Welcome. You came to the right place to ask questions, as I have been doing for months now. I owned a Victory 21 and sailed out of Annapolis for many years. After many years away from sailing, I bought a boat that could fit the whole family. We sail it around Long Island, CT, RI and am planning a trip to Nantucket this summer.
Try the search at the top of the screen to see if anything's been covered before. I think there's lots of threads on "which boat". Much of the decision has to do with the details of what you are looking for.
Also, there are many members in your area, and I'm sure that if you offer to bring a bottle of wine or two, they'd tell you first-hand about their cruising adventures and what they've learned.
Please post pictures of your current boat and places you've been.
Great minds discuss ideas;
Average minds discuss events;
Small minds discuss people.
The best minds discuss sailing. I don't know why. It's a mystery!