One of the toniest mountain towns in America, Aspen is surrounded by towering mountains and affords visitors stunning views from their hikes, paraglides, and kayaking excursions. For those who would prefer to skip the physical exertion, a gondola will take you to the top of a mountain overlooking the town, where you can order truffle fries and rosé.
Palm Springs, CA
A relatively short drive from Los Angeles, Palm Springs is full of outstanding mid-century modern architecture and design. The Parker Palm Springs Hotel receives excellent reviews for its service and its décor, and exploring nearby Joshua Tree is always an option if relaxation becomes a bit too relaxing.
St. Helena, CA
Nestled in the middle of Napa Valley, St. Helena is the ideal place to stay while exploring the surrounding countryside. Charming bed and breakfasts and Michelin-starred restaurants complement the array of world-class wineries surrounding this picturesque California town.
Situated off the coast of Cape Cod, Nantucket is one of the preppiest enclaves in the country. Rose-covered cottages, white picket fences, wild beach dune grass, and early morning fog commingle to create the island’s singular charm.
Key West, FL
Part of the Florida Keys archipelago, Key West has plenty to offer seekers of sun and relaxation. Pristine colonial Spanish architecture will interest the aesthetically inclined, and long stretches of immaculate beachfront will appeal to sun worshipers. And the nightlife options can’t be beat, especially for a resort town, in case you’re the type who prefers to start your night on the later side.
Little St. Simons Island, GA
If you’re really looking to get away from it all, Little St. Simons Island can help you do that. Located off the coast of Georgia, the remote island has just one lodge, which hosts a maximum of 32 guests at a time. Only serious nature enthusiasts need inquire.
The main town in tony Martha’s Vineyard, Edgartown is the ideal base from which Vineyard visitors can embark upon their surfing, biking, or sunning adventures. Martha’s Vineyard is the Obamas’ summer vacation destination of choice, so you never know who you might run into in town.
East Hampton, NY
Beautiful and serene, East Hampton is a quieter alternative to buzzy Southampton and hopping Montauk. The 1770 House is beloved for its charming rooms and hydrangea-filled gardens, as well as its restaurant, which is a favorite with celebrities such as Alec Baldwin.
Lake Geneva, WI
A favored summer destination for Midwesterners, Lake Geneva has plenty to recommend it. Well-heeled Midwesterners have been building in Lake Geneva since the mid-19th century, so opulent historical architecture abounds. Water sports are the main attraction here, but those who prefer to stay dry can opt for horseback riding or hiking.
Hilton Head Island, SC
Hilton Head Island may be small, but it has 26 golf courses, so if you’re a fan, best to consider teeing up. A number of excellent resorts accompany many of the courses.
San Juan Islands, WA
A boat ride or short puddle-jumper plane from Seattle will get you to the San Juan Islands, a gorgeous archipelago that can be explored together or one at a time. The big island is called San Juan, and unless you’re staying at a private house, it’s where you’ll likely be based. Charming shops and sailboats abound.