I think you’ll agree with me when I say it can be overwhelming to plan a road trip.
Especially when you want to go to so many different places and you’re not sure how to budget your time.
I had this problem too. That is, until I planned a 42-day road trip for January and February of 2018.
My itinerary was super flexible, I had a great time, and I made it all the way from San Diego to Florida.
And in this post, I’m going to show you how I planned it all out, step by step.
(And no, I didn’t plan the whole thing out on Google Maps.)
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Step 1: Decide on Length, Endpoints, and When
What kind of road trip are you taking? Cross-country? A loop? What happens to the car once you’ve finished? How do you get home? How much time do you have? Most importantly: where do you want to go?
For the purposes of this tutorial, let’s assume you have a week off from work. With weekends, that makes 9 days for road tripping.
We’re going to plan an epic road trip to a part of the US you want to visit but may have forgotten about. It’s called the Northwest.
We know from our cheap flights masterclass that Frontier, a budget airline, is based in Denver, so we’ll start from there. This means Denver should be affordable to arrive at no matter where you’re coming from.
I’m going to assume you know how to rent a car (no, you don’t need to be 25) and you’ll have the car on the morning of Day 2. Days 2-8 will consist of a 7-day loop. We’ll start in Denver and drive to the Badlands National Park in South Dakota. Then we’ll head to Yellowstone National Park in Wyoming and circle back to Denver. On our last day, we’ll return the car and return home.
Step 2: Deciding on the Main Destinations
When I planned my 6-week road trip across the country I knew I wanted to hit certain places:
- Start in San Diego, CA
- Grand Canyon National Park, AZ
- Santa Fe, NM
- Austin, TX
- New Orleans, LA for Mardi Gras
- Ending in Florida
Everything else grew out of those checkpoints.
The road trip we’re planning in this tutorial will have the following waypoints:
- Denver, Colorado
- Badlands National Park, South Dakota
- Yellowstone National Park, Wyoming
- Salt Lake City, Utah
- Denver, Colorado
I’m a Type-A planner and I like ambitious itineraries, but others might want to spend a couple of days in each place. Janice from Solo Traveler World says she generally needs three days per destination when she’s on a road trip.
I’m going to assume you don’t have that much time. For the purposes of this tutorial, let’s see a new place every day. Our itinerary looks something like this:
- Arrive in Denver, CO
- Drive to Badlands National Park
- Explore Badlands National Park
- Drive to Yellowstone National Park
- Explore Yellowstone National Park
- Drive to Salt Lake City, UT
- Explore Salt Lake City, UT
- Drive to Denver, CO
- Return car rental and return home
We need to research our main destinations and find some places for pit stops before we fill out our days.
But there’s no point in doing research if we don’t have some way to quickly retrieve our knowledge.
Don’t worry—I have to perfect tool for you.
Have you heard of Trello?
Prefer to skip the tutorial and play with the Trello board yourself? Sign up for the Flâneur Files email list to get access.
Step 3: Setting up our Trello Board
Disclaimer: I am a huge Trello nerd.
I think Trello is one of the best road trip planner apps available in 2018.
It’s insanely flexible. You can plan a road trip with multiple stops and have everything you need in one place.
Needless to say, it’s a lifesaver for a busy traveler like yourself.
Our Trello board will be the Source of Truth for our road trip—it’ll contain all our ideas and all the information about our road trip.
The Value of a Trello Board for your Road Trip
Everyone should understand the value of documenting their travels. Trello is a workhorse when it comes to documentation. It makes pictures, notes, and links easily accessible, and it’s easier to navigate than a Word document.
Trello integrates with Google Docs so we can predict and track our expenses. (This is outside the scope of this tutorial—let me know in the comments if you’d like to see a post on this). Trello can link to Google Photos and simplify the retrieval of relevant pictures. Trello can supplement our memories as we reconstruct our trip upon our return when we decide to write our memoir.
The old-school method of logging and planning your travels is analog—keep a calendar, record lists of places, or journal in real time.
