There’s something magical about a long weekend. It’s just enough time to leave the daily grind behind, pack a small bag, and dive into a new place without the pressure of planning a two-week itinerary. While big names like New York, Los Angeles, and Chicago steal the spotlight, some of the most rewarding weekend trips can be found in cities that don’t always make the top of the list. These underrated destinations have everything you’d want—great food, local culture, and plenty to explore—without the overwhelming crowds.
What makes these cities so appealing is their balance of charm and accessibility. They’re easy to get to, affordable compared to bigger hubs, and filled with things that can keep you entertained without needing endless vacation days. Whether you’re craving historic streets, artistic neighborhoods, or outdoor adventures, there’s a hidden gem waiting just a short flight or drive away.
Before we dive into the list, here are some resources that make planning your weekend escape easier. From hotels to unforgettable local experiences, these platforms will save you time and help you get the most out of your trip.
Recommended Hotels
- The Benson Portland, Curio Collection by Hilton (Portland, Oregon)
- Hotel Emma, San Antonio
- 21c Museum Hotel Durham
- The Peabody Memphis
Recommended Experiences
- Food and history walking tour in Portland
- San Antonio River Walk cruise
- Historic walking tour of Charleston
- Graceland skip-the-line ticket in Memphis
Portland, Oregon
How to Get to Portland
Portland International Airport (PDX) is one of the most convenient airports to fly into, offering direct flights from most major U.S. cities. Once you land, hop on the MAX light rail for a smooth ride into downtown without needing a rental car.
Where to Stay
For a mix of elegance and history, check out The Benson Portland, a classic hotel that puts you in the center of it all. If you’re traveling with friends or family, a cozy VRBO rental in the Alberta Arts District gives you more space and a local feel.
Best Things to Do in Portland
Portland is a foodie’s dream, so start with a food cart pod and taste your way through international flavors. Powell’s City of Books is an institution worth getting lost in. Nature lovers can spend a morning hiking in Forest Park or take a day trip to Multnomah Falls, just 30 minutes outside the city. For an insider look, try a food and history walking tour to really soak in the city’s culture.
San Antonio, Texas
How to Get to San Antonio
San Antonio International Airport (SAT) sits just 8 miles north of downtown, making it one of the most convenient city airports. Cabs, ride-shares, or hotel shuttles make the short trip easy.
Where to Stay
Stay at the Hotel Emma, located in the trendy Pearl District, where restaurants, shops, and events are steps away. For a homey stay, consider a VRBO riverfront property that puts you right near the famous River Walk.
Best Things to Do in San Antonio
The Alamo is a must-see, but San Antonio is much more than its history. The River Walk is packed with dining options, live music, and boat rides. Don’t miss a River Walk cruise, which is both scenic and relaxing. In the evenings, the Pearl District offers lively energy, perfect for cocktails and live entertainment.
Durham, North Carolina
How to Get to Durham
Fly into Raleigh-Durham International Airport (RDU), which is about a 20-minute drive from downtown Durham. Public transportation and ride-sharing services are widely available.
Where to Stay
For something artistic and modern, book the 21c Museum Hotel Durham, which doubles as a boutique hotel and a contemporary art museum. Alternatively, a VRBO rental near Duke University gives you easy access to both campus and downtown life.
Best Things to Do in Durham
Durham has become a foodie hotspot, so make sure to explore its farm-to-table restaurants and craft breweries. Visit the Durham Performing Arts Center for a show, or spend a day at the Sarah P. Duke Gardens. Sports fans can catch a game at the iconic Durham Bulls Athletic Park.
Memphis, Tennessee
How to Get to Memphis
Memphis International Airport (MEM) serves as the primary hub, with numerous flights arriving daily. Renting a car makes it easier to explore outside downtown, but staying central means you can walk to many attractions.
Where to Stay
The Peabody Memphis is legendary, especially for its daily duck march through the lobby. For more space, check out a VRBO loft in the South Main Arts District.
