Cheryl Kelly
9 min readJul 3, 2019

How To Plan a Really Remarkable Road Trip

Off the Beaten Highway

Over the past five years I’ve driven a distance equal to two laps around the Earth. My road trips included Seattle to Mexico (Zihuatanejo) driving along the scenic Cartel Coast, round trip from California to the Florida Keys (twice), to Alaska, Arizona, Montana and Utah. Also, I’ve made thirty-plus shorter trips for vacations, medical appointments, or to visit family and friends. In all, I’ve racked up over 50,000 miles on these long distance road trips and I can burn with a case of white line fever that rivals that of a long-haul truck driver. Still, after all that, mention a road trip and my ears will perk up like an excited puppy and I’ll pop open Bing maps quicker than you can say fast food and flat tires. And, driving oh these many miles, I’ve learned what does and doesn’t work and I’d like to share a few of these ideas with you. First, let’s talk about why humans (and some dogs) like to get on the road in the first place…

“Because in the end, you won’t remember the time you spent working in the office or mowing your lawn. Climb that goddamn mountain.” — Jack Kerouac

There’s something about a road trip.

You can fly instead of drive to most places, but you’ll risk missing cultural, scenic and other “unexpected” experiences that you’re sure to have on a road trip. Going to new places, meeting new people and seeing strange and wonderful attractions gets you out of the daily grind allows you to have new adventures, experience personal growth, and to create new memories. There’s something about not knowing what’s around the next corner that enhances the senses and thrills the psyche.

Plus, you can bring a lot more toys.

Like any trip, a road trip begins with some planning:

Half the fun of a road trip is in pre-planning and the other half is in not planning. You don’t want overdo planning to the point of boredom, but it’s good to spend enough time to map out priority stops along the route. On multi-day trips, try to plan for stops every two hours with at least one stop per day for physical exercise. Having stops planned along the way gives you something to anticipate, keeps you awake and motivated, and reinforces the importance of enjoying the journey.

Here are some tools and techniques that are useful for road trip planning:

• Mapping your destination with Google or Bing maps gives you a “high level” view of the trip and the amount of time the trip will take. Switch to aerial or satellite view to note interesting topographical features, bodies of water (lakes or rivers), state and national parks, national monuments and towns along the way. (Note: Google Maps will be enhanced with Google Trips data as of Aug, 2019 integrating its global trip itinerary planning capabilities.)

• Or, skip that step and go straight to one of these two roadtrip planners. AAA’s free TripTik Planner allows you to locate attractions, upcoming events and activities, fuel stations, camping, and restaurants along your route. TripTik’s filters allow you view highly rated restaurants, AAA discount attractions and find gas stations by specific fuel type. You can also set route intervals between 2–12 hours to stop and explore. Roadtrippers offers a planner touting over 10,000 “places of interest” with an annual fee of $29.99 for its ad-free Plus version which includes the ability to share with friends and lets you add more waypoints (from 8 to 150) than the Basic version.

• Next, check out the “Best Things to Do” lists and “Top Tourist Attractions” offered by TripAdvisor, touropia, Fodor’s and Lonely Planet for ideas and inspiration. If the idea of waiting in long lines, or being in a crowded tourist location, sends chills up your spine (the bad kind) then plan to visit popular attractions in the “off season”.

• As you research, think about the activities you most enjoy doing on your days off. For example, if you’re an avid bike rider, check out the Rails-to-Trails TrailLink trail finder to explore trails on your route or at your destination. Hikers can locate trails via paid services like All Trails or by searching state sponsored web sites for free. Or, if bird watching appeals to you, for example, visit the Audubon Society web site for birding and wildlife viewing areas. Associations and groups for every interest are available via a quick web search and list local and national activities on their web sites.

• For more ideas, or to narrow down activities, consider taking a theme-based approach to your planning. Make a pact to stop at every single historical marker and/or museum you see on your trip, for instance. This approach can be fun with kids affording myriad learning moments and children find it exciting to spot the next “brown” sign. Or, follow the route of someone else’s famous (or infamous) road trip. Interactive maps of Jack Kerouac’s route are online if you happen to be a fan of his book “On the Road”, for example.

• Remember to ask friends, family and “locals” for suggestions. The best kept secret spots and coolest places are often gleaned from word-of-mouth recommendations. Don’t forget to stop at Welcome Stations and Information Centers when you can. They offer plenty of free maps and brochures and the astounding encyclopedic knowledge of their volunteers.

It’s a J-O-U-R-N-E-Y!

Clichés become common because they ring of truth and life is a journey not a destination never feels truer than on a road trip. Sure, once in a while you need to blast from the proverbial Point A to Point B, crank up the caffeine, tune into some podcasts or music and drive. Most of the time, though, you can maximize your trip joy by having an “enjoy the journey” attitude.

If unhappiness lies in gap between what we expect and what we experience, then you’re sure to be perpetually unhappy on a road trip if all you think about is getting to the end of the line. Stay connected to the present as you travel and take in your surroundings at a deep level. Don’t be afraid to stop and explore something that isn’t on your itinerary because it appeals to you at that particular moment. Those unplanned diversions are sometimes the most memorable of the trip.

