12 Anniversary Trip Ideas For Every Milestone And Couple

The South is chock-full of charming destinations for a romantic getaway.

Charlottesville VA

Gabriela Herman

Celebrating an anniversary offers the perfect excuse to plan a trip to somewhere new, or even back to a beloved place that you’ve been dreaming to revisit. A romantic getaway is an ideal way to spend quality time with a loved one, and these anniversary trip ideas and itineraries are sure to make more memories as you look back on fond ones. 

Since anniversaries fall on every time of the year, we have different options for every type of couple. Planning for autumn? Consider celebrating with a Blue Ridge Mountains road trip with epic fall color or a bourbon tour in Kentucky. Dreaming of a tropical breeze? The Florida Keys are calling. Want something unique? We’ve got small towns and cities worth wandering. Luckily, the South abounds with charming destinations to experience with your partner. 

For every couple or milestone, there’s a Southern anniversary trip idea for your next vacation. See our list of favorite romantic destinations.

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The Florida Keys

The Moorings Village
Hector Manuel Sanchez

Head out on a road trip on the Overseas Highway, a 113-mile road spanning from Key Largo to Key West—the most famous among Florida’s southernmost archipelago. Beyond the conch-style houses, toes-in-the-sand seafood joints, and general good-living attitude, there’s no bound on what you can explore, starting with How To Spend The Perfect Day in Key West and The Secret Beaches of the Florida Keys Worth Visiting. Make sure to stop for a tour of Ernest Hemingway’s home and its famed six-toed cats. 

02 of 12

Charleston, South Carolina

Charleston's Rainbow Row Homes
Peter Frank Edwards

It’s easy to see the appeal of this charming coastal town for a romantic getaway—it’s been voted the South’s Best City several years running for just that reason. Cobblestone streets and colorful row homes make for easy wandering as you shop down King Street and eat at some of the best restaurants in the South. Get lunch at Leon's Fine Poultry & Oyster Shop (don’t miss the fried chicken), stop in at 100-plus-year-old store Croghan's Jewel Box, and book a room at Hotel Bennett on Marion Square.

03 of 12

Blue Ridge Parkway

Linn Cove Viaduct, Blue Ridge Parkway, NC
Peter Frank Edwards

Running through North Carolina and Virginia, this scenic road winds along the valleys and crests of the Appalachian Mountain range, connecting Great Smoky Mountains National Park to Shenandoah National Park. While there’s no bad time to see the sights, you’re in extra good luck if your trip lands during autumn months when fall color surrounds the drive, or during springtime when the flowers are in full bloom. Make sure to hit our recommendations for Iconic Spots on the Blue Ridge Parkway Everyone Should See and The Best Virginia Towns Along the Blue Ridge Parkway.

04 of 12

Dahlonega, Georgia

Dahlonega, Georgia

Ian Dagnall/Alamy

If you want to see the definition of small-town charm in person, a trip to Dahlonega will do the trick. After spending the morning wandering around the historic town square—which is centered around a courthouse that dates back to the state's early 19th-century gold rush—and grabbing breakfast at Picnic Café and Dessertery, head just outside town for an impressive collection of North Georgia wineries that are open for weekend tours and tastings, such as Wolf Mountain Vineyards, Montaluce Winery & Resort, and Crane Creek Vineyards

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Fort Worth, Texas

Billy Bob's Texas Honky Tonk in Fort Worth, TX
Scott Slusher

For those who enjoy learning about history and having a great time to boot, Fort Worth is like taking a step back into the Wild West. This cattle town recently reinvigorated the Stockyards National Historic District, and you can explore Exchange Avenue and its shops, restaurants, and saloons. Make sure to check out the Cowtown Coliseum, which held the first indoor rodeo arena in the country. Each Friday and Saturday, you can still attend events that showcase barrel racing, roping, and crowd-favorite bull riding. Plan your trip here.

