Planning a Road Trip: A Beginner’s Guide

Planning a road trip can be a lot of fun. In fact, I think it’s almost as fun as the trip itself, because in the planning stages it can be anything you want it to be. Whether you’re new to road trip planning or an experienced road tripper, you’ll want to be sure to consider each of these steps before you take off on an adventure by car.

Planning a road trip, silver car on wooded road

CONTENTS: In this article, you will learn the essential steps and decisions to make when you’re planning a road trip, including:

How to Choose A Destination 

Magnifying glass and car keys on map

One of the biggest challenges to planning a road trip is figuring out where to go. With the world of possibilities around you, it can be hard to narrow down your choices!

There are a few ways you can do this. Here are some ideas.

One way is to plot a radius around your starting point. You can do this by twisting a math compass set to the distance shown on the map’s key.

Or, you can use an online map radius tool.

This approach is really helpful if you know you only want to drive so many hours and/or miles in a day or are looking for a convenient day trip.

For instance, if you want to take a day trip limited to an hour-and-a-half of drive-time, you can plot a radius of 90 miles out (highway), then consider your options.

Of course, you’ll have to account for backroads and delays, but it will give you a general idea of what’s within range.

Another way to choose a destination for your road trip is to base it on your bucket list. Have you always wanted to see the Grand Canyon or see New England’s vibrant fall foliage? Go for it!

A third way to choose your destination is find travel inspiration through experts, such as travel bloggers and by doing online research. You can learn a wealth of information about routes and attractions from those who have already been there.

Regardless of how you decide you want to pick your road trip destination, you’ll want to keep in mind the following:

  • Decide on the amount of time you want to spend en route.
  • Factor in the cost of gas and activities.
  • Determine whether your road trip will include overnight(s) or you’ll return the same day.

Once you have picked a destination factoring those guidelines in mind, you can begin planning the route of your road trip.

Planning a Road Trip Route With Stops

There are number of ways you can plan your route.

1. If You Want to Get There Fast

If you simply want to get from Point A to Point B, Google Maps is an easy, no-nonsense way to map out your route. You can even include multiple stopping points and let Google Maps do all the heavy lifting for you. The only stops you might plan here are pitstops.

Alternatively, Waze helps map out your route and guides with turn-by-turn directions as you drive–even giving you real-time traffic information and detours. You can adjust the filters to avoid highways or tolls.

2. The Multi-Stop Itinerary

If your trip is based on your bucket list stops, simply connect the dots and plan out the route in bite-sized chunks as you from one stop to another.

The same is true if you have multiple friends and relatives who might welcome your visit. This has the advantage of gaining a local’s perspective of each region, and if they are open to overnight guests, it could be a budget-friendly option, too.

3. A Nostalgic Journey

When I planned my road trip from Boston to Nova Scotia, we mostly opted for the familiar driving route my parents traveled each summer to relive some of my mom’s nostalgia. We enjoyed hearing family stories and it made my mother happy to see familiar milestones along the way.

4. Take The Scenic Route

If you’re looking for more of a scenic route, check out to build your itinerary. Once you input an area to their Road Trip Route Planner app, you can explore popular attractions, outdoors & recreation stops, entertainment & nightlife, dining, and other points of interest.

Also, be sure to travel along some beautiful scenic byways when planning a US road trip. This scenic route-planning site is a robust resource, mapping out scenic routes in the United States:

  • By state
  • All-American
  • National
  • Parkway
  • National Forest
  • BLM Black Country byways
  • Other scenic routes.

All the work is done for you!

Planning Tip 1: If you’ll be driving along the coast, such as on a road trip along California’s Pacific Coast Highway, figure out which side of your car you want to face the ocean…driver or passenger?

Planning Tip 2: If you’re an AAA member, you can take advantage of their free planning services. They can help you determine the best stops along the route, too.

Remember, a road trip doesn’t have to be all about getting to your destination. You have the opportunity to enjoy the scenery and sites along the way so plan accordingly.

