Naples

Naples

Naples brings wealthy retirees to the Gulf coast for genuinely some of the prettiest beaches in Florida, and the sunsets at the pier are a community ritual (everyone gathers, no one talks). The downtown along Fifth Avenue is pastel and breezy. Mercato has the upscale restaurants. The Everglades' western edge starts just south of town. Affluent, sunny, and quieter than the east-coast Florida cities.

Tampa

Tampa is the Cuban sandwich's other home (yes, there's a rivalry with Miami), with Ybor City's brick streets, rooster gangs, and cigar shops giving the city a flavor all its own. Bayshore Boulevard claims one of the longest continuous sidewalks in the country, perfect for sunset jogs. The beaches are a short drive west, the Lightning play hockey in the swamp, and the winters feel like other cities' best Aprils.