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Trip for 1 to a US Island in Early May?

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I've never had a real vacation before, but since I've had the year from He** I want one. Even though it will mean that I will have to travel alone. I was diagnosed with a rare genetic disorder this year and I was near death for 2 months even though I'm barely 30. so I'm not looking for a vacation to "hook up" with a guy. I am considered handicapped. I use a rolling walker most of the time. However, if the beach does not consist of a long length to the water of deep, sink in several inches, type sand, I can use a cane. Most of my trip will consist of sitting near the water. I can fly out of any airport around NYC like JFK, LGA, or Newark.
I need something as affordable as possible and here are my requirements:
2. No Cruises
3. I want my vacation to be based in the US for health reasons. I can take a day boat trip to another country's island, for instance.
4. I need an airline that you can pay for extra leg room (because of my health condition) without having the huge price tag of first class. I know Jetblue does this for instance.
5. I want something more on the Quiet and Peaceful side. (no screaming kids please) I don't mind boring :)
6. Air conditioning in the room.
7. Access to reasonably priced meals/food

Here are my wishes/things I would like to have:
1. A massage on the beach (a wish because I know this could make my entire trip much more expensive if the hotel is more of a spa)
2. Wifi available somewhere at the hotel
3. Transportation to a not too touristy but safe (oxymoron I know) market of local merchants (I'm just thinking of what I've seen in movies of locals setting up tables or booths to sell things)
4. A boat trip for sight seeing or to try fishing.

I don't really need any other activities other than those listed above. Obviously, I won't be renting a car. I am very flexible about when I can travel since I cannot work right now, however I am concerned with bad weather, so maybe in early May? I would like to stay as long as I can afford (ie a week?). I know that this would cross St. Thomas off my list lol!

Thanks so much for your advice and suggestions.

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