How to Have the Road Trip of a Lifetime

It was about 5 years before I decided to move to NYC, when I and my four best girlfriends decided to pack up and drive there. Two speeding tickets, one flat tire, and many hours later, we arrived in the big city. By then we’d realized that one girl forgot her wallet, the other her contacts. Two of us forgot pajamas. We all wanted to hook up our phones, but the car we rented didn’t have bluetooth so we had to resort to singing and “i spy” games (trust me — that’s not always a good thing!) It was a fun and memorable time, no doubt, but there are a few things I would’ve done differently had I read an article like this beforehand.

No matter the time of year, I have the itch to travel and explore. But in case you need a reason to go on a road trip, here are a few good ones:

1. America is a great country to road trip in because there are parts of the USA that are warm at any point in the year, making it a great year-round vacation destination.
2. If you’ve had your fill of theme parks and crowded beaches, why not channel your inner Jack Kerouac and plan a long cross-country road trip? If you haven’t already read or listened to his famous novel, “On The Road”, today’s a good day to download it and get inspired.
   

Maybe you’re just ready for a different type of vacation — one where you can see the country, bring your dog, and meet people along the way.

Or maybe you just want to avoid the hassles of air travel — especially with kids. A road trip is the perfect alternative.

You could even do a themed road trip and hit up the best surfing beaches in America, or the best caves.

It’s also a great trip to take if you need to be alone and clear your head. Listening to music or audiobooks and watching the open road go by can be its own form of meditation and therapy.

Or, if you’re wondering how your relationship with your boyfriend will stand up to real life, a road trip is the best on-demand relationship test. With all that time to talk, and all the situations you’ll experience together, you’ll learn how you two interact when situations are stressful. And hey — if he turns out to be a jerk, you can always drop him at the nearest bus stop and keep going!

Either way, now’s the time to hit the road in a way that would make even Kerouac proud. To do this, here’s a guide on how to do road trips the right way:

Let Your Apps Guide You

From tunes to eats, use your phone or tablet along the way. Here are some great apps for the road:

Packing

PackPoint will ask you to answer a few questions — Who are you? Where are you going? What for? And when? It’ll then gather data on the weather, cross-reference your activities and tell you what to pack. Road trips call for comfortable clothes, snacks, walking shoes and sunglasses!

Exploring

If you’re not much of a planner and you like to be spontaneous as you drive through new cities and towns, Field Trip is your guide to interesting and hidden things around you. It tells you the (honestly, really fascinating) history behind buildings near you, what great attractions are nearby, where to eat within a short walk… it’ll even tell you where celebrities live and show you pics. It shows everything on a map, with color-coded cards along the bottom that have useful pics of nearby places. It pulls in all the info you need, including Zagat reviews, hours, prices, etc. and gives a great context to an area, so you can stay spontaneous and learn about the places you’re visiting while on-the-go.

Whether you’re planning ahead or you find yourself on a different route than expected, use an app like Along The Way (iPhone) and On The Way (Android) to map out your route and the restaurants, gas stations, tourist attractions and hotels along the way.

Entertainment

Did you know that you can download your favorite books on WiFi via the Audible app (here’s a free trial) before you head out? You can listen to them with headphones, or share the experience with the whole car over the speakers. I, of course, recommend downloading the 50th Anniversary edition audiobook of On The Road (narrated by Will Patton, one of the best narrators out there) and listening to it while driving. Here’s the synopsis, in case you’re not already familiar:

Few novels have had as profound an impact on American culture as Jack Kerouac’s On the Road. Pulsating with the rhythms of 1950s underground America, jazz, sex, illicit drugs, and the mystery and promise of the open road, Kerouac’s classic novel of freedom and longing defined what it meant to be “beat” and has inspired generations of writers, musicians, artists, poets, and seekers who cite their discovery of the book as the event that “set them free”.

Based on Kerouac’s adventures with Neal Cassady, On the Road tells the story of two friends whose four cross-country road trips are a quest for meaning and true experience. Written with a mixture of sad-eyed naïveté and wild abandon, and imbued with Kerouac’s love of America, his compassion for humanity, and his sense of language as jazz, On the Road is the quintessential American vision of freedom and hope, a book that changed American literature and changed anyone who has ever picked it up.

Food!

