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Spend a private seven-hour day aboard Epiphany, a 44-foot catamaran departing from Harbour Inn & Marina in St. Michaels. Ideal for small groups, with catering and tasting add-ons to customize your Chesapeake experience.
Spend a private seven-hour day aboard Epiphany, a 44-foot catamaran departing from Harbour Inn & Marina in St. Michaels. Ideal for small groups, with catering and tasting add-ons to customize your Chesapeake experience.
Book with St. Michaels Sailing Charters
Verified experiences and guided adventures in the surrounding area.
Operated by St. Michaels Sailing Charters · Saint Michaels, Maryland
Set sail for a day that balances slow coastal luxury with the salty work of the Chesapeake. The Full Day Private Sail on Epiphany launches from Harbour Inn & Marina in St. Michaels, Maryland, and spends seven hours tracing the Miles River out toward open water. Owned and operated by St. Michaels Sailing Charters, the experience puts your group aboard Epiphany, a 44-foot catamaran that combines stable, roomy decks with crisp sailing performance.
From the dock the town’s clapboard waterfront slips by — working docks, waterfront restaurants, and historic boatyards — then the sails come up and wind takes the lead. Key features include the narrow harbor channel, tidal creeks and oyster bars, and the wider expanse of the Miles River where chop and wind deliver authentic sailing moments. The boat’s twin hulls make Epiphany forgiving in light air but quick to respond once you’re outside the shallows. Look for low marsh grasses and the flat, glinting mudflats of the Chesapeake estuary; these estuarine habitats host migrating shorebirds and bay grasses that are the backbone of local fisheries.
This charter is private for up to six guests with options to add a catered lunch, beer and wine tasting, or a champagne sunset upgrade. Because the trip is private you can set the pace—swim off the transom, drift and read, or let the crew teach you sail handling. Meeting point is exact: Harbour Inn, 101 N. Harbor Rd, St. Michaels, MD 21663; arrive 15 minutes before launch.
St. Michaels is small but storied: shipbuilding and oyster harvesting once drove the town’s economy, and today small marinas and museums keep that working-water culture alive. The sail highlights that lineage, moving from intimate harbor lanes past boatyards where you can still see wooden hulls and cradled skiffs.
Practical details make this a smart choice for gatherings: the catamaran’s stability suits mixed-ability groups; local partnerships allow pre-ordered meals to be waiting aboard; and available add-ons make it ideal for birthdays, anniversaries, or corporate outings. Be prepared for sun, wind, and spray—bring layers and non-slip shoes—and consider the beer/wine tasting add-on if you want to toast the sunset. For travelers seeking a private day on the Chesapeake that blends easy comfort with genuine sailing, Epiphany delivers a memorable, flexible, and decidedly local maritime experience.
Crewed by local sailors, the charter includes professional handling while guests relax; gratuity and amusement tax are added to the charter fee. A beer/wine tasting add-on is available for $20 per person, and Epiphany can also be booked as a bareboat charter for larger groups up to 13 guests through St. Michaels Sailing Charters. The operator coordinates with local vendors so dietary needs and timing can be arranged in advance. Book early seasonally.
easy.
7 hours.
Suitable for most fitness levels; ability to step on a dock and move around a boat is required.
Check-in at Harbour Inn & Marina, 101 N. Harbor Rd, St. Michaels, MD 21663; arrive 15 minutes before departure.
This private charter seats up to six guests; Epiphany is also available for bareboat charters up to 13 guests.
Catering is offered as an add-on through local partners; a beer/wine tasting add-on is available for $20 per person.
Standard bookings are crewed by St. Michaels Sailing Charters; bareboat options are available for qualified groups as noted.
Amusement tax and crew gratuity are added to the charter fee, per the booking details.
Cancellation terms are set by the operator and shown on your booking confirmation—check your fareharbor reservation for specifics.
St. Michaels grew on shipbuilding and oyster harvesting, and much of the town’s maritime character remains visible along the waterfront.
The Chesapeake faces ongoing restoration efforts; avoid anchoring on bay grasses, pack out trash, and follow local guidance to protect oyster reefs and seagrass beds.
St. Michaels Sailing Charters operates private catamaran charters from Saint Michaels, Maryland, offering on-water experiences aboard Epiphany, a Leopard 44 catamaran. The company provides private Sailing Catamaran Charters for groups up to 13 people, departing from St. Michaels harbor. Trips focus on relaxed sailing, scenic views of the harbor and tributaries, and private dining or social time on deck. St. Michaels Sailing Charters presents a single primary offering described as the "Private Sailing Catamaran Charter - Up to 13 People." This trip features an open forward cockpit and covered deck spaces on Epiphany, allowing guests to enjoy fresh air and unobstructed views while remaining sheltered if needed. The charters are staged from Saint Michaels, Maryland, a harbor town on Maryland’s Eastern Shore known for maritime activity and waterfront attractions. The operation emphasizes private bookings aboard a defined vessel and accommodates groups up to the listed capacity. Information presented focuses on the vessel type, passenger capacity, departure location, and the experiential highlights of sailing and dining on the water. Third-party references or booking platforms may provide schedules, rates, and availability for the Private Sailing Catamaran Charter offered in Saint Michaels, Maryland.
Book with St. Michaels Sailing Charters