Tips for Planning a Successful Road Trip

Picking your Roadtrip DestinationPlanning your next Road trip
      • Where do you want to go on your road trip?
      • What are your goals along the way?
      • What routes do you plan to take?

These are just some of the crucial questions you need to ask before you head out.
We typically begin with deciding our primary destination goal. Then follow that with how long we intend to spend there, and then how long of a drive it will take to get there. We usually try to break our drive times into a maximum of 6 or 7-hour lengths per day. This drive schedule allows for plenty of time to stop, have meals, and see and do things along the way. It also allows us to take the dogs out for some exercise. See our section on Pet-Friendly Travel.

Planning your road trip accommodations

After you have your route planned out for your road trip, you can decide on where you will stay. Plan your accommodations along the path ahead of time to ensure better pricing and better accommodation options.
We prefer using apps like because you can often get ‘free cancellation’ within 24 hours, plus their rewards program helps us save money on future trips.
You may also wish to drive and see what you find. At many rest stops and tourist information booths, you can find Hotel coupon books which may help you save some money, as well.

Tips for Planning your next Road Trip Vacation
Pick your pack

Choosing who to go on a road trip with can be a bit of a challenge. Often this is a trial and error type of situation. You may have friends (or family) that you like spending a lot of time with but being in a car for several days (or weeks) at a time can bring up conflicts that you may have never recognized before. Just because you are close friends or family, doesn’t mean you have compatible travel personalities. Picking your road trip pack is something you may have to experiment with by merely trying it out.

Start Small

Before you embark on a big adventure with someone, consider taking a shorter trip like a long weekend road trip with these people. This way if conflicts arise, it is only a short trip and will not ruin an otherwise great relationship.
Some key areas to explore before you go away together are:

      • Do they like to stop and shop everywhere?
      • Do they have a relaxed personality when things don’t go as planned?
      • Are you are a hyper-scheduler, while your friends are more of a laid-back kind of traveller?
      • Do your friends prefer an early start to the day or is sleeping in a bit more their speed?
      • Does your travel companion prefer to go from A to B as directly as possible, or are they interested in discovering adventures along the way?
      • How flexible are each of you with where you stay? Do they prefer budget hotels, luxury accommodations, or do your preferences mesh?
      • Do you have similar financial flexibility for a road trip, or is your pack partner on a tighter budget?
      • Are there similar goals and expectations from the road trip?

The best kind of travel companion for a road trip is one who is open to compromise. A little give-and-take is necessary for every relationship; the same applies to road-tripping, as is having open communication. Everything can be worked on and tweaked if you and your road trip companions are willing to discuss it. If something is a deal-breaker, it is better to know before you go.
When you find the perfect (or the best) pack for road tripping, this can make road trips a lot more fun.

Everybody has something to offer

We love taking road trips, and we often go on many with another couple. This squad works out well for us – as we have found the perfect pack (or as close as you can get). In our main road trip squad, we have a decent mix of travel types. Each person brings a unique skill set to the table, that makes road trips more fun, and less stressful.

      • Roguetripper 1 is the person who loves to drive and is very good at it. He is almost always behind the wheel – even though others try to take over. He is also a mechanic, so if something should go wrong, we will be okay.
      • Roguetripper 2 is a very well-travelled person who takes a lot of trips for work and dog shows. As a result, she is good at finding the best dog-friendly accommodations (at the best prices), and activities we can do. She is the one who typically has the best ideas on where we should go.
      • Roguetripper 3 is an excellent navigator with a super-keen sense of direction. He is very good at finding rather obscure places and encouraging others to try new things.
      • Roguetripper 4 (me) likes to plan and schedule. So, I often prepare the routes we take, where we will stay, and look up all of the roadside attractions and other weird activities we may want to incorporate along the way.
Planning the Road Trip Budget

When planning a road trip, there are many costs to consider. Knowing how much money you have to spend on a road trip is an essential first step in the planning process. The variable costs can dictate many things about your trip, such as:

      • Number of days you can be gone on your roadtrip
      • How far you go
      • The type of hotels you stay at
      • Dining options along the way
      • Attractions and activities that you can do

Plan your road trip budget wisely, but also be flexible. It is usually best to expect to pay around 20-25% more than you originally budgeted. Have some freedom with your wallet.
A road trip can be a reasonably inexpensive way to travel, but how much you can spend is up to your budget(s). Check out our tips on how to save Money on a roadtrip.

