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.

Editor’s Note: This article was updated in May, 2022.

This post may contain affiliate links. Please see my disclosure for more information. As an affiliate, I earn a small commission every time you make a qualifying purchase through one of my affiliate links (if applicable).

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
• Planning the Road Trip Route
  • How to Get There Fast
  • Making a Multi-Stop Itinerary
  • Taking a Nostalgic Journey
  • Finding the Scenic Route
  • Making Stops Along the Way
• What’s the Best Departure Time for a Road Trip?
• Car Rental Pros and Cons for A Road Trip
  • Do You Need Additional Auto Insurance?
  • How to Prepare A Car for a Road Trip
• Important Paperwork For A Road Trip
• Additional Road Trip Tips
• Final Thoughts

How to Choose A Destination 

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 like this one. To learn more about how to map a radius, read this article.

Mapping a radius 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.

Related: Be sure to review these pros and cons of traveling by car before planning your road trip.

Planning a Road Trip Route With Stops

There are a 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 pit stops.

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.

This allowed my mother to relive some of her 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 roadtrippers.com to build your itinerary. Once you input an area to their Road Trip Route Planner app, you can explore plenty of stops on the way.

This might include 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.

And if you plan to travel via RV, then you may want to consider joining the Good Sam Club.

The Good Sam Club offers members the following benefits:

• Discounts of up to 10% at associated campgrounds
• Savings of up to 10% at certain outdoor retailers (Like Camping World
• Free shipping on orders of $49 or more
• Discounts on diesel fuel
• Access to online trip planning services
• A 70% discount on the Good Sam Guide,
• 15% off propane purchases
• Free dumping services at select outdoor retailers.

Annual memberships start at just $29 per year. To maximize your investment, you can also subscribe for $50 for two years and $79 for three years. It’s money well-spent, especially if you love to go road tripping!

Stops Along the Way

Typically, you can drive a hundred or so highway miles in about 2 hours. But it’s important not to over-schedule 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). This 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. This is of particular danger if you’re over 40. (Source: The Centers for Disease Control and Prevention)

Food & Lodging Stops

Next, 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. It can be reassuring to 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.

You may even find a place you want to explore further, and why not? That’s the beauty of a road trip.

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.

Perhaps you want to avoid delays from:

• Bridge traffic
• Rush hour
• Construction work
• Festivals, holidays, and parades
• 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. More importantly, so the kids would sleep through most of the trip. That made a more peaceful road trip all around.

And finally, you’ll want to 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 the weather to 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?

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 some place 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. And don’t forget to read the fine print when you sign. Some rental agencies will charge an additional fee if you get a ticket, return the car on empty, dirty, or after hours.

If you’re travelling overseas and don’t have access to your own car, then it’s good to consider a car rental company that offers carbon offsetting or has electric vehicles like Go Rentals. This helps to limit your impact on the environment while still having a great time on your awesome road trip!”

Also, be sure make know how they handle toll payments, mechanical issues, and breakdowns, too.

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. 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.

Now, like with any trip, you’ll also want to purchase travel insurance prior to the start of your road trip. Because even though you may not want to think about bad things happening, it’s always a good idea to be prepared.

And although there are hundreds of travel insurance companies that you can purchase a policy from, I love and use World Nomads travel insurance.

Not only can you quickly and easily buy/make insurance claims online, even after you’ve left home, but World Nomads is also available to people from over 130 countries.

Additionally, their policies are designed for adventurous and slightly less adventurous travelers alike. It will completely cover any overseas medical expenses that you might incur. You will also receive full compensation for emergency evacuations, lost luggage, and so much more.

Additionally, World Nomads Travel Insurance is:

1. Backed by trusted and reliable underwriters.

World Nomads is backed by a suite of strong, secure, specialist travel insurers. They provide you with great coverage, 24-hour emergency assistance, as well as tremendous support and claims management.

That’s why you always get exceptional value for your money.

2. World Nomads focuses only on what you need and leaves out what you don’t.

World Nomads’ prices are some of the most competitive in the industry. As a result, you’ll receive top-notch coverage at a fraction of the price that many other companies offer.

3. Flexibility when you need it the most.

Have a sudden change of plans? Not a problem at all. You can purchase extra coverage, buy an entirely new World Nomads Policy, or file a claim online while you’re traveling.

