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
Bonnie DunkelThe Lady Patty was the perfect way to experience St. Michael’s! The staff made the whole experience seamless and fun and there’s no better way to spend an evening than with a glass of champagne enjoying the sunset on the water. Would absolutely book again if we come back!
Sep 14, 2026 · Google Review
Denise BramhallWe enjoyed the Wine Tasting Sail on Friday afternoon. Both the captain and his first mate were pleasant and made the trip very enjoyable. We were encouraged to sit up front on the bean bag chairs which was the perfect spot. It was so comfortable and allowed us the best view of the Bay.
Sep 13, 2026 · Google Review
TylerVery enjoyable sailing charter. The wind didn't quite cooperate. But it was still a beautiful cruise. Winds typically die down during the summer, so I'd recommend booking a charter in the spring/fall.
Sep 9, 2026 · Google Review
Bob WilliamsMy wife and I did a quick pre-Labor Day getaway to St. Michaels and our afternoon sail with beer/wine tasting was definitely a highlight of that trip. Tim and John were both fantastic and knowledgeable hosts. It was hot the day we went and we reserved the 3pm cruise and had it all to ourselves. Tim joked that we could have rented out the whole boat, or just made a reservation and gotten lucky (we did!). We sailed on the Lady Patty. It's an older boat, but you can tell that the owners took love in restoring her and meticulously care for her. There was ample space for at least another 20-25 people aboard and it still wouldn't have felt cramped. It was a wonderful experience. We felt the stress melt away the further into our sail we went. I'd highly recommend St. Michaels Sailing Charters for anybody visiting St. Michaels, or who lives nearby and doesn't have their own sailing vessel.
Sep 9, 2026 · Google Review
Teal BakerTom & Steph were a great crew on a beautiful morning on the Bay!
Sep 7, 2026 · Google Review
Jason LombardWe had a great time out on the water with Rob (captain) and Steph. They not only sailed us around the Miles River, but also shared a general history of St. Michaels and the area. It was an enjoyable trip, and we would happily do it again!
Sep 1, 2026 · Google Review
Court LEasy sail boat ride with wine tasting. We took the lady paddy, which was beautiful.
Aug 23, 2026 · Google Review
RoseAnn MargolisCaptain Jim and mate Josee were phenomenal hosts. They made our cruise one of the most memorable experiences of a lifetime. Our sunset cruise was enchanting and the Epiphany is a beautiful ship with all the comfort and amenities one could ever wish for while on a cruise. The sunset was beautiful and this extraordinary cruise will forever hold a special place in our hearts. It was a pleasure meeting Daniel and Andrea as well. Everyone was so friendly and accommodating. Much success to them all!
Aug 19, 2026 · Google Review
Lisa WarnkeWe took the sunset cruise on the Lady Patty this past Sunday and we had an amazing time. Cpt Yvonne and her first mate (I am so sorry that I forgot his name) were absolutely amazing. They were so knowledgeable about the surrounding area and told great stories as we sailed. We had never been on a sailboat before and it was so much fun. Highly recommend this tour.
Aug 18, 2026 · Google Review
Sam PalmerBeautiful boat with a fascinating history and a Captain and First Mate who made it even better. I arrived on probably the most calm day of the month but we still managed to sail the majority of the trip. I can only imagine the ride when the wind picks up! Lovely scenery, can't go wrong!
Aug 16, 2026 · Google Review