Road Trips (Part 1): How to Plan an Awesome Adventure

The weather is warm, the road is calling, and adventure awaits. Why not take a road trip?!
They have to be fun, right? I mean, look at all the movies that have centered around them:
- Vacation (Chevy Chase & Beverly D’Angelo – a classic!)
- Tommy Boy (Chris Farley & David Spade)
- Planes, Trains & Automobiles (Steve Martin & John Candy)
- Identity Thief (Melissa McCarthy & Jason Bateman)
- Due Date (Robert Downey Jr. & Zack Galifanakis)
- Guilt Trip (Seth Rogan & Barbara Streisand)
What do these all of these movies have in common? The main characters encounter crazy people (sometimes the person they’re traveling with) and even crazier situations.
In reality, road trips can be a blast (alone or with 1+ travel buddies) with a little advance planning.
START YOUR PLANNING BY ANSWERING SOME IMPORTANT QUESTIONS
Before you jump in your car and head out on the open road with the radio cranked up and the wind in your hair, you need to do some planning.
Start by asking yourself the important “Who, What, Where, When, Why, and How” questions, as in…
1. “WHO will be going on the trip?”
The answer to this question is very important.
- If you are going alone, you can do whatever you want whenever you want.
- If you are going with others, you will have to find activities that everyone will enjoy and be able to compromise on your itinerary.
2. “WHAT is my budget?”
Money is always a consideration when traveling (or doing anything else, for that matter).
Don’t have a budget limit? Lucky you! Skip this section and go to #3.
If you do have a limited budget, be sure to take into consideration all trip-related expenses so you can estimate how much you’ll need.
Your trip budget should include an estimate of the following expenses:
- Gas – How many tanks of gas will you need to travel round-trip?
- Meals – Where will you eat? Fast food restaurants? Chain restaurants such as Ruby Tuesday, etc.? Or will you buy groceries?
- Lodging – Where will you stay while you’re away? The home of a friend/family member? Campground? Hotel? Airbnb? Hostel? Or will you couch surf?
- Incidentals – Will you need money for tolls, parking, tips for hotel staff? Admission fees for sights you want to see?
- Spending Money – Do you plan on shopping, buying gifts, etc.?
If the total is more than you have or are comfortable spending, you can make the necessary adjustments in advance.
3. “WHAT do I want to see and/or do?”
If you’re like me, you enjoy doing some of the touristy things (like one or more of these weird roadside attractions) combined with exploring. If you just want to go with the flow, that’s fine, too. It’s your trip. You can do whatever you want!
4. “WHERE do I want to go?”
If you have an idea of where you want to go in mind, great! That’s half the battle.
If you don’t know where you want to go, don’t freak out. There are a few things you can do that will help you narrow down your destination(s).
- Ask your friends/family – If you know anyone whose gone on a road trip or two, ask them where they went, how long they were gone, and if they enjoyed the trip
- Google “road trip itineraries for [geographic area]” and see what comes up
- Use a website or app to help you plan (*Check out my next post after you finish this one)
5. “WHEN will I go?”
Depending on the answer to #2, you can take a spontaneous trip or you may have to ask for time off far in advance.
6. “WHY am I going?”
Do you want some R&R? Do you want to see and/or do as much as possible? Or a combination of the two?
7. “HOW long will my trip be?”
If you are only going for a weekend, your destination will be much closer to your home than if you have a week or more.
Once you answer these questions and come up with your budget, you can plan your route.
ROAD TRIP ROUTE EXAMPLE: MY TRIP TO NC & TN
Awhile back, I took a road trip through North Carolina and Tennessee with my boyfriend. The total trip ended up being 1,462 miles.
To plan, I started out by asking myself and answering the 6 questions mentioned above:
- WHO will be going on the trip? – Originally, I was going alone, but due to a change of plans, my boyfriend went with me.
- WHAT is our budget? – The less money, the better! Since my boyfriend went on the trip, we split everything 50/50 which made it much more affordable.
- WHAT do we want to do and/or see? – The must-sees on my trip were The Biltmore in Asheville, NC and Music Row in Nashville. Everything else was open.
- WHERE do we want to go? – Asheville, North Carolina and Nashville, TN
- WHEN will we go? – I was planning on going 3-4 weeks from when I asked off from work (unless they needed more advance notice)
- WHY am I going? – To get some time to rest, relax and explore
- How long will my trip be – Mine was 10 days
Next, I looked on the map to see where things were in relation to each other. Then, I added a few stops to fill out my trip.
In addition to stops in Asheville and Nashville, we added a few days in Raleigh, NC, to stay with one of my friends for a few days and a stop in Knoxville, TN, to explore.
Figure out how much time you want to spend in the car each day, then start plotting your course. This may take a little bit of tweaking, but it is doable.
I planned my route specifically so:
- We wouldn’t be driving a huge amount of time each day, and
- We had 2 days in (almost) each place, giving us some time to recover from all the sitting we’d be doing.
Here’s what our route looked like:

PLANNED ITINERARY
Day 1 – McLean, VA ⇒ Raleigh, NC (4 hours)
Day 2 – Stay in Raleigh with my friend
Day 3 – Stay in Raleigh with my friend
Day 4 – Raleigh, NC ⇒ Asheville, NC (4 hours)
Day 5 – Stay in Asheville; visit The Biltmore
Day 6 – Asheville, NC ⇒ Nashville, TN (4-1/2 hours)
Day 7 – Stay in Nashville
Day 8 – Nashville, TN ⇒ Knoxville, TN (2-2/3 hours) ⇒ Abingdon, VA (2 hours
Day 9 – Abingdon, VA ⇒ McLean, VA (5-1/4 hours)
The only diversion from how I planned the trip occurred in the last 2 days. We ended up leaving Nashville after dinner and driving as far as Knoxville, where we spent the night. The next day, we spent the afternoon exploring Knoxville, then drove all the way home.
WHAT WE ACTUALLY DID
Day 1 – McLean, VA ⇒ Raleigh, NC (4 hours)
Day 2 – Stayed in Raleigh with my friend
Day 3 – Stayed in Raleigh with my friend
Day 4 – Raleigh, NC ⇒ Asheville, NC (4 hours)
Day 5 – Stayed in Asheville
Day 6 – Asheville, NC ⇒ Nashville, TN (4-1/2 hours)
Day 7 – Stayed in Nashville
Day 8 – Nashville, TN ⇒ Knoxville, TN (2-2/3 hours)
Day 9 – Knoxville, TN ⇒ McLean, VA (7+ hours – ugh!)
Due to our change in itinerary, the ride home was way longer than I wanted it to be, but we got home safely at about 1am (*yaaaawn*).
I hope this post gave you some things to consider when you start to think about going on your first (or next) road trip.
Now that you know what to consider when planning your trip, you’ll need some tools. Check out my favorite trip planning websites and apps.
Hahahaha great advice with humor! Love it ?