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.

Anchorage

Anchorage is the city where moose sometimes wander into downtown, the Chugach Mountains tower right behind your office, and summer days run 19 hours long. The Iditarod sled-dog race kicks off from here every March. The food scene leans heavily on the world-class salmon and halibut coming off the boats. Winter brings the northern lights flickering above the mountains and the kind of quiet you only find this far north. Wild edge.