Tolls: Make sure you have a good variety of cash on hand for tolls along your route. 


The Roadtrip Vehicle
Roguetrippers drive their Nissan Rogue through a giant Route 66 sign
Roguetrippers Route 66

Choosing the road trip vehicle is very important, for the comfort, safety, and peace of mind of everyone involved.
Do you take your vehicle, or do you rent a car?
There are benefits to each, and factoring both into the decision-making is necessary. If a personal vehicle is preferred, who’s, do you choose? You want a car that is roadworthy, safe, and comfortable for all passengers as well as have enough room for the expected luggage (plus purchases along the way).

Please read our article on getting your vehicle road-trip-ready.


Driver Shift Change

How many licensed and able drivers are in your pack? When you are planning your road trip, having a discussion about driving shifts is a good idea. Some people operate better in the morning, others at night. Perhaps that is a great way to divvy up the duties? Other ways to break up the drive times is to change drivers when you refuel or stop for meals, etc. No one person should take on 100% of the driving unless necessary (or if they want to). You need to stay alert and focused, so take regular breaks. Also, don’t underestimate the need to get out and stretch your legs.

Music & Entertainment

Music not only entertains, but it can be a way for the driver to stay alert and energized. One rule of thumb we have for group road trips is that the driver chooses the music. You may not like their taste in music, but the same can be said about your choices when you are the driver. When planning a road trip, we suggest everyone have a playlist of the music they like. Or they can select from satellite radio stations that they prefer etc.
Podcasts and audiobooks are also popular. For long drives, before leaving download several PodCasts that might be of interest to you, and your pack.

Planning road trip snacks

As you are planning your road trip, you may wish to pack some snacks and drinks to get you going. Having a variety of snacks to munch on will keep you from getting hungry and irritable between meals. Some suggestions are to keep it healthy but have some fun snacks as well. Pack some chewing gum, water, protein-rich snacks, and items that will not spoil in the vehicle.
There are plenty of places to stop and pick up more snacks or fresher snacks, so there is no need to overpack. Also, if you are crossing the border do not bring any fresh fruits and vegetables, meats or other items forbidden from crossing the border.

Check out our Tips for Road Trip Snacks: What to Pack

Split the costs

We have a general rule of thumb when it comes to prices on a road trip with other people, and that is, we always split the costs evenly.

  • Meals should have the bills split accordingly.
  • Alternate who fills the fuel tank for fairness
  • Book hotel rooms where each couple can pay for their own, or at least divide the costs at checkout.
  • If someone buys a coffee, snacks, or something for the group, then the other couple or person does it next time.
Road Trip Planning Resources

The right books, maps, and trip planners can be invaluable. We love offbeat adventures & attractions, and so we use websites and books that are geared to helping us find those things. Other books that we love are the city version of DK Books. They have great maps, ideas on what to do, where to stay, eat, etc.

Don’t forget to pick up FREE travel guides at the provincial, city, or state tourism bureaus you will find along the route of your road trips. They are a great resource. Click for more Money-Saving Tips

Mistakes Happen

How you plan your road trip is entirely up to you. Regardless of how well you plan, there will be mistakes along the way, and you will learn from that. The first time Nick & I went on a road trip together, it did not go well at many points along the road. However, it was still a lot of fun, and we learned from our mistakes. Each consecutive road trip has been better, and we now have most of the stressors figured out. That doesn’t mean it always goes perfectly, but we figured out how to make it work as well as possible for us.

Fifteen years later since that first (poorly planned) road trip, and we still look forward to the next. We have found the right balance between my hyper-scheduling, and his attitude of “let’s see what happens”. I schedule less, and he plans a little more. Now, we plan a less intense road trip schedule, so that we can incorporate more flex into our days, thus reducing the stress.

Planning the perfect road trip is all about making compromises and working together so that everyone has a fun vacation.


Adventurer, gastro-tourist, avid road tripper, and butter tart aficionado. Exploring the road less travelled and the adventures that exist for all to see if you open yourself up to new possibilities. Greg and his husband Nick are residents of Guelph, and their greatest joys in life are exploring the world around them. Road trips with no real destination are a favourite past time. Get off the beaten path and discover somewhere they have never been before. Sometimes the best vacations are the ones you don't really plan. Life is about the journey together and not the destination.

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