How to Go On a Solo Cross-Country Road Trip Without Getting Lonely

Going on the road alone is exciting—but can be daunting, too. Smart planning ensures you get much-needed social time.

Bram Berkowitz
Dec 31, 2019 · 14 min read
Me at Rocky Mountain National Park. All images provided by the author.

To some, the thought of going on a cross-country road trip around the United States is the dream: the open road without a familiar place or person in sight. That feeling of being removed from normal life. An adventure.

A solo road trip is a way to get off the grid, to do something spontaneous, to challenge yourself, and have lots of fun. But let’s be realistic: To many of us, it can also seem downright scary.

We may not admit it, but most of us enjoy the routine of our 9-to-5 jobs, the friends we’ve had forever, and that exact same cup of coffee every morning. I am one of those people. I liked working and grew up in the bustling city of Boston. I valued my career and have a great group of friends.

But as I began to get older, I started to worry that I might never see the world. Sure, I had been on plenty of family vacations, gone on birthright to Israel and studied abroad in Madrid, Spain during college. But I had always wanted to see the U.S. I felt like I should really see and experience the country I was born in at least once in my life.

However, after finally deciding to take the leap, I soon realized that I would be on my own. When I pitched a few of my friends on the idea of joining me, most of them quickly said “no”—they had other obligations, and either couldn’t or didn’t want to take off months to go with me.

Wouldn’t I get lonely being on my own for three months? Who would I talk to? Wouldn’t it be more dangerous not having someone by my side? Wouldn’t the driving be too much to handle? I almost didn’t go until I realized just how much of a golden opportunity I had.

I was ready to quit my job; I had enough money saved up to cover a few months of unemployment; I had no apartment lease hanging over my head and no real responsibilities to anyone other than myself.

No, if I was going to travel, now was the time. And I did.

I hit the road on August 9, starting in Toronto, Canada, and for three months made a counter-clockwise loop around the U.S., with a little zig-zagging mixed in.

I hit Chicago, Colorado, Wyoming, Montana, Idaho, Utah, and then went out to California. Then I came home along the bottom of the country, passing through states like Arizona, New Mexico, Texas, and Louisiana.

Overview of my trip.

Now, having completed the trip, I can truly say that it was a great experience.

There were certainly bumps along the road and some weeks that were better than others, but there is no better way to test yourself than by traveling alone.

For all of the downsides, there are advantages, too. You get to make your own plan, go where you want to go, and you have the power to stay or leave anywhere at anytime. Pure unadulterated freedom.

I will admit, however, that getting lonely on a solo road trip is a real thing.

In this article, I will walk you through some strategies for how to plan and go on a solo cross-country road trip. If done properly, you will be able to enjoy the challenges and excitement that come with a trip like this, without getting too lonely.

Planning the Overall Route and Duration of Your Trip

The first thing I did was pick places I wanted to visit. I knew I wanted to head West and see some of the states that seem foreign to an East Coast person like me: Wyoming, Montana, and Idaho. I also knew I wanted to visit some national parks. So there were some easy places I could begin with. And I definitely wanted to go to California and drive down the Pacific Coast Highway through most of the state.

Knowing that it was best to visit the national parks before it gets too cold, I decided I would start with them. I wasn’t going to leave until August, and if I waited too long to get there, it would get too cold, and some of the parks might even be closed for the season.

This ultimately led me to decide on a counter-clockwise loop around the U.S., starting with the northern national parks and then going to California. Then it naturally made sense to come home across the bottom of the country.

The other way I chose places to visit was to consider where I had friends and family. During my trip, I ended up staying with cousins scattered on the East Coast; Washington, D.C.; and California. I also visited various friends in states such as Philadelphia, Chicago, California, and Texas.

Not only was it great to catch up with friends and family I don’t always get to see, but these are also often places to crash for a few nights.

Then you need to consider other routing options. For example, you can decide that you want to see almost every state and make plans to try to pass through each and every one, or you can pick a bunch of places you want to go and spend more days in places you want to see. There is no wrong choice here: It depends on your preference. But you need to consider the type of trip you’d like to have.

I chose to do the latter because I didn’t want to be driving every day, and there were states I had no desire to visit.

Next, I had to figure out a timeline.

Luckily, some of my cousins had gone cross-country, so I was able to consult them on how long they spent traveling when they did their trips. They told me their trips had lasted six to seven weeks, but felt a little rushed—they were driving pretty much every day.

After doing a very general overview of how many days I thought I wanted to spend in some of the main places I wanted to go, I set a loose timeline of two-and-a-half to three months for the trip.

This also helped me do some loose budgeting to make sure I could afford the trip and wouldn’t run out of money halfway through.

