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.

Tulsa

Tulsa was built by 1920s oil money and the downtown looks the part: Art Deco everywhere, like Gatsby moved to Oklahoma and never left. The Greenwood district, once known as Black Wall Street, now holds one of the most powerful civil rights museums in the country. The Tulsa Remote program pays new arrivals $10,000 to move here, and enough have taken the deal that there's a real scene now. The Gathering Place park alone is worth a flight.