Learn how to plan a road trip to ensure an incredible time from start to finish. A comprehensive guide to planning & surviving. By A Pair of Passports

How to Plan an Unforgettable Road Trip

It’s so much fun to just hop on a plane, nap for two hours, and step back off the plane into a completely different world. It’s also incredible to be on a train for a few hours, driving through gorgeous fields, around bright blue lakes, and up snowy mountains. However, nothing beats a road trip. The spontaneity that comes with being able to stop whenever you want, eat whatever you want, and go wherever you want is what makes road trips so special.

From our mini road trips like the day spent driving around the Cotswolds and the day spent driving down the Alsace Wine Route, to our more serious future plans (driving around the U.S.), we absolutely love going on road trips, and think the best memories are those made on the road. However, the idea of planning a road trip can be daunting – how can you possible make being in a car for hours on end worth it? How much should you plan on driving each day? Is it worth it to go out of the way for an attraction?

We want to help you answer these questions.

And to do that, we have created the ultimate road trip planning guide. We start out by going through the actual planning steps and finish with a list of our road trip packing essentials. So go ahead and find a travel buddy, because you’re going to want to get straight on the road after reading this!

How to Plan a Road Trip

Choose your destination

Learn how to plan a road trip to ensure an incredible time from start to finish. A comprehensive guide to planning & surviving. By A Pair of Passports
Tuscany would be an incredibly scenic road trip destination, but not so wise if the theme of the trip is wine tasting and everyone wants to participate!

We said this in our guide to planning a weekend trip, and we will probably say it in every planning post we ever write. You cannot do anything until you pick a destination! For road trips, your destination depends on a few things: 1) will you be starting at home with your car, or will you be hiring a car once you reach your destination? 2) if you are hiring a car, do you have a mileage limit?, and 3) how much area are you looking to cover?

Where are you getting your car from?

If you are starting at home, you probably want to do a local road trip or at least a road trip within your country. Of course, you can drive to any destination and then start the “road trip”, but we do not necessarily recommend that. A long drive followed by days of shorter, scenic drives with frequent stops can be exhausting!

If the plan is to hire a car, there is a lot more flexibility. You can fly or take a train to your starting point, hire a car there, and then explore the surrounding area. However, when you hire a car, you are also bound to the company’s policies on where you can go, how far you can go, etc.

Does your car hire involve restrictions?

When hiring a car, know the restrictions. For example, there might be a mileage limit or a rule on whether you can or cannot leave the country you hire the car in. When we hired a car in Basel for our Alsace road trip, we made sure we could take the car from Switzerland to France. Within Europe, you should be able to drive freely; however, it is always safe to double check!

If you have a mileage limit, consider how much area you are looking to cover. With a limit, it’s probably isn’t wise to go somewhere where the different stops are very far apart. Instead, opt for a specific area where you can still see a lot – a drive around the Ring of Kerry, for example, or all around a specific wine region.

So…do you have an idea of where you want to go? Now start thinking about the details!

Ask (and answer) the important planning questions

Start asking yourself questions to determine exactly what type of road trip you are looking for. This will help you determine the duration of your trip, how many stops you will make, if your trip has a theme, etc.

  • Is there a reason for this road trip?
  • Is the road trip your entire trip, or are you just trying to make the most of the drive to your end destination?
  • Does your road trip have a theme? Some examples: drive through all 50 states, visit all of the castles in a specific region of England, or drive around the Ring of Kerry.
  • What shape will your route follow? Is this one way, or will you need to make a complete route? Do you want to go East to West, North to South? Get to an understanding on exactly what this road trip should look like, before you start planning it.
  • How long will this trip be? Do you have the option to extend during the trip if you want to?

Go through questions like these with your travel partner in order to make sure you are on the same page, as well as develop a base layer for your travel plans. There is nothing worse than planning an entire trip and then realizing there is no way it is going to work, and needing to start from scratch!

As we continue to travel around the UK, we usually focus on shorter road trips, with one main destination, but stop as many places on the way to and from that destination. That’s what we did while we were staying at The Fish Hotel in the Cotswolds!

Choose your stopover points

Learn how to plan a road trip to ensure an incredible time from start to finish. A comprehensive guide to planning & surviving. By A Pair of Passports
Pull out your map and your planning kit and start drawing out your plans. Listening to your Road Trip playlist for inspiration is highly encouraged!

