Spend a weekend on Nantucket
While summer is the traditional season to travel to this Massachusetts island, fall can be an ideal time to visit instead. The fog that rolls over the island’s cranberry bogs in the autumn is particularly beautiful. If you can’t make it in fall, spring is good too, especially when the Nantucket Wine and Food Festival takes place; it should give any foodie reason enough to want to visit.
Go on a foodie tour of St. Louis
By your thirties, you’ll have hopefully gained an appreciation for good food you may have lacked in your twenties, making the under-the-radar foodie city of St. Louis an ideal spot for a weekend escape. Start with happy hour at the beautiful Bar Les Freres in Clayton, and then head to Soulard for dinner at Sidney Street Café—Chef Kevin Nash has won countless national awards for his inspired French cooking.
See fall foliage in Vermont
Stay at the historic Shelburne Farms, one of the best cheese farms in America, and enjoy some sharp cheddar with your leaf-peeping.
Go antiquing in Connecticut
The Brimfield Antique Show is famous to collectors all over the world for its impeccable selection—travel to Connecticut in July to partake in the fun.
Visit the San Juan Islands
The perfect low-key long weekend escape for a group of 30-somethings, the San Juan Islands are a beautiful cluster of islands just off the coast of Seattle. Hop on a sea plane to the main island where you can rent a house or hotel, and charter boat rides to the neighboring, pine-scrubbed islands.
Attend South by Southwest in Austin
The ultimate techie festival, the annual South by Southwest festival in Austin also features marquee music acts alongside talks by the CEOs of major tech companies such as Twitter, which was founded at the festival.
Go skiing in Aspen
Aspen is one of the most beautiful ski towns in America. You’ll swear you stepped off the plane into Switzerland in this scenic Colorado town, which has plenty of black diamond trails for accomplished skiers and lodges, such as Ajax with truffle fries and rosé on tap, for those who are more into the aprés.
Drive from L.A. to San Francisco along the ocean
California’s famous Pacific Coast Highway can take you from L.A. all the way up to San Francisco along the ocean, making it one of the most beautiful drives in the world. Rent a convertible, and spend the first night in Santa Barbara and the second in Big Sur.
Partake in outdoor adventures in Alaska
Between dog-sledding, skiing, rafting, hiking, camping, and climbing, Alaska is hard to beat in terms of outdoor opportunities it affords. Incredible scenery, especially when covered with snow and ice, makes Alaska a true bucket list destination.
Spend a weekend in Santa Fe
One of the most unique and historic spots in America, Santa Fe was established by the Spanish in the 16th century. The entire city center is made up of Navajo-style adobe clay structures, with courtyards in the center, and turquoise trim. Stock up on turquoise jewelry and visit the famous Ten Thousand Waves Spa in the hills outside the city.
Visit Savannah, Georgia
If you’ve read the cult classic Midnight in the Garden of Good and Evil, you doubtlessly already want to go to Savannah. But besides a serious cast of eccentric characters, Savannah also has killer food and no open-container laws; therefore, you can enjoy your mint julep while on that antebellum architecture tour.
Take an Art Deco architecture tour of Miami
After the allure of partying all night in Miami fades, the city’s incredible Art Deco architecture remains. Cap off your tour with a visit to the hot new Faena Museum, and take your pick of many excellent restaurants.
Walk the Freedom Trail in Boston
College may be a distant memory, and perhaps your American history lessons will be as well by the time you reach 30. Rectify that by walking the Freedom Trail in Boston, which will take you through incredible Revolutionary War sites. Finish with dinner at the Beehive, a jazzy dinner spot in the hip South End.
Eat a lobster roll in Maine
The lobster roll is an American delicacy, and no state lies as great a claim to making the best as does Maine. Whether in Kennebunkport or Cape Elizabeth, pick a shack right on the water where the lobsters are caught right out back.
Visit historic Newport
The seaside town of Newport, Rhode Island, has stunning Gilded Age mansions that look as they did 100 years ago, complete, in some cases, with historic reenactors. Spend the afternoon touring, and then grab dinner on the harbor.
Run (or watch) the Cherry Blossom Marathon in D.C.
Whether running or watching, the Cherry Blossom Marathon in D.C. is a beautiful rite of spring, perfect for a 30-something group of friends. Have a celebratory dinner afterward at Oyamel—a favorite of the Obamas.
Visit Niagara Falls
It may be touristy, but it’s impossible not to get into the spirit of Niagra Falls once the boat captain hands you your poncho. Try the Maid of the Mist for an excellent narrated tour.
Spend a night at the Chateau Marmont
Hollywood’s most legendary hotel, the Chateau Marmont is tucked into the hills just off Sunset and is an ideal place to get away for a weekend or even just a night. Celebrities pack the restaurant (for guests and A-listers only) and the hotel’s bungalows, which lie nestled in the hills behind a locked gate to keep the paparazzi away.
Chateau Marmont, 8221 Sunset Blvd, Hollywood, CA, USA, +1 323 656 1010
Go to Napa
Spend a weekend with friends at a winery in Napa, where you’ll find beautiful scenery, Michelin-starred food, and, of course, some of the best wine in America.
Stay at a classic New York hotel
Whether it’s the chic Gramercy Park Hotel (designed by Ian Schrager) downtown or The Carlyle uptown (with its restaurant wallpaper painted by Ludwig Behmelmann), treat yourself to a night at a proper New York City hotel.
Go shopping in Dallas
Arguably one of the flashiest cities in America, Dallas is a mecca for high-end shopping. Start at the original Neiman Marcus (make sure to try the popovers in the café) and then make your way to beloved indie boutique Forty Five Ten.
Check out the art in Chicago
There is enough in the world-famous Art Institute of Chicago to interest an art history fiend for days. Fuel up before at RL Restaurant—the posh and preppy hot spot located right inside the Ralph Lauren store. And don’t forget a photo of the reflective bean sculpture in Millennium Park.
Go to Chez Panisse
The paragon of California cooking, Chez Panisse is Chef Alice Waters’ restaurant in Berkeley and is as excellent now as the day it opened 40 years ago. If you’re lucky, Waters will be in the kitchen that day and can sign one of her cookbooks for you.
Chez Panisse, 1517 Shattuck Ave, Berkeley, CA, USA, +1 510 548 5525
Stay at a dude ranch
Grab some friends and head to a dude ranch perched high on a hill somewhere out West. Whether in Montana, Wyoming, or Colorado, the views of nature around you will be awe-inspiring, and the memories hard to beat.
Check out Marfa
An upscale hippy arts town in the middle of the Texas desert, Marfa isn’t the easiest to get to. But those who make the journey will be rewarded with incredible, conceptual contemporary art, including the famous Prada Marfa store—a statue of a Prada store that is always lit and never open.
Spend a summer weekend in The Hamptons
Get a share house or a hotel room, and spend a summer weekend sipping rosé, playing tennis, and relaxing at the beach in this preppiest of American enclaves.
Tour a whiskey distillery in Kentucky
Options abound, but Johnny Walker is a classic for a reason.
Vacation in Michigan’s Upper Peninsula
Deep, dark blue lake waters and excellent, ever-lasting barbeques await summer travelers to Michigan’s Upper Peninsula. The Fourth of July is a particularly good time to travel to this all-American enclave.
Go to the New Orleans Jazz Festival
The New Orleans Jazz Festival is a far cry from the din of Mardi Gras. Stay at a historic bed and breakfast during this long weekend in May, and enjoy the jazz along with the Café du Monde beignets.
Visit Puerto Rico
No passport required to feel like you’ve entered an entirely separate country.