Hippie, outdoorsy, and sophisticated, this western North Carolina town in the Appalachians has long drawn independent thinkers, including George Vanderbilt, whose Biltmore estate put Asheville on the map. “There’s a creative spirit nurtured in the mountain air of the Blue Ridge that runs through the eateries, breweries, galleries, and music halls,” says Victoria Isely, a former Washingtonian who is now CEO of Explore Asheville. Besides downtown, neighborhoods to check out include the River Arts District and up-and-coming West Asheville and South Slope, known for their funky shops. Already, the summer schedule is packed: Asheville Beer Week is late May into early June; Saturdays in June mean Art in the Park; and early August brings one of the nation’s longest-running folk-music gatherings—the Mountain Dance and Folk Festival, nearing 100 years of celebration.
Street for strolling: The area around Eagle and South Market streets, at one time the commercial center for the African American community, is once again a hub for Black-owned businesses and makers. Wander “the Block,” a redeveloped area of shops, restaurants, and creative spaces.
Local bite: Pulled-pork sandwich. Try it at Buxton Hall BBQ, where hogs are smoked in the eastern North Carolina style, with a vinegar-based sauce.
Sustainable stay: The Cottages on Biltmore Estate—with their solar panels and butterfly-friendly landscaping—carry on Vanderbilt’s environmental legacy.
Nature fix: The Mount Mitchell summit, highest peak east of the Mississippi, rewards visitors with views of some of the oldest mountains in the world. Get to it via a short but steep walk from the parking area or a strenuous two-mile climb.
New nonstop: From Reagan National on American Airlines (seasonally from May to October).
At the tip of a 125-mile chain of islands connected by the Overseas Highway, Key West is closer to Cuba than to the Florida mainland. This tiny island—a little more than seven square miles—has an outsize personality, from the nightly antic-filled sunset celebration in Mallory Square to the haunts of famous residents such as Ernest Hemingway and Jimmy Buffett to high-adrenaline marine pursuits like sport fishing. This year, the island marks the 200th anniversary of its first permanent settlement, and yearlong activities are planned.
Street for strolling: Whitehead Street—parallel to the main drag of Duval Street and running from the Gulf of Mexico to the Atlantic Ocean—has Mile Marker Zero (the starting point of US Route 1, which goes to Canada), the Hemingway House Museum, Mallory Square, and the marker for the southernmost point of the continental United States.
Local bite: A slice of Key-lime pie, natch. Try it at Kermit’s Key Lime Shoppe, which also sells a gluten-free version.
Sustainable stay: Key West Marriott Beachside Hotel, a Florida Green Lodging–designated property.
Nature fix: Kayak among the mangroves and spot ospreys, queen conchs, small sharks, and stingrays through a tour outfitter such as Blue Planet Kayak Eco-Tours.
New nonstop: From Dulles on United (year-round).
This 48-square-mile spit of land off the coast of Cape Cod, Massachusetts, is a favored getaway for Washingtonians—famous and not—perhaps because of its uncrowded, dune-backed beaches; cedar-shingled, weather-worn buildings; and landscapes that melt worries away. “It’s surrounded by water and 30 miles from the mainland, so it feels cut off from the world, in a good way,” says Washingtonian Susan O’Keefe, whose family has vacationed there for decades. “You leave behind chain stores and traffic lights and slip into life in a seaside village with rose-covered cottages and uninterrupted white-sand beaches—all with public access.” The town’s cobblestone streets are lined with boutiques, restaurants, and galleries—all great and all pricey. Be sure to visit the Whaling Museum to understand the island’s role in the 19th-century whaling industry.
Street for strolling: Main Street has coffee shops, a pharmacy with a soda-fountain counter, and historical wood houses of sea captains and whale-oil merchants.
Local bite: Boiled lobster with all the sides. Try it at Nantucket Lobster Trap.
Sustainable stay: The Cottages at Nantucket Boat Basin participates in hotel recycling-and-reuse programs and promotes oyster restoration off Nantucket Island.
Nature fix: Bike to Siasconset, a former fishing hamlet about ten miles from town where a hidden bluff walk offers wide ocean views and sprawling summer homes with steps leading to ’Sconset beach, as locals call it.
New nonstop: From Dulles on United (seasonally from June to September).
Big Sky Gateway
Seeding an Old West cow town with creative millennial makers has turned Bozeman, Montana, into one cool city. Cafes, bike shops, upcycled-furniture stores, and breweries dot the downtown, and an old grain mill has been converted into a gallery and workshop. A landmark Art Deco building, circa 1941, is now the Kimpton Armory Hotel. All this isn’t even the main attraction. Ringing the town of 53,000 is the great outdoors. Make that grand: a half dozen mountain ranges, and Yellowstone National Park practically in its backyard. Wild to mild, any activity is possible, from hot-spring hopping to ziplining.
Street for strolling: Make it Main Street, with its mix of architectural styles plus storefronts that sell everything from hand-stitched leather boots (Boot Barn) to hand-pulled espressos (Wild Joe*s Coffee Spot).
Tasty bite: A burger made of Montana cattle or bison. Try it at Backcountry Burger Bar.
Sustainable stay: In the heart of downtown, the Lark Bozeman used recyclable materials in the redesign of a 1960s property and opts for digital directories.
Nature fix: A horseback ride through the sagebrush meadows of the Gallatin Range is classic Montana. Try it at 320 Guest Ranch.
New nonstop: From Dulles on United (seasonally from July to September).
Despite being Georgia’s oldest city, Savannah has a youthful and visionary aesthetic. That’s thanks in part to the renowned Savannah College of Art and Design, or SCAD, whose alumni have, over the last four decades, helped shape the city’s culture and economy. Against the backdrop of the largest National Historic Landmark District in the US—22 city squares, encompassing sights such as the oldest Black church in North America—the creative spark of the Hostess City shines everywhere, including the contemporary-art museum, Jepson Center; the high-end Downtown Design District; and a dining scene ranging from down-home eateries to Michelin-starred restaurants.
Street for strolling: Often called the prettiest street in Savannah, red-brick-paved Jones Street is lined with southern live oaks and Victorian homes.
Tasty bite: Fingerlickin’ fried chicken and hoecakes (pancakes made with cornmeal). Try them at the Grey, housed in a restored Art Deco former Greyhound bus terminal.
Sustainable stay: Kimpton Brice Hotel is certified by the Green Key Eco-Rating Program and partners with Clean the World, which collects and recycles discarded soap.
Nature fix: Stretch out on a sandy beach on Tybee Island, a barrier island 20 minutes from downtown.
New nonstop: From BWI on Southwest Airlines (year-round).
This article appears in the April 2022 issue of Washingtonian. An earlier version of this article also included Berlin, Germany, but United Airlines since changed its plans to begin nonstop service this summer from Dulles to Berlin.