Experience the serene beauty of Chesapeake Bay on a Private Sailing Catamaran in St. Michaels. Enjoy personalized service, stunning views, and a relaxing cruise on this exclusive boat tour.
More ways to explore the area's outdoor wonders
Hang tight — photos are loading
This usually takes just a second.
Difficulty
easy
Duration
2–4 hours
Fitness Level
Suitable for most fitness levels; minimal physical activity required
Wildlife
History
St. Michaels has a rich maritime heritage, once serving as a hub for shipbuilding and maritime trade in the Chesapeake Bay area.
Conservation
The Chesapeake Bay area emphasizes sustainable boating practices to protect local ecosystems and wildlife.
St. Michael's Sailing Charters
Experience the serene beauty of Chesapeake Bay on a Private Sailing Catamaran in St. Michaels. Enjoy personalized service, stunning views, and a relaxing cruise on this exclusive boat tour.
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.
Prepare for variable weather
Check the weather forecast before your trip and bring layered clothing for comfort during changing conditions.
Bring sun protection
Sunscreen, hats, and sunglasses are essential for comfort and protection during the sunny sailing hours.
Secure personal items
Keep valuables in waterproof containers or secure pockets to prevent loss overboard.
Arrive early
Arriving 15-30 minutes before your scheduled departure ensures a smooth check-in and briefing.
Sunscreen
Protect your skin from sunburn during day-long cruises.
summer
Hat and sunglasses
Shield your eyes and face from direct sunlight while on deck.
summer
Light jacket or layers
Stay warm during cooler days or evenings on the water.
spring|fall|winter
Waterproof bag
Keep electronics and valuables dry and secure during your trip.