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
Amber KodgesFantastic experience! We sailed on the Epiphany on Veteran’s Day for a mid-day 2-hour wine tasting cruise. Captain Jim and First Mate? Stephanie were so welcoming and friendly. Very relaxed atmosphere. Peaceful on the water. The boat was clean and well-maintained with lots of room and various options for seating. A lovely time and absolutely would go again. Thank you!
Nov 13, 2026 · Google Review
Elena CookeAmazing trip. Friendly crew and lovely companions. Will come back. Repeatedly. 🫶🏼
Oct 15, 2026 · Google Review
Rick DrakeWe enjoyed a relaxing mid-week cruise on Miss Patty. GM and Steph regaled us with historic anecdotes and current news. Do this you just want to enjoy the air and breeze on your face.
Oct 14, 2026 · Google Review
Matthew RevisMy wife and I had a lovely time on the sunset champagne cruise aboard Lady Patty during our honeymoon. It was a peaceful time on the water led by delightful crew. We would highly recommend.
Oct 3, 2026 · Google Review
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