When: February 4-7, 2027Where: Orlando to Gilbert's Resort, Key Largo, FL

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A convoy of classic trucks driving down a palm-lined highway

Friday, February 5 · Wheels rolling 5:30 AM

The Road to the Keys

We wake up before sunrise and head south together. Palm trees replace pine trees, the windows come down, and US-1 carries us across the water into the Florida Keys.

Join the road tripSee the route
When
Friday, February 5Staging 5:00 AM · wheels rolling 5:30 AM
Start
Embassy Suites, OrlandoInternational Drive
Lunch
Sunset Grille, MarathonMM 47 Early afternoon
Cost
Free to joinSign up so we know you're rolling

The adventure begins

5:00. 5:15. 5:30 sharp.

Meet at the Embassy Suites with your vehicle fueled, checked over, and ready to drive.

  1. 5:00 AM

    Staging

    Embassy Suites lot. Fueled, checked over, and ready to drive.

  2. 5:15 AM

    Driver meeting

    Route, stops, caravan etiquette, and what to do if you get separated.

  3. 5:30 AM

    Wheels rolling

    Sharp. We head south.

The day in three stops

South together. Back north at your own pace.

  1. Wheels rolling5:30 AM

    Orlando

    Embassy Suites, I-Drive

    ~323 misouth, together
  2. Early afternoonLunch

    Marathon

    Sunset GrilleMM 47

    ~62 miback north, your pace
  3. Rooms open4:00 PM

    Key Largo

    Gilbert's ResortMM 108

About 385 miles of Florida

Don't just put Gilbert's in your GPS.

A navigation app will pick its own way, and that defeats the point. We drive one route together: south through interior Florida, down Krome Avenue to Florida City, and onto US-1, the Overseas Highway, across the water into the Keys.

Friday route schematicOrlando south through interior Florida and two fuel waypoints to Krome Avenue and Florida City, then US-1 across the Keys to lunch at Sunset Grille in Marathon, mile marker 47, then back north about 62 miles to Gilbert's Resort at mile marker 108 in Key Largo.ORLANDOFRI 5:30 AMWAYPOINT · TBAWAYPOINT · TBAKROME AVEFLORIDA CITYGILBERT'SMM 108 · KEY LARGOUS-1OVERSEAS HWYMARATHONSUNSET GRILLE · MM 47SOUTH TOGETHERNORTH, OWN PACE

  1. Orlando

    Embassy Suites, 5:30 AM

  2. Interior Florida

    South through the middle of the state

  3. Waypoint 1

    To be announced

    Fuel and rest, to be announced

  4. Waypoint 2

    To be announced

    Fuel and rest, to be announced

  5. Krome Avenue

    Down to Florida City

  6. US-1, the Overseas Highway

    Across the water into the Keys

  7. Key Largo and Islamorada

    Island by island, south

  8. Marathon

    MM 47

    Lunch at Sunset Grille

  9. Gilbert's Resort

    MM 108

    Back north about 62 miles

The shared route

Everyone gets the route and the official regrouping points before departure.

Google Maps route link coming soon

Before you roll

Don't race. Bring a transponder.

Mile47

Lunch in paradise

Sunset Grille & Raw Bar

7 Knights Key Blvd, Marathon, FL 33050

By Marathon we're in the heart of the Keys, looking out at the Seven Mile Bridge. We stop together for lunch, drinks, photos, and conversation, and let the trucks cool down. Target arrival is roughly 1:00 to 3:00 PM. Everyone orders individually.

Then there's no rush. From Sunset Grille, everyone makes the roughly 62-mile drive back north to Gilbert's at their own pace. That's the moment the caravan becomes a vacation.

Mile108

Arrive in Key Largo

Welcome to Gilbert's.

107900 Overseas Highway, Key Largo, FL 33037

Hotel check-in begins at 4:00 PM. Check in. Unpack. Wash the windshield. Grab a drink. Find your friends. Put your feet in the sand.

The Beach Party presented by F100 Squad starts at 6:00 PM.

Your road trip, your way

Not coming from Orlando? Join where it works.

  1. 1

    From Orlando

    The full day. Staging 5:00 AM at the Embassy Suites, wheels rolling 5:30 AM.

  2. 2

    At a waypoint

    Meet the convoy at a published fuel and rest stop along the route.

    Waypoints to be announced

  3. 3

    At lunch

    Meet everyone for lunch at Sunset Grille in Marathon, then head north at your own pace.

  4. 4

    At Gilbert's

    Skip the drive, meet us in Key Largo. Rooms open at 4:00 PM.

Driving in from across the country? Lead or join a caravan to Orlando.

Free to join

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