If you're more likely to want to shop and go to Fort Myers, consider Portofino, an Italian village-style community. It's close to the Minnesota Twins complex (and soon-to-be Boston Red Sox complex). It takes about the same amount of time to get to Fort Myers Beach or Sanibel from either community. HOA fees are about $1089 per quarter.
Your choice may come down to floor plans and value. I'd be glad to send you details on the options in both communities: feel free to contact me at 239-440-1069 or email firstname.lastname@example.org.
Southwest Florida Residential Specialist
Sellstate Select Realty
It truly is all a matter of personal taste. Emerson Square is a very nice community centrally located close to both Ft. Myers and Bonita Beaches and of course10 mile canal and mullet creek marina for fishing, boating, canoeing etc .... Portofino is also a very nice community with a Mediterranean feel and resort like atmosphere and ammenities. This is also centrally located about 20-25 mins to Fort Myers Beach and 10-15 minutes to the airport. Both would make a very nice home or seasonal residence . i suggest you visit both to get a feel for them. Feel free to contact me if you would like to visit them. Good Luck in your search!