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Discussion Starter #1
The Family is contemplating a major change in life direction. So as part of this years summer vacation we've decided to take a drive down to the chesapeake. We want to charter/rent a sailboat in the 26-28 foot range for 3 days or so. does anyone have tips on finding a place that is in that market? so far all I can find are operations that charter the "Big boats" ( those over 36 feet! hey we're Canadian!)

We have 2 young kids (10 and under) who have not sailed before and I was hoping to introduce them to sailing this way. We're also going to wanter around and go to the Maritime museum, see what they have in Norfolk for Naval museums, etc. so the whole week wont be on a boat.
 

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You aren't going to see much of the Bay in 3 days. You could do the Annapolis area, or Norfolk/Tidewater, but not both.

I've never done business with these folks, but they have the size boat you are looking for:
South River Boat Rentals.
 

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Discussion Starter #4
Thanks for the tips. The 3 days is less about trying to see alot and more about just trying it out. I have a 10 year old boy who is excited about the idea but hasn't been on a boat in 6 years. I also have a 7 year old girl who wants to try it but often gets cold feet about trying something new! hence the short 3 day window.
 

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You aren't going to see much of the Bay in 3 days. You could do the Annapolis area, or Norfolk/Tidewater, but not both.

I've never done business with these folks, but they have the size boat you are looking for:
South River Boat Rentals.
Exploring Annapolis and crossing the bay to St Michaels (Chesapeake Bay Maritime Museum) would be a nice trip and doable in a couple days. You might consider a stop in Baltimore on the way, kids love the aquarium and visiting the USS Constellation.
 

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Some will argue this... Jun/July is the worse time of the year for sailing the Bay. The prevailing winds die off in June and don't seem to return until late summer.
 

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Some will argue this... Jun/July is the worse time of the year for sailing the Bay. The prevailing winds die off in June and don't seem to return until late summer.
A bad day sailing on the bay is still better than.....just about any other day :)
Last season may have been unusual, perhaps it is the new normal - either way we had good air much of the time, weekends with good sailing weather and it seemed fewer days of doldrums and scorching heat. Then again even if it was awful (anything other than snowing) all things considered I'd rather be on a boat.
Early June may be better than July, but July 4th brings fireworks that kids from the north country would enjoy.
 

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You might also consider a day charter on the York River, near Williamsburg, to get a sense of what the lower Bay is like. See williamsburgchartersails.com
 

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For a short cruise, I second the motion for the Annapolis, Baltimore, St. Michaels area - much more to see in shorter distances.

Wind is typically light, from the south, southeast, southwest with a Bermuda high parked offshore during those months, but you will likely experience increasing winds after noon as the land masses heat up, then dying down at sunset, with the possibility of late afternnon/evening thunderstorms. Wind picks up again several hours after sunset. Plan on doing some motoring if you need to put miles under the keel in any direction.
 

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I'd go a little larger, if you have the experience to handle a larger boat. 26-28' can be a little tight for a family of four, even for a couple nights.

A larger boat is also likely to have air conditioning, which could make a big difference that time of year. When we chartered a couple years ago, we thought AC would be totally unnecessary, but there was one hot, muggy, stagnant night where it made a huge difference. We rented a slip to get shore power and were very comfortable.

We used Haven Charters in Rock Hall.
 

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28 foot IP in the slip next to mine. I think Dolphin Charters has it.
 
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