Size Guidelines

[mpc7002]

I am sure that this kind of question has been posted before, so my apologies. If someone can point me in the right direction that would be great.

I am getting back into sailing, and my wife and I are looking for our first boat. My experience has been in the Tampa Bay area, about half and half inter coastal, and Gulf. I have rarely sailed beyond sight of land. And its always been as crew on other peoples boats. So here is my question...

What would be the appropriate size boat for two adults, and a 10y/o to:

1) be out for the weekend
2) sail from Tampa to the Keys
3) sail to the Bahamas
4) sail across the Gulf to Mexico

I am not looking to buy a boat tomorrow and do these things next week, of course it would be based on experience, and what size boat we had.

I was thinking of starting out with something manageable like a 25 footer, and work my way up.