It’s not a road trip without snacks. But, only eating junk food will leave you feeling bloated and blah. In addition to your go-to sweet snacks, pack a variety of nuts, granola bars, dried fruit and wheat-based crackers. When you stop for something more substantial, plan ahead using an app like Clean Plates or Food Tripping. Clean Plates lets you browse nearby eating options, and you can even filter by cuisine, price and diet. Food Tripping focuses on finding local, sustainable stops like farmers’ markets, juice bars and green eateries.

It may be tempting to eat junk food while on the road, but in order to keep your strength (and mood) up, it’s more important than ever to find healthy plant-based meals while on the road. Thankfully, HappyCow is the perfect app for this. It caters to herbivores and healthy eaters on the go, letting you search by area for healthy restaurants wherever you’re traveling.

Other Essentials

One of the nicest things you can do for your parents (no matter what age you are), is use a postcard app to send your family and friends postcards along the way. Just take a great photo, write a quick message, and the app will print and mail it for you for between $1 and $3 per postcard, depending on the app you choose.

Need a bathroom ASAP? If this is the classic problem of the road trip, Sit or Squat is your best friend. This app will locate the nearest restrooms, rate their cleanliness, and make your pit stops quick and easy.

Conversation Starters

Excitement and music may get you through the first few day, but you can prepare for inevitable conversation lulls by bringing along a few ice-breaking activities. For example, try conversation-starter cards made by funny-girl Mindy Kaling to ensure hours of girl-time gabbing.

Making Memories

All you need is each other to make memories. But, it doesn’t hurt to have something to record them along the way. Don’t forget to pack must-have items like a journal and pen, address book (so you can easily send postcards from each destination) and camera. Capture every moment with a GoPro mounted to the rear view mirror or planted in the sand when you stop to relax on the beach.

Of course you also can take plenty of selfies and use a group hashtag to let others follow your adventures. Consider downloading a picture-pretty photo filter app like A Beautiful Mess to personalize all of your photos.

Expect the Unexpected

As Sal and Dean found out during the book, even the best-planned road trip will never go completely as expected. And you know what? That’s perfectly okay. With this in mind, plan on a variety of little annoyances and delays to pop up during your trip. This mindset will help keep you on an even keel. Also, just because things like road construction, detours, headaches and flat tires may throw a wrench into your plans, this doesn’t mean you can’t prepare for at least some of the delays.

Although there will be plenty of pit stops along the way, you don’t want to find yourself empty handed and in a pickle without a city in sight. Be sure your car is well-tuned and you have at least one spare tire in the trunk. Carry a well-stocked first-aid kit filled with plenty of Band-Aids and Advil. Before you leave, gather the girls and make an emergency kit. In addition to the obvious items—a spare tire, AAA card, flashlight and an actual paper map—use small plastic tubs to collect the often forgotten essentials for the trunk. Some necessities include:

• Several water bottles (about 2 liters per person)
• Blankets and sweatshirts
• A portable cell phone charger and one that plugs into your car
• Flares
• Pepper spray
• Running shoes and socks
• Hand sanitizer & tea tree oil

To be sure you don’t have any unexpected run-ins with Johnny Law, take some time to become familiar with the driving laws in each state you’ll be passing through. New York laws differ from California, for example. This will help you to be as safe as possible during your journey and avoid any unpleasant traffic tickets.

Even after hours of planning, you’ll likely find yourself lost or hours from you original destination at least once on the trip. Embrace it! Enjoy this time with your girls on the open road with just the radio on and the wind in your hair. You may even stumble upon something better than you imagined.

Hit Some of the Same Highlights as the Novel

If your planned route will take you to some of the same spots that were featured in Jack Kerouac’s “On The Road,” try to experience a few of the same activities as the characters in the book/movie.

If you end up in the mile-high city, pretend you are Sal Paradise for an afternoon and enjoy a baseball game at Coors Field. If you happen to come across a neighborhood pickup game while you are in Denver, you can stop to watch it too — just as Sal did. Now that sounds truly script-worthy!

Enjoy Yourself!

The best way to get the most out of a cross-country road trip is to slow down and take your time. Just like the main protagonists did in Kerouac’s book, a road trip should not involve seeing how long you can be behind the wheel before your eyes begin to glaze over. A road trip is not about where you are going, but how you are getting there; this means it’s okay to spend a few hours lingering over strawberry shortcake and coffee at a roadside diner, and stopping to check out the world’s largest ball of string or hugest frying pan. It’s amazing how much more you will see when you’re not in a hurry.

Want more? Check out these great American road trip destinations, and here are some more great products for your next road trip:

This is a sponsored conversation written by me on behalf of Audible. The opinions and text are all mine.