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
Veronica BarnettWe had an absolutely incredible evening on the Champagne Sunset Tour with St. Michaels Sailing Charters! The Epiphany catamaran was spotless, spacious, and extremely comfortable. The captain and first mate were warm, attentive, and so knowledgeable, making the whole trip feel relaxed and special for our family. We even had food from a local shop delivered directly to the sailboat—it was delicious and the portions were huge! The sunset views were breathtaking and made for a truly memorable night. Highly recommend this company to anyone visiting the area!
Aug 8, 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
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