The advantages of a virtual planner are it’s utility, portability, replicability. You can share your Trello board to keep friends updated even as you change your plans.
The disadvantage is you have to learn how to use Trello. But don’t worry—I’m here to help. It’s not hard. Promise.
What is Trello?
I imagine Trello as a virtual board of index cards organized in columns. Each column has a title, and each index card has a front and a back. I can also attach photos, links, or files to any cards, and I can label them as I choose.
This structure lends itself well to organizing a road trip. Each column will represent a day of our road trip. The cards in each column will contain information about each activity or site we want to do or visit.
Getting Started with Trello
Navigate to trello.com and you’ll see this lovely welcome page.
Let’s click “Sign Up”. You’ll need to provide your name—this can be anything, but if you’re collaborating with someone you should probably use your real name instead of a username—an email address you have access to, and a simple password.
Once you sign up, Trello will try to confirm your email address. Go to your email, open the message from Trello, and click “Verify Address”.
Afterwards, you’ll arrive at the Trello homepage for logged-in users. Mine looks like this:
Let’s open the Welcome Board by clicking on it.
There’s a lot going on here, but don’t worry. Trello gives you instructions on how to get familiar with its basic functionality. Let’s try some of them.
Follow the instructions on the first card, dragging it to the second list. Your lists should now resemble this:
Next, click on the new topmost card in the left list. This opens the back of the card, which looks like this:
Get familiar with the back of Trello cards. We’ll be using them a lot.
Don’t worry if the number of options on the back of the card is overwhelming. I’ll guide you through the process later.
The rest of the cards in the Welcome Board are things we don’t need to worry about right now. Let’s return to the homepage and set up our road trip board.
Creating Our Road Trip Board
Back on the homepage, click “Create New Board”.
Trello will ask you to name your new board. I like to give my boards descriptive names because it makes navigating a lot easier, so let’s call this “Flâneur Files Road Trip Tutorial”.
Then create the board.
Yay! You created a brand-new board! It should look like this:
Like I mentioned earlier, we want each list to represent a day. So let’s change the titles of the existing lists. If you already know your dates, put those in the title too. Here’s what mine looks like:
I format my titles like this: DAY #: LOCATION/ROUTE, STATE (DAY OF THE WEEK, MONTH DATE, YEAR). That’s because I like knowing how many days into my trip I am, where I’ll be, the calendar date, and what day of the week that is.
All this information comes in handy once we start doing research. If you know you’ll be in Denver on a Saturday, you can plan Saturday activities. Likewise, being at Badlands National park on a Monday means we’ll probably miss the weekend crowds.
You’ll notice we need to add more lists. Let’s do that.
I like to minimize the right-hand menu with the X to keep my board clean. Click “Add a list…” and type in the name of the fourth day.
Your new list should look like this:
Let’s continue until we have nine lists, one for each day.
You will need to scroll to the right to continue adding lists.
These are what my lists look like:
I picked some random dates in August in case you want to take this road trip.
Now let’s add some cards. I like the topmost card on each list be a description of the location, or, if it’s a transit day, of the route.
Adding a card to your Trello board is simple. Click where it says “Add a card…” under the list where you’d like to add the card. A text box will appear and you can give the card a title.
You can click the green “Add” button or simply press the Enter key to finish making the card.
Cool! We made a card! Now what? Let’s click on it and open the back.
First, I add a link to some useful resource. Since this is the city of Denver, let’s add a link to the Visit Denver tourism site. (https://www.denver.org/)
On the right-hand side of the card, find the “Attachment” button. Click that. A new box will appear; halfway down it’ll say “Attach a link”. Paste the URL to the Visit Denver site there and another field will appear, which lets you name the link.
Click “Attach” and your link will appear on the back of the card in a new “Attachments” section.
If you’re feeling lazy, you can simply Ctrl + V on the back of the card (paste the link to the card) and Trello will automatically add the link. It won’t be named.
It doesn’t matter how you prefer to add your links. I like to name links to files on Google Drive but I like to paste the entire URL for web pages.
