15 US Cities Perfect for a Long Weekend Trip
Recently one of our editors took a long weekend trip to one of our favorite destinations (Nashville, Tennessee) for no real reason at all… except for having some extra cash after winning Super Bowl Squares this year & she had the best time. That spontaneous vacation, combined with this article from Thrillist inspired us to come up with our own list of 15 cities in the United States that we’d love to head to for a weekend trip – either solo, for a romantic getaway, or a fun girls’ trip with a couple close friends. While we love a great international trip, there are so many cities in our own country that we either love or have never been to & they’re most certainly worth a visit, even if just for a couple nights. Note: These are listed in no particular order!
This city truly feels like our home away from home and we love it more and more every time we visit. It’s called “Little Big Town” for a reason – it’s the perfect mix of a small town & a big city with tons of great restaurants, plenty of live music, and lots of things to do for all ages. The locals are also super friendly & it’s definitely a must-visit destination for anyone who loves music – especially country! Check out our Nashville travel guide for more tips on where to stay, what to do & (most importantly) what to eat and drink!
Charleston, South Carolina
This Southern city has been on our list of must-visit places – it just looks so charming! Julia Engel of Gal Meets Glam has a great Charleston guide since moving there from San Francisco, and we're excited to follow her advice once we book our own trip. We can't wait to explore the French Quarter, the famous Rainbow Row, and nearby Hilton Head Island or even Palmetto Bluff to see all that the Lowcountry has to offer. It seems like the perfect destination for a relaxing girls’ weekend with your best gals filled with shopping & bicycling – or even a mother/daughter or sister trip!
New York, New York
The “Big Apple” is one of those destinations that captures the hearts of tourists from around the world – just look at how many people travel there for New Year’s Eve alone (despite the cold temperatures)! It’s been years since we’ve visited New York City & with so many places to stay, neighborhoods to explore, and food to enjoy, it would make a wonderful weekend destination. Another perk is the public subway system that makes it easy to spend the morning in Central Park, grab lunch at one of Brooklyn’s trendy hot spots, and then watch one of many Broadway shows after dinner.
We have heard amazing things about the city of Austin, Texas & we can’t wait to experience it for ourselves. Most people say that it’s very similar to Nashville since there’s a small-town vibe with tons of live music and delicious food. Dallas & San Antonio are other cities in Texas that we’ve been to that would make good weekend trips, but everyone raves about Austin… so put this destination at the top of your Texas list!
If you’re looking for a city with Midwest charm & a metropolitan vibe, we’ve heard wonderful things about Chicago. With tons of tourist activities to enjoy – like The Bean at Millennium Park, the Willis Tower (formerly the Sears Tower), Navy Pier, and great museums – it’s sure to be a fun trip. We’ve also heard amazing things about the food (hello, deep-dish pizza!) & can’t wait to go on the Chicago Architecture Tour along the river. One of our favorite sites, The Everygirl, is based in Chicago & they have a great weekend guide here that we’ll definitely be referencing for our future trip.
Santa Barbara, California
Also known as The American Riviera, Santa Barbara is a beautiful city on California's central coast. We love the Mediterranean-style buildings with white exteriors & red roofs that reflect the locale's Spanish colonial heritage. Spend the day exploring the many shops & restaurants along State Street, visit museums & missions, and go wine tasting downtown along the urban Funk Zone wine trail or in nearby Santa Ynez or Los Olivos. We can’t resist Los Agaves for Mexican food, The Lark for a special occasion dinner, Lucky Penny for tasty pizza & McConnell’s for ice cream!
Like Charleston, Savannah is one of those Southern cities that we’ve heard so much about and can’t wait to visit. A weekend trip would be the perfect opportunity to unwind & take in the fresh air, beautiful greenery, and homey vibe the city has to offer. The Everygirl also has a weekend guide for Savannah that shares where to stay, what to do & what to eat when visiting the charming locale featuring cobblestone squares & historic architecture.
