How to organize your own road trip


Does it seem daunting to organize your own road trip? It really shouldn’t! Follow these steps and make it your perfect holiday.

Going on a trip or vacation is exhilarating, the prospect of time off, new experiences, different weather and spending it either alone or with your family is the bomb. Well, for me it is.

Booking it, however, often is tedious and rife with ifs, buts, and maybes. You’ve decided where you want to go but you can only go on particular days of the week. Or a specific month.

The flights only leave mid-day, robbing you of an extra workday thus vacation time. It could also be contingent on the number of interested parties whether the trip will take place at all. What if you want to bring the kids?

By taking all of that into your own hands, you can make it entirely tailor-made. You keep track of the costs, go on your preferred travel dates and pick and choose just those activities that suit you.

How I organize it – Georgia – Florida example

Did you see my blog on the first few days of our Georgia – Florida road trip, last Tuesday? I always find it hard to read the generic ‘How-to’ blogs as I always seem to hit tons of ‘but what if’ -scenarios.

That’s why I thought, I’d do this organizational blog-series alongside my blogs on our trip last March.

It’ll hopefully show you what issues I consider when planning and/or why I organize things the way I do. Let me know if it works for you or what you run into, so we can tackle those issues together, okay?

Today, we’ll consider some of the more generic information at the planning stage, and the booking of your first big-ticket items, flights, first and last accommodation and car rental.

Organize phase 1

Though these steps are easy to follow, you do need to set aside some time. For that reason, I’d recommend booking it in steps.  

Let’s start with the set variables: who you plan this for.

Travelers: Number and Ages

Are you traveling alone, as a couple, a family or group of friends and what are your ages? As students, with groups or over 50, 60 and 65 years old, you may get discounts and can travel out of season.

If you have kids younger than 4 years old you may benefit from similar initiatives. When your kids are older, however, you may be obliged to travel at certain times of the year.

With three kids or more you need to book earlier if you want everyone to sleep in one (family) room or be able to book enough rooms for your family or a group. And from 11 years onwards keep in mind they may be deemed an adult in terms of pricing.

Budget and Travel dates

Your budget thus depends on the travelers, their ages and when you’re allowed to travel. Depending on when you go, high-or low season, and the number of travelers, this will make all the difference. Going low season could mean an extra few days of holiday, that one experience that you could pay for or traveling on a day that otherwise would be too expensive.

Keep in mind that if you want to travel over the summer period, make sure to organize a few things in advance (approx.6 months ahead) such as flights or accommodation if you’re going to popular places. Finding flight deals is easier when you have some time to contemplate what a good deal is for you.

At the same time however, don’t overthink this. Bag a good enough deal that gives you some money to play with but also secure that trip so you can tick that part as done. Don’t add any unnecessary stress and an option for added costs by waiting for the perfect deal to come around. They won’t and it’ll cost too much.


So how much do you need, or how much should you count on to spend?

There are several schools of thought on how to set a budget or deciding how much you’re going to need:

  • 5-12% of your overall (combined) income;
  • $1400 per person per trip (based on a 2-week holiday usually on the same continent);
  • Not spending more than just 1 month of your annual pay/income;
  • Savings.
Breaking up of costs % of Budget Budget $10.000 Budget $5000 Budget $2000
Travel 40-50% $4000-5000 $2000-2500 $800-$1000
Accommodation 25-33% $2500 – 3300 $1250- 1650 $500-700
Food 20-25% $2000-2500 $1000-1250 $400-500
Excursions/cultural visits/experiences 10-20% $1000-2000 $500-1000 $200-400
Contingency/emergency fund 5% $500 $250 $100

This is a pretty rough guide for something that is very important at this stage. If you’d like a more detailed idea of what your trip will cost, try tools like: this online travel cost calculator,

Booking stage

By now, you have a fairly good idea who will be traveling, when and how much you have to spend. Time to start securing part of your trip.

Organize and keep track

One of the very first things I do, when I start to organize our road trips, is setting up a dedicated folder on my computer.

In it, I have one file usually a Word or Excel file where I keep track of all that I know, have organized and/or still need to follow up on. It grows along with my plans and once we’re ready to go, I can either bring it electronically or print it off.

Hard-copy folder

In fact, I often also dedicate a hard-copy binder to our trip. It’ll have the print-off with all of our dates, but also the hotel reservations with highlighted areas about whether or not the breakfast is included, or if we need to double-check for say, a roll-away bed.

Besides the fact that you sometimes don’t have access to electronic files, I often use it as an impromptu diary of our trip. I make notes on what I saw that day, remind myself where we’ll go next and keep receipts or leaflets of the activities we took part in.

