top of page
  • Writer's pictureAshleen Chappuis

Ultimate Guide to Planning a Road Trip

Updated: Nov 28, 2023

Whether you are traveling from California to Maine or New York to Chicago, your road trip ultimately starts with a plan. This guide will give you a template to build your own adventure, including everything you need to figure out before you get in the car (and space to let your plans change after you've hit the road).


One of the stereotypes I've heard about Americans is that we think nothing of driving hours for something. Even amongst Americans, my family loved driving when I was growing up. We drove from near Cape Cod, Massachusetts to near the Canadian boarder in Maine, a minimum of a 7 hour drive, every summer. We drove from Massachusetts to Montana in the US, from Paris to Perpignan in France, and from Canterbury in England to Fort William in Scotland. As an adult, I drove cross country when I moved from Boston to Seattle.


All this is to say that I have logged a lot of hours in a car and have gone on enough roadtrips to learn what works and what doesn't. I'd like to share what I've learned and give you some tips and tricks to the perfect road trip.


Table of Contents



How Important is Planning a Roadtrip?


With any new adventure, there is a wide variety of personal preference. Some people want to have every detail ironed out a month before they hit the road. Others don't know where they're going to end up later today let alone what the plan is for tomorrow. In my experience, to have the best adventure, you need to find the sweet spot between inflexible and under-prepared.


Maybe you know you want to travel the American Southwest during wildflower season, or you need to move Boston before school starts this fall, or you and your besties are just dying to do a road trip regardless of the time or the place. You can plan all of these road trips will use the same basic template.



Before You Leave: The Essentials


Step 1: Who Are You Going With?

Before you can get too deep into the planning phase, you need to know who will be traveling with you.


If you are going alone, that gives you a lot of flexibility. You can do whatever you want, whenever you want. You do not need a group decision, you won't have to skip anything on your bucket list, and you don't have to stop at anything that does not interest you. However, you will have to plan each step of the trip, do all of the driving, and be more cautious than you would be with a group. That means you need to come up with back-up plans should anything go wrong, like your phone dying or forgetting where you parked the car, because you do not have anyone to help.


If you are going with a group, you'll (hopefully) never be lonely. You can all sing along to your favorite songs, laugh over dinner together, and see sites you would have never picked yourself. However, you will need to get agreement from the group on each step, align on the overall budget for the trip, and exect to get in at least one argument if you're trapped in the car with someone for too long.


Step 2: Decide on When and Where

Once you know who's in on this trip, you need to decide on where you're going.


There are a number of different ways you can plan a road trip, but they all require you to have a rough idea of where you want to go and when.


A cross country trip will change dramatically if you plan to go from coast to coast in a week or over the course of the whole summer. More common road trips, like traveling with your friends to a concert or helping a loved one move, have set dates that you will need to work around. So before you do anything else, you need to decide when and where you want to start and end your trip.


Depending on your situation, you may be able to extend your trip or have a more flexible end location, but it is still helpful to have a rough idea of the timing so that you can determine the right pace for your travels.



Step 3: Create a Rough Map of Your Route

There is always more than one way to get from point A to point B, so it is important that you go online and look at a map of where you will be driving.


I like to start with the most efficent route. This gives you an idea of the fastest the trip could possibly go or the minmum amount of time you need to make this journey. Since you already determined in Step 1 how long you have for the roadtrip, you can take the amount of time you have and substract the amount of time you need based on what the map is telling you.


For example, let's say I wanted to drive from NYC to Chicago and only had one day to do so. I would look at the map and see that it takes about 13 hours of straight driving to do that, which means that this trip would be a very long day of driving and there would be no room the schedule to stop for sightseeing. This kind of roadtrip would not be for fun and would instead have to focus on being as practical as possible.


However, if I had a 4-day weekend to do the same thing, I I would have a lot of time to stop and see things. With the extra time, I could make this a fun roadtrip that visits a bunch of places.


Using this equation (the maximum time you have for the trip minus the minim time you need to get there) will help you get an idea of the pace for your road trip, which you will need to complete the next steps.


Step 4: Pick Your Must-see Stops

Now that you know your destination, timing, and pacing, you can start to build out your roadtrip, starting by adding a few important stops. To do this, keep your map (or Google Maps) open and look at where your route goes.


To continue with the example above, if I were traveling from New York to Chiago and had a lot of time to explore, I would look at the map and see that the route is near Philidelphia, Pitsburg, Cleveland, and Detroit. From here, I could decide if I want to visit any or all of these citites and make them my high level stops. One of my personal goals is to visit all of the US National Parks, and a quick search shows that this route is also close to Cuyahoga Valley National Park and Indiana Dunes National Park and I could decide if I want to visit these places as well. However, given that, in this example, I only have 4 days for this trip, I would not be able to visit all 6 of these places, and I would need to pick which ones to see and which ones would need to wait for a future trip.


