SailNet Community banner
  • SailNet is a forum community dedicated to Sailing enthusiasts. Come join the discussion about sailing, modifications, classifieds, troubleshooting, repairs, reviews, maintenance, and more!

Good bareboat charters on Chesapeake?

12K views 19 replies 18 participants last post by  scottyt 
#1 ·
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?
 
#2 ·
Wingman,

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.
 
#5 ·
Wingman,
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
 
#8 ·
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.

Sam
Island Bound Charters
 
#9 ·
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
 
#12 ·
I also vote for Haven Charters--have chartered from them for several years now, each time on a different boat. They don't have all new boats (some are, some aren't), but the prices reflect that. In addition, the boats are generally well-maintained and equipped. The website gives you the list of ammenities, and the couple who manages the company are very helpful with things like telling you which boats are better than others for your needs.

Haven's not the fleet of all new boats type of place, but that's what we like about them.
-J
 
#14 ·
It's probably to late to be of any help to the O.P., but for others that come across this page, I'll vote for Haven also. I chartered with them for a four day charter last summer. The owners are really nice and laid back. The boats range from new and nice to older and not as nice but, like others have said, the condition is reflected in the price. We went from Rock Hall to St. Michaels, to Annapolis, to Baltimore, and back to Rock Hall. That's a nice four day cruise if anyone is interested.

I'll also point out Baysail, which is located in Harve de Grace, MD (northern tip of the Bay). It used to be owned and operated by a lady named Kim who was quite controlling (although generally nice). As of about two years ago it was sold and the new owners are much more laid back. A guy named Steve manages (not sure if he's an owner) and he's really nice and helpful. I've chartered with them about four times and I also received my ASA certifications from them (great instructors).
 
#16 ·
Harbor Sail, Fells Point

I chartered a 25' C&C from Harbor Sail, the condition was immaculate and the owner was extremely kind courteous and helpful. The rates are fantastic at $200/1st day and 65/day thereafter. Good people

Coincidentally the picture above was taken on the Luv II

Harbor Sail LLC
 
#19 ·
One of the great things about Haven Charter is all the great destinations within reach in one day (maybe a little more than 8 hours). The list would include, Georgetown on the Sassafras River, Havre de Grace, Baltimore, Annapolis, Kent island and the Kent Narrows, St. Michaels, the Wye River, Oxford and the Tred Avon River. These are all great places to visit. Then there's the list of great resturants, but I'll let someone else do that.
 
#20 ·
wing man if you want a single day test i can do a 8 hour day with you and yours, out of the harbor area. i have a 27 foot hunter with plenty of life vests, she not perfect yet but its free. basicly we can get out and play on the bay in an hour maybe 2 from where my boat is
 
This is an older thread, you may not receive a response, and could be reviving an old thread. Please consider creating a new thread.
Top