Stops Along the Way

Typically, you can drive a hundred or so highway miles in about 2 hours. But it’s important not to overschedule your trip. The best road trips leave time for unexpected detours, interesting attractions, and a little downtime.

If you love nature and are planning to check out U.S. National Parks, it can be cost-effective to invest in an annual National Parks Pass ($80), which covers entrance fees to thousands of National Parks & Federal Recreational Lands.

Stops for Extended Trips

For extended trips, don’t forget to plan for necessary stops along the way, such as:

  • Bathroom breaks
  • ATM/Banks stops
  • Convenience or supermarkets stops
  • Laundry

As a general rule, you’ll want to plan some stops just to stretch your legs, especially if you’ve been driving for four hours or more. Otherwise, you could be at risk for blood clots, or deep vein thrombosis (DVT), which is more likely during long-distance travel, particularly if you’re over 40. (Source: The Centers for Disease Control and Prevention)

Food & Lodging Stops

Consider whether you’ll want to stop for food and overnights. Depending on your comfort level, you may want to decide on where you’ll eat or stay as you go or have firm plans in place ahead of time.

Either way, do some research before stopping. You can check out Zagat or Yelp for dining reviews and look to Momondo for Unique accommodations.

When it comes to planning out routes and stops, take time estimates with a grain of salt. Remember that on the day of your travel you might end up hitting traffic or construction delays, or find a place you want to explore further.

What’s the Best Departure Time When Planning a Road Trip?

I always like an early start, especially for long trips. It makes me feel like I’ve covered a lot of ground by noon.

But there are exceptions to the rule.

Say, for instance, your travel partner isn’t an early riser.

Or, you have day commitments to keep before leaving for the long weekend.

Maybe your overnight accommodation on the route offers an incredible brunch or, you really wanted to see a few more things in that cute village before heading off on the next leg of your journey.

Or, perhaps you want to avoid delays from bridge traffic, rush hour, construction works, festivals, holidays, parades…or otherwise generally busy travel times.

When my children were toddlers, we would arrange our Sunday night departures from Cape Cod for after 8 pm to avoid traffic jams–and more importantly, so the kids would sleep through most of the trip.

And finally, check for weather delays. For one thing, bad weather might ruin your day trip. And it will certainly extend your drive time. (At the very least, dress for it and be prepared.)

So, is there a best departure time when planning a road trip?

Not really.

But there are better times depending on your circumstances.

Should You Rent a Car for A Road Trip?

Jackie Gately of Enjoy Travel Life in a yellow sports car

There are pros and cons to renting a car for a road trip.

Some of the Pros include:

  • Less wear and tear on your personal vehicle
  • More desirable car for the trip (better gas mileage, more space, specialty car, more reliable)
  • May offer roadside support/replacement vehicle

Some of the Cons to renting a car for a road trip include:

  • Additional rental expense
  • Requires a credit card deposit upwards of $300 (some companies will accept a debit card hold on funds)
  • Unfamiliar vehicle
  • Mileage or state/country line limitations
  • Speed or other trackers (privacy)

To make sure you get the best deal, do some shopping online and ask for price-matching.

Also, some rental car agencies run very affordable weekend rental rates.

The best deals offer unlimited mileage and allow you to cross state/country lines without additional fees. You may also want to drop the car off someplace different from where you got it.

If you decide to rent a car for your road trip, book it in advance for the best odds of getting the car you want.

Additional Insurance Coverage on a Road Trip

Your existing auto insurance policy (assuming you have a car) may offer some coverages for your car rental, but most likely won’t include Supplemental Liability insurance (SLI). And if it does, it’ll be pricy.

Simply defined, Supplemental Liability Insurance or (SLI) covers you for injuries to other drivers and their cars. In some states, like California, New York, Nevada, and Florida, you are required by law to carry SLI on your rental car. But even if it’s not required on your route, getting a short-term policy will minimize your financial risk.

Check with your insurance agent and the rental agency about the availability and pricing of SLI.

