Try Punta Gorda
There are good areas all along the SW FL coast, but consider Punta Gorda. Charlotte Harbor is great regardless of weather because it is protected water, shallow & warm water, nice trip out to Cayo Costa for beach, cruise canals to look truely "affordable" (not like Naples)homes, boat rental available at Fisherman's Village along with shopping, eating, etc. King Fisher Fleet Charter has day trips on nice group charter to Cayo Costa, nature charters, sunset cruise, etc. Try looking at www.liveonthewater.com It is a realtor's site, but has great photo album, links, etc. We are not retired but wanted to move to FL to be on water. Looked in Naples, Cape Coral, Ft. Myers, Venice, Sarasota and bought in Punta Gorda. Waterfront property is not cheap, but it is more reasonable here than anywhere else. We live on canal, have a Catalina 320 at our backyard dock. The sailing here is great - there are shoals, but we have had no problems. The canals in Punta Gorda Isles are beautiful at Christmas with boats and canal fronts decorated with Christmas lights. King Fisher Fleet also does canal cruises to see lights, but not sure if they continue after Christmas. They have a web site with their cruise options and times. Also, traffic in Punta Gorda is not even close to the mess it is in Naples or any of the other areas we looked at.