How to Prepare for a Road Trip: Don’t Overplan—Just Go!

Road-tripping is hands down one of my favorite ways to travel. Now, I’m not talking about those full-sized RVs with kitchens and queen-sized beds (though, let’s be real, that would be awesome). I mean packing up my Elantra, grabbing my friends, and hitting the road with no set destination—just a general direction and a willingness to see where we end up.

The Best Road Trips Are the Ones You Don’t Overplan

Of course, there’s some level of preparation involved, but the magic of a road trip comes from spontaneity. You’re not waiting on flight schedules, tour groups, or anyone else’s itinerary—you’re fully in control of where you go and when. The best moments often come from unexpected stops, last-minute detours, and the people you meet along the way.

A Route with No Set Plan: My Spontaneous Trip to Florida

One of my most memorable road trips started in Kingston, Ontario, with two of my closest friends. We crossed the border with zero set plans, just a rough idea of heading south down the East Coast of the U.S..

Driving to Florida

What our itinerary looked like:

• Washington, D.C. – After an all-night drive, we pulled into a random gas station for a few hours of sleep (we didn’t book a hotel).

• Myrtle Beach, SC – We stopped here for two nights, soaking up the sun and playing TopGolf with a group of new friends we met along the way. We would have stayed longer, but when the temperature suddenly dropped to 13°C (55°F), we made a quick decision—keep driving south.

• St. Augustine, FL – A hidden gem! Right on the water, with stunning architecture and quiet beaches, it instantly became my favorite spot in Florida. We stayed here for two days before starting the drive back north.

• New York City – A quick stop to break up the long drive home, because why not? Check out this budget friendly guide to travelling New York.

If I could combine this trip with a previous Florida road trip, I’d also highly recommend adding Miami and South Beach to the mix. There’s a certain energy to those cities that I can’t fully explain—just a non-stop, lively atmosphere. You don’t need to spend hundreds of dollars on theme parks to have a great time.

The True Freedom of Road Trips

More than anything, road trips are about freedom. Unlike a typical vacation where everything is pre-planned, you can go wherever feels right in the moment. There are, of course, some basic things to keep in mind (which I talk about in my blog post 3 Must-Know Travel Tips for Young Adventurers (Avoid These Costly Mistakes!), but overall, it’s about embracing the adventure.

That Time I Hit a Giant Weasel…

Of course, there are some practicalities to consider—like car insurance. Make sure anyone driving is covered, because trust me, you don’t want to deal with car damage without it. I learned this lesson firsthand when I hit an animal (still not sure what it was, but we’re calling it a giant weasel) and ripped off part of the bumper in a rental car.

Beyond that, though, there’s not much to stress about. Pick a general direction, make sure your car is in good shape, and hit the road.

Who You Travel With Matters More Than the Destination

A road trip is only as good as the people you take it with. You’re trapped in a car together for hours (or days) on end, so choosing the right travel companions is crucial.

Before setting off, ask yourself:

• Can I truly spend X hours/days in a car with this person?

• Are they adaptable, or will they freak out if plans change?

• Can we handle disagreements without ruining the trip (or a friendship)?

Also, make sure you’re able to answer these questions about yourself as well.

Unlike a regular vacation where you can go back to your hotel room at the end of the day, there’s no escape on a road trip. Make sure your group is on the same wavelength before you hit the road.

Food & Accommodation: The Unspoken Road Trip Conversations

Here are a couple of arguments I’ve had around so you can avoid them:

Food will be a topic that comes up often. Before embarking, make sure you discuss the expectations.

• Are we grabbing fast food to save time and money, or is it important to sit down for meals?

• Does everyone agree on stopping when hungry, or are we just pushing through until we reach our next stop?

Hotels & Budgeting

• What level of accommodation are we looking for? (Are we okay with budget motels, or do we need a higher star rating at a higher price?)

• If there’s nothing available within budget, is sleeping in the car an option?

• Is going over budget every now and then okay, or do we need to stick to strict spending limits?

There’s no right or wrong answer to these questions, but everyone needs to be on the same page. The last thing you want is tension over money or expectations halfway through your trip.

Final Thoughts: Why Road Trips Are the Best Way to Travel

For me, road trips are about the journey, not the destination. Sure, picking a few must-visit spots is great, but the real magic happens in the unexpected moments, last-minute detours, and hilarious mishaps along the way.

There’s no necessary over-planning, or rigid schedules. Just good company, a playlist, and an open road.

So, if you’re thinking about planning a road trip, my advice? Don’t overthink it—just go.