We can also add images to Trello cards using either method. Copy the image and paste it using the keyboard, or upload it as an attachment.
I took this image from the Visit Denver website, but you can feel free to use whatever image you’d like.
Your card should look something like this:
In addition to links and images, we can attach files (PDFs, Google Drive links, videos) and we can link to other Trello cards.
Let’s also add a small description. This is what mine looks like:
How did I get the headings to be big and bold? Trello uses Markdown to format its descriptions. Markdown translates to HTML but it’s faster to write. Here’s what the Markdown looks like:
Easy enough, right? You can click the “Formatting help” in the bottom-right corner and Trello will give you a Markdown cheat sheet that should answer most of your formatting questions.
I also like to add a checklist for anything I have to do for that card. For Day 1, maybe we still need to book our flights, reserve a car rental, and find out where we’re going to spend the night. And since it’s Saturday, maybe we want to go out for a nice dinner or something before heading out on the road.
To add a checklist, look at the right-side of the card back under the Add column. Click “Checklist” and a new box will appear and Trello will ask you to name the checklist. I called mine “Preparation”.
Then you can add items to your checklist the same way up added a card to a list.
My example checklist looks like this:
As you complete each item, Trello will show you what percentage of the checklist you’ve finished.
If you’re so inclined, you can set a deadline for when you need to have everyone on this card completed. The option for this is between “Checklist” and “Attachment” under the Add column.
Return to the Trello board by clicking anywhere on the screen that isn’t the card. Your first list should look something like this:
You see all that new information on the bottom of the card? That’s metadata. It lets you know, at a glance, what fields on that card are filled out. We added two attachments (a link and an image), a description, and a checklist consisting of five items.
Pretty neat, right?
Let’s set up the first card on the rest of our columns in a similar fashion.
For transit days, I like to make a card called “Route & Itinerary” which contains some driving directions I’ve scouted ahead of time via Google Maps. We can’t figure out what route we’ll be driving or roughly how much time we’ll need until we decide what we’re doing.
My board looks like this:
Notice how my Route & Itinerary cards are untouched. Those are placeholders for now—we don’t have enough information to fill them out right now, but we will want them at the top of the list and putting them in now saves us the trouble of moving them to the top later.
You can change your background if you don’t like whatever background Trello defaults to. Open the right-hand menu and click “Change Background”. Then you can either change to one of Trello’s built-in background or you can choose a stock photo from Unsplash.
I changed my background to a road since this is a board for a road trip. But pick whatever you like.
Step 4: Researching our Destinations
Now that we’ve set up our scaffolding, it’s time to fill up this board. There are several ways to research a destination—I assume you know all about Google, so I’m not going to bother with that. Here are four other places you might not have thought of: the Atlas Obscura, Instagram, Pinterest, and a nifty tool called BuzzSumo.
At this point, we’re capturing the possibilities for our road trip. We won’t be able to do everything we encounter, and that’s fine. We’re going to record everything on Trello now and prune and prioritize at a later step.
Use Trello Labels to Organize Your Research
Trello is a great visual tool when you only have 4 cards in a list and don’t have to do much scrolling, but by the end of this section, we’ll have 20+ cards on our lists. We need some quick method of surfacing the cards we want.
We can do this by using Trello labels.
I like to label my cards as “must-do”, “food”, “reservation required”, and “time-intensive”.
Cards with the must-do label are important. These are the essential activities.
Cards with the food label denote restaurants or regional dishes I want to try. We’ll take a look at some food-finding tools at the end of this section.
Cards labeled “reservation required” represent popular activities that subsequently get booked (tours, concert or sports game tickets, theatrical productions, etc.).
Cards with the time-intensive label indicate long hikes or activities that will take a significant chunk of the day. It’s best to dedicate an entire day to these activities.
Trello labels are easy to use. First, open the back of a card and look at the right-hand side.
Select “Labels” and click on one of the color bands.
From there, you can click the pencil to the right of the label you want to edit. Give it a title and save it. Click the label and it’ll be added to the card.
You can add multiple labels to a single card.
To search for all cards with the same label, open the menu on the right-hand side of the board.
