‘Twas the night before TS12 and all through the South, the Swifties were stirring, 12 new songs at the mouth. The bracelets were stacked, (orange) glitter sprinkled with care, in hopes that Taylor soon would be there.
The road leading up to “The Life of a Showgirl” has woven Swifties through eras marked by fairytales and romance, whimsy and change, heartbreak and revenge. Whether you find yourself dancing in your best dress or you’ve only bought it to, well, take it off… we’re sharing the ultimate guide to traveling the South like a Taylor Swift era.
Happy listening 🧡✨
Debut | Nashville, Tennessee
“Someday you’ll turn your radio on – I hope it takes you back to that place.”
The lyric still feels like “The Prophecy,” because over the years, her lyrics have transported me directly to a place, a feeling, a moment in time. Taylor’s debut era features big hair and a twang that has suspiciously disappeared throughout the eras. But alas, “Our Song,” “Teardrops on My Guitar,” and “Tim McGraw” will always live in infamy.
For Taylor, Nashville was where it all began and is the clear choice for living out your debut daydreams. When Taylor was just a teenager, spiral notebook and glittery guitar in hand, she caught her big break at the Bluebird Café in Green Hills. Since then, she has recorded hits along 16th Avenue (Music Row) and has referenced the town in songs like “Invisible String” and “I Think He Knows.”
A visit to Nashville is steeped in ambition, just like Taylor had when she first came to town. Hopeful artists belt their hearts out from sunup to sundown on Lower Broadway, girls in their glittering prime saunter boot-clad through the city streets, and unsuspecting tranquil pockets like Centennial Park and suburban Franklin feel like stumbling upon those comforting deep tracks that feel like she’s speaking just to you.
Where to stay: The Hutton Hotel, a music industry favorite located steps from Music Row. While you’re walking down the hallway well on your way to your lovin’ bed, you may even pass a secret songwriting room and an onsite music venue, Analog.
Fearless | Fairhope, Alabama
The Fearless era is marked by glitter and gold – it’s the album that first showed that Taylor’s reach could stretch beyond Nashville, carrying her from romance in high school halls to selling out arenas.
“Love Story,” “You Belong With Me,” and “Fifteen” still play like rites of passage at every live band bar in the world, and sucker punches like “White Horse” and “The Way I Loved You” gave us just enough of a peek behind Taylor’s curtain to feel like we’re not only friends, but that she understands what we’re going through, too.
Fairhope, Alabama, carries that same whimsy and fairytale glow. A town perched on the edge of Mobile Bay, Fairhope sunsets are famous for sparkling atop the water in hues of yellow and gold. The downtown is trimmed with galleries, bookstores, and music floating from patios at night, creating a sweetness that feels like growing up while still holding onto childlike wonder.
The waterfront setting means gardens aplenty ripe for sneaking out, screaming, crying, and kissing in the rain.
Where to stay: Write your “Love Story” at the Grand Hotel Golf Resort and Spa, a spectacular waterfront property guaranteed to give you “The Best Day.”
Speak Now | Asheville, North Carolina
Speak Now is the era of fairytales and fighting dragons. We were “Enchanted” to meet Taylor’s more mature side, which set the scene for the diabolical call-outs we’d learn to love her for. Seriously, our “Dear John” is probably still icing that burn.
The album is packed with ballads about growing up, preserving innocence, failed romances, and storybook tales, all inciting feelings of castles and candles and feeling a little “Haunted.”
That’s Asheville, North Carolina. Tucked in the Blue Ridge Mountains, you’ll find mist curling around ridges, the Biltmore Estate perched like a fictional palace, and countless cozy breweries, art galleries, and craft shops line downtown streets that round out an experience that’s whimsical but with sharp edges — just like Speak Now.
Where to stay: “Long Live” all the mountains surrounding the Omni Grove Park Inn, one of the South’s most dazzling properties, doubling as a spa and vineyard.
