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wingman 08-27-2008 08:41 PM

Good bareboat charters on Chesapeake?
I'm an experienced sailor currently without a boat looking to charter for weekends and week-long cruises on the Chesapeake Bay. Eventually I would like to buy a boat, but I'd like to let my family see what it's like to spend some time on a boat before I make that kind of commitment.

Anyone know of agencies or individuals that have "fully equipped" boats for rental on the Chesapeake? It has been many years since I've chartered on the Chesapeake. It was always a good experience, the boats were new, most of the details were taken care of, but I recall that they were really bare boats, not much more than minimal equipment.

We rented a beach house this summer that was completely equipped with everything you might need for a week at the beach, from kitchen equipment to bbq grill to beach chairs and umbrellas and everything else. Made me realize that that is the kind of sailboat rental I'm looking for. A well-equipped boat that has all the gear to make a week-long cruise on the Bay enjoyable.

Any suggestions?

JohnRPollard 08-31-2008 12:22 PM


You might check with some of the larger charter companies in Annapolis. But I'm not sure if they will be quite as turnkey as you might hope -- maybe.

Another option would be to search on-line for a private party that charters their family boat. This might give you a better chance of getting all the goodies along with the boat.

I would think that a decently equipped boat from a major charter company would still be a good way to introduce your family to Chesapeake sailing. Make sure the boat has a good bimini system and a dinghy. Then choose a fun itinerary and it should be a memorable experience. Good luck.

Yamsailor 09-04-2008 09:56 PM

jjablonowski 09-04-2008 10:10 PM

I've used Haven Charters in Rock Hall successfully. Hyperlink in previous post.

nursinadream 09-10-2008 08:52 PM

We chartered with "getaway sailing" in Baltimore. They have a small fleet, good variety. We were looking for something small, had a Cal 22, and it was in very good shape. We enjoyed being up in the Baltimore harbor, never even got to the bay that weekend. Too windy!
Deb in KY

northbay 09-12-2008 04:15 PM

Haven charters has a good reputation, good clean boats and ran by a great
sailing couple.

harryrezz 09-29-2008 11:18 AM

Chartered with Haven years ago - quite satisfied.

stadros 10-24-2008 07:41 PM

Sailing in the Chesappeake
I own and run a 50' sailboat as a crewed charter yacht. For the winter season I am in the Caribbean however right now I am in the Chesapeake Bay waiting until the end of hurricane season to head south. Please message me if you would like to go for a sail.

Island Bound Charters

sck5 10-24-2008 10:12 PM

Another vote for Haven Charters. I chartered from them last month and they were great. Easy to deal with and nice clean boats - enough of them so that when they didnt have my first choice available there were three others in the same size range that were perfectly fine for what I needed

camaraderie 10-24-2008 10:46 PM

If you want to get away from it all and try the mid and lower bay...try Nortons...

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