Then navigate to “Filter Cards”. You can enter the name of your label in the search or you can click on your label. You can filter for multiple labels at a time.
Trello lets you know when you’re filtering and shows you the total number of cards in a list.
To turn off filtering, click the green “x” next to the filtering message.
How to Find the Weirdest Stuff in the World to See on your Road Trip
The Atlas Obscura is one of my favorite places on the Internet. (It’s also a fascinating rabbit hole if you ever need to waste some time.) While there is a print edition of the Atlas Obscura, it’s (obviously) not as current as the online version.
What is the Atlas Obscura? It’s a collection of all the wacky things on Earth—both natural and manmade. They recently included a food section (called “Gastro Obscura”) and you’re welcome to peruse that in addition to the Atlas, but I won’t cover it in this tutorial.
If you want to hit up the weird stuff on your road trip, look no further.
From the Atlas Obscura home page, head to the map.
The map is super overwhelming. I’ll let you stare at that for a few seconds.
12,500 places and counting. That’s ridiculous. I can’t even convey how ridiculous that number is.
(Also, can we talk about how weird the USA is? I’m sure there some reporting bias there because most of the contributors to the Atlas are probably American, but still. America is weird.)
Each pin on the map represents a different entry in the Atlas. The circles with numbers represent pins clustered so closely together it’s not feasible to show them all on the map.
Clicking on these circles of larger numbers will zoom us in. Let’s zoom in until we find Denver.
We’re not so concerned with Denver right now. Instead, we want to follow the road between Denver and Badlands National Park.
To view a pin, click on it. Clicking on a pin creates a preview of the Atlas entry.
How do you open the entry? Click on the item’s name.
My Strategy for Successful Comb through the Atlas Obscura
Open a new browser window containing two tabs: my Trello board and the map.
Going top to bottom (or bottom to top), I open 15-20 pins in a new tab.
Create a new card under the appropriate list on the Trello board for each tab. In Google Chrome, I use keyboard shortcuts to speed this up. Here’s how:
- Let the Trello board be on the first tab, Tab #1. Let the map be Tab #2 and Tab #3 be one of the pins you opened from the Atlas Obscura.
- We can quickly switch between tabs by using the Command + Number combinations. So I can press Command + 1 to switch my current tab to the Trello board.
On Tab #3, I copy the entry’s name and location and switch to Tab #1 to create a new Trello card, like so:
Then, on the back of this new card, I copy the URL to the Atlas Obscura and add it as an attachment, again using the keyboard shortcuts to save a few seconds:
I also copy one of the images from the Atlas Obscura entry and add it to the card as the card cover.
Finally, if there’s anything important in the “Know Before You Go” section on the Atlas Obscura entry, I’ll copy it into the Trello description.
My finished card looks like this:
Now close Tab #3. The next tab becomes Tab #3 and you can continue switching between Tab #1 and Tab #3 until you’ve added all the entries to your Trello board.
Once I’ve processed all my open tabs, I move the map and repeat until I’ve finished going along my route.
Since I’m not sure what my exact route will be at this point, I like to grab from all over the place. I’d rather take all day to get somewhere and stop in lots of interesting places along the way.
Don’t worry about capturing everything in the Atlas Obscura—there’s too much. If something looks cool but you can’t see yourself going there, don’t clutter your Trello board with it.
How to get Up Close and Personal with your Destinations
Instagram can be an even more powerful search engine than Google.
Why? Because Instagram is updated in real time. Instagram is also more visual than Google, which makes it perfect for researching destinations.
Let’s try to look up Badlands National Park.
Launch Instagram on your phone. Click the search icon on the bottom nav and then hit the Places tab on the upper-right. Type in “Badlands National Park”.
You get a feed of the photos that have been geotagged at Badlands National Park. (This means the person who posted them on Instagram indicated the photo was taken at Badlands National Park.)
Let’s click on a photo and look for hashtags. Usually, people add five rows of dots and then hide their hashtags, or they add their hashtags to a comment.
