Ready-Made Itineraries

52 curated Southern road trips, from long weekends to a four-week grand loop.

Open the trip builder →

By length

Long Weekend (2–3 days)

Delta 101
3 days · ~420 mi · from Memphis · 🎶 Music · 🏛️ History
The essential first taste: down the Blues Highway to the Crossroads and the Delta's shrines, back through Faulkner's Oxford. Music every night if…
Grant's Campaign Weekend
2 days · ~180 mi · from Vicksburg · 🏛️ History
The 1863 campaign in two days, exactly as the user manual (Grant's memoirs) describes it — five battles, one siege, county roads the whole way.
Mosby to the Bloody Angle
3 days · ~240 mi · from Alexandria / DC · 🏛️ History
The Northern Virginia war loop, run counterclockwise so the history happens in order — First Manassas to Jackson's deathbed.
Lowcountry Long Weekend
3 days · ~210 mi · from Charleston · 🍽️ Food · 🏛️ History · 🎭 Culture
Charleston to Savannah the slow way — oyster sheds, ruined churches, Gullah history and two of America's most beautiful (and complicated) cities.
Forgotten Coast Oyster Run
3 days · ~250 mi · from Pensacola · 🏞️ Outdoors · 🍽️ Food
Dune lakes, Truman Show streets, a phone-booth police station and the springs where Hollywood kept its monsters — Old Florida in one weekend.
Presidents & Pinot
3 days · ~160 mi · from Charlottesville · 🏛️ History · 🍽️ Food
Monticello and Montpelier with the Monticello AVA poured between them, then Virginia's prettiest road north — grafting onto the Civil War loop at…
Crooked Road Ramble
3 days · ~220 mi · from Bristol (start Thursday) · 🎶 Music · 🏞️ Outdoors
Mountain music's living calendar: Floyd on Friday, the Carter Fold on Saturday — drive the prettiest gaps in Virginia between shows.
The Overseas Highway
3 days · ~210 mi · from Miami · 🏞️ Outdoors · 🍽️ Food · 🏛️ History
US 1 to the end of the road: forty-two bridges over turquoise water to Key West, with a hurricane monument, a rescued movie boat, tiny key deer and…
Florida's Mystic Coast
3 days · ~280 mi · from St. Augustine · ⛪ Faith · 🎭 Culture · 🏛️ History
The nation's oldest city, the beach where speed was born, and inland to a genuine 1890s Spiritualist camp — a weekend of Old Florida faith, art and…
Cracker Trail & the Big Water
2 days · ~260 mi · from Bradenton · 🏛️ History · 🏞️ Outdoors
The old cattle-drive route across Florida's forgotten middle, then a loop of the vast lake at its heart — muck-city football towns, a hand-built…
The Scenic Seven & the Pig Trail
3 days · ~340 mi · from Hot Springs, AR · 🏞️ Outdoors · ⛪ Faith
Arkansas's two great mountain drives back to back: bathhouse steam and gangster lore, then the Buffalo River highlands and the Pig Trail's tight…
Crowley's Ridge & the Arkansas Delta
3 days · ~420 mi · from Piggott, AR · 🎶 Music · 🏛️ History
Down the strange loess spine of Crowley's Ridge — Hemingway's writing barn, Johnny Cash's boyhood home — then into the flat Delta's hard history…
Sherman's March to the Sea
2 days · ~210 mi · from Milledgeville, GA · 🏛️ History
Georgia's antebellum capital to the sea by the route the Union army burned across in 1864 — old statehouses, market squares, a prison camp and the…
Bourbon, Bluegrass & Shakers
3 days · ~300 mi · from Lexington, KY · 🍽️ Food · ⛪ Faith · 🏛️ History
Horse country to cave country the reverent way: a preserved Shaker village, a Trappist abbey, Lincoln's birthplace and the bourbon trail's holiest…
Golden Isles Getaway
3 days · ~260 mi · from Savannah · 🏞️ Outdoors · 🏛️ History · 🍽️ Food
Georgia's marsh coast at low speed: the smallest church in America, wild horses and driftwood beaches, a millionaires' island club and the tabby…
Cradle & Surrender: Jamestown to Appomattox
3 days · ~260 mi · from Williamsburg · 🏛️ History
The bookends of American history in one Virginia weekend: the first permanent English colony and the Yorktown victory that won independence, then…
A Reader's Central Kentucky: Bardstown to Shaker Village
3 days · ~160 mi · from Bardstown, KY · 🏛️ History · 🍽️ Food · 🎭 Culture
Sent in by a reader who came home with a Shaker Village membership: three unhurried days of Civil War museums, an 1845 inn, a Main Street café's Pig…
Houston to New Orleans the Old US 90 Way
3 days · ~430 mi · from Houston · 🍽️ Food · 🎶 Music · 🏞️ Outdoors
Leave I-10 at the Sabine and take the Old Spanish Trail through rice country and Acadiana: boudin at gas stations, a Saturday accordion jam…
The Smokies, Every Road That Matters
3 days · ~280 mi · from Gatlinburg · 🏞️ Outdoors · 🎭 Culture
The whole park and its two famous roads in one long weekend: over Newfound Gap, out to the Cherohala Skyway, back by the Dragon and Cades Cove.
Nashville to Atlanta on the Dixie Highway
3 days · ~340 mi · from Nashville · 🏛️ History · 🍽️ Food
The old Dixie Highway's whole Tennessee-to-Georgia act: whiskey country and the plateau to Chattanooga, then the General's road down the Atlanta…
Nashville Day Trips: the Dixie Highway Sampler
3 days · ~300 mi · from Nashville · 🍽️ Food · 🏛️ History · 🏞️ Outdoors
Three separate days out of Nashville and back, each on the old Dixie Highway: the battlefield and the whiskey, the plateau and its waterfalls, the…
Buffalo River Weekend
2 days · ~120 mi · from Harrison · 🏞️ Outdoors · 🎭 Culture
The Ozarks' river in two days: the canyon overlook and Jasper, then elk at dawn in Boxley, the Crag, Lost Valley and the loop home.
Gulf Shores & the Forts
2 days · ~100 mi · from Mobile · 🏞️ Outdoors · 🏛️ History · 🍽️ Food
Both forts, the ferry and all 32 miles of Alabama beach in a weekend, with the Flora-Bama for the finale.

A Short Week (4–5 days)

About a Week (6–8 days)

Two Weeks (12–16 days)

The Epic (3–4+ weeks)

Foodways Tours (eat the map)

By theme

🏞️ Outdoors (26)

🍽️ Food (27)

🎭 Culture (11)

🎶 Music (18)

🏛️ History (35)

⛪ Faith (4)