A Beginner’s Guide to Planning an Extraordinary Road Trip

woman in black aviator sunglasses sitting on car s passenger seat
Photo Andrea Piacquadio

Here we are five months into the pandemic, jonesing to travel and 2020 just won’t cut us a break. Leisure travel on planes, trains, and buses is risky, but the good ole fashion road trip is capturing the imagination of those intrepid travelers anxious to explore the world, albeit closer to home.

With all the interest in road trips, I wanted to post a beginner’s guide, and therein lies the rub. I haven’t been on that many, so I asked veteran road tripper, Carolyn Heller, for help. Carolyn has been on countless road trips in the United States, Canada, and Europe, and her guide for beginners is just what I was looking for to help me plan my future adventures––you’ll think so too.

~Susan

How to Plan an Extraordinary Road Trip

By Carolyn B. Heller

I’ve been road-tripping since I was a child, when my dad would spread a map on the hood of our red station wagon and show me the route from our Indiana home to New York City, the Thousand Islands, or all the way to California, depending on where that summer’s journey would take us.

As an adult, I’ve continued that road tripping tradition, both on my own and with my own children. I’ve done solo road trips from Vancouver to Los Angeles, through the Canadian Rockies, across New England, and along Ontario’s Lake Superior.

Looking down the centerline of a paved road in the country taken while on a road trip
Photo: Susan Portnoy

My twin daughters and I spent six weeks road tripping across the United States where we camped at Yellowstone National Park, searched out quirky attractions like Wisconsin’s Mustard Museum, and ate mashed potatoes and gravy in 14 states.

If you’re organizing a road trip for the first time or looking to improve the way you road trip, read on. I’ve put together an easy guide to help you make the most of your time on the road.

Researching Your Road Trip Route

Do you have a destination you’re dreaming of visiting or are you looking for a close-to-home getaway? Are you more interested in hopping from city to city or spending time outdoors? Are you traveling to a festival or other event? Think about the kind of trip you want, then pull up a map and start figuring out how to get there. Roadtrippers has an online planner that can help you organize your trip.

Two hikers on a trail in Bryce Canyon, Utah
Photo: Carolyn Heller

Consider buying a guidebook to the regions you’ll be visiting. Moon Guides publishes a road trip series specifically designed for car travel (including my own book, Moon Vancouver & Canadian Rockies Road Trip). Check the websites of local or regional visitor centers for things to do, too.

How Much Time Do You Have?

Once you have ideas of where to go, figure out what’s realistic for the time you have. I try not to travel more than 300 miles or 5-6 hours a day, so I have more time to stop in each destination, but you may choose to cover more ground. If you’re the only driver, plan more frequent stops.

Budgeting for a Road Trip

On a road trip, your largest budget items will be accommodations, food, gas, and admission fees for attractions.

Road-tripping campers on a budget can seek out free spots to sleep at sites like FreeRoam or Campendium, or look for lesser-known camping options at Hipcamp.com. Other camping alternatives include national parks, state or provincial parks, National Forest Land, and private campgrounds. If you don’t want to camp, consider AirBnB, VRBO, or other rental options and compare prices to hotels, hostels, and bed-and-breakfast accommodations.

At the Continental Divide, Wyoming Photo: Carolyn Heller

Save money by bringing food from home, or buying food at grocery stores and farm markets. Food trucks can be an economical and more interesting alternative to fast food. 

To estimate how much you’ll spend on gas, plug your trip details into the GasBuddy Trip Cost Calculator. Track gas prices through the American Automobile Association or Canadian Automobile Association.

What Should You Book in Advance?

Are you road tripping in the peak summer season, on a holiday weekend, or other busy time? Is there a popular festival in a destination you’ll visit? The busier the season, and the shorter your trip, the more important it is to book your accommodations in advance.

On weekend trips, I’ll plan most of my route and where I’ll stay in advance. But if I have at least two weeks on the road, I’ll leave more of my trip unplanned and open to discoveries.

Lobster Roll |Photo: Carolyn Heller

Tip: Build in unstructured time, even on relatively short road trips. You might want to stay longer at a park you’re enjoying, or a detour to a cool town.      

