something genuinely different find that the combination of a Forbes Four-Star waterfront resort and a private vessel charter is difficult to improve upon. Whatever the occasion, our Guest Services team can help tailor the experience, from vessel selection and duration to food and beverage arrangements and timing around the sunset.

Inn at Perry Cabin's private charter fleet includes six distinct vessels, each chosen for its character, quality, and ability to deliver a genuinely memorable experience on the Miles River and Chesapeake Bay. Sailing vessels range from the sleek and responsive Alerion Express 33 and Alerion Sport 38 to the classic Friendship 40 Stargazer, a fast and beautifully crafted sailing yacht with 360-degree views from the helm and a spacious teak cockpit suited for longer voyages. For guests who prefer to motor rather than sail, the Harbor Star Andreyale 33 French Canal Commuter offers elegant appointed salon seating for up to six passengers and reaches 18 knots with a whisper-quiet diesel engine, making it ideal for exploring the quieter reaches of the Bay and Miles River. The Hinckley Talaria 55 Five Star is the flagship of the fleet, a highly customized flybridge motor yacht capable of 40 knots and available through November, making it the natural choice for the Explore the Chesapeake voyage to Annapolis and any guest who wants the finest vessel on the Bay for their private charter. And for a private charter unlike anything else on the Eastern Shore, the 1902 Stanley Norman Skipjack is available for full vessel private bookings at a flat rate, offering exclusive access to a National Historic landmark vessel with its own captain and crew.