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Plan a 3-day road trip from Miami to Key West along the Overseas Highway with best stops

Kick off your journey from Miami, heading south through the Everglades' edge before hitting the iconic Overseas Highway. Today is all about getting into the 'Island Time' mindset.

3days
10stops
DAY01

Miami → Islamorada

Overnight in Islamorada
  1. 09:00
    Miami· start
  3. 10:30
    Robert Is Here Fruit Stand
  5. 13:00
    John Pennekamp
  7. 17:30
    Islamorada· overnight
Island Eats
  • Mrs. Mac's Kitchen · Classic Key Largo spot. Get the world-famous Key Lime Pie and a fish sandwich.
  • Lorelei Restaurant & Cabana Bar · Perfect sunset views in Islamorada with your feet in the sand.
Day 1 Budget
Snorkeling Tour
$60
Islamorada Hotel
$250
DAY02

Islamorada → Key West

Overnight in Key West
  1. 09:00
    Islamorada· start
  3. 10:00
    Robbie's of Islamorada
  5. 13:00
    Bahia Honda
  7. 16:30
    Key West· overnight
Local Favorites
  • No Name Pub · Hidden gem on Big Pine Key. The walls are covered in dollar bills.
  • Blue Heaven · Al fresco dining in Key West. The lobster benedict is legendary.
Daily Spend
Tarpon Feeding
$5
Key West Parking
$40
DAY03

Southernmost Point → Miami

  1. 08:00
    Southernmost Point· start
  3. 09:30
    Hemingway Home
  5. 11:30
    Mallory Square
  7. 17:00
    Miami
Last Bites
  • El Siboney Restaurant · Authentic Cuban food. The Puerco Asado is a must-try.
  • Kermit’s Key Lime Shoppe · Grab a chocolate-dipped Key Lime pie on a stick for the road.
Final Costs
Hemingway House Entry
$18
Gas for Return
$45
Heads Up
  • Traffic on US-1 can be slow on weekends
  • Sunscreen is non-negotiable
  • Book Key West hotels early