If you want to camp at many national, state, or provincial parks, reserve early. Campgrounds at popular destinations like Banff National Park normally book completely on the first day that reservations open for the season in January.

Check to see whether you need to purchase national park passes, tickets for museum exhibits, or other attractions in advance.  

How to Add Local Culture to Your Road Trip

Road trippers often focus on national parks and other outdoor destinations – and with good reason. Nearly anywhere you can road trip, you can enjoy the outdoors, whether it’s the rust-hued rocks of Utah’s Bryce Canyon, the turquoise lakes in Jasper National Park, or the spectacular seashore along California’s Highway 1. Yet, it’s often the encounters I’ve had with local people (albeit six feet away for the time being) and culture that leave the most long-lasting impression.

Research the region’s culture before your trip.

Young girl holds up a can of spam from the SPAM Museum, Minnesota during a family roadtrip
SPAM Museum, Minnesota | Photo: Carolyn Heller

What quirky roadside attractions or local museums, like Minnesota’s SPAM Museum or Ontario’s much-photographed Wawa Goose, can you visit? Are there places to learn about the diversity of the area you’re visiting, like Seattle’s National Nordic Museum, or the Buxton National Historic Site & Museum, which illuminates the history of formerly enslaved people who followed the Underground Railroad to Canada?

Eat your way along the Dumpling Trail in British Columbia or do a taco tasting along Tucson’s South 12th Avenue.

Take time to chat with people in cafés, markets, or the town’s craft brewery. Maybe you’ll learn that a local band is playing in the plaza or that you’ve arrived in time for an indigenous community’s powwow. All these activities will make your road trip richer.

Getting Ready for Your Road Trip

What to Pack

Here’s a short list of things to pack. For greater detail see How to Pack For a Road Trip.

(For Susan’s favorite gear, check out The Insatiable Traveler Amazon Store)


A highway sign warning of waves on the road Gaspé Peninsula, Quebec
Warning sign, Gaspé Peninsula, Quebec | Photo: Carolyn Heller

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Before You Go

Download Maps and Apps

Download Google Maps that you can access even if you’re out of cell range. Navigational apps like Waze will help you avoid traffic tie-ups or road closures.

Check Your Insurance

Make sure your car insurance is up to date and that it covers you in the destinations you’re going. Confirm that your travel medical coverage is valid for the times and places you’ll be visiting.

Young man offering a lemonade to camera
A lemonade stand at the Corn Festival in Alberta, CA

Clean Your Car

Expect that your car will get messy as you travel, so clean it before you set out.

Get Your Car Tuned Up

Book an appointment for an oil change and a tune-up in advance, especially if you’ll be traveling for more than a few days.

Check the Weather

Confirm whether you’ll need winter tires on your car. Many mountain regions in Canada, for example, require you to have winter tires or carry tire chains if you’re traveling between October and March.

If you’re heading anywhere it could possibly snow, make sure you have a snow scraper or brush to clear your windshield, and ideally, a small snow shovel.

Beautiful flowers and mountains Olympic National Park, Washington
Olympic National Park, Washington | Photo: Carolyn Heller

How to Organize Your Car for a Road Trip

Pack like things together. Designate a bag or box for camping gear, another for food supplies, and another for anything you’d want at the beach.

Tip: Bring reusable shopping bags, some for grocery shopping and others to sort things in the car. Or use stackable plastic containers to organize your stuff.

Think about what you’ll need daily. I pack separate bags with anything that doesn’t need to be unpacked every day, such as extra jackets, sports equipment, or beach towels. That way, you’re not dragging everything out of your car every night.

Keep bags for trash and recycling handy, and empty them regularly.