Stopover points are your bases. Whether these are determined by where you are planning to sleep, or just what major areas you want to spend a good chunk of time in, these stops will help determine your route. Do not try to cram too many bases into your trip. We recommend 1 base for a 1-3 day road trip, and 3-4 for a week. This makes it a bit easier to book accommodation. If you have a camper van or are planning to camp in a tent, everything becomes more flexible. However, it is still smart to have a general understanding of where you want to stop so you can research campsites and important places in that area.

Planning Tip: Lonely Planet has a great range of guides written specifically for road trips. They feature themed routes, with recommended hotels and attractions along the way. We prefer to pick accommodation on our own, but love using the guides to help us plan our route and which attractions we want to visit. We are currently planning a Ring of Kerry trip using the Ireland’s Best Trips book!

Fill your days with stops and adventures

Learn how to plan a road trip to ensure an incredible time from start to finish. A comprehensive guide to planning & surviving. By A Pair of Passports
Blenheim Palace was probably our favourite stop when we decided to make our trip back from the Cotswolds a mini road trip!

You now know how many major stopping points you are going to have, and how much time you have to get from one to another. With that information, you can start planning the mini stops and adventures in between.

Yes, it’s time to decide exactly where you want to go and what you want to do! This includes tourist attractions, national parks, bookable experiences, walking routes, and even restaurants and shops. Only get as detailed as you are comfortable with. For example, we love having at least one restaurant lined up that we researched and hand picked, but generally wing our food choices the rest of the time!

Planning Tip: Keep in mind what type of car you have while making plans – it’s probably not wise to drive up a mountain if you don’t have four wheel drive; likewise, if it isn’t your car, plan an extra stop at the car wash if you might be bringing mud or sand back into the car with you. The fee you pay to get it cleaned will be less than the extra charges the hire company smacks on you!

Map it out

Use the map tool of your preference to outline your route and download directions. We love building custom itineraries on Google Maps and printing directions from each point to the next. If you want to be more flexible, though, at least make sure you have a map of all of your stopping points. That way, you at least know if you are heading in the right direction when driving aimlessly! If you’re Type A like me, this is also a great opportunity to gather information for the attractions you want to visit – opening times, admission prices, etc.

Once you hit the road, it’s also a good idea to get a paper map just in case. You can find maps of the area at nearly every petrol station or rest stop.

Remember to remain flexible!

Learn how to plan a road trip to ensure an incredible time from start to finish. A comprehensive guide to planning & surviving. By A Pair of Passports
When we couldn’t find parking near one winery in Alsace, we just went looking for another one. Road trips offer that flexibility, so make sure you are flexible in return!

Road trips are meant to be fun. And spontaneous! While it is great to have a plan (believe me, I’m a great planner), it’s also important to remain flexible. You may hit traffic or see a sign for a landmark you have never heard of. This could take you off your course and you may miss something else as a result. Your car could break down, forcing you to cancel your accommodation plans and find something in the town closest to the repair shop. When these things happen, it’s so easy to get stressed, but don’t let it ruin your whole trip! Regroup, adjust your plans, and make the most of it. You always have next time to get to the things you didn’t get to.

Road Trip Essentials


Music, podcasts, and games are all great entertainment options for road trips. If you remained entertained, you will remain more awake and more sane. This means fewer arguments, better memories, and a better attitude when you arrive at your destination!


A great playlist can make a road trip. After all, can you think of anything more fun than belting a song at the top of your lungs while driving down an empty road with the windows down? Before you head on your trip, put your favourite tunes into a playlist or two that you can jam to on end. We like to mix country with pop and some classics, but build something that suits your taste.

Our current top 10 road trip songs:

  1. Think of You – Chris Young
  2. Mayday – Cam
  3. Make You Miss Me – Sam Hunt
  4. Huntin’, Fishin’ and Lovin’ Everyday – Luke Bryan
  5. Shut Up and Dance – Walk the Moon
  6. Wagon Wheel – Darius Rucker
  7. 22 – Taylor Swift
  8. Break Up in a Small Town – Sam Hunt
  9. Vacation – Thomas Rhett
  10. Can’t Stop the Feeling – Justin Timberlake

If country isn’t your thing (there’s a lot on our playlist!), check out this incredible travel playlist from The Nomad’s Scrapbook!