06 of 12

Georgia’s Golden Isles

Jekyll Island, GA
Peter Frank Edwards

Yes, Georgia has a coast, and it’s draped in beautiful oaks and marshes. Two neighboring islands, Sea Island and St. Simons Island are both inviting places to visit anytime of the year, but it’s an especially welcoming destination during the holidays if you want to Celebrate A Lowcountry Christmas for your winter anniversary. For a more outdoorsy and warm-weather Georgia island, Jekyll Island offers biking on wide wooden pathways, kayaking on the marshlands, and relaxing on the beach. 

07 of 12

Gatlinburg, Tennessee

Gatlinburg SkyBridge
Marcus Watson

The Smoky Mountains are calling, and luckily there are two popular towns to visit in between oohing and aahing at the mountain vistas and natural wonders. Head to Gatlinburg for the scenic SkyBridge, North America’s longest pedestrian suspension bridge, which leads up to a viewing deck, the SkyLift Park, that offers unobstructed views. Book a room at Dollywood's DreamMore Resort and Spa in neighboring Pigeon Forge.

08 of 12

Charlottesville, Virginia

The Monticello Wine Trail in Charlottesville, VA
Gabriela Herman

With over 500-plus miles of Blue Ridge trails, a restaurant-per-capita density that rivals major cities like New York City, easy access to breweries and wineries, and Thomas Jefferson’s Monticello estate nearby for touring, Charlottesville is packed full of things to do. The Monticello Wine Trail has 40 wineries in a 25-mile radius of Charlottesville. Head to Pippin Hill Farm & Vineyards—which is known for its landscape, food, wines, and verdant grounds—for a relaxing day date. 

09 of 12

Kentucky’s Bourbon Country

Fall color leaves along a road in Kentucky Horse Country
Brown W. Cannon III

There’s not a bad time of the year to head out to the rolling hills of Kentucky’s bourbon and horse country. In the spring and fall, hit the horse races at Keeneland in Lexington, head to our South’s Best-voted favorite distillery, and stop into Bardstown, a historic small town in the countryside an hour outside Louisville. Make sure to stop in at the Old Talbott Tavern, one of the oldest stagecoach stops in the country, for Kentucky cuisine. The building was constructed in 1779. 

10 of 12

Orange Beach, Alabama

Orange Beach Sunset
Jenna Sims

Ask any Alabama native their favorite thing about the 32-mile stretch that makes up the beaches of Orange Beach and Gulf Shores, and it’d be hard to count the many reasons why families flock to this destination year after year. A good place to start would be The Best Things To Do In Orange Beach (including locally-beloved fried shrimp), but don’t miss the area’s biggest natural wonder, Gulf State Park, which boasts over 6,000 acres of land that includes a tranquil beach away from the busy crowds.

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North Carolina’s Outer Banks

Airstream Bambi Sport 16 at Cape Hatteras National Seashore - Ocracoke Campground
Peter Frank Edwards

Make a beach trip into an adventure by embarking on an anniversary RV trip to North Carolina’s Outer Banks. The coastline is lined with wide, flat beaches that are perfect for long bike rides and often dog-friendly. Additionally, you can travel between towns like Nags Head, Duck, and Kitty Hawk. State Road 12 passes through lighthouses and beach villages for nearly 150 miles and culminates on the northernmost Currituck Banks, where you can spot wild horses.

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Anna Maria Island, Florida

Bike in front of Trees in Anna Maria, FL
Jessica Sample

This seahorse-shaped barrier island runs for 7 miles along the Gulf Coast and, despite being a gorgeous enclave of sandy beaches with a strong local community, it has happily remained a hidden gem thanks to residents that have helped preserve its laid-back village vibe. Instead of high-rises, you’ll rent out charming beach cottages. Stroll Pine Avenue, the town’s original main street, where you’ll find a friendly mix of galleries, bakeries, boutiques, and restaurants. A quiet, breezy, relaxing anniversary? See our recommendations.

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