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Your first overland trip: Step-by-step

Overlanding 101

An interview with

An interview with

Your first overland trip: Step-by-step

January 28, 2026
7
min read
by
Charles Forman
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Goal: Help you plan a first trip that feels achievable, not overwhelming.

This is about getting out there, not doing it perfectly.

Step 1: Redefine “first trip”

Your first overland trip should be:

  • close to home
  • low commitment
  • easy to exit

A perfect first trip might be:

  • a day drive + one night
  • familiar terrain
  • mobile signal nearby

This is intentional.

Step 2: Choose the right location

Look for:

  • legal access routes
  • somewhere you’ve heard of
  • simple tracks or roads

Avoid:

  • unknown technical trails
  • remote areas “just because”
  • anywhere that feels stressful to reach

Confidence grows through small wins.

Step 3: Plan the route (lightly)

You don’t need a military plan.

You do need:

  • a start point
  • a rough route
  • a backup option

Ask yourself:

  • Where could I turn around?
  • Where could I leave early?
  • Where could I stay if plans change?

Flexibility > precision.

Step 4: Decide on one overnight (optional but recommended)

Your first overnight teaches you more than ten day trips.

Choose:

  • an official campsite
  • a legal wild camping spot (where allowed)
    somewhere with facilities if it helps

There’s no shame in easing in.

Step 5: Pack the basics (not everything)

You need:

  • food
  • water
  • warmth
  • sleep
  • navigation
  • phone charger

You don’t need:

  • backup gear for backup gear
  • every “just in case” item
  • gear you don’t know how to use

If you didn’t use it — that’s learning, not failure.

Step 6: Set expectations

Things may:

  • take longer
  • change last minute
  • not go to plan

That is overlanding.

The goal isn’t perfection.

The goal is experience.

Step 7: Go slower than you think

Slow driving:

  • reduces stress
  • improves safety
  • helps you notice more

You’re not rushing anywhere.

Step 8: Reflect after the trip

When you get home, ask:

  • What worked?
  • What didn’t?
  • What would I change next time?

This reflection is where confidence is built.

Your takeaway

Your first trip doesn’t need to be impressive.

It needs to happen.

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Charles Forman
Charles is the founder and curator of explmore. He is also the proud son of Alec and Jan Forman, the authors of the book Strangers Like Angels - With a Devil or Two to Boot and the inspiration behind the creation of explmore. He has spent the majority of his life living outside his original passport country. Today, when he is not running the operations behind explmore you will find him hiking, camping and enjoying the outdoors (overlanding of course) with his family.
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