We see some relevant hashtags: #Badlands, #BadlandsNationalPark, #SouthDakota, and #badlandsnps. Let’s click on the #BadlandsNationalPark and see what’s there.
This hashtag has over 45,000 posts. We can also see some other relevant hashtags people are using; we can follow those to find more photos of the Badlands National Park.
Notice we can follow this hashtag. When you’re using Instagram to research a destination, following a hashtag is a smart idea. Instagram will show relevant posts in your default feed when you’re scrolling through the app, so you don’t have to think so much about visiting the hashtag page.
I encountered a picture of Mt. Rushmore, which I had totally forgotten about, as I scrolled down this hashtag page. It turns out Mt. Rushmore is between the Badlands and Yellowstone, so we’re adding that to our itinerary.
I’ve found people on Instagram are quite responsive when you ask them questions about their photos. Instagram might be full of meaningless and annoying emoji comments, but it’s also full of photographers and travelers who are more than happy to learn their photos and storytelling have inspired and informed someone else.
How to Get Pinfinite Destination Ideas
I think Pinterest is too often written off as the stay-at-home mom social media platform. That’s a shame because Pinterest can be a powerful tool to use when researching a destination and planning a road trip. (Also, Pinterest isn’t a social media platform. Pinterest is a search engine.)
What advantages does Pinterest have on Google?
- Infinite scroll. This means you don’t have to go to the second page of Pinterest to get more information about your search query. There is no such thing as the second page of Pinterest. You just keep scrolling. This might seem like a little thing, but it makes a difference. You can be exposed to 50 articles much more quickly on Pinterest than Google.
- It’s highly visual. When scrolling through Pinterest, I immediately notice the titles of well-designed pins. The subject of the post is related to a visual. This marriage of image and text creates a wholly different experience from Google, where Google Image search often turns up nothing and many of the unique perspectives on a topic are buried on page 17.
- Pinterest has more independent bloggers and fewer big companies. While TripAdvisor and Travel & Leisure can be wonderful, they’re not my top choice when it comes to research a destination. I’d rather read a post about a place or experience from an independent blogger than a faceless brand.
You can also use Pinterest to hoard information. Here’s what I do:
First, you need to go to Pinterest and create a board.
Give your board a name and make it secret. I like to include some relevant keywords in my board titles to make it easier for other people to find my board.
Once you’ve created your board, you need to search for pins about your topic.
As you type, Pinterest will offer suggestions the same way Google does.
Let’s search for “Badlands National Park”. You’ll get a screen that looks something like this:
Let’s go over each of these.
The first row is a list of suggested keywords. You can click on these and Pinterest will run a search with the new keywords appended. If I clicked “Things To Do”, Pinterest would run the search “Badlands National Park Things To Do”.
The second row lets you toggle your search between pins and boards. Right now we’re seeing the pins Pinterest thinks are most relevant—you can think of these as the highest-ranking results on the first page of Google search. If we switch to Boards, we can view the boards that other people have created which contain many relevant pins.
The third point I want you to notice is the pin itself. Pins are images. The title for each pin is at the bottom of the pin.
Let’s try to pin the post I’ve indicated.
Hover over the pin and a Save button will appear.
Click this Save button and Pinterest will ask you which board you want to pin it to. Sometimes it’s smart and matches the keywords in your board title and the pin, but here I had to give it some help.
Hover over your board name and the Save button will appear again. Click this button and now that Pin is saved to your board.
You can repeat this process for any number of pins in the smart feed, or you can switch to look at some boards.
The images you see on each group board are from pins. In the bottom-left corner, you can see the profile picture of the person who made the board. Beneath that is the board name and the name and the board’s owner. Finally, you have the option of following the board, which means pins from that board are more likely to show up in your feed.
Click on some of these boards and you can repin that content the same way you pinned from the smart feed.
Once you’re done, head back to your profile (click your profile in the upper-right corner) and open your board. You might need to refresh your browser due to a bug in Pinterest, but you should see all your pins there.
Now you can click on each pin to open it.
