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History of St. Michaels Sailing Charters, St. Michaels, Maryland

St. Michaels Sailing Charters History on the Eastern Shore of Chesapeake Bay

Hop Aboard St. Michaels Sailing Charters for your personalized boat tour

Ahoy from the team at St. Michaels Sailing Charters! Providing the most personalized and enjoyable boat tour on the Eastern Shore of the Chesapeake Bay is our top priority.

Pictured to the right are owners GM and Laura Bell. GM has been sailing since childhood and previously taught sailing at the Miles River Yacht Club in St. Michaels, Maryland. His sailing adventures have taken him across the Mediterranean Sea, Mexico, Hawaii, California, the U.S. East Coast from Rhode Island to Florida, the Delaware River, and much of the Bahamas and Chesapeake Bay. He has held a U.S. Coast Guard captain’s license since 2014. Laura also grew up sailing with her family on various monohull sailboats and now has several years of experience sailing Epiphany along the East Coast and throughout the Bahamas. She is also the owner and photographer behind Laura’s Focus Photography.

GM spent several summers serving as first mate to Captain Iris aboard the historic Selina II. In 2025, we are honored to “take the helm” of Iris’s company, Sail Selina, as we continue to grow St. Michaels Sailing Charters. After several seasons operating on Broad Creek, we will be moving across the harbor for the 2026 season and beyond, sailing from the same Harbour Inn & Marina dock previously home to the Selina II.

We’re thrilled to offer two unique sailing experiences: a historic journey aboard our 1935 ketch, Lady Patty, or a modern adventure on our 44-foot luxury catamaran, Epiphany. Both yachts can accommodate up to 13 guests.

We are very excited about our addition of historic Lady Patty to our fleet. This 1935 Maryland built boat brings nearly a century of maritime history back to the Chesapeake Bay. You can read more in this What’s Up Media feature article!

Black and white photo of a sailboat with two sails on water.

Whether you join a public tour or book a private charter, every sail includes a relaxing cruise with our knowledgeable captains and friendly crew. Booking your adventure is simple—our online system lets you reserve your boat cruise in just a few clicks.

Your journey begins with a peaceful glide through the harbor, passing the Chesapeake Bay Maritime Museum and the iconic Hooper Strait Lighthouse. We’ll also cruise by the Inn at Perry Cabin, famously featured in the movie Wedding Crashers. As we head out into the Miles River, keep an eye out for wildlife—osprey, bald eagles, and local watermen harvesting the Chesapeake Bay’s renowned blue crabs. Once we reach open water, you’re welcome to help raise the sails or simply sit back and relax as the wind fills the canvas.

Don’t miss out on this unforgettable experience! For more details, give us a call at 410-849-9864. Ready to set sail? Book your cruise tickets today and start your adventure!

 

Smiling couple in sunglasses on a boat deck with ocean and sailboat in the background.
Choose Your Sailing Trip
Comfortable Seating on Selina II.Sturdy Double Settees on either side of the ship’s wheel offer seating on cushions for 2 big people. Or sit in our vintage captains chairs with cloth seats located on the cockpit sole for seats that offer back support. All seating offers good visibility from the cockpit area where you will be sitting. Occasionally guests ask to go forward and sit on the hard cabin top. You are welcome to do so if you have good balance, are sure footed, and can hold a hand rail.

Seating

Both of our sailing yachts have lots of cushioned seating. Epiphany also offers shaded areas and lounging chairs.

Tasty Champagne onboard Selina II, a cava from Spain. Enjoy our bubbly from custom etched champagne flutes created specially for our exclusive guests aboard sail selina in st michaels md

Refreshments

Soda, Cold Craft Beer, Wine, and Champagne are available for sale during all trips. Bottled water is complimentary.

Onboard Bathroom Facilities, Yes, we have a very clean marine head onboard for your convenience; however, it is limited and located down four steps. To ensure your maximum comfort during your journey, we recommend you make use of the shore-side facilities inside the Harbour Inn before embarking.

Toilet

There are marine heads onboard; however, it is limited, so we recommend that guests take advantage of the shore-side facilities inside the Harbour Inn before embarking.