Fort Myers (RSW) is the closest, and Jet Blue and Spirit have a non-stop out of logan to RSW.

You can do a 1 stop with almost any airline out of Boston, Jet blue (thru JFK) $292; USAir (Thru Philly or Charlot) $309; Delta (Thru Atlanta) $311

Or the non-stops jet blue is $368 and Spirit is $326. Fairs are from Expedia for 2/5 in and 2/9 out.

Fort Myers is nice airport and rental cars are at the terminal building.

The charlotte harbor regatta website has a link at the top for lodging in the area, I stay at home, so no experience with any of the hotels listed.