5 Steps to Planning a Month-Long Roadtrip
Written by Casey Wilson
I was bit by the travel bug at a very young age. From swinging from the trees in the Cayman Islands, to marveling at Cinderella's castle in Florida, to attending a luau in Hawaii, to cruising through the water in Alaska, and to everything in-between, I was fortunate enough to have two parents who loved to give us ("us" being my brother and I) incredible travel experiences. Though, what I didn’t realize at the time was that the travel bug would bite me hard, and that it would leave its venom in me for the rest of my life.
Traveling is my escape, my happy place, and my absolute favorite thing to do. Add a camera in my hands, and you can barely wipe the stupid smile from my face.
As I look back on my vacations from my childhood, I remember how organized and fun they were. A lot of that is owed to my Dad who was the travel/vacation planning KING. And I, his travel princess, secretly watched and soaked up his every move, so that one day, I could wear the crown and plan trips as well as he did/does.
So, here YOU are in my Dad and I’s travel kingdom- okay I’ll drop the metaphor already- BUT I’m here to give you some of my tricks that I use, most of which I learned from watching/listening to my dad, but some that I have picked up along the way.
My husband, Ethan, and I booked a 27 day road trip out west this past summer, and I'm so excited to share with you all of our adventures. But before we begin, I want to share how I organized the trip in the first place!
Step 1: Map Your Journey
This, in my opinion, is the trickiest (and lengthiest) part. Grab yourself a notebook and a pen, pull up a map of the place you are going, open up Pinterest and Google, and get started.
The first thing that I did after picking our destination(s) was decide which stops to make. My first list I made was a “tourist city” list. There, I listed all the major cities that most people travel to and/or talk about. Next, I typed each city into Pinterest and/or Google and started reading blog posts about what there is to do in each of those cities. If a city did’t appeal to me, then I crossed it off my list. I kept going until I felt that I had found out enough information about each place to make a decision.
Along the way, you will start to notice the places that get mentioned over and over in different blog posts, and that helps make decisions a little easier.
Once I had a pretty solid list of major tourist cities, I then created my second list called “hidden gems.” I like to Google and search on Pinterest "unique places to go in _____." Sometimes you have to really dig to read about these places, but if you have the patience to read and search, you will be led to some pretty picturesque/interesting places. I walked through the same process of elimination with these places.
Step 2: Create Your Route
If you road trip a lot and you have not downloaded the app Roadtrippers, then you are missing out! If you are new to road trips, then I high recommend you start with this app (it is also available in a desktop format at www.roadtrippers.com).
Once I had my list of “tourist cities” and “hidden gems,” I pulled up my Roadtrippers map. I marked the tourist cities and the hidden gems on the map. I then looked for patterns to see if they were clustered together, or if they were far away from each other. Roadtrippers allows you to click around and re-route as many times as you want. This process allowed me to begin eliminating places from my list.
Roadtrippers also gives you information and recommendations about cool places to stop that are along your route. The app/website will also tell you how long it will take you to get from place to place (much like Google Maps).
After I had I pretty good idea of the stops we wanted to make, my next step was to decide how long to stay in each city. I wanted to stay at least two days in each city so that it didn't feel like we were in the car more than we stopped. Once I decided how many days would be spent where, I started looking for accommodations.
BONUS TIP: Roadtrippers will also tell you an estimate on how much you will spend on gas!
Step 3: Book Your Accommodations
The two websites I use to book accommodations are booking.com and airbnb.com. I generally only use booking.com if I want to book a hotel; otherwise, I prefer Airbnb because I like that Airbnbs have kitchens, living spaces, character, backyards, and other unique amenities. Plus, most of the time you get to stay in local areas and get a vibe for what it is like to live in that city.
One thing I always do when booking an Airbnb or hotel is use the map view to see how close the Airbnb is to the places we want to visit, and if it is located in a safe area. You can find safe areas and places to avoid by using a simple Google search "Safe places in ______." Or "dangerous places in _______."
For this trip, Ethan and I took our dog, Oakley. Therefore, we also had to make sure that the places we stayed at were dog-friendly! There are MANY places on Airbnb that let you bring your dogs, and most places that are dog-friendly have backyards that you can let your dog go to the restroom in (unlike most hotels).
Bonus Dog-Lover Tip: Make sure you read the house rules about the SIZE of your dog. Some places have limits on the size of dogs that can stay at their place.
One of the SUPER cute AirBNB places we stayed at in Lake Tahoe!
Step 4: Read Other's Reviews
This tip I owe all to my Dad! We always stayed at the best places, ate at the best restaurants, and had the best excursions/adventures on our trips. Why? Because my Dad always did his research on which places were the best by reading the REVIEWS. Read the good reviews AND the bad reviews- then make your choice. You can learn A LOT about a place by the reviews.
I never choose an Airbnb or hotel if it has less that 20 reviews. It is important to me that I am choosing the safest, cleanest, most comfortable, and most convenient place. This goes for excursions/adventures as well. There are a lot of activities to do via Trip Advisor; however, if you look closely, a lot of adventures are named similarly to one another, and the only differences between them are the REVIEWS. You have to look closely at what you are booking before you click the “purchase” button.
We only booked a couple excursions for our road trip before we left, and the rest we planned on deciding while we were there (Ethan's idea). This was really hard for me; I am NOT a “go with the flow” person. I would be lying if I said I wasn't freaking out about not doing all my research before we left on our trip. However, I also learned to find beauty in “living in the moment” ← that one is for you, Mom!
Moral of the Story: The excursions you REALLY, TRULY care about, you should research, read reviews on, and book ahead of time.
One of my FAVORITE spontaneous things we did, and one of my LEAST FAVORITE spontaneous things we did. I'll let you guess which one was which...
Step 5: Write Your Itinerary
Once I mapped our journey, created our route, booked our accommodations, and read reviews, I put together an itinerary.
This can be done via Google Docs, Word, or just plain ol' pen and paper. I like to use Google Docs and create a table with three columns labeled, Place/Date, Accommodations, and Things to Do/Know.
Under the "Place/Date" column I listed the cities and the dates we would be in that city as well as the driving time.
Under the “Accommodations” column, I put the confirmation number of the place I booked, the check-in and check-out times, the Host or Hotel name and their contact information, and the address of the place. I also listed any special rules that the accommodation had.
Under the “Things to Do/Know” column I listed all the places/things we booked and/or wanted to see/do.
Lastly, in classic-Casey fashion, I color-coded it, formatted it, and printed it!
**IMPORTANT SAFETY SUGGESTION/TIP: SHARE YOUR ITINERARY!! Share your itinerary with your close friends and family. That way, if something happens, they know where you are supposed to be.
Here is an example of what my itinerary looked like. For the privacy of the Airbnb owners, I have removed the address. I also have not included the confirmation numbers.
HAPPY PLANNING!
