Best Historic Sailing Yacht Tours and Luxury Catamaran Sailing Experiences on the Chesapeake Bay!
Looking for a relaxing boat tour in Saint Michaels on the Chesapeake Bay? Hoping to get out on the water, unwind, and spend some time in nature? If you’re searching for things to do in St. Michaels, MD or exploring the top local attractions, our luxury sailing yachts—Lady Patty and Epiphany—are the perfect choice. From historic charm to modern comfort, St. Michaels Sailing Charters will take you out for a memorable and peaceful day under sail.
Choose between our two stunning sailing yachts: the historic Lady Patty, a 1935 Maryland-built ketch, or Epiphany, a spacious and modern 44-foot Leopard catamaran. Each sail includes a two-hour (or longer) cruise with knowledgeable, first-class captains and a friendly crew dedicated to creating an unforgettable experience. Enjoy our popular day sails or opt for specialty outings like sailing lessons, wine and beer tasting cruises, and more.
Our sailing yachts are docked at the Harbour Inn & Marina in the heart of St. Michaels, Maryland—a charming Eastern Shore town known for its incredible seafood and inviting small-town atmosphere. Whether you’re planning a day trip to St. Michaels or seeking a sailing charter on the Eastern Shore of the Chesapeake Bay, our relaxing sailboat excursions are conveniently located just 90 minutes from Philadelphia, Baltimore, and Washington, D.C., and only an hour from Annapolis.
Out on the open water, our sailboats offer your choice of a public or private cruise in one of the most beautiful places to sail. Chesapeake Bay sailing is renowned for its stunning scenery and unforgettable sunsets. Your charter begins with a peaceful glide through the harbor before heading out into the Miles River, where you’ll enjoy sweeping views and, if you’re lucky, wildlife sightings like osprey and bald eagles. This year, we’ve even spotted porpoises!
Learn more about the history of our sailboats and all the fun outdoor activities in St. Michaels, MD here:
Our Popular St. Michaels Maryland Sailing Charters and Relaxing Chesapeake Sailboat Cruises
The #1 Boat Tour in St. Michaels!
A 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!
– Erin Parfitt, Google Reviews
We had a fantastic experience with Captain Scott and First Mate Diane on board the Epiphany during a wedding weekend getaway with our family of six. The catamaran was beautiful, spacious, clean, and perfect for cruising the Chesapeake Bay. Captain Scott was professional, knowledgeable, and shared great insight about the area, making the tour both relaxing and informative. First Mate Diane was incredibly warm and welcoming from the moment we stepped on board. It was our first time in St. Michael’s, and seeing the region by water was the perfect way to take in the charm and natural beauty of the Bay. A wonderful memory for all of us—we highly recommend this experience to anyone visiting the area!
– Angeli Breen, Google Reviews
I surprised my boyfriend with a sunset cruise with St. Michael’s Sailing Charters for his birthday. We had such an amazing time! Laura and GM were amazing hosts and we felt truly pampered. The catamaran is stunning and so comfortable. I highly recommend it!
– Jennifer Fowler, Google Reviews
AMAZING! Words cannot describe how perfect everything was aboard the gorgeous and spacious Epiphany, and the friendly and fun atmosphere with Captain Scott & First Mate Diane! We celebrated my parents 50th anniversary and they surprised us with decorations! They were also extremely welcoming and accommodating to my 6 year old daughter who was so excited to explore the boat as well as my husband who was newly on crutches. We loved every minute and will absolutely do this again in the future!
– Kelly Upton, Google Reviews
Hands down the best way to see Maryland! We had such a fabulous time on the water in such a beautiful boat. Diane is amazing! She went out of here way to make sure it was a memorial event and Captain Scott knew all the best places for the perfect views. We will definitely be back next time we visit. Thank you both so much!
– Tamara Lawrence, Google ReviewsWhy St. Michaels Sailing Charters?
Rated #1
When looking for things to do in St. Michaels MD, our reviews tell the story! St. Michaels Sailing Charters is ranked the #1 Maryland sail boat tour in St. Michaels.
Everything Is Included
Sit back and relax. Want a drink? We’ve got it! Cold beer, red & white wines, Champagne, and soda are available for sale on all our sailboat rides and are included on our evening charters.
Over 90 Years of Experience
Our top-notch captains have a combined sailing history of 90+ years, and our friendly crew has a combined sailing history of 30+ years. We all love to sail and we love taking people for sailboat rides!
Spacious & Beautiful Boats
Lady Patty was built in 1935 in Solomons Island, Maryland as an off shore racing boat and later restored as a charter sailboat. She spent her early days in Florida racing for the Southern Ocean Racing Conference circuit and won a race from St. Petersburg to Havana, Florida.
Epiphany is a modern 44 foot Leopard catamaran built in South Africa. This spacious sailboat has forward and rear shaded areas, dining tables, and a large trampoline area for stretching out and enjoying the sun. Both of our boats can accommodate 13 of your family and friends.
The Best Captains
Our St. Michaels boat tour captains are known for their storytelling skills and offer a boat trip balanced with some touring, some sailing, and some time to simply relax, unwind and kick back. When sailing on the Chesapeake in St. Michaels, choose from a basic sailboat ride, or opt for a specialty outing like a local craft brew beer tasting cruise or a sunset champagne charter.