ST. MICHAELS BOAT TOUR FIELD GUIDE
Leopard 44 Days: A Private Catamaran Passage on Chesapeake Bay from St. Michaels
A private, three-hour-plus sailing aboard the Leopard 44 catamaran Epiphany from St. Michaels, offering spacious cockpits, customizable routes, and waterfront views of the Chesapeake Bay.
Leopard 44 Days: A Private Catamaran Passage on Chesapeake Bay from St. Michaels.
Adventure brief
Leopard 44 Days: A Private Catamaran Passage on Chesapeake Bay from St. Michaels
From the historic harbor of St. Michaels, Maryland, the Leopard 44 Epiphany slips onto the Chesapeake with an open-forward cockpit and covered living spaces that make three-hour charters feel like a taste of coastal cruising luxury; the vessel’s layout and customizable routes let groups trade the town’s piers for sweeping bay horizons and sheltered cockpit dining.
Embark on an unforgettable adventure with St. Michael's Sailing Charters' Private Sailing Catamaran Charter in St. Michaels, Maryland. This exclusive boat tour offers travelers a chance to experience the Chesapeake Bay's stunning waters aboard a luxurious, private catamaran. Whether you're celebrating a special occasion or simply seeking a peaceful escape, this sailing trip provides a perfect blend of relaxation and adventure. Glide through calm waters, enjoy panoramic views of the shoreline, and possibly catch glimpses of local wildlife while basking in the sun. The experienced crew ensures a safe, customized experience, guiding you through scenic routes and sharing insights about the area's rich maritime history. Bring along your favorite snacks and beverages to savor on deck as you enjoy the gentle sea breeze. Perfect for groups or couples, this private charter allows you to set your own pace and make memories that will last a lifetime. Discover why sailing in Maryland is a favorite outdoor activity and create unforgettable moments on the Chesapeake Bay with this luxurious, personalized boating experience.
Route Schematic
Typical route schematic
Stops are flexible but generally follow an out-and-back pattern from St. Michaels with time to cruise the local bay waters and return to the harbor.
Embark in St. Michaels
Boarding typically begins at the operator’s St. Michaels berth; Epiphany’s home base for most charters is St. Michaels, Maryland.
Cruise the Chesapeake Bay
Spend the bulk of the charter cruising the Bay from St. Michaels, enjoying open-water views and sheltered cockpit seating aboard the Leopard 44.
Return (or alternate finish)
Most trips return to St. Michaels at the end of the outing; trips can also be started or ended at alternate locations for an additional fee.
Provided facts do not list specific physical requirements; routes are customizable and may be adjusted by the operator—confirm details and any accessibility questions with the charter operator in advance.
Highlights
Outing Highlights
Leopard 44 Epiphany — modern cruising comfort
Built by Robertson & Caine in 2016, Epiphany is a Leopard 44 catamaran with a three-cabin layout, an open forward cockpit with direct saloon access, and covered forward and aft cockpits designed for visibility, ventilation and protected living space.
Spacious cockpits and tailored routes
The catamaran’s open cockpits and a large aft seating and dining area make the charter comfortable for relaxing or socializing, while routes are customizable so the outing can be shaped to your group’s preferences.
Chesapeake Bay from St. Michaels
Charters operate from St. Michaels and use the waters of the Chesapeake Bay, offering broad water views and the option to start or end at alternate locations for an additional fee.
What the day feels like
What the charter feels like
This private sailing charter moves at an easy rhythm: embark in St. Michaels, settle into the shaded forward or aft cockpit, and spend two to three hours (or longer) cruising the bay on a Leopard 44 whose layout emphasizes open sightlines, covered seating and a social dining area—an experience calibrated for comfort and adaptable to your group’s wishes.
Suitability
Who it's for
Who this private charter suits best.
Practical planner
Details to review before reserving
Charters typically run two or three hours in St. Michaels; the advertised experience is a three-hour sailing adventure and the vessel can be booked for three or more hours.
Embarkation is listed at 23672 Mt Pleasant Landing Circle, St. Michaels, MD 21663 (Epiphany’s home base is St. Michaels, though alternate start/end locations are possible for an additional fee).
Bring food and drinks if desired; also recommended are sunscreen, hats, life jackets for any children (adult life jackets and generic child life jackets are provided aboard), and a jacket or coat for chilly weather.
The charter uses Epiphany, a 2016 Leopard 44 catamaran with a three-cabin layout, an open forward cockpit and covered forward and aft cockpits for dining and seating.
Review cancellation policies before reserving.
Frequently asked questions
Planning Your Outing
How long is a typical charter?
Most charters last two or three hours; the advertised experience is a three-hour sailing adventure and trips can be three or more hours.
Where do I meet the boat?
The listed meeting location is 23672 Mt Pleasant Landing Circle, St. Michaels, MD 21663; Epiphany’s home base is in St. Michaels.
What boat will we sail on?
Charters are aboard Epiphany, a Leopard 44 catamaran produced by Robertson & Caine in 2016 with a three-cabin layout and an open forward cockpit.
What should I bring aboard?
Bring food and drinks if you wish, plus sunscreen, hats, a jacket or coat for chilly weather; adult life jackets and generic child life jackets are provided, though you may want specialized child jackets if needed.
Can the charter start or end somewhere other than St. Michaels?
Yes — trips can be started or ended at alternate locations for an additional fee.
Is the experience private?
Yes — this is a private sailing catamaran charter tailored for your group operating out of St. Michaels.
How this guide was prepared
This field guide is synthesized using verified supplier specifications, route descriptions, and destination data. Some booking links may generate affiliate revenue for ADV Guides.
- Verified: 2026-08-10T12:44:05.140Z
Some booking links may generate revenue for ADV Guides or The Adventure Collective.
Availability, pricing, schedules and operating details can change.
Trip details and contextual sources were reviewed by ADV Guides Editorial.