Hello and welcome to the forum. You are in a great area to sail. You have so many destinations all over LI Sound.
If you are boat shopping
there are so many options. Which one will depend on your preferences and budget
. Most boats can be set up for easy single
handing so focus on finding the boat you like and set it up for how you sail.
My daughter just moved to Martha's Vineyard
. I was lucky enough to plan a visit the week Irene showed up but still had several nice days. Her boyfriend has a boat in Tashmoo and we made it up to Edgartown for a day. He's also in the building business and looking for something on the island.
Good luck on the boat search and let us know how it's going.