Most pins should link to a blog post or a web page. Click “Read It” and a new tab will open up. If you find that information useful, add it to your Trello board. If not, delete the pin from your board.
Once I have 30+ pins on my board, I make it public so other people can find the pins I found useful.
By making Pinterest boards about your destination, you can create a highly curated library and knowledge base about your destination. It’s also a great way of collecting information you’ll want to read later.
See What in your Destinations People are Buzzing about
You might know I do SEO (search engine optimization) consulting for some monies. An important part of SEO is getting people to link to you. Another important part of SEO is getting traffic—the more people that link to you, the more traffic you get. The more traffic you get, the more times your content gets shared. The more times your content gets shared, the more people link to you. It’s a virtuous cycle.
(By the way, it would mean a lot if you shared this post. Thanks!)
BuzzSumo tracks these share counts. You enter a keyword (say, “Badlands National Park”) and BuzzSumo returns a list of the most-shared articles for that keyword. You can sort these results by Total, Facebook, Twitter, Pinterest, and LinkedIn.
First, let’s visit buzzsumo.com in our web browser.
Then we can enter our search query into the BuzzSumo. You can enter a keyword (for example: “Badlands National Park”) or enter a question much like you’d use Google (“what to do in Badlands National Park”).
BuzzSumo will then return a list, sorted by the number of total shares, of the results.
News, news, news. Boring. This is to be expected, but the news isn’t quite what we’re looking for. It gets dated quickly and it doesn’t help us plan an exciting itinerary that’s filled with fun and interesting things to do.
We can choose to sort by number of Facebook, Twitter, LinkedIn, or Pinterest shares. Facebook, Twitter, and LinkedIn tend to follow the same pattern as Total Shares. More news.
But sorting by the number of Pinterest shares unearths a different trend.
Voilà! Tons of posts from independent bloggers and smaller websites that are packed with useful information to help you plan your road trip.
Pinterest is the social network of choice for finding posts by independent bloggers, especially if they’re travel bloggers. (There’s a reason I add Pinterest-friendly images to the end of all my blog posts.)
How to Find the Best Places to Eat on your Road Trip
We here at Flâneur Files take food very seriously. It’s fun to try new food and go to new restaurants. American cuisine is so wildly varied and contains such a mixture of influences that it’s impossible to run out of things to try.
It’s no secret Americans love diners, even if they’re becoming cultural artifacts to my generation. If you’re taking a road trip you deserve better than the old fast food standbys.
Use TVFoodMaps to Find Featured Restaurants
This is the most important tool you’ll ever find. TVFoodMaps is a map of several restaurants that have been featured on 50+ television programs that are dedicated to food.
It’s nothing short of amazing.
You can search for restaurants by a television show or by state. Let’s look for restaurants along our route that have been featured on Diners, Drive-ins and Dives.
To do this, I click on the TV Show image in the screenshot above. Then it takes me to a page containing all the television shows TVFoodMaps traces.
From there, I can use my browser’s Find function (Cmd + F for macs and Ctrl + F for Windows), type in the name of the TV show I’m looking for, and it’ll navigate there automatically.
Let’s click on that link.
This gives you two different views: a list view of restaurants (useful if you know exactly where you’re looking) and a map. The map view is what we want.
Let’s zoom in until we can see our loop route.
It looks like there’s not much going north from Colorado or West to Yellowstone until we reach Jackson, WY. Let’s click on one of those pins.
Much like the Atlas Obscura, we get a little blurb. If you click on the name in red you’ll see a page that profiles this particular restaurant.
From here, we can add the relevant information—Name, Address, Website, Hours, and any notes from TVFoodMaps—to a new card in our Trello board.
You can even copy the episode title and watch the relevant episode on Food Network. This is expressly for the purpose of doing research, of course.
If you’d rather search TVFoodMaps on the go, they also have a mobile app.
RoadFood is another food-finding tool you can use for your adventures. While TVFoodMaps was dedicated to restaurants that have been profiled on television, RoadFood wants to help you discover great restaurants that highlight regional cuisine while you’re on your road trip.
