Enjoy a private 2-3 hour bareboat sailing experience aboard a Leopard 44 catamaran from Saint Michaels, Maryland. Discover Chesapeake Bay’s stunning views and peaceful waters on your own terms.
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Difficulty
moderate
Duration
2–3 hours
Fitness Level
Participants should be in reasonable physical condition to move around the boat safely and handle occasional moderate exertion.
Wildlife
History
Saint Michaels played a significant role in the War of 1812 and remains a vibrant maritime town with preserved colonial architecture.
Conservation
Efforts in this area focus on sustaining Chesapeake Bay’s water quality and protecting native aquatic species from overfishing and pollution.
St. Michael's Sailing Charters
Enjoy a private 2-3 hour bareboat sailing experience aboard a Leopard 44 catamaran from Saint Michaels, Maryland. Discover Chesapeake Bay’s stunning views and peaceful waters on your own terms.
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.
Arrive Early for Safety Briefing
Plan to arrive 15 minutes early to receive a comprehensive safety briefing and charter orientation.
Wear Non-Slip Footwear
Boat decks can be slippery—wear shoes with good grip to avoid falls and ensure safety onboard.
Pack Sun Protection
Bring sunscreen, sunglasses, and a hat to shield yourself from intense midday sun.
Bring a Waterproof Bag
Protect your valuables and electronics in a dry bag as splashes and sea spray are common.
UV-protective Sunscreen
Prevents sunburn during extended exposure on open water.
summer
Non-slip Boat Shoes
Provides secure footing on wet and slippery boat decks.
Light Windbreaker Jacket
Protects against cool winds and spray while sailing.
spring
Waterproof Dry Bag
Keeps electronics and personal items safe from splashes.