Music Up, Windows Down: Here's Exactly How to Plan a Road Trip to Remember

Updated 06/28/18
How to Plan a Road Trip

True story: My friend and I once drove from L.A. to Montreal in 48 hours. I don't recommend it to anyone—I was 20 years old and much more cavalier back then, and my pull for the all-American road trip was strong. On another occasion, I patiently sat in the back seat of a Mini Cooper SUV (yes, these exist) as my Parisian stepdad and Australian then-boyfriend argued over directions on the road from Antibes to Paris. 

My experience with road trips reaches far and wide, from the majestic coast of Big Sur to the perched villages around Monaco. That said, having traversed the country from coast to coast on two occasions now (once in a much more lengthy fashion), I've learned a thing or two about how to plan a road trip to remember—and, more important, what to avoid.

So if you're thinking of planning your own road trip this summer, there are a few basics to know: Plan your route wisely, pack for all eventualities, and have a really solid playlist that includes as much top 40 as it does Johnny Cash classics and compelling audiobooks. Beyond the basics, here is everything you need to know to plan the ultimate all-American road trip.

Step 1: Plan Your Route

Map out all the places where you might want to stop on your way and plan realistically. Apps like Roadtrippers can help you plan your routes, stops, and any meals or interesting things you should see on the way. That way, you can have a better sense of how many days your road trip should take based on how many things you want to see and the distance between each attraction.

Step 2: Have Your Car Serviced

This may sound like an obvious one, but if you're taking a relatively long road trip in remote areas, make sure you do an oil change and have your car serviced before you leave. Fill up your gas tank in advance to avoid an extra stop on departure day. These small precautions will save you many potential troubles along the way.

How to Plan an American Road Trip

Step 3: Prepare Your Entertainment

Now, the fun part. Road trips are notoriously fun, but they can also have long stretches of boredom. To keep everyone in the car entertained, prepare playlists, podcasts, and audiobooks to listen to. Think of creative games to play, quizzes to take, and anything else you could only do while stuck in a car for hours with your nearest and dearest.

Step 4: Book Flexible Accommodations

Even the best-laid plans can go awry. While you may want to check out that cute new lodge that just opened upstate or a historic property on the shores of Rhode Island, make sure to book accommodations that have flexible cancellation policies. You'll thank us when you decide to switch course last minute to see an unplanned attraction, or when a storm or accident keeps you from getting to your destination in a timely way.

How to Plan the Perfect Road Trip

Step 5: Pack an Emergency Kit

I would roll my eyes so hard when my mom packed my trunk with an emergency kit: filled with warm blankets, matches, flashlights, jumper cables, even chocolate. But these kits can be lifesavers if your car breaks down in the middle of nowhere. Think to pack anything that could help you make quick car repairs (if you're an amateur mechanic), but also remember basics like non-perishable snacks and bottled water. 

Step 6: Map Out Your Meals

Food on the road is notoriously bad (save for the once-a-year jaunt to McDonald's that never fails to remind us how good McNuggets are), so try to plan your meals in advance. There might be a lovely farm-to-table restaurant just minutes away from that dreary highway rest area and, if there isn't, that's what homemade snacks are for. Try to sample local cuisine as much as possible wherever you go.

Step 7: Don't Forget All the Essentials

Without going overboard, try to pack for as many eventualities as possible. The great thing about road trips is that a car trunk can fit much more than a standard suitcase, so bring those extra beach towels, outdoor games, and picnic baskets. You never know when you'll want to throw an impromptu bond fire barbecue on the beach, so better be prepared.

Voyager Leather-trimmed Printed Canvas Weekend Bag
Eddie Harrop Voyager Leather-Trimmed Printed Canvas Weekend Bag $850
Lalita Crocheted Cotton Swimsuit
She Made Me Lalita Crocheted Cotton Swimsuit $260
Pembroke Beach Umbrella
Serena & Lily Pembroke Beach Umbrella $288
Capri Beach Towel
Serena & Lily Capri Beach Towel $38
Pamela Cat-eye Acetate Sunglasses
Illesteva Pamela Cat-Eye Acetate Sunglasses $220
Leather-Handled Picnic Basket - Crate and Barrel
Crate & Barrel Leather-Handled Picnic Basket $70

Next up: 26 essential (but oft-forgotten) items on a road trip.

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