I think their website is easier to use, too. Let’s take a look.
First, navigate to roadfood.com in your web browser. Immediately, you’ll see a map with your location and some restaurants around you.
This is helpful when you’re already on the road, but if you want to do some advance research, you’ll need to enter a location in the search box or move the map to your location.
I think moving the map produces better results. I’m going to position it over Badlands National park and Rapid City, SD, which we’ll probably route through.
Here I clicked on the pin in Rapid City. Clicking auto scrolls me so the restaurant profile, Essence of Coffee, is at the top of the screen. (This is only marginally annoying.)
Like with TVFoodMaps and the Atlas Obscura, clicking on the name of the restaurant takes me to a dedicated page with photos, some information about the restaurant, and recommended dishes.
Add this to your Trello board the same way we’ve been adding cards. I’d add the name, the address, a link to the RoadFood page, a link to the restaurant’s website, hours, and any other important information (like dish recommendations).
Once you think your Trello board is pretty filled up, move to the next step.
Step 5: Deciding What to Prioritize
Now that you’ve done your idea dump, start by prioritizing the things you’re sure you want to do. Here are my best tips for knocking items off your to-do list:
- Aspire to do or see 1-2 big things for each day—a morning activity and an afternoon activity.
- Consider what time attractions are open. Some places are only open 8-5, and if you get there at 2 you’ll have to wait in a long line to get in.
- Label cards using a “High Priority” or “Must-Do” label to have a visual indicator of what you’re committing to
- Consider how much you can realistically accomplish in a day by making a timetable.
- This might mean putting all your destinations in Google Maps and adding in the hours spent at each destination. If you plan to arrive at the Badlands at 9 am, stay there until 2:30 pm, then drive to Mt. Rushmore, you’ll have to consider when Mt. Rushmore closes and be generous with how long the drive will take.
After I’ve decided on my one or two big things for the day, I look at the other items on my list and sort those into “would like to do” and “optional”. That way, if I’ve given myself way too much time at one place, I have plenty of other activities to fill the time with.
Conversely, prioritizing my activities like this gives me a degree of flexibility, as I have activities I can put on the chopping block if I decide to spend more time at one location.
As you travel and share your plans in real time, you’ll get some feedback from friends and family (or Instagram followers) recommending something you didn’t plan for. There’s nothing wrong with a little detour, but make sure you know where you’re going before you head out on a 10-mile hike in the Utah wilderness.
Not like I’ve ever made that mistake or anything. No sir.
Step 6: Share Your Plans and get Feedback
Trello boards can be made public, so you can share them with everyone. I posted mine on Facebook and texted it to friends and got some fantastic feedback—I wouldn’t have changed my itinerary to visit Vegas, Utah, or Taos if I hadn’t done this.
You’ll need to change your board’s permissions to share your Trello board on somewhere like Facebook.
This is easy to do. Navigate to where your board says “Private”, to the right of the board name.
Click on this and a menu will appear.
You want to make your board Public, which is what I’ve highlighted in this screenshot. Click on Public to change your board’s permissions.
Now confirm your board says it’s Public.
To share the board, you need to open the right-hand menu. Then click More.
At the bottom of the menu, you’ll see the link to the Trello board. Copy this link.
You can copy and paste this link to Facebook, Twitter, email, a text message—to whatever. Then everybody can view your Trello board and give you feedback on your itinerary.
Like Trello says, nobody can edit your board unless you add them to your board. So you don’t need to worry about someone accidentally deleting everything.
You’ll probably iterate on this research/prune process a couple of times as you continue searching Instagram and Pinterest and soliciting feedback from friends.
Step 7: Iterate through Steps 4, 5, and 6
I revised my 6-week road trip several times. At first, I wasn’t going to spend any time in Nevada or Utah, and then I added those in. I was going to spend time in the Gila National Forest and in Tulsa, and then I removed those detours.
My plans changed because I continued to research the area after I “finalized” my trip. I continued to tell people about my plans and I continued to think about what my priorities were on this trip.
