Give us some more information. Do you want good hurricane protection inland for the best protection or do you want to retain access for sailing the boat at times during this summer? By "East Coast" are you thinking more of Florida or anyplace up to Maine? - Canada? I think you'll get better answers with a more defined question.
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I have never seen a man-of-war in the Bay. They are more of an ocean creature. I have seen them in Florida and we used to pop them when we found them on the beach and and I have dodged them swimming in Bermuda. Jellyfish are a seasonal nuisance that come and go with temperature and salinity. They do not like fresh water and never get to the northern parts of the Bay that are essentially fresh. In the Annapolis area they arrive some years by July . Some years never. This year the cold winter and wet spring have kept them away - I have not seen one yet 
You can either keep a boat at the north end or go up there on a cruise to get away from them. Other alternatives are getting a nettle net, wearing a rash guard, or going places with swimming pools When we were young we ran our ski boats up the Chester River to Chestertown to ski in nettle free water and get lunch. Someone from the southern end may chime in, it may be they don't like the very southern end of the Bay either due to too much salt. Do keep in mind jellyfish are annoying, not dangerous. My dog tried to eat one once with comical results - he would drop it, bark at it about 5 times, and then get really mad when it stung his tongue again LOL. Recruiting for our yacht club - if you are a member you can put in a mooring. OTOH it is a fair drive from the airport and way out in the country. Likely an hour from BWI. Speaking of which, you might want to think about how and when you would be getting from airport to boat. Some areas have heavy traffic at certain times. If you have your own airplane there is at least one airport/marina combo, but no such luck if you fly commercial.
You can either keep a boat at the north end or go up there on a cruise to get away from them. Other alternatives are getting a nettle net, wearing a rash guard, or going places with swimming pools
When we were young we ran our ski boats up the Chester River to Chestertown to ski in nettle free water and get lunch. Someone from the southern end may chime in, it may be they don't like the very southern end of the Bay either due to too much salt. Do keep in mind jellyfish are annoying, not dangerous. My dog tried to eat one once with comical results - he would drop it, bark at it about 5 times, and then get really mad when it stung his tongue again LOL. Recruiting for our yacht club - if you are a member you can put in a mooring. OTOH it is a fair drive from the airport and way out in the country. Likely an hour from BWI. Speaking of which, you might want to think about how and when you would be getting from airport to boat. Some areas have heavy traffic at certain times. If you have your own airplane there is at least one airport/marina combo, but no such luck if you fly commercial.
The Chesapeake is 180 miles long with about 3500 miles of shoreline. SOME of it is pretty nasty - say Baltimore Harbor, Washington DC, the Annacostia River. A lot of areas can be bad right after a heavy rainfall. Standard advice is to wait 48 hours after major storms to swim. It is also highly variable with time of year and weather. This August is the coolest in living memory, but many years when August rolls around and water temps head past 80 towards 90 it doesn't look as nice as it did in June. Note that the water at Cape Charles, litterally around the corner from the Atlantic, would be very different from the water in a major city and very different again from a rural fresh water river on the Eastern Shore.
I can't think of any area that would come close the Virgin Islands type water anyplace in the USA except sort-of in the Keys. If swimming in clear warm ocean water is a requirement then the Florida Keys are about the only choice and if swimming in ocean water in general is a requirement then new England or someplace near enough the barrier islands of NC to walk across to the ocean side would do. If you want clear fresh water then maybe Lake Champlain would be OK. I think you can drink it straight from the lake because it is so friggin cold nothing could grow in it
I can't think of any area that would come close the Virgin Islands type water anyplace in the USA except sort-of in the Keys. If swimming in clear warm ocean water is a requirement then the Florida Keys are about the only choice and if swimming in ocean water in general is a requirement then new England or someplace near enough the barrier islands of NC to walk across to the ocean side would do. If you want clear fresh water then maybe Lake Champlain would be OK. I think you can drink it straight from the lake because it is so friggin cold nothing could grow in it
Note that any issue the Bay has with water quality the areas trapped behind the barrier islands in NC have at least as bad or worse once you get away from the inlets. I went to school in Florida and the water inside (ICW) was nasty and many of the fresh water lakes were worth your life to put your hand in
My relatives live on the Westport River north of Newport RI. There is a nice ocean beach there and interesting places nearby to sail to, but you don't seem to want to be that far north.
My relatives live on the Westport River north of Newport RI. There is a nice ocean beach there and interesting places nearby to sail to, but you don't seem to want to be that far north.
If you want clear fresh water then maybe Lake Champlain would be OK. I think you can drink it straight from the lake because it is so friggin cold nothing could grow in it
Great wreck diving in the Great Lakes and the St. Lawrence River..thanks to the Zebra muscle infestation the viz can be 70 ft or more. In the St. Lawrence River temps are a constant 70F from top to bottom this time of the year but the current can be running between 3-5 kts.
Viz in the upper to middle portion of the Chesapeake Bay can run from several inches to a couple of feet. Temps this time of the year has been running around 80F. I usually dive on my boat up some tributary creek,as we have several popular swimming areas on the Eastern side of the Bay, to check on running gear but not taking any chances I do wash with soap and fresh water immediately afterwards.
I actually do live on Lake Champlain. Water temps in the mid 70s right now. We don't have perfectly pristine water quality everywhere on the lake, but having lived on this lake my entire life (35 years) I've never given a second thought to spending hours a day in the water. For us, swimming and playing in the water is a huge part of sailing and one of the reasons we got a sailboat. Because the OP mentioned swimming as a priority, thought I'd throw out the question about water quality in the Chesapeake.If you want clear fresh water then maybe Lake Champlain would be OK. I think you can drink it straight from the lake because it is so friggin cold nothing could grow in it
Typical afternoon for us off the back of the boat after sailing and/or when wind isn't blowing.
I pretty much have spent much of my life in the Bay. Since I was a kid our sailing schedule has been go south first and move north to avoid the nettles. I wouldn't swim in Baltimore Harbor, but other than that most places we go are good for swimming. Now if you are used to air-clear Bahamas water, everything on the East Coast will be
EDIT - Speaking of north and south, I have a suggestion for the OP that might work better than picking one spot. Why be limited since you don't live here anyway? Start in Florida in the spring and cross the hurricane line into the Bay by June 1. Make it up to Maine by August and then head south again for the winter and pick a handy spot for winter storage. If I could figure out how to be in Annapolis in May and Portland in August I would do it in a second. Plently of marinas to leave the boat in all the states on the way up and back.
EDIT - Speaking of north and south, I have a suggestion for the OP that might work better than picking one spot. Why be limited since you don't live here anyway? Start in Florida in the spring and cross the hurricane line into the Bay by June 1. Make it up to Maine by August and then head south again for the winter and pick a handy spot for winter storage. If I could figure out how to be in Annapolis in May and Portland in August I would do it in a second. Plently of marinas to leave the boat in all the states on the way up and back.
I'll bet at the 30ft depth there is a thermocline diff. like most lakes
I'd suggest you consider areas north of NYC, in my opinion southern New England offers you the most options, and better sailing/cruising... I love a spot like Charleston as much as anyone, but for the SUMMER ??? No thank you...
No offense to the folks on the Chesapeake, but I think someone like yourself who has been keeping their boat in the Caribbean would find sailing on the Bay in summertime to be pretty lame, in general... Moving the boat back down there in the fall, however, now that would be more like it...
Not sure if you intend to spend the entire summer on the boat, or would be commuting back and forth, but I think having the boat near a place like Newport would offer the best blend of good sailing, the widest variety of interesting destinations and cruising grounds, and relative ease of access to major airports, etc...
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