Or, opt for a more affordable option: Bonzah’s car rental SLI is under $12/day and covers up to $1M in liability. You can buy it online through their website or the Bonzah app and have instant coverage. 

While you ideally don’t have any accidents on your road trip, SLI offers an additional level of comfort and assurance if you do.

Preparing Your Car for A Road Trip

If you decide to bring your own car on a road trip, you’ll want to:

  • Clean it out
  • Ensure the insurance, registration, inspection is up to date
  • Have a trusted mechanic safety-check it and top off fluids as needed
  • Make sure your EZ Pass toll responder is working and funded

While you’re at it, make sure your license is current and you have no outstanding tickets or driving violations.

Important Paperwork Before You Begin Your Road Trip

It’s a good idea before you go on your road trip to print out any rental agreements for reference on the road. That means hotel reservations, admission tickets, tour receipts, and other purchases made at home. While you may have access to the files electronically, remember that Wi-Fi may not always be available. I recommend storing printed copies together in a handy folder.

You should also take photos of all of your important documents in case your car is stolen. That includes your car registration and insurance documents, or your car rental agreement. It’s a good idea to have copies of your license, passport, and credit cards, too.

Take a photo of your license plate for the same reason, and also for convenience when checking into hotels. (Who can remember a license plate, even your own?)

If you take medications, make sure you have documentation for refills as needed.

Lastly, prepare a written or digital itinerary with dates, locations, and contact info and share it so someone knows where you are. If you are leaving children, pets, or elderly parents behind, make sure caretakers have detailed instructions and know how to reach you or a relative in an emergency.

I also recommend downloading route maps so if the Wi-Fi is spotty and you lose GPS, you won’t risk getting lost.

Additional Road Trip Tips

Here are a few more items for your road trip checklist:

  • Check Easy Pass/tolls and bring some quarters and singles in case there’s a problem.
  • Bring a trash bag for the ride and extra windshield wiper fluid.
  • Add a rooftop cargo bin for additional storage.
  • If you’re crossing international borders, check for your phone plan. Many plans offer unlimited talk and text in all of North America, but if not, you may want to look at skype or whatsapp to keep in touch for free.
  • Back up the photos from your phone to the cloud before you leave and make sure you have plenty of space for new photos.
  • Download any files you may need to access to your laptop hard drive in case you don’t have wifi access.

Hit the Road!

Finally, the big day is here. You’ve planned it out and you are ready to have an amazing road trip! 

But wait.

Final Thoughts

There’s one last thing I forgot to tell you…

Expect the unexpected.

That might mean rerouting because of an unexpected road closure, or it might mean exiting off the planned route to explore a country road. Once your planning is done and you hit the road, be prepared for the adventure to unfold.

After all, that’s the best part.

Have you ever planned an epic road trip? I’d love to hear about your experiences and tips in the comments below.

Essentials for Road Trips | What to Know Before You Go!
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Jackie Gately

Jackie Gately is a seasoned travel writer, photographer, and marketing consultant who is passionate about travel. She loves casual-luxury experiences, coastal getaways, cultural attractions, and local, wholesome food and wine pairings. A perfect day ends with her toes in the sand or by chasing the sunset with her camera--ideally both.

18 thoughts on “Planning a Road Trip: A Beginner’s Guide

  • July 4, 2020 at 12:18 pm

    I love road trips and just did my first one of the summer last weekend. It was a short one but still a lot of fun. The compass idea is great for a day or weekend trip! The best road trips are the longer ones and you can stop and explore along the way. I loved the tip about the Pacific coast highway. This is very high on my bucket list and of course, I would want to be driving on the same side as the ocean. I never would have thought of this.

    • July 4, 2020 at 1:39 pm

      I love the longer trips, too, Kelly! But sometimes, a weekend fix does the trick for me. Hope you get to the PCH soon (and make sure you’re on the “correct” side). Glad you can think about that now, before you go!