Photo album Georgia – Florida

It’s a great reminder of when and what we did once I start putting together a photo-album or want to blog about it and need to add details like driving distance, or what made the day special.

Electronic organization file

So, what is on that file of mine? Typically, the following:

Time Travel dates what details cost distance highlights

Furthermore, I add a folder to my email inbox where all trip-related emails such as booking confirmation, hotel communication and car rental agreements go. Handy to have when you need to check details in your email box on your phone while underway.

Organize now

As we lived in Toronto (I miss you TO!) and wanted to go during March Break, our dates were set early on: March 22nd  – March 31st. Plus, it meant flights needed to be organized. Driving over 1500 km /950 mi would take too long.

Flights – Things to think about when you organize:

Flight times:

  • When are you off work, depending on the proposed flight time, could you fly out after work and/or school?
  • Night flights can be cheap but as you need to be at the airport at least 2 hours in advance for international flights – consider if this is feasible for your travelers. Are they morning people, will their inner clocks be off for days, how about feeds for babies, extra time to recuperate when you arrive, etc.?
  • Transport/parking: Will you (need) to take your car to the airport? Who will drive, pay for parking for the duration of your stay? Is a taxi better? How much will it cost? Will all family members fit with your luggage? My kids are 9-11 and 13 y/o now and we start to have a problem if we want a taxi now.

Destination and packing:

  • Are you going somewhere warm? How many clothes and/or what equipment are you bringing? How important is it to you to look your very best? Where is your trip going and how can you reduce the number of items you bring?

    Example: over time we realized that we consistently used about half of the clothes we packed on any trip. We also found we often stayed at hotels that had washing machines and dryers (make a note on your organization sheet which ones).

    So, we now each have a small carryon suitcase (everyone is responsible for their own suitcase) and bring about 4-5 days’ worth of clothing. We pack less, pay less and are in and out of the airports twice as fast. Even when we decide to hand in our luggage on certain flights.
  • You’re flying somewhere warm but out of a wintry locale and you need your heavy coat on the way in and back? Either leave them in your car and get a VIP service that’ll park your car. Or leave your heavy jackets in an airport storage locker.
  • How much room will you have in your rental car? Did you book a big SUV? If you’re outside of North America, count on smaller cars and boot size. Will, what you’ve packed fit?

Booking your flight

To find the best flight deals I usually open a bunch of websites, comparison and airline websites, at the same time: 

Most of them compare airlines for me already.

Of course, there are myriad of ways to find the absolute bottom line price for flights. Unfortunately, as a family with 5 people, we often have to travel on particular days and times related to work and school.

My focus is on finding a reasonable deal flying at a reasonable time (with kids) which will maximize our holiday time.

Booking sites

Alongside the comparison sites, I also look at the booking sites such as,, www. They sometimes have a great combination deal with flight and hotel, sometimes also including car rental.

In this event, I needed all. After some comparisons (over 1 week, checking different websites a few hours here and there), I organized separate flights, hotel, and rental car. While I tried to combine the three the ‘combination’ website(s) kept telling me there wouldn’t be a rental car available. Also, the cost of combining the flight and hotel for the first night was more expensive by $500 compared to booking it all separately.

So, it is beneficial to take some time to compare websites. It meant an extra two hotel nights had ‘paid for’ themselves.

Organized thus far:

Due to some uncertainty with our planned move to Europe, we didn’t book this trip too far in advance. By January 20th though, nine weeks ahead of the trip, this is what I booked:

Flights – leave Friday night and return early Sunday morning (6 am)

The flight was at 8.40 pm, allowing to fly on Friday night, in time to finish work and school and because the flight is just over 2 hours. Dinner could be done before we left for the airport and the kids are a little older, so they’ll manage the one day with less sleep.

Hotels – first and last day to ensure to be close to the airport. This allowed for pick-up of the rental car after arrival, and return thereof the day before our return flight. An airport shuttle was available to take us from the hotel to the terminal.

Tip: don’t forget to contact the hotel to let them know you’ll arrive late that day or maybe technically the next day!

Rental car: Pick up late at night, thus full day use on first road trip day. Drop off on the last full day.

Rental companies are often open at all hours, especially when you book them for pick up at the airport.

Next steps

Next week we’ll look at the further organization of this road trip. We’ll discuss travel distances, what to visit, the costs and how to balance it all.

What would be your number one concern if you’d organize a trip like this? What tools would you like to find or which do you use for these types of trips?


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