Red | Bardstown, Kentucky
This album burns with passion, heartache, confessions, and longing. We get a little “Sad Beautiful Tragic” with lyrics like “so casually cruel in the name of being honest” in arguably one of her best songs, “All Too Well.” We get a little “Treacherous” in songs like “We Are Never Ever Getting Back Together” (like, ever). But then we also get some quintessential Taylor Swift bangers like “Red” and “22,” speaking of which…
Now that Taylor is of a legal drinking age, we head to Bourbon Country to be cursed by her first Old Fashioned. Bardstown has all the makings of Red – bourbon that burns on the way down, autumn leaves falling down like pieces into place each fall, and a historic downtown that grounds it all.
Where to stay: The Trail Hotel is Bardstown’s newest “Holy Ground.” It’s in a stunning historic property with plenty of character, an onsite restaurant, pool, bourbon lounge, and more to keep you happy, free, confused, and (not) lonely at the same time.
1989 | Wilmington, North Carolina
1989 is the rebirth – Taylor is a pop artist now. This era is where Taylor traded cowboy boots for crop tops, and country twang for synth beats. She shook it off, stepped into the spotlight of New York, asked if we’re “Out Of The Woods” 38 times, and shared her “Wildest Dreams.”
The era is synonymous with both Taylor’s departure from Nashville and her entry into the Big Apple, but it has also grown to reflect beach scenes and seagulls, thanks to her personal “Style” and coastal album artwork.
Which is why Wilmington, North Carolina, is the perfect place to embody the 1989 era. Don your red lips and rosy cheeks, salt spray your hair, and chase the seagulls during a coastal Carolina getaway.
The town feels cinematic, just like 1989 — clear blue water, high tide that came and brought you in, bikes cruising down sandy streets, and plenty of spots to stand in a nice dress staring at the sunset, babe. Plus, we all fell in love with Conrad the use of Taylor’s songs in The Summer I Turned Pretty, which was filmed here.
Where to Stay: Trust me, “I Know Places.” Book a stay at Arrive Wilmington, a spectacular new property with high design and coastal details that’ll never go out of style.
Reputation | Savannah, Georgia
Dare I say, the best era has arrived. Are you “…Ready For It?”
Reputation is synonymous with snakes, seduction, and sweet, sweet revenge. The old Taylor rises from the dead in “Look What You Made Me Do,” shoots her shot boldly in “So It Goes…” professes her love in “King of My Heart,” and takes us on a thrill ride in her “Getaway Car.”
Gone are the days of twirling, giggling, and fairytales; we’re in the big leagues now. The Reputation album infused confidence, power, and passion into listeners proud of Taylor for reemerging after a public fallout.
Grab your real friends and head to Savannah for a Rep-inspired getaway – after dark, gas lamps flicker in the streets, Spanish moss drips from oak trees, cobbled streets and quiet courtyards are equal parts spooky and romantic. On River Street, there’s glitter on the floor after the party
Where to Stay: Hold on to the memories made at The Alida, a River Street boutique hotel with in-room record players, a rooftop bar, and a pool club (read: champagne sea). You’ll be feeling so Gatsby for that whole stay.
Lover | Charleston, South Carolina
And just like that, the dark cloud parts to reveal pastel skies and cotton candy vibes. If Rep is after hours, Lover is all “Daylight.” For the first time in years, the joy is louder than the heartbreak for an entire album.
In this era, we may walk “Cornelia Street” and pine after a “London Boy,” but no Southern city embodies the colorful and carefree vibes of the album quite like Charleston. It’s cool, that’s what I tell ‘em.
It’s an eternal “Cruel Summer” in this coastal paradise, complete with candy-colored homes along Rainbow Row, wisteria curls through hidden courtyards, and horse-drawn carriages saunter past towering historic homes not on “Cornelia Street,” but South Battery instead. And while Taylor tells us that in Lover the altar is her hips, in Charleston, the altar is just about everywhere else. It’s the Holy City after all.
Where to Stay: While “It’s Nice to Have a Friend,” 86 Cannon is a boutique property perfect for lovers. Sneak in through the garden gate (not really, use the provided code) to unveil pastel-colored guest rooms, luxury amenities, and a charming private pool.
