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Old 07-02-2011
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Best Maryland/Chesapeake bay Charters

Does anyone know of a good charter place for a 27-32 foot sailboat on the Chesapeake?
Chesapeake Bay area

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Old 07-02-2011
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check out haven charters in rock hall - it has been a few years but i had a great experience with them and now keep my boat in the same marina they are in

Haven Charters - Bareboat sailboat charters on the Chesapeake Bay, within easy sailing distance of Annapolis, Baltimore, Oxford, St. Michaels. Caribbean BVI's sailing vacation yacht charters with captain and crew or join our flotilla and follow the l

rock hall is a good place to start from with lots of good destinations less than a day away
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Old 07-02-2011
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I researched the charter options in the mid-Chessy region earlier this year. We ended up not chartering and had 6 grown men on a 32' sailboat instead.
Here is what I think I remember:
There is an outfit on the South River that rents both power and sail boats in the size range you asked about. IIRC they had pretty reasonable rates.
Sailboat and Power boat rentals and charters in Annapolis, Maryland - Chesapeake Bay
Annapolis Bay Charters has bigger boats then 30' Annapolis Bay Charters :: Charters in their fleet. Midweek time is cheapest. I was advised by a reliable source that I should thoroughly check out the condition of the boats as they are sometimes used hard and put away wet. You may be able to negotiate the price.
There is another outfit in Rock Hall on the eastern shore that also has newer Bendytoes > 30' and the rental prices reflected that.
Keep in mind I have never chartered from any of these places, yet.
"The cure for anything is salt water~ sweat, tears, or the sea." ~Isak Denesen

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Old 07-03-2011
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I rented from South River Boat Rentals a couple of years ago and they had nice boats for reasonable prices. The boat we took out developed a tear in the main sail in 15-20kt winds and we had to bring her back, and they offered to either replace the main or give us another half-day sail later on. I'd definitely rent from them again.
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Old 01-22-2012
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which charter did you eventually go with?
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