1 / 5

The Southern Charm Run

This is a classic 10-day crawl across the Gulf Coast and the Deep South, taking you from the jazz-filled streets of New Orleans all the way to the tip of Key West.

10days
30stops
DAY01

French Quarter → Frenchmen Street

Overnight in Frenchmen Street
  1. 10:00
    ⭐ French Quarter· start
  3. 14:00
    Garden District
  5. 17:30
    Frenchmen Street· overnight
Accommodation
French Quarter or Marigny
DAY02

Ocean Springs → Fairhope

Overnight in Fairhope
  1. 11:00
    ⭐ Ocean Springs· start
  3. 15:00
    Mobile Bay
  5. 17:30
    Fairhope· overnight
Accommodation
Fairhope
DAY03

Gulf Islands National Seashore → Seaside

Overnight in Seaside
  1. 11:00
    ⭐ Gulf Islands National Seashore· start
  3. 15:00
    Destin Harbor Boardwalk
  5. 17:30
    Seaside· overnight
Accommodation
Santa Rosa Beach or Seaside
DAY04

Apalachicola → Wakulla Springs

Overnight in Wakulla Springs
  1. 12:00
    ⭐ Apalachicola· start
  3. 15:30
    St. George Island
  5. 17:30
    Wakulla Springs· overnight
Accommodation
Tallahassee or Crawfordville
DAY05

Crystal River → Tarpon Springs

Overnight in Tarpon Springs
  1. 11:30
    ⭐ Crystal River· start
  3. 15:00
    Homosassa Springs
  5. 17:30
    Tarpon Springs· overnight
Accommodation
Dunedin or Clearwater
DAY06

St. Pete Beach → Siesta Key

Overnight in Siesta Key
  1. 10:30
    ⭐ St. Pete Beach· start
  3. 14:00
    The Dali Museum
  5. 17:00
    Siesta Key· overnight
Accommodation
Sarasota
DAY07

Gasparilla Island → Naples

Overnight in Naples Pier
  1. 11:00
    ⭐ Gasparilla Island· start
  3. 15:00
    Sanibel Island
  5. 17:30
    Naples Pier· overnight
Accommodation
Naples
DAY08

Shark Valley → Robert Is Here Fruit Stand

Overnight in Robert Is Here Fruit Stand
  1. 11:00
    ⭐ Shark Valley· start
  3. 14:30
    Big Cypress National Preserve
  5. 17:00
    Robert Is Here Fruit Stand· overnight
Accommodation
Key Largo
DAY09

John Pennekamp Coral Reef → Bahia Honda

Overnight in Bahia Honda
  1. 11:00
    ⭐ John Pennekamp Coral Reef· start
  3. 14:30
    Seven Mile Bridge
  5. 17:30
    Bahia Honda· overnight
Accommodation
Key West
DAY10

Ernest Hemingway Home → Mallory Square

  1. 09:00
    ⭐ Ernest Hemingway Home· start
  3. 13:00
    Southernmost Point
  5. 17:30
    Mallory Square
Accommodation
Key West
Heads Up
  • Pack reef-safe sunscreen and polarized sunglasses—the glare off the white sand and turquoise water is intense!
  • Download offline maps for the Everglades (Day 8) as cell service can be spotty.