Folklore | Ozark Mountains, Arkansas
If you think you’ve seen this film before, you haven’t. Born from pandemic isolation, Folklore was perhaps Taylor’s greatest genre pivot to date. The vibes took us out to a secluded cabin and bathed the world in black and white as she reflected on what could have been “the 1,” told us the story of a teenage love triangle in three clever parts, and “exile”d us with the help of Bon Iver’s Justin Vernon.
When you think of stories and seclusion, Arkansas’ Ozark Mountains come to mind. “The lakes” glisten like mirrors, the towering forests are where “my tears ricochet,” and cabin retreats offer a fire that’ll keep your brittle heart warm, all of which is surely enough to give you peace.
Where to Stay: Become one with the woods at Beckham Creek Cave Lodge, a hotel tucked into a literal cave. It may not be the Windermere peaks, but the cave is probably still a perfect place to cry.
Evermore | Roanoke, Virginia
Folklore’s sister album brings us fully into winter and even more whimsy. We’re getting a little colder, moodier, and less rooted in reality with an influx of stories (or at least, let’s hope that’s the case with “no body, no crime”).
If evermore was a “willow,” it’s bending right to Roanoke. Fall and winter “‘tis the damn season” to visit this mountain town that thrives when the air is crisp and the leaves have already given way to bare branches. Independent bookstores, coffee shops, international dining (or saloons if you’re a “cowboy like me”) buzz in town, while the mountains beyond feel like the perfect place to wander for “evermore.” There are more than 1,000 miles of trails, after all.
Where to Stay: There are plenty of cabins and B&Bs in the surrounding Blue Ridge Mountains, but “long story short,” we recommend The Liberty Trust for a downtown stay. The bank-turned-luxury hotel has no shortage of “champagne problems” — we mean vault dining and sparkling cocktails, of course.
Midnights | New Orleans, Louisiana
It’s the story of 13 sleepless nights (well, 23 when it was all said and done). Midnights is an album filled with restless confessions, where Taylor whisks us through the “Lavender Haze,” what once was red now glows “Maroon,” takes us to “Paris,” and brings us along in “The Great War.”
To fully step into Midnights energy, you “Would’ve, Could’ve, Should’ve” visited New Orleans, arguably the South’s most sleepless city. Be it on Mardi Gras or a regular Tuesday, revelers are known to make the whole place shimmer.
Everybody agreessssss, the food here “Hits Different,” “Karma” comes through the city’s spiritual lore (tarot readers, voodoo shops), and the whole town feels a little spooky if you’re working the graveyard shift.
Where to Stay: “Dear Reader,” when visiting New Orleans, plenty of chain hotels and B&Bs await. But The Chloe is our pick for a Midnights-approved vacation – the historic property-turned-boutique-hotel is feminine with hidden bookshelves, record players, and cozy interiors fit for sprinkler splashes to fireplace ashes.
The Tortured Poets Department | Oxford, Mississippi
Taylor took us all back to school when she unveiled The Tortured Poets Department, an album full of bruised ballads that read like pages torn from a diary you weren’t supposed to see. For at least a “Fortnight,” we grieved alongside piercing tracks like “So Long, London,” “loml,” and “How Did It End,” and raised a collective middle finger during “The Smallest Man Who Ever Lived.”
Through it all, we broke out our thesaurus to cry, scream, heal, and move forward alongside her most raw and sophisticated collection yet.
If there’s anywhere in the South that understands tortured poets, it’s Oxford, Mississippi. Home to William Faulkner, a centuries-old university, and plenty of Southern Gothic lore, the town has no shortage of bookstores, an adorable town square, and plenty of bars (though “The Black Dog” isn’t one of them).
As a staunch Mississippi State fan, I wish I could say “I Hate It Here.” But the truth is, how could you? It’s unexpected, beautiful, and fit for a poet.
Where to Stay: There may not be a Chelsea Hotel, but there is The Oliver, a premier boutique lodging option right off the square. From stunning guest rooms to an onsite restaurant and a speakeasy perfect for catching up with “Chloe or Sam or Sophia or Marcus,” it has everything you need for your poetry-filled Oxford visit.
Life of a Showgirl | TBD!
Where will Taylor’s newest album take us? We’ll have to wait and see together.
Find more travel inspiration from around the South here.
