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.
More ways to explore the area's outdoor wonders
Hang tight — photos are loading
This usually takes just a second.
Difficulty
easy
Duration
2 hours
Fitness Level
No advanced fitness needed; suitable for most ages and mobility levels, though some light walking on deck is required.
Wildlife
History
Saint Michaels is known for its rich maritime heritage and role in the War of 1812, reflected in its museums and architecture.
Conservation
Operators adhere to environmental guidelines to protect Chesapeake Bay’s delicate ecosystem, promoting responsible boating practices.
St. Michael's Sailing Charters
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.
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.
Departure Port
St. Michaels, MD
Private charters depart from St. Michaels
Vessel
Leopard 44 (Epiphany)
2016 Leopard 44 catamaran listed
Trip Length
2–3 hours
Typical charter durations offered
Capacity
Up to 13
Private charter option notes 13 people
Book a tailored 2–3 hour Epiphany charter for weddings, engagements, Oxford fireworks, or a private day sail — customizable routes and onboard crew service.
Book in Advance
Due to limited availability, reserving your private charter early secures your preferred date and time.
Bring Sun Protection
Even when on water, UV exposure is strong—wear sunscreen, hats, and sunglasses to protect your skin and eyes.
Wear Non-Slip Shoes
Deck surfaces can be slippery when wet, so shoes with good grip ensure safe movement onboard.
Stay Hydrated
Even on shorter cruises, bring water or request drinks to stay well hydrated, especially on warm days.
Sunscreen
Protects your skin from strong UV rays while exposed on the open water.
summer
Light Jacket
Keeps you comfortable against cool breezes on the bay.
spring
Comfortable Non-Slip Shoes
Ensures safety by providing good footing on potentially slippery surfaces.
Sunglasses
Reduces glare from the water, enhancing visibility and comfort.