The main point of this step is to decide what on your route is a must-see and what sites you will need to drive past. I would recommend picking between 1 and 3 big stops a day, depending on the pace of your trip.



Before You Leave: Nice to Have/ Non-essentials

At this point, you should know who you're traveling with, where you're going, and have a few spots you know you will be visiting.


If you think this is enough and can't wait to get out on the road, then skip ahead to the On the Road Essentials. If you want want to keep planning things before you leave, such as mapping out your first day and picking the right playlist, keep reading.


Tip 1: Make Multiple Playlists

Long drives can get boring, so you need to have a variity of things to listen to on your roadtrip. I recommend making a few different playlists that you can alternate between and making sure you can listen to a couple of them even if you lose cell service. Some key playlists include:

  • A relaxed vibe to start the day off strong

  • A high-energy or pump-up playlist for driving in the dark or when you start to get tired in the afternoon

  • A podcast series to help time pass faster

  • Some good throwbacks

  • Songs you will never get tired of listening to

Tip 2: Pack Snacks

Roadtrips need snacks! You don't want to get too hungry while driving and depending on how remote you get, you may not be able to quickly find somewhere to stop and eat. Instead, pack a bag of snacks to take with you on your trip. My biggest tip is to start the trip with healthy snacks. As you drive, you'll probably end up stopping for fast food or restocking your snack bag at the gas station, so it's nice to hold off as long as you can and to have something fresh and different at the start.


Tip 3: Get Roadside Assistance and Insurance

If there is ever a time when you want to make sure your car is running right and that you have someone who can help you if you get stuck on the side of the road, it's during a roadtrip.


Be sure to get car insurance that covers you throughout your trip. This means if you are crossing national boarders, checking with your insurance before you leave to make sure they cover you internationally, or if you use a small, local insurance compnay that they will cover you nation-wide.


Additionally, be sure to get a roadside assitance program. This is sometimes part of your insurance or can be purchased sperately from groups like AAA. You can always cancel this once you get back from your roadtrip, but it is better to be safe than sorry when traveling unfamiliar roads.



Tip 4: Check for Passes

If you plan on visiting multple national parks, consider getting an America the Beautiful Pass, which will let you into the national parks and a number of federal sites. It costs $80 (or less if you are eligible for a discounted pass), which means that it pays for itself if you visit at least 3 national parks in the year.


Tip 5: Map Out Your First Day

While you can never map out every minute of your trip (and I would recommend not bothering th try), I would recommend coming up with a few options for your first day. Think of this as a practice round. It gives you a chance to see how easy it is to find the information you need (and a chance to see what you never thought about and what you never ended up neededing to know). My recommendation is to look into a few different stops and places to have lunch so you have options depending on what pace you end up moving at once the road trip actually starts.



While Driving: the Essentials

Step 1: Check Your Tank

Each morning of your roadtrip should start by checking how much gas (or battery) you have left in the tank. Depending on where you go on yout trip, you may end up in a big stretch where its hard to fuel up your vehicle so you want to plan ahead and make sure your tank never gets to empty.


Step 2: Make a Driving Plan

Whether you are driving alone or switching off drivers, you will want to take some breaks to stretch your legs. I would recommend stopping every couple of hours to use the bathroom and go for a short walk. If you can switch drivers, I would recommend switching drivers every 3 or 4 hours so you can stay fresh and alert behind the wheel.


Step 3: Book a Place to Stay At Dinner

Whether you are sitting down to eat or eating in the car, when dinner time comes around it is a good time to start thinking about where you want to end the night. You'll have a good idea of how much longer you want to drive and where you will end up at the end of the day so you can use this time to book a hotel or a campsite (or at least research them).





While Driving : Nice to Have/ Non-essentials

Tip 1: Make the Most of Dinner

When you start the road trip, everything is new and exciting. But by day 5, you and your travel buddies have run out of things to talk to. Use your dinners (and your diner's wifi) to plan our your next day in more detail. Talk about breakfast plans, any sites you want to visit, and a rough idea of where you want to end up at night. Additionally use this time to book a hotel for that night


Tip 2: Charge Your Phone While Driving

You'll want to have a full battery when you get to your stops, so be sure to charge your phone while driving. Additionally, if you have mutiple people in the car, make sure everyone has a chance to use the charger.


Tip 3: Always Stop for the Unexpected

Driving across the US, you will find a number of stange things, from a Jolly Green Giant to the World's Largest Prarrie Dog. These are the things you can only find on a roadtrip and a key par of the Americana vibe. Don't let these things pass you by! Yes, it is toursty to stop at a themed resturaunt, but how often do you get to eat at a Wild, Wild West themed bar in the Wild, Wild West? You are a tourist so be a tourist!



Tip 4: Enjoy the Ride

You can never go on the same trip twice. Each one will be unique because you'll tavel with different people or at a different time. Be sure to take everything in and savor the adventure you're on. Make memories, take photos, and enjoy your roadtrip!

Recent Posts

See All
bottom of page