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Step aboard a restored 1950s Chesapeake Bay deadrise and design your own private half-day or full-day charter from St. Michaels. Perfect for small groups, celebrations, and wildlife-focused outings on the tidal estuary.
Step aboard a restored 1950s Chesapeake Bay deadrise and design your own private half-day or full-day charter from St. Michaels. Perfect for small groups, celebrations, and wildlife-focused outings on the tidal estuary.
Book with Escape by Boat
Verified experiences and guided adventures in the surrounding area.
Operated by Escape by Boat · Saint Michaels, Maryland
On the Eastern Shore of Maryland, the town of Saint Michaels sits along the upper Chesapeake Bay, and Escape by Boat offers private charters from St. Michaels Harbour Inn, Marina & Spa that let small groups shape a day on the water. Boarding a carefully maintained, classic 1950s Chesapeake Bay deadrise, you choose a half-day or full-day cruise that can be built around relaxation, wildlife viewing, or a special celebration. The boat’s broad deadrise hull handles chop and wakes with an old-school grace, while modern comforts—Bluetooth speakers, shaded seating, and a captain experienced in local tides—keep the outing easy.
Routes are flexible: drift past tidal marshes threaded with spartina grass, circle historic oyster reefs, cruise river arms where blue crabs and blinds of canvasback ducks feed, or slide along the bay margin watching sailboats skimming toward Tilghman Island. For photographers, the geometry of low-angle light on oyster shell bars and the contrast of dark water and pale marsh grass are signature Chesapeake shots. Wildlife is abundant—great blue herons, osprey hovering over schools of menhaden, and the occasional river otter slipping between pilings.
This private experience is intimate by design: maximum six guests means space to spread out and time to tailor the day. Bring food and drink for a picnic at anchor, cue a playlist for a sunset cruise, or request an itinerary that includes a quiet anchorage for swimming in protected coves. The meeting point is St. Michaels Harbour Inn, Marina & Spa; the slip is just past the public boat ramp on the left. If needed, call 410-443-2615 for directions.
Escape by Boat’s classic deadrise connects to the Chesapeake’s working-water heritage—the hull form evolved for hauling oysters and crab pots in quick, chop-prone waters—and the region’s history shows in every pier and channel marker. On calm mornings you can hear the call of bald eagles and the creak of wooden docks; on windier days the deadrise’s hull hums through chop with steady progress.
Practical notes: choose a full day to explore farther reaches of the bay and shallow creeks, or a half day for a relaxed harbor tour. The captain monitors tides and weather closely and offers free cancellations up to 48 hours before departure. Whether you want a family outing, a proposal at golden hour, or simply a slow day with the horizon, this private charter is a direct, personal way to experience Chesapeake Country from the water.
Book early for weekend dates and consider a sunrise cruise for glassy water and active ospreys; late-season trips highlight migrating shorebirds and quieter marinas. The captain adjusts routing for weather and tides, making this a safe, customizable way to see the Chesapeake’s living shoreline with friends aboard a classic deadrise.
The charter carries a maximum of six passengers to ensure comfort and maneuverability.
Meet at St. Michaels Harbour Inn, Marina & Spa; the slip is just past the public boat ramp on the left.
You can bring food and non-commercial beverages for a picnic at anchor; confirm alcohol policies with the operator when booking.
Free cancellation is available up to 48 hours before departure; cancellations inside 48 hours receive a rescheduling credit. If the captain cancels for safety, a full refund is issued.
Half-day and full-day durations are offered; typical time ranges run about 4–8 hours depending on routing and preferences.
Yes—private charters accommodate families, but confirm safety arrangements for young children and bring appropriate flotation devices if needed.
Escape by Boat is a Chesapeake City–based operator offering private boat charters that depart from St. Michaels and explore the Chesapeake Bay and Miles River. The fleet includes a vintage 1950s deadrise and the vessel Sweet Tilly, used for private sails that accommodate up to six guests. Trips are designed to be customizable, with options for morning, midday, half-day, full-day, and sunset departures depending on the selected cruise. Trip highlights include the Escape Before Noon! morning cruise that passes historic waterfronts and the Chesapeake Bay Maritime Museum, and the Midday Maritime Escape, a compact one-hour harbor cruise through St. Michaels. The Miles River Escape and the flexible Escape All Day! option let guests choose routes through tranquil creeks and scenic bays. Sunset Escape features wine aboard Sweet Tilly while the sky turns gold over the Miles River. Several cruises pass locations featured in the film Wedding Crashers, offering photo opportunities and local storytelling. Escape by Boat emphasizes private, small-group experiences for families, couples, celebrations, and photo-focused outings. Boats offer shade and onboard music on longer excursions, and cruises can be tailored to the group's pace and interests. All descriptions are based on offered trip summaries; schedules and exact departure details are provided at booking. Escape by Boat positions itself as a local option for private, scenic sailing on the Chesapeake Bay, focusing on flexibility, intimate groups, and classic Chesapeake watercraft.
Book with Escape by Boat