On the Road

How to Find Healthy Food on the Road

Anyone who’s driven across North America’s major highways knows that it’s easy to find fast food but challenging to track down healthier options. With a little effort, you can avoid the fast food trap. Here’s how:

  • Get off the highway: Make even a short detour from the main highway, and you’re more likely to find options beyond fast food.
  • Go to the grocery store: Instead of pulling into the drive-thru, shop for cheese, hummus, nut butters, and other sandwich makings, along with fresh fruit and vegetables, at a local grocery store. Assemble a salad from the salad bar or look for economical prepared foods. A roast chicken can be dinner today and leftovers for sandwiches tomorrow.
view of a lake and the shore with trees from a kayak in Kayaking on Okanagan Lake, British Columbia during a road trip
Kayaking on Okanagan Lake, British Columbia | Photo: Carolyn Heller
  • Eat Locally: Buy produce at farmer’s markets or roadside farm stands. Visit cafés, diners, and anywhere that serves regional specialties, from barbecue to butter tarts. Road tripping through Quebec’s Gaspe Peninsula during lobster season, I bought a pre-cooked, ready-to-eat lobster from a seafood shop. Back at my hotel room, it was a delicious picnic.
  • Tip: Pack a lobster cracker if you’re traveling in a lobster-eating region. It’s not easy to crack open a lobster shell with your bare hands.

The Best Road Trip Snacks

The best road trip snacks are easy to eat, don’t require constant refrigeration, and aren’t horribly messy. Good choices include dried fruit, nuts, protein bars or other snack bars, hard cheeses, nut or seed butters, and crackers. I often bring packets of oatmeal or other hot cereal for a quick breakfast.

If you’re a chocolate lover like I am, keep your chocolate in the cooler.

Fresh fruit is healthy and refreshing, so look for fruits that don’t smash easily or that you can keep protected. Apples and grapes travel pretty well, and I love cherries, so even though they’re fragile, I stop for fresh cherries whenever they’re in season.

Yoho National Park, British Columbia
Yoho National Park, British Columbia | Photo: Carolyn Heller

Tip: Bananas are easy to eat on the road, but they quickly get overripe, and your car will smell like bananas for the rest of your trip. Buy bananas in small quantities and dispose of the peels as soon as possible.

More Food and Drink Trips

Carry an extra jug of water, in addition to whatever each person has in their water bottles, so you can refill your bottles between stops.

Clean out your cooler at least daily. Melting ice, leaking drinks, and food that’s past its prime all make coolers get gross really fast. 

If your accommodations have a freezer, refreeze your ice packs overnight. Set a reminder to repack your ice packs in the morning.

Kootenay Lake, British Columbia
Kootenay Lake, British Columbia | Photo: Carolyn Heller

Road Trip Entertainment

Assemble a playlist of sing-along songs that will keep you occupied in the car, or choose songs by artists from the region where you’re traveling. I’m a fan of podcasts and audiobooks, which can be good entertainment for the whole family.

Listen to local radio, too. On a solo road trip along New Brunswick’s Acadian Coast, I found a French-language country music station – the perfect tunes to listen to between stops for seafood and pets de soeurs, a pastry known as “nun’s farts.”

Staying Safe

Keep your gas tank filled, especially in remote areas. You don’t want to be running on empty and find that you’re 100 miles from the next service station.

Stop before dark. It’s safer to drive during the day, and you’ll appreciate the scenery more in the daylight. 

Keep your cell phone handy and make sure it’s charged.

Snow Canyon State Park, Utah
Snow Canyon State Park, Utah | Photo: Carolyn Heller

Check the weather regularly. Remember when you’re driving through the mountains that the weather can be very different at different elevations. Traveling through the Canadian Rockies one August, it was drizzly in town and snowing heavily higher up the mountain. Yes, in August.

Consider joining the American Automobile Association (AAA) or Canadian Automobile Association (CAA), so you can call for help if you get a flat tire or have other car issues.

Research what wildlife lives in the areas you’ll be visiting and any precautions you should take. If you want to watch wildlife from the car, pull off the road as far as possible. Don’t get out of your car or disturb the animals. Remember you’re intruding on their habitat.

Cottage at John Henry’s Resort, Pender Harbour, British Columbia
Cottage at John Henry’s Resort, Pender Harbour, British Columbia | Photo: Carolyn Heller

Tips for Solo Travelers

All road trippers should let a friend or family member know where you’re planning to go, which is even more important when you’re traveling solo. I check in with my husband regularly, and I’ve given him access to my electronic calendar, where I record where I’m planning to stay. This calendar ends up being a handy trip diary, too.

