The Best Trips To Take With Your Girlfriends in 2020

Magic City Living

There’s more to the “Magic City” than meets the eye. Spend most of your time outside at Railroad Park, Regions Field for a ballgame, or Pepper Place Market on Saturday mornings, or crossing off titles on the rockstar lineup of restaurants. Meander between downtown Homewood, Mountain Brook Village, English Village, and Avondale to see the best of the city. 

A perfect day? Start at Woodlawn Cycle Café (and get the sweet potato biscuit!), head to Ghost Train or Back Forty for one of Birmingham’s signature brews, enjoy the weather at Railroad Park or the stunning Botanical Gardens, and then make sure to hit one of Frank Stitt’s places, particularly Chez Fonfon (get the coconut cake!), or one of Chris Hasting’s, like ultra-hip Ovenbird. 

Horse Country Escape

In Lexington you’re right in the heart of Horse Country, the Bourbon Trail, and everything downtown Lexington has to offer—Dudley’s on Short is a must-hit brunch spot. 

Spend your days right outside of town touring horse farms (and meeting Kentucky Derby winners!) and famed distilleries like Woodford or Buffalo Trace before heading back into town to enjoy more urban pursuits. The Distillery District boasts restaurants and bars worth a visit. 

Hot tip: If you’re in town around Keeneland’s spring or fall meets, hit the track to watch thoroughbred racehorses barrel around the track—and make a bet, or two. 

Harbor Town Haunt 

For a laidback girls’ trip, look no further than this funky beach town on the Atlantic. A harbor town at heart, this spot has come a long way since pirates and brothels and casinos ruled the roost. Think more along the lines of old-fashioned ice cream parlors, a charming French restaurant in a tiny house, called Le Clos, and The Palace Saloon, Florida’s oldest bar that stayed open through Prohibition. 

You’re more than likely to hit it during one of the town’s festivals, whether it be a shrimp festival in May, jazz fest in October, or Charles Dickens-inspired festival at Christmastime. Round out your trip with a jaunt along the area’s gorgeous beaches and lush wildlife. 

Antique Adventure

This tiny Texas town is full of quirky surprises, which makes it perfect for a group that wants to blaze a trail and try something new. For starters, people from all over come into town twice a year for the biannual antiques fair that is basically an antique diver or flea market finder’s dream. If you act quick, reserve one of The Silos at 159’s rentals, which have fashioned Anthropologie-worthy tiny abodes from old converted silos. 

Beyond the booths, you’ll find year-round shops like Junk Gypsy and Humble Donkey Studio that will send you home with plenty of unique finds. But, really, you can’t leave without gathering the gang and heading to Royers Round Top Café where pie is a must-get. Choose between Not My Mom’s Apple, Texas Trash, Junk Berry, and more. The menu jokes that it’ll cost you more to get a slice without a scoop of ice cream—and that’s our kind of rule. 

Virginia Wine Country

This spot is just the thing for a group that wants R&R with a side of stunning views and lowkey activities. Located in the middle of historic sites like James Madison’s Montpelier, wineries along the Monticello Wine Trail (make sure to hit Barboursville Vineyards, a vineyard built on grounds that also host the impressive ruins of former Virginia governor James Barbour's mansion, designed by Thomas Jefferson!), and charming Main Street shops and restaurants. 

Stay at the Inn at Willow Grove, a striking inn owned by couple Charlene and David Scibal that was renovated from a circa-1778 estate. If you can stand to drag yourself out of the plush accommodations, join the flocks of people visiting nearby Shenandoah National Park, especially if traveling during the months of peak fall color.

Do the Carolina Shag

Ever seen Shag? Myrtle Beach is practically made for running around with your girlfriends like you’re 18 again. Head to The Bowery for the house band and dance the night away—The Shag, of course!—after getting the local-favorite She Crab Soup at oceanfront spot, Sea Captain’s House. Another famous spot to dance the Carolina Shag to “beach music” is Fat Harold’s Beach Club. With a name like that, you’re bound to make some new memories with your gals. 

The New Nashville

Let’s get something out of the way: We know this is the ultimate girlfriend getaway destination of all time. But this time around, we’ve got the best brand spankin’ new spots to hit to make your trip to Nashville feel like the first time again. 

The Bluebird Café has long been the ultimate stop for singers destined to become country stars, but if you want a place a little less touristy, try out The Listening Room Café in the SoBro district. Make a reservation at Pearl Diver and sit amongst palm-frond wallpaper, seafoam booths, and coral stools. The bar cranks out very girls’ trip-friendly drinks, such as a classic daiquiri with rum, pressed sugarcane, and lime. 

