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A Little Planning Creates a Stellar Vacation

I have always had strong organizational skills.  Planning, mapping, organizing, and creating systems and processes come naturally and easily.

But that’s not the case for everyone.  Some people fly by the seat of their pants, and that can lead to a lackluster vacation; or worse, it can result in missed opportunities and wasted money.

To solve this problem, I’ve organized my process into an easy to follow solution.  It can be applied to any trip, and help you create the ultimate road trip, the perfect experience that packs ALL the excitement into your time touring.

Of course, if you don’t care to plan, hit me up.  I’ll plan it for you so you can have an itinerary worth bragging about.


My Five Step Method to Creating the Best Road Trip of All Time

Why 5 steps?  Because that’s what it came out to be.  It isn’t a magical number, that’s just how many steps this thing ended up at.  What is important, however, is the order of the steps.  Well, the first one has to come first anyway.

1 – Choose Your Road Trip Theme

Road trips, by definition, aren’t a means to an end.  The trip itself is what you’re all about.  So if you want to “road trip” from Billings, Montana to Miami, Florida, you’re not really road tripping.  You’re traveling from Billings to Florida and just happen to be taking the roadways to get there instead of air or train travel.

Road trippin with the Serys travel blogger

The road trip, however, is all about the journey rather than the destination.  The “destination” is the trip, it’s what you do along the way; each stretch is the adventure.  But just driving for the sake of driving ends up being boring.  You have to plan your “destination” around a theme.

In March, 2022 we took a road trip for spring break.  Our theme: State Capitals and Capitols.  In fact our next several vacations are revolving around this theme until we knock off all 50 of them (Alaska and Hawaii, naturally won’t be included in the road trippin’ aspect).


New Mexico
State Capitols Road Trippin with the Serys

Mapping things from Billings, we saw a distinct route that would take us south through Utah, Nevada, and Arizona.  Then we completed the loop heading east to New Mexico, and north through Colorado, Wyoming, and back into Montana.  It was an ambitious loop, but we would knock off 5 state capitals along the way (Nevada’s capital was way out of the way).

This theme got us the basis for the road trip.  Now it was a matter of filling in the gaps.

2 – Choose Your Road Trip Duration

How long do you want to be away from home?  For some people they can leave and never look back.  For others, three or four days and they’re longing for the comfort of their own bed.  With pets at home, work that you have to return to, or other “things” drawing you back, the shorter you want to make your road trip.

For some, you’re stuck with how much time you get off work.

On our spring break trip, we had two weekends and the week that was sammiched between them.  Naturally you want some recuperation time at the end of the trip, so don’t plan to be gone right up to the time you have to return to work.

The duration will help you understand the location, or rather locations, of your road trip.

3 – Choose Your Road Trip Location

You know what you want to see, and you know how long you can be gone.  Now it’s time to figure out which locations your journey will pass through.  This step is actually more time consuming than you might think because you have to account for multiple stops, travel, and the inevitable potty breaks even though we just filled up for gas 15 minutes ago.


Most people can travel 12 to 14 hours per day.  And you spend the entire time in the car without experiencing the journey.  You simply drive.  When you’re destination traveling, as opposed to road trippin’, that’s fine.  My son and I drove to Minneapolis in 12 hours because our goal was to get to Minneapolis.

But the destination is the journey on your road trip.  Your goal is to have fun, and sitting in a car for 12 hours a day is far from fun.

Planning a road trip is finding that fine line of how long you can sit between the things you want to experience.  Sometimes it’s only a couple hours, sometimes it can be more.

For our spring break capital trip, we had a couple of days that were 9 hours in the car.  The first day of the trip (getting from Billings to Salt Lake City), was traveling through areas where we had largely been before.  Nothing new, nothing incredibly exciting, and mostly just hurry up and get there.  Of course part of our “hit every state and state capital” means we stop for a picture by the sign leading into that state.  So at the Montana/Idaho border and the Idaho/Utah border we stopped and got a couple of quick pictures.


