Where to start
Planning a trip of any type can be overwhelming at first, so I broke down the first baby steps I took in planning mine. I figured these things out the hard way, so hopefully you don't have to.
Step 1: Pick your time frame
The allure surrounding a summer road trip adventure, while cliche, is magical. If possible, take your trip in the wild summer months, because it opens up opportunities that wouldn’t otherwise be available. In the summer you can usually count on good weather and outdoor activities, which means camping at night and exploring the great outdoors in the day. After all, if you travel far and wide, what's the point in staying inside? Warm weather also means no bad driving conditions and gorgeous sunsets. As for picking a length, it really depends on what you’re up to and free for. While my most recent trip lasted a month, I’ve also had a blast spending a week or even a weekend on the road. Truly, with the right route, any amount of time is well worth it.
Step 2: Plan your route
You can’t have a road trip without a route! Before deciding on a route I spent many late nights overwhelmed with the endless possibilities. We ended up having about a month to get from Portland to Philadelphia, and we knew our priorities were San Francisco, Moab and Steamboat. We also wanted to dip down the the Outer Banks in North Carolina and spend some time there, so we definitely needed a good way to map out our journey. I used Roadtrippers, which lets you punch in destinations in a certain order and it shows you the time and milage it takes to get to each place. It was amazing to see how much ground we were going to cover, and mapping it out made it seem so real. Roadtrippers also lets you see what popular locations are along your route, and you can filter for hotels, camping spots, attractions and gas stations. You can see our map here.
Step 3: Find your crew
Whether it’s a group of friends or just your favorite adventure buddy, the people you go with will make or break the trip. Luckily, I had one of my closest friends along for the ride. A lot of people told me that we would definitely get tired of each other, or run out of things to talk about, but I can honestly say there was never a dull moment or a conflict that lasted longer that two minutes. I got pretty lucky with my road trip partner, and I don’t think it would have gone as smoothly with any of my other friends, so it is important to make sure you pick the right person. If you are going with a group, make sure everyone has similar motives for the trip. If half of your group wants to just have a rough direction to head in and see where the road takes them, and half the group wants a detailed itinerary, you’re going to end up with unhappy campers. That being said, it’s smart to have a balance between planners and followers, so at least one person is prepared at all times. Realistically, not everyone will be bright and shiny all the time, but as long as your group has a good dynamic, the trip will end up on everyone's list of favorite memories.