Actually the rooftop lounge at The Weyvern Hotel is a spectacular place to watch the sunset over Charlotte Harbor. Fisherman’s Village in Punta Gorda is a quaint collection of shops with restaurants at the end of the pier that have spectacular views of Charlotte Harbor. Port Charlotte, next door to Punta Gorda is very affordable. Boca Grande, about 45 minutes to the West of Punta Gorda on the Gulf is a very nice very upscale island (with a toll bridge that limits problems) with nice beaches and a lot of famous conservative folks as residents.
Port Charlotte has no downtown, but Punta Gorda is right across the bridge and is quaint and pretty quiet. I like the Celtic Ray pub, an authentic Irish pub. The tiki bar by the bridge is a bit more upscale. The Ice House is an authentic British pub, just down the street. Laisley Crab house is an open air restaurant and bar overlooking the harbor from an upstairs level. There are lots of dumps for lower class guys like me too.
Venice is 20 miles north and is a slightly younger, more upscale community with all sorts of restaurants and bars in the downtown walking area. It is closer to Sarasota and very close to the beach.
Did I mention that it's hot in the summer?