St. Michaels Sailing Charters
St. Michaels Sailing Charters offers relaxing and scenic sailing experiences on the Chesapeake Bay aboard the historic 1935 ketch Lady Patty and the 44-foot modern sailing catamaran Epiphany. With her classic wooden construction, tall masts, and traditional rigging, Lady Patty delivers a sailing experience that feels timeless, while Epiphany offers a spacious, smooth, and comfortable ride designed for effortless cruising.
Whether you’re looking for a relaxing cruise on the Miles River, a sunset sail, or a private charter with friends and family, each vessel provides a unique way to experience the Chesapeake. Guests can also enjoy wine and beer tastings and special events, all led by experienced captains.
Lady Patty and Epiphany can accommodate up to 13 guests for an intimate experience. Charters depart from Harbour Inn Marina & Spa in the heart of St. Michaels, Maryland.
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Google Reviews
Maria CabellAwesome sunset cruise on a beautiful sail boat. The captain and first mate were informative and were wonderful to talk to. The weather was very cooperative as well and we enjoyed a peaceful sail with a wonderful sunset. A free glass of champagne, soda or wine was a nice added touch. We definitely recommend this company.
Jul 18, 2026 · Google Review
Suzanne PacittiWe just had the most wonderful afternoon with Captain Jim and first mate Andrew! We sailed the Epiphany at 4 pm. BEAUTIFUL, comfortable boat. Fantastic seating options – lots of shade. My fave were the bean bag chairs on the bow. Highly recommend this for a relaxing, fun experience. Thanks guys!
Jul 27, 2026 · Google Review
Emily BarnesWe went out on Epiphany for a sunset sail with Captain Mike and first mate Brian (sp?) last night, a Saturday. It was truly unforgettable for many reasons. 1 -The team – we were in great hands with Capt Mike and he is a superb and genial sailor. We spent most of the time on the bow with FM Brian and he was a most scintillating company. Our faces are still recovering from unending smiles and laughter. It felt like we’d known him our entire lives and we will never forget his company. 2 – we saw several bald eagles and two did the courting death spiral. Seeing this was once in a lifetime and we couldn’t have asked for better people to experience it with (also shout out to the other fine couple who we enjoyed the sail with). 3 – the catamaran was most comfortable and conducive to relaxation. 4 – the views of St. Michael’s never cease to cause us wonder. It was, indubitably, our favorite and most memorable of all our sails.
May 3, 2026 · Google Review
Zachary PrehnTook my wife to St. Michaels for her 40th birthday and went sailing with captain Rob C and John H. Both were amazing! The boat was beautiful and very well maintained. Would highly recommend if you’re in St. Michaels.
Jul 1, 2026 · Google Review
Erin PhilbinA simply magical experience on the water with Captain GM and first mate Laura. Consummate hosts! The boat is gorgeous and spotless. We had our choice of great seating at the front and the back of the boat. Laura served us our champagne and offered to prepare our charcuterie. (We were too engrossed in the sailing to want to eat though!) It was a perfect day for a sail and everything was amazing. Can’t imagine a better day on the water. Highly recommend this experience! Don’t miss it!
Oct 22, 2025 · Google Review