Wellington, Florida

Situated in sunny South Florida about 30 minutes west of West Palm Beach, Wellington makes the list for the second year in a row. It’s a well-manicured and wealthy village also known as “the Winter Equestrian Capital of the World”; every year, Wellington International hosts the 40-week Winter Equestrian Festival. The village also plays host to the Palm Beach Polo Season for four months, as well as the International Gay Polo Tournament.

Wellington’s claim to fame is that Bill Gates snapped up real estate in the area, when daughter Jennifer used to train there for equestrian events. Other boldface names, like Michael Bloomberg and Laurene Powell Jobs, also have ties to the area.

For everyday locals, the rural but pristine village is family-friendly, providing a high quality of life, great schools, three nearby hospitals, and numerous recreational activities. There’s a tennis complex, aquatics center, and acres of golf country. You can easily spend a day teeing up at Wellington National Golf Club or the Wanderers Club. 

And for those who want to enjoy the outdoors, Wellington offers a 65-mile bridle trail system. Peaceful Waters Sanctuary, a 30-acre wetlands park, showcases the best of Florida’s natural world, and Wellington Environmental Preserve, at the Marjory Stoneman Douglas Everglades Habitat, provides 365 acres of trails for hiking and horseback riding.

While South Florida traffic doesn’t have the best reputation, Wellington is close enough to several major cities outside of West Palm Beach for weekend excursions. Fort Lauderdale and Miami are both pulsing with nightlife and cultural attractions.