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On the Chesapeake Bay


sailboat charters chesapeake bay

Picturesque, historic, idyllic – sailing the Chesapeake Bay is the perfect way to explore the shorelines of Maryland and Virginia. Approximately 200 miles long from the Susquehanna River in the North to the Atlantic Ocean in the South, the Chesapeake Bay is the largest estuary in the United States with 11,684 miles of shoreline and tributaries of cruising ground. The Chesapeake Bay offers the sailor/explorer a treasure trove of historic points of interest as well as hundreds of rivers and creeks offering quiet anchorages, access to local towns and villages, where the local watermen carry on the Bay’s tradition.

Click on any Boat listed below for more information.

Sailboat Rentals in Chesapeake Bay

Captain & Instructor Fee’s: $100/half day $200/per day
All prices in US Dollars ($)

Sailboats Rentals and Charters

Boat Size ½ Day Full Day Multi-Day
Rainbow(s) 24′ 160 300 Call
J-Boat 24′ 300 500 Call
S2 26′ 300 500 Call
Hunter 26′ 300 500 Call
O’Day 272 28′ 400 600 Call
O’Day 28′ 400 600 Call
Ranger 29′ 400 600 Call
Hunter 33′ 450 700 Call
Hunter 37′ 500 900 Call

Rental Times

Full Day 10:00 am – 6:00 pm
Half Day 10:00 am – 2:00 pm or 2:00 pm – 6:00 pm
Multi Day 10:00 am (multi-day charters start at 10:00am the first day and end at 6:00pm the last day of the charter)

You can contact us by phone at (410)956-9729 or please fill out the form below. All information will be kept confidential. We do not share email addresses in any way.

First and Last Name:



Rental Date (example: 4/4):

Rental Duration:

What type of boat are you interested in renting/chartering?: sailboat powerboat

Is this a Gift Certificate?: yes no

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Telephone. 410-956-9729
Location. 2802 Solomons Island Road
Edgewater, MD 21037
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