Planning is an iterative process. If you want the perfect road trip, you need to revise and edit your trip like you would a story. Perfection is the result of iteration.
Or, as Anne Lamott puts it, write a shitty first draft. Then make it better.
That road trip plan we’ve made in Steps 1-6? That’s your shitty first draft. Now make it better.
How to Revise your Road Trip Plan
Tweaking your plans is personal and perhaps more work than what you want to put in when planning your vacation. And that’s fine—it’s your vacation. But I’m a firm believer that preparation is time well spent, and if you’re dedicated to having a great road trip then I want to ensure the time you spend planning is spent wisely.
Let’s say, for the purposes of this tutorial, that after some research we’ve decided that we don’t really care to see Salt Lake City. Instead, we want to spend two days at Yellowstone.
Since we’ve decided that each list in Trello should represent a day of our trip, we need to shift the lists accordingly.
Our original itinerary looks like this:
- Arrive in Denver
- Drive to Badlands National Park
- Badlands National Park
- Drive to Yellowstone National Park
- Yellowstone National Park
- Drive to Salt Lake City
- Salt Lake City
- Drive to Denver
- Go home from Denver
Our new itinerary is going to be as follows:
- Arrive in Denver
- Drive to Badlands National Park
- Badlands National Park
- Drive to Yellowstone National Park
- Yellowstone National Park
- Yellowstone National Park
- Drive to Salt Lake City
- Drive to Denver
- Go home from Denver
Let’s reflect this change in Trello.
Since we’re not going to spend any time in Salt Lake City except to sleep, we can archive all the cards in the Salt Lake City list.
Now we have an empty list, but our lists are out of order and their headings are wrong. Let’s change the empty list’s title to “DAY 6: Yellowstone National Park (Thursday, August 16, 2018)” and move it to the right of our first Yellowstone list.
Now we need to fix the day number and date in the card that reads “DAY 6: Yellowstone National Park, WY –> Salt Lake City, UT (Thursday< August 16, 2018)”.
The days, dates, and locations on the list titles in our Trello board should flow correctly:
Now we can populate the empty list with what we’d like to do during our second day at Yellowstone National Park.
Step 8: Determine Where to Sleep
Depending on the popularity of your destination and whether or not its high season, you should beginning booking accommodation 1-6 months in advance. (For example, remember the Great American Solar Eclipse? That occurred in August and I booked accommodation for it in April.)
There are plenty of places to book accommodation. I’m not going to show you how to use them in this post, but you’re welcome to take each in turn and consider it:
- Couchsurfing works by requesting to stay on a stranger’s couch for free for a couple of nights.
- Airbnb lets you rent a bed or a couch from someone.
- Agoda scours the web to find you the best hotel prices, often at large discounts. Sometimes their prices are cheaper than Airbnb!
- Hotel Tonight lets you book off-market hotel rooms at a large discount.
- Trivago compares hotel prices to help you save money.
- Roomer Travel lets you buy a hotel reservation from someone who can’t use it.
I don’t own any camping gear, so I can’t advise you on finding campgrounds, but Bear Foot Theory has you covered with their Ultimate Guide to Finding Free Campsites in the US.
If you’re budgeting hardcore, you can always sleep in your car, but I don’t recommend that be your first option. (And don’t sleep in your car during cold nights. That will end poorly.)
Don’t forget your personal network, either. A friend’s fiancée might have family in Wyoming, or an old college roommate might be living in Denver. You can save some money by relying on your friends.
Now that you have a pretty solid itinerary, you should do the following:
- Find plane tickets if necessary
- Decide who you’re bringing, or if you’re going solo
- Rent a car, if necessary
- Decide if you need an Annual Interagency Pass (sometimes called a National Parks Pass)
- If you plan on visiting any number of national parks in a given year, this will save you hundreds of dollars in entry fees.
- Determine a budget
You can get full access to this road trip plan along with my entire resource library by signing up for the Flâneur Files mailing list.
What are your favorite road trip-planning tools and hacks? Do you want to go on this road trip now? Let me know in the comments!
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Also published on Medium.