Check in at the dockside at Harbour Inn, 101 N. Harbor Rd, St. Michaels, MD 21663 and arrive 15 minutes before departure.

How long is the cruise?

The scheduled sail runs two hours, allowing time to traverse the Miles River and sample open Chesapeake Bay views.

What is the capacity?

Public sails accommodate up to six passengers; Epiphany is available for private charters for up to 13 guests.

Is alcohol available?

There’s a beer and wine tasting add-on for $20 per person; guests must be 21 or older to participate.

Are children allowed?

Children are permitted; age minimums aren’t specified in the listing—contact the booking provider if you have specific concerns about youth safety or seating.

What about seasickness?

Short two-hour sails are low-commitment, but anyone prone to motion sickness should bring medication or acupressure bands and sit mid-boat where motion is minimized.

Two-Hour Chesapeake Day Sail on Epiphany in St. Michaels | Catamaran | Sailing

Adventure Brief

Spend two easy hours aboard the 44-foot Leopard catamaran Epiphany, departing from Harbour Inn in St. Michaels to chase osprey, bald eagles, and occasional dolphins across the Miles River and Chesapeake Bay. Choose a public sail or book the boat privately for an intimate waterside escape.

2 hours

easy

From $204.75

On the tide-scored waters off Saint Michaels, Maryland, the 44-foot Leopard catamaran Epiphany unhooks routine and replaces it with a two-hour loop of bay light, salt breeze, and low-key wildlife theatre. Departing from Harbour Inn, 101 N. Harbor Rd, St. Michaels, MD 21663, this short cruise follows the Miles River out into the Chesapeake Bay, where wide water opens against a shoreline of marsh grass, historic clippers, and weathered boathouses. The modern deck layout gives passengers room to move—covered dining areas for shade, open rail lines for lookouts—and a crew whose local knowledge turns simple sightings into stories. Wildlife is the headline: osprey hover over shallow flats, bald eagles quarter the river edges, and on lucky days dolphins arc alongside the hull. The estuary here is a productive mix of tidal creeks and mudflats, a living shoreline that supports migrating birds and bay fish, so binoculars or a camera with a long lens will pay off. Epiphany can be booked as a shared public sail or reserved privately for groups; the vessel accommodates up to six passengers on public trips and can be chartered for up to 13 guests privately, making it equally suited to solo travelers, couples, or small celebrations. Logistics are simple but specific: the sail lasts two hours, fares run at $175 per passenger or $895 for a private charter, and there’s an optional beer and wine tasting add-on for $20 per person (21+). Guests should plan to arrive 15 minutes before departure time at the Harbour Inn dock. The short duration makes this a perfect late-afternoon outing that still leaves time to wander St. Michaels’ historic main street or visit nearby nature preserves. What makes this trip stand out in the region is its blend of accessibility and authenticity. You don’t need to be a sailor to appreciate the quiet choreography of tides and birds, yet the vessel is a true performance platform—a Leopard catamaran built in 2016 with thoughtful deck space that invites lingering and conversation. It’s an ideal way to sample Chesapeake Bay ecology and coastal culture without committing to a full-day expedition. Whether you chase sunset colors across the Miles River or plan a private small-group celebration, this two-hour voyage on Epiphany is a compact, memorable way to experience Maryland’s Eastern Shore from the water. Plan clothing in layers and bring sun protection: even short sails can expose you to reflected light and wind; non-marking deck shoes keep footing secure. If you’re photographing birds, a 300mm lens helps; for groups celebrating, ask crew about shade and cooler space. The short itinerary makes this a flexible addition to a weekend on the Eastern Shore, pairing salt air with up-close encounters with Chesapeake Bay life.