If you’re looking for a trendy spot with a group activity, head to Pinewood Social. It’s a hip restaurant with a bowling alley for your best-ever group dinner yet. 

Lakeside Living 

If your crew is into mega views (or Instagramming them), head up to the Blue Ridge Mountains to this large private lake that’s so pretty it was once referred to as, “America’s Switzerland,” since it favored the Alp’s characteristic mountainside lakes. It even served as the getaway destination of industry giants like the Rockefellers. 

Stay at either the historic Greystone Inn or rent a home that comes with club amenities at the Lake Toxaway Country Club (things like tennis, golf, water activities, and dining). We’d vote for an autumn trip date to catch all of the fall color reflecting off the crystal waters, but summer makes an equally fun pick. You’ll be just minutes away from Cashiers and Brevard for when you need a few more creature comforts. 

Port City Charm

Historic Charleston, South Carolina: It's a charmer. Walk the city and shop ‘til you drop, or settle in on a carriage or minibus tour to see the sights sans Google maps. Grab a park bench or a patch of grass in Riley Waterfront Park, and watch the boats come and go. If gardens are your speed, you won’t want to miss the gorgeous landscaped ones at Middleton Place. Later in the day, wander over to FIG or Husk for a delicious dinner with your best pals—and don’t even think about skipping dessert. Need more reasons to visit Charleston? Here are 23.

Capital Fun

Hear that? Jackson's calling your name. For a fun weekend getaway, visit Mississippi’s state capital, which has plenty of up-and-coming areas to explore. No visit to Jackson is complete without a stop in the Fondren District, where you’ll find cool shops and restaurants like Saltine, Fondren Public, and Brent’s Drugs diner and soda fountain. In the evenings, the latter turns into The Apothecary at Brent’s Drugs (pictured), where you can find a menu of expertly mixed cocktails. Don’t miss Lemuria Book Store or the Mississippi Museum of Art, either.

The Pioneer Getaway

Pawhuska, Oklahoma, is the home base of Ree Drummond, The Pioneer Woman, and she has turned this tiny town into a fun weekend destination. When planning a pioneer getaway in Pawhuska, book a room at Drummond’s boutique hotel The Boarding House, and be sure to stop into the Mercantile (pictured), a restaurant and shopping hub that'll charm you as soon as you set foot in the door. (Just be sure to book early—Pawhuska is becoming more popular by the day!) Still working on your itinerary? Check out these four things everyone should do when visiting Pawhuska.

A Getaway Fit for a Queen (City)

Set your sights on the Queen City for a low-key vacation in a metro hub with plenty to do, eat, and see. Check out Freedom Park for a long walk, Blumenthal Performing Arts Center for a fun show, and SouthPark for plenty of shopping. Don’t miss Kindred, Good Food on Montford, and Nova's Bakery for delicious eats. In Charlotte, you’ll have your pick of places to stay; we’d recommend The Ivey’s Hotel or The Park Hotel. Want more Charlotte recs? We have you covered.

Southernmost and Feeling Fine

Point your compass south for a visit to Key West, and you’ll be greeted with charming streets, gorgeous architecture, and tropical trees as far as the eye can see. Rent bikes to pedal around the island, or settle in on a public beach after buying a box of Kermit’s Frozen Key Lime Pie on a Stick. (It lives up to the hype.) Take a photo at the Southernmost Point (pictured), stop into the Hemingway House, and catch the sunset at Mallory Square. Even better? Make a week of it and plan a Keys road trip from Key Largo to Key West.

Choose Your Own (Texas) Adventure

This sprawling Texas city should be at the top of your to-visit list. There are a million things to do in Houston, so choose a neighborhood, book a hotel, and explore a pocket of this ever-growing metropolis. For a manageable slice of the city, book a room at the swanky Hotel ZaZa, shop your way through nearby Rice Village, and meander the Museum District, which is just blocks away. Then set your sights on Montrose or Upper Kirby. The time to head to Houston is right now.

Georgia on Your Mind

If you plan a trip to Savannah, then Georgia's sure to be on your mind. This port city is a gorgeous coastal gem with leafy parks, plenty of great shopping, and a bustling historic district and riverwalk, where you’ll find great restaurants like Huey’s and Vic’s on the River. Don’t even think about skipping a trip to Moon River Brewing Company, River Street Sweets, or the Savannah Bee Company either. It’s a lovely destination for a three-day getaway—have you heard about the secret gardens?