THE ADVENTURE COLLECTIVE® · Independent discovery and booking for outdoor travel
Discover the charm of Chesapeake Bay aboard a luxurious catamaran. Customize your 2-hour sailing charter near Saint Michaels with food, drinks, and onboard fun.
Discover the charm of Chesapeake Bay aboard a luxurious catamaran. Customize your 2-hour sailing charter near Saint Michaels with food, drinks, and onboard fun.
Book with St. Michael's Sailing Charters
Verified experiences and guided adventures in the surrounding area.
Operated by St. Michael's Sailing Charters · Saint Michaels, Maryland
Set sail on the beautiful Chesapeake Bay aboard the Leopard 44 catamaran, Epiphany, with St. Michael's Sailing Charters. This exclusive 2-hour private charter offers the perfect blend of relaxation and adventure, with customizable options to suit your preferences. Whether you want to lounge on deck soaking up the sun, take part in the sailing experience by learning to handle the boat, or simply enjoy personalized food and drink service, this trip has something for everyone. The calm waters around Saint Michaels provide an ideal setting for unforgettable moments with friends and family while taking in panoramic views of Maryland’s scenic coastline. The spacious and luxurious catamaran ensures comfort throughout your voyage, and the crew’s local knowledge adds an enriching touch to your experience. This exclusive offer is a fantastic way to explore the Chesapeake Bay's natural beauty in style.
easy.
2 hours.
No advanced fitness needed; suitable for most ages and mobility levels, though some light walking on deck is required.
You can bring your own, but personalized food and drink service is available and recommended for the best experience.
No prior sailing experience is needed. The crew can guide you if you want to participate in operations or just relax.
Cancellation policies vary, but generally, full refunds are available up to 48 hours before the charter date.
Pets are not allowed to ensure safety and comfort for all guests.
Due to the boat’s design, wheelchair access is limited, so please contact the company for specific accommodations.
Dress in layers with comfortable shoes, and bring sun protection such as hats and sunglasses.
Saint Michaels is known for its rich maritime heritage and role in the War of 1812, reflected in its museums and architecture.
Operators adhere to environmental guidelines to protect Chesapeake Bay’s delicate ecosystem, promoting responsible boating practices.
St. Michael's Sailing Charters operates private sailing experiences from St. Michaels, Maryland, aboard Epiphany, a modern 2016 Leopard 44 catamaran. Epiphany features a unique open forward cockpit and a spacious aft seating area designed for passenger comfort and panoramic views of the Chesapeake Bay. Charter options include 2-hour and 2–3-hour sails with customizable routes departing from St. Michaels. Experiences are offered as private charters for groups, including options listed for engagements, weddings, elopements, photo shoots, special occasions, and seasonal events such as July 3rd fireworks sailings. One listed offering includes a private bareboat charter option for the Oxford fireworks event. Guest capacity and trip length vary by listing; one specific private charter notes capacity for groups up to 13 people. Onboard arrangements allow passengers to bring their own food and drinks; crew service is available to assist with onboard needs during the charter. Guests may choose relaxed sightseeing sails or may participate in sailing operations per the chosen charter. Several listed experiences reference customizable start and end locations and private itineraries tailored to the group's preferences. St. Michael's Sailing Charters is featured on The Adventure Collective and markets private Leopard 44 catamaran charters focused on comfort, scenic Chesapeake Bay cruising, and single-event bookings such as engagement shoots, weddings, and holiday fireworks sailings. All descriptions reference the Epiphany Leopard 44 and departures from St. Michaels, Maryland.
Book with St. Michael's Sailing Charters