We lived in Boston all of our lives but decided that the city was not for us in retirement, however access to it was. Second criteria was some proximity to the ocean. We thought about moving out of state but grandchildren here are a magnet.
Ultimately we bought a house in an active 55 community in Plymouth, Mass. (aka America's home town). About 50 miles to the city, accessible by car or train within an hour. Close to Plymouth harbor and beaches. Good restaurants etc nearby. The community offers the opportunity to be involved in as much or as little as you desire. The downside remains the weather.
So for two years we have traveled to warmer climes for month or so in the winter, 30 days in Aruba last year, and 30 days in Florida starting next week for 2011 and maybe another couple of weeks in the Carribean in Dec.
We decided against buying in a warmer climate so that we could try different places, if we really fall in love with some area then we might buy. We are also fortunate to have a place on Cape Cod (Truro) and spend time there as well. But highly recommend this area.