Private Tours & Charters- "Escapes"

Escape all day
-Custom duration
-Custom departure time
-Custom itinerary
-Custom PRICE
-Up to 6 passengers
You need to get out on the water and stay- all day. What sets Escape by Boat apart is our understanding of what you need: a classic 1950's Chesapeake Bay deadrise, obsessively maintained, outfitted to carry you and your party on a custom charter experience that lasts all day long. We have the latest bluetooth speakers, Starlink internet connectivity, comfortable setting, shade, and most importantly a wide open river or Bay for you to explore.

Escape Before Noon
-Private harbor & river tour
-1.5 hours
-10am-11:30am
-$175
-Up to 6 passengers
When you need a fast escape first thing in the morning, you can meet Sweet Tilly at the dock in St. Michaels and GO! Enjoy the sites of historic St. Michaels harbor followed by a cruise along the Miles River.

Midday Maritime Escape
-Private harbor tour
-1 hour
-12:30pm-1:30pm
-$125
-Up to 6 passengers
This tour may be small, but she is mighty! There is a lot more to see around the St. Michaels harbor than you might think. We will maneuver through the marine hustle & bustle of this iconic Chesapeake Bay town and take in the scenery to include the historic grounds of the Chesapeake Bay Maritime Museum, the place where they filmed the movie "Wedding Crashers," all of those beautiful yachts anchored in the harbor, all the gorgeous waterfront houses, and that's all before you get to hear about the history of the "town that fooled the British."

Miles River Escape
-Private Miles River tour
-2 hours
-3pm-5pm
-$275
-Up to 6 passengers
Escape either up or down the Miles River in a tour that lets you flex some curiosity about what is out there. Like most tributaries of the Chesapeake Bay, the Miles River has its own creeks, small bays; places to go and cool things to see. After boarding we will slip out of the harbor and ask you where you would like to head next. But don't worry, as long as you don't want to go up or down, there is no bad choice of direction.
Sunset Escape
-Private harbor & river tour
-2.5 hours
-Departs 2 hours before sunset
-$375
-Up to 6 passengers
Watch the sun set over the waters of the Miles River. This is the classic sunset cruise experience. Whether you toast with wine, champagne or a juice box, Sweet Tilly will transport you and your party to another place, literally and in your soul, to send off another day of living that could not possibly have a better ending. We have years of sunsetting experience at Escape by Boat. We would be honored to host your next Chesapeake Bay sunset experience, our signature and most meaningful escape.

