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How to Plan the Best Road Trip and the Top Road Trip Destinations

Adventure Team | Jan 10, 2022

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How to Plan a Road Trip

Once you’ve picked from the variety of road trip destinations the USA has to offer, you need to start planning. Knowing where to begin in the planning process and when you’re ready to hit the road can be difficult, which is why we’ve made it so easy. Below are the steps to follow before starting your journey to one of the best road trip destinations in the USA. When selecting a location from our list of recommendations, you can’t go wrong.

Rv on a road trip in the mountains.

1. Select the Right Vehicle

You may have thought to consider the number of travelers and amount of luggage, but don’t forget to consider your activities and destination. For my most recent road trip in Scotland, my husband and I opted for a car. However, once on the adventure, FOMO set in when we realized we neglected to consider a camper van. We longingly watched adventurers set up camp on the breathtaking cliffs in Orkney and along the coast on the North Coast 500. We won't miss out on opportunities like that again.

2. Keep Two Separate Bags

One perk of a road trip is that all of your belongings are with you at all times. Even so, we always pack a second "Go Bag. " You never know what may greet you around the next bend of your adventure. You’ll want your camera, charger, hiking shoes, and bathing suit within arm’s reach to grasp the spontaneity of your road trip without having to dig through your luggage and toiletries on the side of the road. We sometimes make a list to help ensure we pack everything we could possibly need.

3. Pack Snacks

Maybe tip two should mention three bags. Always pack snacks! If you pull over for a swim or sightseeing, you’ll be thankful you have snacks for an impromptu scenic picnic. Maybe you got off schedule during the day but want to make it to your destination to watch the sunset. Having snacks will allow you to power through any last-minute changes in your trip without a hangry travel partner.

4. Use Social Media

Many adventurers limit their social media and disconnect on vacation, but don’t underestimate the power of social media to give you a local experience. We were a bit too flexible with our time in Orkney. We would have missed the Yesnaby Castle and a local winery and painter that were less than a mile from our accommodations had it not been for Instagram.

Search local places and use the map feature on Instagram to find recent posts in the area or ask for recommendations on Facebook to get a more local experience.

Traveler on an arctic adventure to see a real-life glacier.

5. Have A Plan But Be Flexible

Again, we love to plan! We rough out a draft of our journey before we leave, deciding on what route, what cities, and we secure big-ticket activities.

We download all of our apps to be prepared, including Gasbuddy, Roadtripper, VanLife, etc. And that’s it — from there, we let the adventure decide the rest!

During our road trip through Scotland, we discovered the world's best fish and chips along with a must-have Fisher and Donaldson fudge doughnut for dessert after chatting with a friendly local in St. Andrews. And our distillery guide in Speyside invited us to a lovely afternoon tea with his kids, where we learned about lambing in the Highlands.

The balance of detail and spontaneity is what makes a road trip unforgettable. Plan enough to be prepared but let the rest of your adventure unfold one mile at a time.

6. Consider Road Trip Travel Insurance

Just because you're traveling on the road doesn't mean you won't get sick or hurt.

If you're investing a material amount of money in your trip expenses for a road trip here in the U.S., consider purchasing a trip protection plan like our Get Away USA plan. It allows you to customize your plan so you buy only the benefits you need. Why pay for baggage protection if you’re traveling by car?


What to Pack for a Road Trip

Knowing what to pack for a road trip before you leave for your destination is crucial. Roadtrippers like yourself need the right food, equipment, clothing, and much more if you plan on having a good time traveling in the USA. Look at what the weather will be like and pack clothes that will prepare you for it, be sure to bring chargers, batteries, things to sleep with, a tent if necessary, etc. And, of course, don’t leave home without an insurance plan that will have you covered if things go south.


Best Road Trip Destinations

It’s a big ol’ world out there, and it’s difficult to see it all. That’s why some of us prefer to jump into our cars and take to the road, soaking up scenery and culture at highway speeds!

So, if your idea of a perfect holiday is hitting the open road in your car, you’re in the right place.

Here are my picks for the three best road trips in the USA.

1. Route 66, USA

  • Distance: 3,950 kilometers
  • Highlights: Chicago, the Grand Canyon, Barringer Crater

I don’t think it’s an exaggeration to call Route 66 the king of road trips. I mean, it’s the most famous route on this list by quite some margin and probably always will be!

Running from Chicago to California on the Pacific Coast, Route 66 is a behemoth road trip, taking in some of the best American scenery and culture.

At almost 4,000kilometers, Route 66 runs through some incredibly varied states, including Illinois, Missouri, Arizona, and California.

2. Big Sur, USA

  • Distance: 140 kilometers
  • Highlights: Julia Pfeiffer Burns State Park, Point Sur State Historic Park, Los Padres National Forest, Partington Cove, Bixby Bridge

Big Sur is probably the second most well-known U.S. road trip after Route 66. Confined to a small section of California, Big Sur follows Highway 1 through California’s central coast between Carmel and San Simeon.

Yes, it’s a short road trip, but 140 kilometers is all you need when you’ve got such a beautiful coast packed with painfully pretty beaches, grand redwood forests, striking canyons, and bedrock cliffs.

3. The Road to Hana, Hawaii

  • Distance: 100 kilometers
  • Highlights: Maui Tropical Plantation, Haleakala National Park, Koki Beach, Hana Lava Tube, Hanawi Falls, Ho'okipa lookout

The Road to Hana is a short road trip of under 110 kilometers, but it includes some of the best scenery Maui offers.

The road trip starts in Kahului and runs east along the coast towards Hana. While it starts pretty easily, the road quickly grows more intense and erratic. By the end, you’ll have enjoyed (or endured) 600 tight twists, 50 narrow single-track bridges, and more blind summits and corners than you thought were possible.

The white knuckles are more than worth it, though, as the road trip passes through lush jungle, cascading waterfalls (weather permitting), and steep cliffs.


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