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
rene tywangWhat a wonderful experience! Very intimate short trip, just 2 hours. Just six passengers with Captain Iris and first mate John. We were not experienced sailors and we were made to feel very comfortable while getting the real "on the water" vibe. Lovely early afternoon spin in the beautiful "Selena II" with some wine and lovely conversation. Highly recommend! Glad to be a tiny part of her 100 year journey. Would have done the evening sail but they were sold out. Charming.
Oct 10, 2025 · 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
Sarah MorganAmazing Experience! We sailed on the Lady Patty (but also admired the catamaran Epiphany) and had an absolutely lovely experience. Our captain (John), first mate (Ren), and owner treated us to two hours of sailing, gorgeous sights, and fun stories. They were all the perfect mix of easy and fun to chat with while simultaneously giving you space to enjoy the experience with friends and family. We already have plans to come back to St Michael’s and when we do, we’ll for sure be booking another cruise with St Michael’s Sailing Charters!
May 31, 2026 · Google Review
Spencer BlakeMy captain, Amy, and deck mate, Brian, were the definition of outstanding service. I had an absolutely incredible experience aboard the Epiphany. I was initially concerned about whether my emotional support dog would be accommodated, but they welcomed both of us without hesitation and made us feel completely at ease. Amy took the time to show me the functions of the impressive 44-foot sailboat and patiently answered all of my questions. I truly appreciated her knowledge, curiosity, and willingness to share her expertise. Brian was equally exceptional—professional, thoughtful, and attentive throughout the trip. He made sure my dog was comfortable and well cared for, which meant a great deal to me. The sunset cruise exceeded all of my expectations. St. Michaels is a beautiful destination, and experiencing it from the water made it even more memorable. The sailing was smooth, relaxing, and enjoyable from start to finish. I cannot thank Amy and Brian enough for making this outing so special. I will absolutely recommend St. Michaels Sailing Charters to my friends and family. Thank you for a wonderful experience and a truly unforgettable evening! ⭐⭐⭐⭐⭐
Jun 22, 2026 · Google Review
Tiffany PhillipsMy daughter and I absolutely LOVED our two hour sailboat ride aboard the Selina II and recommend it highly. Iris, our captain, and Matt were wonderful and engaged us in great conversation and imparted a wealth of knowledge about their unique boat, the beautiful area including it’s history, and all things nautical. I also enjoyed a delicious glass of champagne onboard. If you are traveling to St. Michaels, I highly recommend you book a trip on the Selina II. You will disembark feeling relaxed and refreshed and wanting to do it again the next time you visit! Thank you, Iris and Matt for an amazing adventure!
Sep 28, 2025 · Google Review