12 Naples, FL

PopulationMetro: 372,880
Money can’t buy happiness, but in prosperous Naples, it can buy a lifestyle among some of America’s richest oceanfront bounty.

The Place category is our deepest and most complex, so we tend to surface cities that don’t register high on the overall ranking yet excel in the Place category as outliers among the overall winners. And Naples, which ranks #3 among small cities for Place, has much to offer, despite finishing #12 overall.

Considerably sleepier than its Atlantic counterpart, the Gulf Coast is a place to slow down and relax. Cultured, chic and set at the edge of one of the most serene beaches in southwest Florida, Naples is welcoming and always up for packed itineraries. The city comes in at #2 for Parks & Outdoors, with surfing, fishing and all kinds of on-the-water tours (mangrove and manatee eco-tours, anyone?).

Place 65
Product 37
Programming 41
People 71
Prosperity 63
Promotion 47

Its solid Shopping, Restaurants and Culture rankings also powered its Top 20 score for Programming.

Napes offers the kind of laid-back, leisure lifestyle one would expect from the #14 most prosperous small city in America, boasting the highest Household Income in the country, according to our research, and a Top 5 finish for Educational Attainment.