If you get tired of music or just aren’t in the mood, podcasts are a great alternative. You can choose something information, something funny, even something suspenseful. Listening to a podcast is like having a friend tell you a really long story. Our favourites include Serial, Ted Talks, and Stuff You Should Know. I also secretly love etiquette podcasts (Awesome Etiquette & The Simple Sophisticate).

If you are heading somewhere historic, it’s a great idea to listen to podcasts on the location. You’ll save money later when you can turn down the audio guide! Although we weren’t on a road trip when we visited Paris, I planned our day in Le Marais by listening to a Join Us in France podcast!

Learn how to plan a road trip to ensure an incredible time from start to finish. A comprehensive guide to planning & surviving. By A Pair of Passports
When you get stuck, create your own fun! It’s amazing how the littlest things amuse us…

Even to this day, I love playing the license plate game in the U.S., or a simple game of I Spy anywhere! Playing games in the car takes me back to my childhood days, before iPods and tablets, where I would give literally anything to be entertained.


Learn how to plan a road trip to ensure an incredible time from start to finish. A comprehensive guide to planning & surviving. By A Pair of Passports
Even Giorgio gets his own bag of snacks and toys for our road trips!

Food is also a create cure to boredom. The excuse to have junk food is probably the single best thing about road trips. After all, you need some sugar to keep you awake – and service stations don’t have many healthy options (so long as you don’t look for them!). Sean always jokes about how, when he was younger and going on long drives with his family to football matches, his parents promised that he could have Burger King on the way back if he behaved. He tries to get me to offer him the same deal every time we are on the road together. It sometimes works.

Essential Cables

We are quite proud of the “cable kit” we have built over the last year or so. After one of our rental cars did not have an Aux cord or Bluetooth capability (meaning we couldn’t listen to our music!), we decided to be prepared for all of our future trips. Our kit contains an aux cord, a USB iPhone cable, a car charger converter, and any other essential charging cables we need. These keep us powered and listening to music our entire trip!

Emergency Kit & Information

As with any trip, safety comes first. Make sure you (and your car) are equipped with anything you might need in an emergency. This includes, but is not limited to, the following items:

  • Spare tire & jack
  • Jump cables
  • First Aid kit – our friends at Pages of Travel have a great guide on building a first aid kit
  • Insurance information
  • Contact number for recovery
  • Warning triangle
  • Emergency blanket
  • Flashlight
  • Water bottles

Get on the Road!

Learn how to plan a road trip to ensure an incredible time from start to finish. A comprehensive guide to planning & surviving. By A Pair of Passports
You’re now ready for gorgeous landscapes like this – so get on the road!

Now that you’re fully ready for a road trip, it’s time to get on the road! Grab your travel buddy, make your plans, and head out on your next adventure. Don’t forget to send us your road trip route and photos. We’d love to feature you here on A Pair of Passports!



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What’s your dream road trip route?

Let us know in the comments below!

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A handy guide for planning road trips. Everything you need - where to start, planning tips, and road trip essentials. By A Pair of Passports

9 thoughts on “How to Plan an Unforgettable Road Trip

  1. Meg says:

    Fabulous tips! I really liked the list of questions to ask yourself when planning the road trip – to make sure you know what your purpose is. I’ve never really thought about clarifying things like that before but it makes sense! I have had some great road trips and they definitely provide me with some of my favourite travel memories.

    • apairofpassports says:

      Happy to hear that you liked it 🙂 You just have to know what you’re looking for – even if it’s to be spontaneous and go with no plan, as long as everyone is on the same page about that, that’s technically your trip’s theme!

  2. Christie says:

    OMG I love this! Very timely also as I’m planning a road trip up the California coast. I especially love that you included road trip songs – what a great idea!!! Pinning this as well 🙂

    • apairofpassports says:

      We would love to do the California coast – I’m sure you’ll have a great time. And yes, if you like country music, some of those will be PERFECT for driving along the coast with the windows down.

  3. Katie Dickinson says:

    Yesss to podcasts! I make a 7hr drive between Boston and friends in Ontario a few times each year, and swapping over to podcasts (particularly for the highway portions) was a lifesaver. I would get bored so fast with just music and I would end up stopping more often that I needed.

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