How I plan a road trip

By Jess Shanahan | Guides

Dec 13

I’ve planned alot of road trips over the years from mind-blowing personal trips to PR stunts that have been documented in the national press.

Planning is road trip is a huge part of the fun for me. I love discovering new places and thinking about what it would be like to drive there. I dream of muscle cars and capable 4x4s and the terrain they’ll be traversing. I think of all the culture I’ll be able to absorb and the food I’ll be able to eat.

Put real time into planning you’re trip and it’ll make it all the more exciting once you’re there. (Oh, and if you’ve got kids, get them involved in the planning process!)

Every time I plan a trip. I learn something new but I wanted to take you through my process.

Where do I want to go?

I start by thinking about where in the world I’d like to go. I usually have a vague idea. For the Austrian trip, I knew I wanted to visit Auschwitz and some family graves in Berlin, the Alps seemed like a great precursor to the more serious side of that trip.

When planning the Croatia trip, I knew I wanted to go to Bosnia too. And for the USA road trip, I knew I wanted to visit a friend in Chicago.

This is a great way to find a start, central or end point to your journey and start to build a road trip around it.

Look at a map

From there I look at a map and usually, the trip will start to form from there.

In Austria, driving the Grossglockner High Alpine road was high on our list of priorities. That meant that Heiligenblut was one must-stop place as it was the perfect place to go hiking.

As Liechtenstein was nearby, Vaduz became a stop. Then Vienna, then Brno, both of which were on the way to Poland. The route came together pretty quickly from there once we’d added in a few stops in Germany at the beginning of the trip and that final one in Berlin.

For your trip, open Google maps (or find a real one) and get a sense of what is nearby. Start to make a list of nearby places you could visit within your road trip’s time frame. Highlight any stops that look really good or are home to an attraction you’ve been desperate to visit for years.

Plan a list of places you’d like to visit

This list might change but you need a starting point. It’s ok at this stage to add in a bit of flexi­bility if you’re going to have some days just seeing where you’re going to end up.

A list of places is going to form the outline of your trip in this draft stage but next comes the tricky bit, planning distances. 

Look at the distance between each destination and how long it’d take you to drive (again, Google Maps is great for this). Make sure you have a sense of how much driving you’d like to be doing each day.

For me, I don’t like more than four or five hours per day, with two of us driving. In an ideal world, I won’t be driving for more than two hours a day on a road trip.

If any destination seems a little too far, you might need to add another stop. This is where things can get difficult if you’re limited for time. Can you afford to drive for six hours to get somewhere you’re only going to stop in for one night?

Think long and hard about your travelling time because you’ll be disappointed if you don’t get long enough in a place you instantly fall in love with.

Start looking at attractions

Once you have a hit list of places you’d like to visit, start to look at what there is to do in each place.

I love gorgeous architecture, abandoned buildings, caves, nuclear bunkers and grand churches. These are the things I look for in a new place. Oh and food markets, I love a local market.

Sometimes, though, a place won’t excite me from an initial Google, which is when I look for advice from the communities of travellers and digital nomads I hang out with. Facebook groups are fantastic for getting recommendations for places. (Check out our Road Trip Lovers group on Facebook.)

Look for accommodation

Once you feel like you have a semi-concrete list of places to stop, you can start to look at accommodation. I normally start with Hotels.com (because if you buy 10 nights, you get one free) or Laterooms.com depending on how soon my departure date is. I’ll also look at Airbnb and Booking.com if necessary and if all that fails, I hunt down accommodation via Google and other recommendations.

Book a car

This is the most important part of any road trip (in my petrolhead opinion). If you’re not taking your own vehicle, you’ll need something suitable for the stops you’ve planned.

If you know that you’ll only be visiting cities and towns via beautiful highways then you can book your car earlier but I tend to wait until I know my route. The reason for this is that I like a car that can handle the terrain I’m going to be tackling. If you add in a surprise mountain pass, four-wheel-drive might be best, for example.

Planning a road trip can be a lot of work but it’s so rewarding. Once you’ve planned your first trip the next will seem like a doddle. I went on my first big road trip almost nine years ago and we made so many mistakes on that trip that I now have planning down to a fine art.

What’s your road trip planning process?

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About the Author

Jess Shanahan is a road trip journalist and motorsport consultant who loves high heels, V8s and the open road. You can find her on Twitter @Jetlbomb.