Discover the beauty of Chesapeake Bay on a private sailing catamaran trip in St. Michaels, Maryland. Perfect for relaxation, wildlife spotting, and enjoying scenic vistas, this adventure offers a personalized maritime experience you won't forget.
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Difficulty
easy
Duration
2–4 hours
Fitness Level
Suitable for all fitness levels, with minimal physical activity involved
Wildlife
History
St. Michaels has a rich maritime history dating back to the 19th century, once serving as a major center for shipbuilding and seafood processing.
Conservation
The Chesapeake Bay faces environmental challenges, but local initiatives and responsible boating help preserve this vital ecosystem for future generations.
St. Michael's Sailing Charters
Discover the beauty of Chesapeake Bay on a private sailing catamaran trip in St. Michaels, Maryland. Perfect for relaxation, wildlife spotting, and enjoying scenic vistas, this adventure offers a personalized maritime experience you won't forget.
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.
Wear Weather-Appropriate Clothing
Bring layered clothing and sunglasses to stay comfortable during variable weather conditions on the water.
Arrive Early for a Briefing
Getting to your private charter early allows time for safety instructions and to customize your sailing experience.
Bring Sun Protection
Apply sunscreen and wear hats or visors to protect yourself from sun exposure while on the water.
Capture the Moment
Use waterproof gear or cases for your camera to take advantage of stunning sunset views and scenic landscapes.
Sunscreen
Protect your skin from UV rays while sailing on sunny days.
summer
Light Jacket or Sweater
Layer up for warmth during cooler weather, especially in early spring or late fall.
spring|fall|winter
Waterproof Camera
Capture scenic views and wildlife comfortably without worry about water exposure.
Hat and Sunglasses
Shield your eyes and face from sun exposure while onboard.
summer