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.

Manchester

Manchester is built around the Amoskeag Mills, once the largest cotton mill complex in the world, now converted into apartments, restaurants, and offices along the Merrimack River. The downtown's grown into a real food and brewery scene. It's the largest city in New Hampshire (still relatively small) and a quick drive to the lakes, the mountains, or Boston. Plus there's no state income tax or sales tax.