Mississippi Fly Drive

Fly Drive Itinerary

• Day 1: Arrive in Jackson

  Touch down in Jackson, Mississippi’s spirited capital, and dive straight into its cultural heartbeat. Visit some of the best museums in Mississippi and explore the Fondren District for artsy flair and Southern fare.

• Day 2: Jackson to Natchez

  Day two brings the journey south to Natchez, where mansions whisper tales of old-world opulence. Wander the bluffs overlooking the mighty Mississippi, then catch sunset from the iconic Under-the-Hill district with a carefully crafted cocktail in hand.

• Day 3: Natchez to Vicksburg

  Drive north along the scenic Natchez Trace Parkway to Vicksburg. Discover gripping history at the Vicksburg National Military Park and stroll past the city’s famous riverfront murals, a must-see destination where past and present meet in full colour.

• Day 4: Vicksburg to Clarksdale

  Hit the Delta and head to Clarksdale, the cradle of the blues. Visit the Delta Blues Museum, then spend the evening soaking up soul-drenched sounds at Red’s Lounge or Ground Zero Blues Club.

• Day 5: Clarksdale

  Board the bullet train (Shinkansen) to Kyoto*, Japan’s ancient capital. The trip takes only around 2 hours and 15 minutes, and the train can reach speeds of 300 km/h! Enjoy the rest of the day exploring Kyoto at your own pace. Linger in this living, breathing blues town. Follow the Crossroads legend where Robert Johnson allegedly sold his soul to be a musical genius, or hunt down hidden juke joints where the music still stirs the spirit.

• Day 6: Clarksdale to Tupelo

  Trade blues for blue suede shoes in Tupelo, the birthplace of Elvis Presley. Tour his childhood home and museum, then grab a bite downtown where vintage diners serve up rock ’n’ roll nostalgia with a side of fried green tomatoes.

• Day 7: Tupelo to Oxford

  Head west to Oxford, a literary haven steeped in Southern charm. Explore Faulkner’s Rowan Oak and take a lazy loop around the historic Square, where indie bookshops and cocktail bars make the perfect pairing.

• Day 8: Oxford to Tupelo

  Return to Tupelo and dig deeper into its musical roots or stretch your legs in the nearby Natchez Trace Parkway scenic trails. Take day eight at a slower pace, perfect for soaking up those Delta vibes.

• Day 9: Tupelo to Jackson

  Circle back to Jackson for one final night of Southern hospitality. Enjoy a farewell feast, perhaps at the award-winning Saltine or Walker’s Drive-In, and reflect on a journey rich in rhythm, history and heart.