Don’t broadcast the fact that you’re traveling alone on social media or when you stop at a gas station, restaurant, or attraction.

Read accommodations reviews carefully before you book. If something doesn’t feel safe, leave right away.

Tips for Family Road Trippers

Involve the kids in planning your trip. Read about places you’re considering and talk about what they find interesting. Some families suggest letting each child choose one activity that they most want to do.

Even young children will likely be calmer if they understand the day’s plan. Road tripping through Spain when our kids were only three, my husband and I eventually realized – after a couple of days of backseat fussing – that our toddlers were happier when they knew what to expect, even if all we told them was “we’re going to drive until it’s lunchtime, then have a picnic.”

Before you go, decide your policy about electronics. Will you let the kids watch movies or play games in the car or at your overnight stops?

A small red car drives through Canmore, Alberta
Road-tripping through Canmore

Look for kids’ books set in the region you’re visiting. Stop into a local bookstore to find works by area authors.

Build in enough flexibility to adapt to the kids’ moods on any particular day. When my daughters and I crossed the U.S., we had days when they wanted to be hiking, swimming, or doing pretty much anything but sitting in the car, so we’d find a place to stay early and get outdoors.

On other days, the kids were content driving for longer stretches. Even adults have similar moods – days when you can’t wait to get out of the car and others when you feel like you can drive forever.

COVID-19 Precautions

Road trippers should consider these additional preparations during this time of the coronavirus:

  • Research the communities, parks, and regions you want to visit, including places you’ll be driving through, to make sure they’re open to travelers.
  • Check for any quarantine requirements, both where you live and where you’re going.
  • Book campsites or other accommodations in advance, as choices may be more limited.
  • Check refund policies for anything that you prepay, in case you need to change your plans.
  • Wear masks, wash your hands whenever you stop and use hand sanitizer regularly.
  • If you or anyone in your traveling group has any symptoms of illness, stay home.

Tip: Check here for more details on how to plan a safe holiday on the road.

Have a great trip!


Carolyn Heller

Carolyn B. Heller is a Vancouver (Canada)-based travel writer and author of the road trip guide, Moon Vancouver & Canadian Rockies Road Trip. She’s also written two other Canada travel guides and contributed to more than 50 other travel titles for Lonely Planet, Moon, Fodor’s, Forbes Travel Guide, and other publishers. She writes about road trips, food and drink, art and culture, and offbeat experiences.

Follow her adventures on Twitter or Instagram.


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11 thoughts on “A Beginner’s Guide to Planning an Extraordinary Road Trip

  1. Susan Portnoy says:

    Hey Lavanya, I’m glad you felt the post would be of value to you. That’s what it’s all about. Tip… tomorrow, I’m going to post Carolyn’s Road Trip Packing List. 🙂

  2. Lavanya says:

    Great post and very informative. I have never been on road trips but I dream of going on. it would be different and an experience to share with my grand kids. your post will be my first resource when i will plan that trip. all my travel plans for this year are now put off. I hope these difficult times are over soon and i can start travelling again. And hopefully, go on a road trip.

  3. Veronica says:

    I wish I could go somewhere this year! I really want to go visit my brother back home in Chicago, and my relatives in Florida, but it will have to wait due to the pandemic.

    And I bring an atlas if I am traveling to an unfamiliar place, or I think there’s a chance that GPS might fail.

  4. Arpan Chaudhary says:

    Absolutely magnificent. You provided very vital information with real ease. It’s really a post that helps any traveller especially the beginners to overcome their fear and plan accordingly… Thank you so much 🙌🙌

  5. Laura (PA Pict) says:

    Great article packed with good advice. It is giving me itchy feet. We are a family of road trippers and are very sad to not be travelling this summer – though we were actually supposed to go home to the UK instead of road tripping. I really hope the time will come when we can start planning another road trip.

I would love to hear from you! What did you think of the post?