[ricki]

June and July (and August) typically are off wind months in Florida. There is still lots of great things to do and see in Florida, but useable winds usually are scarce. From what I have experienced later August can be an off wind time in other areas. So, if you can choose I would shoot for travel in June and July. There are lots of areas with reasonable winds in those months. In the mainland USA, Padre Island in Texas, the Outer Banks of North Carolina, Cape Cod in Massachusetts, Sherman Island and the Gorge in the northwest to name a few. For best value for accommodations you might do well in Padre Island perhaps the Outer Banks from that list.

The Bahamas seems to have similar wind prospects to Florida over the summer. Cabarete in the Dominican Republic can have excellent winds particularly in July as long as tropical weather systems don't alter things. Historically, accommodations were very reasonable there too. Today, less so but I think there still are some bargains to be had there. You may also find some reasonable rates down around Margarita just above South America. Happy looking, hope you have a great summer!