Filled with rich history, Boston would be a fun place to spend a long weekend mixing tourist activities with tasty New England food. There are plenty of national landmarks and museums to visit (like the Freedom Trail – a 2.5-mile walking route of historic sites) & baseball fans can watch a game at the famous Fenway Park. Side note: We're also watching A Million Little Things right now, which takes place in Boston & it's definitely making us want to plan a trip even more!
Portland is one of those US cities that we've always planned to visit but never have. We have friends from Portland & friends who have moved to Portland, but we've surprisingly never made the trip! We've heard incredible things about the food & craft breweries, and we love how the city is so close to some great outdoor adventures. It might rain a lot, but that could be part of the fun!
Sedona was one of our favorite weekend getaway spots when we lived in Arizona – it’s gorgeous! We would love to stay at the stunning Enchantment Resort someday since its design pays tribute to the natural beauty of the region. The small town is perfect for outdoorsy types who want to hike and take in the red-rock buttes, canyon walls & pine forests, and it's also a New Age favorite since there are tons of shops, spas, and art galleries that honor the unique vortexes & calming properties of the destination. We also recommend visiting Oak Creek Brewing Co. for tasty craft beer – be sure to try the Nut Brown Ale while sitting on the patio!
We used to visit Carmel every year when our grandparents had a summer home there, but we haven’t been back in almost two decades & it’s time to start planning a trip! Located on the Monterey Peninsula, the coastal town is known for its charming storybook streets, cottages, and art galleries (think: all the cute Big Little Lies moments & Thomas Kincaid paintings). It's also super close to the famous Pebble Beach golf courses & the gorgeous 17-Mile Drive, which is a great way to spend an afternoon. If you're planning a trip to Big Sur (another beautiful place we’d add to this list!), definitely take the extra drive farther north to this super cute & romantic place.
Tales of the rain & gloomy skies may have kept us away all of these years, but we’re so excited to visit Seattle someday. We've heard great things about their famous "hot tub boats" that you can rent while cruising the lakes, and of course we’ll be stopping by the Space Needle, catching fish (or watching people catch fish) at Pike Place Market, and maybe leaving some gum behind at the famous Gum Wall. For those who like to hike or just take in the beauty of nature, Mt. Rainier is just a quick day trip away – perfect for a long weekend excursion!
New Orleans, Louisiana
Some realists say you should see New Orleans before it really starts sinking & while that probably won’t happen in our lifetime, we’re still adding this city to our must-visit list! If the beignets at Café Du Monde weren’t enough to get us to buy a plane ticket, we're looking forward to eating in the French Quarter, drinking and listening to live jazz music on Bourbon Street, and maybe even checking out one of the spooky haunted history tours!
La Jolla, California
A small seaside community within the city of San Diego (which we also recommend!), this upscale coastal town is the perfect place to spend a weekend getaway. Coming from LA, it’s a great spot to unwind since the lifestyle seems more laid-back & we love how despite the shopping malls and city feel, they embrace the beauty of the area and coastal vibe – many parts of the highways don’t even have streetlights! We recommend sitting on the patio for lunch or dinner at Piatti and stopping at La Jolla Cove for the gorgeous ocean views & to see sea lions up close.
Though we’ve never been, the capital of Colorado is on our list of US destinations to see. While we probably couldn’t handle a winter visit in the cold – unless we were staying at one of the nearby ski resorts in the Rocky Mountains – the crisp air & blend of urban sophistication with outdoor adventure makes it a great weekend spot. We’d also love to go see a show at Red Rocks Amphitheatre in nearby Morrison, Colorado – definitely a bucket list experience!
Have you visited any of these cities? If so, let us know what we have to try when we go! Did we leave off one of your favorite US cities that you think is perfect for a long weekend trip? Please share in the comments… We’re constantly adding to our travel bucket lists! For more ideas & inspiration, view 11 well-designed Airbnbs we’d love to book, discover our Cabo travel guide, and get 75 ideas on what to do this spring & summer.