4. Coverage for a range of adventure activities

Between skiing in New Zealand and whitewater rafting in Colorado, World Nomads provides an amazing level of coverage for an array of adventure-related activities. You might want to participate in while you’re away from home, and have insurance for any unexpected mishaps.

5. World Nomads gives you peace of mind since it allows you to travel safely.

All policyholders and members of the World Nomads family have access to up-to-date travel safety alerts, as well as travel safety advice and tips online through the World Nomads Travel Safety Hub.

This company also prides itself on a commitment to high-quality customer service and wants to ensure that you get the most out of your travel insurance.

Therefore, if you have any questions about your travel insurance policy or travel safety in general, always feel free to contact WorldNomads.com directly.

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 using this amazing, portable vacuum cleaner. It’s a small, hand-held vacuum that is incredibly powerful. This makes it easy to instantly detail your car with the long, 16-foot power cord. It also features fantastic suction, a transparent trash container (allowing you to instantly see when it needs to be emptied), and three different nozzles that will help you satisfy all your cleaning needs.
• Quickly and easily detail the exterior of your car with this Snow Eagle, 10-piece car cleaning tool kit. When you order it, you’ll receive the following: a window water scraper, car duster, tire brush, wheel brush a handle, microfiber sponge, mini-duster for the air Vent, plastic blow storage box, and three towels. What a bargain!
• Organize the interior of your car with this Trello, three-door, plastic storage bin for your trunk. You might also like this Tidify front seat organizer. It features a dedicated tablet/laptop holder, stabilizing side straps, soft adjustable shoulder strap and hardened buckles. Check out this sun visor organizer, too.
• 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.
• In case of an emergency, also make sure that you can have a premium roadside assistance kit in your trunk. I personally use this kit from AAA since it’s affordable and includes 42 incredibly useful items. The kit includes things like jumper cables, flashlight, first aid kit, rain poncho, and more. You’ll also want to bring a comprehensive, up-to-date first aid kit.

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

Related: If you really want to get your car organized for a road trip, learn these easy tips next.

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
• Other purchases made at home

While you may have access to the files electronically, remember that Wi-Fi may not always be available. That’s why 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 It’s 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.

If you’re traveling with anything expensive, like your laptop or a professional camera, make note of the Serial Numbers. Then, if they get stolen, they are easier to identify.

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.
• Bring an auxiliary cable that you can plug into your car stereo and that you can use to charge various electronic devices while you’re on the road.
• Bring all of your favorite radio programs on the road with you, with a subscription to Sirius XM Satelite Radio. You’ll get a complete Sirius installation kit as well as a three-month subscription to their associated satellite streaming service. This way, you’ll be able to listen to your favorite shows, regardless of where you are in the country.
• Pack all your travel essentials into a chic, MyMealivos Canvas Weekender Bag. Each bag is affordable and available in three hand-crafted designs with brown faux leather accents. The interior finished with a luxurious brown cotton lining. Plus, its dimensions meet standard airline carry on restrictions, too. This handy bag also has a separate shoe compartment, an ergonomic design, and seven zippered compartments to help you stay organized.
• A high-quality, extra-durable, vacuum insulated, stainless steel, YETI 18 ounce Rambler, or the 30-ounce YETI Tumbler. Both drink holders feature DuraCoat Color that is built to last, are BPA-free and dishwasher safe. They have a leakproof triple haul cap, a vacuum insulated double wall that will keep your drinks either hot or cold for hours at a time. YETI’s unique, sweat-proof design makes them easy to carry, too.

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 from the planned route to explore a country road. Once your planning is done, you’re dressed for the trip, and you hit the road, be prepared for the adventure to unfold.

After all, that’s the best part.

For more how-to tips on Road Trips, continue reading:

• How to plan the best food snacks for the trip
• Family road trip packing list
• Helpful tips for planning a road trip
• Planning the best outfit for a road trip
• The best tips for organizing your car for a road trip
• Most useful travel accessories for a road trip
• How to plan the perfect road trip
• Things to know before renting a VW Bus

For destination related road trips, check these out:

• Road trip essentials for a UK driving tour
• Best US road trips from Chicago to LA on Route 66
• Scenic self-drive holidays in Canada
• Best New England road trips
• Driving Barcelona to Madrid Spain
• Where to stay on a road trip to Nova Scotia
• Driving from San Francisco to San Diego on the PCH

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

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