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

The ultimate Florida Keys road trip — 255km of bridges, beaches, and key lime pie from Miami to the southernmost point.

3days
8stops
DAY01

Miami → Islamorada

Overnight in Islamorada
  1. 08:00
    Miami· start
  3. 10:00
    Key Largo
  5. 15:00
    Islamorada· overnight
Where to Eat
  • Robert Is Here · Famous fruit stand since 1960. Grab a key lime milkshake and whatever's in season.
  • Chef Michael's · Islamorada institution. Hogfish snapper or yellowtail, dockside with live music.
  • Morada Bay Beach Cafe · Sunset dinner on the sand. Get there early for a beachfront table.
Today's Spend
Boutique motel (Islamorada)
$180-250
Gas + tolls
$45
DAY02

Islamorada → Key West

Overnight in Key West
  1. 08:30
    Islamorada· start
  3. 11:00
    Marathon
  5. 14:00
    Bahia Honda
  7. 17:00
    Key West· overnight
Key Eats
  • Hobo's Cafe · Local dive in Marathon. Conch fritters and cold beer, zero pretension.
  • Seven Fish · Key West dinner reservation. Fresh catch, intimate spot — book now.
  • Kermit's Key West Key Lime Shoppe · Frozen key lime pie on a stick. Touristy but totally worth it.
Cash You'll Drop
Guesthouse (Key West)
$220-350
Pigeon Key ferry
$25
DAY03

Key West → Dry Tortugas

  1. 09:00
    Key West· start
  3. 12:00
    Fort Zachary Taylor
  5. optional
    Dry Tortugas
  7. 18:00
    Key West
Last Meals
  • Blue Heaven · Breakfast in a courtyard with roaming chickens. Pancakes bigger than your face.
  • El Siboney · Cuban spot locals actually eat at. Ropa vieja, plantains, strong coffee.
  • Sunset Pier · Last night, last sunset. Grab a rum runner and toast the trip.
Today's Tab
Bike rental
$15
Hemingway House
$18
Seaplane to Dry Tortugas (optional)
$380
Heads Up
  • Book Key West lodging early — it fills up fast
  • Pennekamp snorkel trips sell out by 10am
  • Cash for Robbie's tarpon feeding and Mallory Square tips
  • Sunscreen + hat — the reflection off water is brutal