Best Things to Do in Memphis
Music lovers can’t miss Beale Street, packed with blues clubs and live performances. Graceland is one of the city’s top draws, and booking a skip-the-line ticket saves you time. Food is another highlight: from classic barbecue to innovative Southern cuisine, your taste buds won’t leave disappointed.
Charleston, South Carolina
How to Get to Charleston
Charleston International Airport (CHS) is just a quick 20-minute drive from downtown. Ride-shares are common, though many visitors prefer renting a car for nearby day trips.
Where to Stay
Historic charm is everywhere here, but The Dewberry Hotel stands out for its unique blend of Southern warmth and style. If you’d rather have more privacy, a historic VRBO home rental gives you the chance to live like a local.
Best Things to Do in Charleston
Take a stroll down King Street for shopping and dining, or hop on a historic walking tour to dive deeper into the city’s past. Rainbow Row and the Battery make for picture-perfect walks, while nearby plantations and gardens showcase the area’s natural beauty. The food scene, which is heavily influenced by seafood and Lowcountry flavors, is another reason to spend your weekend here.
Boise, Idaho
How to Get to Boise
Boise Airport (BOI) is a small yet efficient airport, offering connections to major hubs. The city center is just a 10-minute drive from the airport.
Where to Stay
For a comfortable stay, The Grove Hotel offers a prime downtown location. Families or groups may prefer a VRBO home near the Boise River Greenbelt.
Best Things to Do in Boise
Boise combines city energy with outdoor adventure. Spend time exploring the Boise River Greenbelt, a 25-mile trail perfect for biking and walking. Downtown boasts excellent restaurants and breweries, and the Boise Art Museum provides a cultural attraction. For a bit more adventure, hike the nearby foothills or take a short drive to Bogus Basin for year-round outdoor activities.
Milwaukee, Wisconsin
How to Get to Milwaukee
Milwaukee Mitchell International Airport (MKE) is the city’s main gateway, with plenty of direct flights from major Midwest hubs. Amtrak also connects Milwaukee to Chicago in just 90 minutes, making it an ideal destination for a quick weekend getaway.
Where to Stay
The Pfister Hotel is an elegant downtown choice with a touch of old-world charm. For a different vibe, book a VRBO lakefront condo and wake up to Lake Michigan views.
Best Things to Do in Milwaukee
Beer culture runs deep here, and touring the city’s breweries is a must. Visit the Harley-Davidson Museum, or spend an afternoon along the lakefront exploring the Milwaukee Art Museum with its striking architecture. Summer weekends are filled with festivals, live music, and lake cruises, making this city far livelier than most travelers expect.
Santa Fe, New Mexico
How to Get to Santa Fe
Santa Fe Regional Airport has limited flights, but most visitors fly into Albuquerque International Sunport (ABQ) and drive an hour north through scenic desert landscapes.
Where to Stay
Stay at La Fonda on the Plaza, a historic hotel filled with Southwestern charm. Or opt for a cozy VRBO Adobe rental, where you can fully immerse yourself in the local vibe.
Best Things to Do in Santa Fe
Santa Fe is an art lover’s dream, with Canyon Road offering hundreds of galleries and studios. The city’s architecture, infused with Pueblo-style design, makes even a simple walk feel inspiring. Don’t miss the Santa Fe Plaza, where shops, food stalls, and local music create a lively atmosphere. Outdoor enthusiasts can head to the Sangre de Cristo Mountains for hiking and breathtaking views.
Conclusion
From the desert beauty of Santa Fe to the lakefront charm of Milwaukee, these underrated U.S. cities prove that the best weekend getaways often fly under the radar. Each offers its own character, filled with history, food, and culture, without the crowds or stress of bigger destinations. The next time a long weekend rolls around, skip the obvious choices and try one of these gems—you may find yourself planning a return trip before you’ve even left.