  • July 4, 2020 at 4:57 am

    Didn’t know about that road tripping app, that sounds an excellent idea. I love road trips and I’ve finally learned not to over schedule the trip. Go slow, take the scenic route and enjoy. But it’s taken me a lot of road trips to reach that stage lol.

    • July 4, 2020 at 12:02 pm

      I agree, Sarah! Overscheduling is probably one of the biggest mistakes when planning a road trip.

  • July 3, 2020 at 11:46 pm

    We really love road trips for the immersive experiences they foster and also the freedom of being able to stop wherever and whenever. Your post is a ready-reckoner for planning a road trip and covers each and every aspect. Having the right paperwork is so important, for example in India in some regions you need to have special passes to enter some regions, and these need to be procured online before the trip.

    • July 4, 2020 at 12:04 pm

      Paperwork is crucial! My daughter was almost denied entry to Vietnam without the right paperwork. I can’t stress enough how important that is on any road trip, as you have described likewise for regions in India. (Thanks for the kind words.)

  • July 3, 2020 at 11:29 pm

    I love a good road trip and take them as often as possible. My daughter and I took a two week road trip last summer and had so much fun. We planned our route and bought good snacks, which are always necessary. It was so fun, with many stops. Great tips for a newby road tripper. I think there will be a lot of those this summer. .

    • July 4, 2020 at 12:05 pm

      Yes, I’m sure there will be an uptick in newbie road trippers. I would love to take a road trip with my daughter or son. It’s on my bucket list. I am glad you enjoyed yours. (Good snacks=essential!)

  • July 3, 2020 at 5:25 pm

    Love all of these tips! I love road trippin’ and it’s our families go-to travel of choice. You’re right, it’s a lot of work to plan a good road trip- much more than just booking a flight BUT you get the reward of fun on the road!

    • July 4, 2020 at 12:06 pm

      It truly is an adventure of a different kind compared to taking a flight somewhere. I thoroughly enjoy it, too!

  • July 3, 2020 at 11:21 am

    Thanks Jackie for putting together tips for road trips. This is exactly what we need this summer. The only other tip I need is how to get an older teen into a car for a road trip 😂😂.
    A tip I can share is to use the brand new Guides in Apple Maps. There are amazing guides and it’s just getting started.

    • July 3, 2020 at 2:13 pm

      Haha, I totally understand, Jyoti! Thanks for the kind words, too. I will definitely check out the new Guides in Apple Maps. Thanks for sharing this tip!

  • July 3, 2020 at 6:21 am

    Wow. The tips are great. As far as the car rental is considered, I always opted for it. As driving an unfamiliar car is a bit risky, I do look for a similar model first 😋. Also keeping a handful of snacks helps a lot on the way, as we never know what is coming up along the way. Being prepared is everything we need.

    • July 3, 2020 at 2:15 pm

      What a great idea to rent a car similar to the one you’re familiar with. I would have never thought of that but it makes good sense so I will keep that in mind going forward. Thanks!

  • July 3, 2020 at 2:03 am

    This is a great checklist Jackie. We’ll be looking to do more local trips over the next few months and your post will be handy to make sure we’ve thought of everything. Food and lodging are the essentials but I wonder how many people think about bathroom breaks in between, I know I’ve had to try and work this out on the fly before 🙂

    • July 3, 2020 at 2:17 pm

      Thanks, Freya! I find especially as I get older, those bathroom breaks are an essential part of a road trip! LOL Glad you enjoyed the tips and will put them to good use on your journeys.

  • July 2, 2020 at 7:00 pm

    You offer so many great tips here! Road trips are going to be the most popular way to travel for the foreseeable future and I think it’s really important for people to see how much work goes into them. Picking a Destination is the fun part and it’s time to start planning

    • July 3, 2020 at 12:17 am

      I’m glad you found these tips helpful, Jenn. You’re right about the work that goes into planning a road trip. It is both a good thing and the bad thing, LOL. I love dreaming about my next destination (and then making it happen)!


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