Keep a travel journal

Travel journals allow you to keep track of where you were and when, what you liked about a place (or didn’t) and gives you a place to record what you’ve learned about the places you’ve visited and what you’ve learned about yourself in the process. Years from now, when you read about your adventures, you’ll appreciate the details you’d forgotten until reading them in your journal. Practical details like the best campsites at a campground, meals at a particular restaurant and the most useful gear are invaluable on future trips.

But, don’t wait until the trip to start a travel journal. Use it in the planning phase and jot down a few experiences that you absolutely don’t want to miss. When you make final plans, you can refer back to that information to stay on track.

Options for cloud-based and physical journaling are plentiful. I use a not-so-obvious tool called Microsoft OneNote. It can be used whether you’re offline or connected and allows you to insert images, web links, etc. and it is part of the Office 365 suite. Dedicated travel journal apps may also be downloaded and used on your phone. Or, you can buy a notebook or travel journal and write trip notes with an actual pen. With a physical notebook you can add ticket stubs, menus, and brochures to your notebook giving it more of a scrap booking feel.

Whatever the method, the most important thing is consistency. Write each day in your journal even for 5 minutes — it’s guaranteed to be the best souvenir of your trip.

Cars are where pack rats go to die…happily

Packing for a road trip is pretty much like packing for any trip except that you can bring a lot more gear. Thus, it’s sometimes more challenging deciding what not to bring. Here again is an opportunity to pick a theme. For example, if you make your trip about hiking and mountain biking then the two activities will require similar supplies and take place in the same types of environment. That makes it easier to leave behind unrelated items.

When you think about essentials, be sure not to overlook the obvious like food and water. It’s easy to assume that you’ll have access to both, but when you’re on the road there can be long stretches in remote areas where you’ll have access to neither. At those times, you’ll appreciate having taken the time to fill a few gallon jugs with water and having loaded up a cooler with sandwiches and healthy snacks.

Here are some not-so-obvious items that are useful on road trips:

• Coffee kit: water, a JetBoil, filters, pour-over cone, cups and freshly ground coffee. With this set-up;, you add water and you can make an energizing cup of coffee (or tea) …anywhere.

• Drybags: Why drybags? Because they’re waterproof, come in different colors allowing you to organize gear by color, and hold water in as well as out in case you need to fill up a dry bag with hot water to soak your feet because they get too cold in your kayak. (Not that that’s happened to me.) Lightweight bags like the Hotcore are great and come in a variety of sizes: 5L, 10L, 20L, 30L

• Go Girl (or similar): “GoGirl is a helpful, independent bathroom solution” for women. This, or similar product, is great to have on hand for emergency bathroom situation involving standing behind a tree to relieve oneself or an icky port-a-potty.

• Ropes: Carry ropes in different sizes and a handful of bungee cords. Their uses will be only limited by your imagination.

• Rags and garbage bags: Spills, motion sickness, greasy food, trash…need I say more.

• Toolkit: The least amount of tools to carry include a wrench or two, Philips and Flathead screwdrivers, duct tape (of course) and a pair of pliers.

• Spare Tire: Ha! You think you have one, don’t you? Check to make sure, because some manufacturers no longer include one routinely, providing you instead with a “repair kit”

By the way, it’s a good idea to keep the items you’ll need with frequency at the outside of the packing pile so you can get to them without unpacking the whole car.

Potty party

All that most of us want when it comes to a bathroom is that it’s clean, safe and available when we need it. This becomes even more important on a long road trip. Here, then, are some potty pointers:

• Proving that there truly is an ‘app for everything’ several restroom finder apps: Sit or Squat, Toilet Finder and Bathroom Scout are among the highest rated.

• Starbucks, Grocery Store Chains like Safeway, and Fast Food restaurants: clean, safe and available to the public.

• Truck Stops: Clean, safe, easy on and off and open 24 hours/day.

• Rest Stops: Avoid at night and when traveling alone. Some rest stops have security now. Best to find alternatives if possible.

• Campgrounds and Day Use Areas: Often the best alternative in rural areas and convenient for day time use.

• Find a tree (see Go Girl above for women), but please not in plain sight of the road and not next to river or lakes.

Tread lightly

At the risk of sounding preachy, driving long distances uses fossil fuel and emits carbon dioxide. If you can take your trip in a hybrid, electric or bio-diesel vehicle then that certainly helps. In any case, consider buying carbon offsets. Reduce waste and single use plastic by bringing along your own eco-kit comprised of a dish set, utensils, refillable water bottle, reusable straws and travel mug. Where possible, try to stop and eat at a real restaurant instead of buying fast food in wasteful packaging. Your body and the planet will thank you for it.

ANY drive can take on the fun and adventure of a road trip…

Whether you’re taking a long trip, or driving to work, why not plan for some fun along the route? According to AAA, the average American spends 17,600 minutes driving each year. If you multiply that times the average lifespan in the US (79.8 years to be exact) that equates to 23,144 hours or about 2–1/2 years of your life! Jazz up your mundane drives. Queue up some new music, a podcast or two, leave early and stop at a park for ten minutes, or pack a special snack for the drive home.

Cheryl Kelly

Self-described generalist with a high-tech background and a penchant for creative writing across a broad spectrum of topics