Ideally your road trip should be four to six hours between stopping points, maximum.  Sometimes your stopping points are along the way, so you might do two hours, then have an hour or two stop, then two more hours with an hour or two stop, then two more hours.

You get the idea.  Time in the car simply traveling should be kept to around 6 hours per day if you can.

4 – Choose Your Road Trip Budget

One of the reasons families will travel by car instead of air is the cost savings.  Current gas prices mean it will cost somewhere around $200 to get a vehicle to Denver and back, but if you were to fly it would be $400 per person.

Fuel isn’t really an issue here.  The true costs, the things you have to really budget for are lodging and attractions.  We’ll get into attractions soon, but first: the budget.


But be sure to account for food, souvenirs, attractions and more.  Hotels are one thing, but if you’re eating out (as opposed to grabbing things at the grocery store that can travel with you) you will spend more.  Some meals are more than others.  Know your budget, and know how much you can spend each day so you don’t come home with some massive credit card debt.

5 – Choose Your Road Trip Attractions

The first thing to cut from your trip, if you’re going over budget, are the attractions.  If you’re in Vegas and you want to do ALL the things, trim that back to a few that you absolutely cannot live without doing.


How does this look?

Your budget includes gas, lodging, and food.  Now you know that you have a certain amount left over for attractions and things-to-experience while you’re on your road trip.  Keep in mind that everything is going to end up costing more than you expect.  If it says $100 per ticket, remember to account for taxes, and the fact that you probably misread that, and it’s really $125 because you’re there during peak hours.  You will get thirsty and water is $4 per bottle.  You want that souvenir, and it’s another ten bucks.  You’re irritated so you need a beer; there’s another $8 a pint… you get it.

Make a list of all the things you would love to do.  Most likely there won’t be time for all of them, so you can easily whittle away at that list.  As you taper it down, keep in mind your budget and how much time you have in every location.  When it’s finalized, then it’s time to organize everything to keep you on track, on schedule, and on budget.


Road trippin with the Serys
Spotting exotic license plates is a road trippin' hobby

Literally Map it Out and Create an Itemized Itinerary

You have your theme, you have your budget, you have your destinations and your attractions.  Now it’s a matter of putting all that information together in one easy-to-see place so you know just what you’re doing and where you’re going.

Personally, I like to create a one-sheet that I print off, and a printed map with my highlighted route.  But there are a number of planning apps or software programs that can be used instead.

On the left-hand side of the sheet I have the date.  In the next column I have my starting point for the day, then a column for travel duration, and then a column for destination.  Next to the destination I have the hotel where we will stay and the confirmation number and contact phone number.

Beneath that day I include the activities that we will experience along the way, including the time when we are to do them if they required a reservation.  Some destinations have considerable free time to explore, so I indicate that on the daily activities.  When you’re planning activities, always plan considerable free time between them otherwise you’re bound to get stuck in traffic, feel rushed, miss the start of the program, or otherwise not have enough time.


Normally I will get this sheet ready well before the trip, and then keep it in a folder with other receipts and confirmations as we go along.  Because I like to crunch the numbers after the trip, I print off the fuel receipts and calculate mileage from each fill up.  It’s not necessary, but I find it enjoyable.

Itinerary in hand, knowing where you’ll go, and having plenty of free time at each stop means that when you arrive and you see the sign for the world largest donut, you can say “that looks like fun, we will add that to the list.”

Here’s a quick look at how this itinerary looks when printed, and what my map looks like; I’ll update this with a better copy after my next road trip.


Road trippin with the serys
Yes, I know it's terrible, I don't have a clean version yet.

Scott Sery is the Ultimate Road Trip Planner

Planning the perfect road trip takes time.  It takes a bit of dedication to look into each aspect.  And, most of all, it takes organization to keep things all in the right place so they’re easy find and easy to read.

Over the years I have found that most people don’t want to put the effort into it, nor do they have the organizational skills to make it happen.

So, if you’re in that boat, let’s connect.  I’ll plan your ultimate perfect most awesome road trip for you, so you can get out there and experience life on the road.

HMU with an email if you’re interested and let’s see where this goes.


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