Make An Actual Guide

Now, you don’t need or want this guide to be a strict timetable. For example, you don’t need to plan to be crossing the Utah state line on October 24 at 10 a.m.

But create a list of where you plan to visit and estimate how many days you think you want to spend in a certain place. This will help keep you on track, particularly as money can become become an issue and the traveling can become tiring. If you have your trip outlined, you can use that information to make changes as you go.

I used a Google Doc to make a list of places I planned on seeing, rough dates, and the number of days I wanted to stay. I also tried to include driving times in the guide because that’s an important factor, given the amount of time you will spend in the car.

Part of my guide.

As you begin to lay out the guide, try to plan for a visit to a friend or relative at least every few weeks. Driving on the open road can get lonely, so it’s good to have these visits mixed in with your other destinations along the way.

I found it ideal to have a week or two on my own and then a few days with friends or relatives.

Toward the beginning of my trip, I saw nine national parks in Wyoming, Montana, Idaho, and Utah. I didn’t really know anyone in these states, so I had about a three-week period without seeing anyone familiar, and while I met lots of people at the national parks, it definitely started to get lonely toward the end of that stretch.

A good way to prevent getting lonely on a long stretch is by asking friends or family to come meet you for a week or weekend. They may not be willing to take two or three months off to do an entire trip with you, but a long weekend or maybe even a week is often appealing and quite manageable.

That’s another reason to get your trip outlined at least a month or two in advance: You can give friends and family time to plan. I definitely could have done a better job at this. Still, I was lucky enough to coordinate two weekend trips with friends during my trip.

Fortunately, one of my friends from college said he was going to be in Toronto around the time I wanted to depart. While that wasn’t originally on my list, it was sort of on the way to my first big destination in Denver, Colorado. Another one of my college friends wanted to go along for that, and I had never been to Canada, so we ended up making a weekend of it. This became the first weekend of my trip.

Having done that, I would recommend making your first weekend a casual visit with friends. It’s a great way to ease into the trip with just a normal weekend away. The only difference is when the weekend is over and everyone goes home, your real trip is just beginning.

Another weekend I set up was a golf weekend in Palm Springs, California with three of my other college friends. This weekend had already been somewhat in motion, and I was able to work things out so it marked the halfway point of my trip.

Having this middle point was super helpful because it kept me moving and on schedule. I always had my eyes on that weekend, which turned into a key deadline.

When you have no deadlines or timestamps, it’s easy to lose a sense of urgency. Some people don’t want any timestamps or deadlines — I met plenty of them on the road — but for first-time travelers, I think this kind of milestone is helpful.

Although I had that middle date firmly implanted in my schedule, things changed all the time. I would stay in one place a few extra days longer than normal, one place shorter than expected, and some places I skipped entirely.

Listen to your gut and go with the flow — a road trip should never feel like a 9-to-5 schedule.

Stay at Hostels

I set up a little camper cot in the back of my minivan and stuck to this strategy in the beginning, especially while I was touring the national parks and some of the more rural states.

The back of my minivan. Photo by the author.

However, I quickly learned that you won’t meet a lot of people by sleeping in Walmart parking lots. The easiest way to meet people in the major cities was by staying in hostels.

Hostels are less expensive than hotels. Typically, you get a bunk bed in a dormitory and share a common bathroom, lounge, and sometimes a kitchen. Dorm rooms can be mixed or single-sex. Some have private rooms available for a higher cost.

Hostels are an extremely popular way to travel for the common backpacker in Europe. Even though they are less known in the U.S., almost every major city has one. They are a bit pricier in the U.S. than Europe, but you can typically get a bed for $20 to $40 per night.

Many of the hostels provide breakfast, have laundry machines, and are situated in the heart of popular downtown areas, making them useful pitstops and fun places to meet people and go out at night.

I won’t lie: Some of them aren’t always the nicest accommodations in the world, and once in a while you get stuck in a dorm room with a person that might have a diagnosable snoring problem.

Nonetheless, I enjoyed most of my nights in hostels. I had an absolute blast at hostels in Bozeman, Montana; San Diego; Austin, Texas; and New Orleans. Every time I stayed at one in a major city on the weekend, it was easy to meet people that wanted to explore the city and hit the bars at night. Some hostels (New Orleans!) even ran bar crawls and other activities once a week or every night.

Another great thing is that most of the people staying in hostels are traveling like you, so not only do they understand the lifestyle, but, like you, they’re probably only staying in a city for a few days and trying to soak up every minute of it.

And because hostels are so popular in Europe and other parts of the world, many international travelers choose to stay at them when they travel in the U.S. I met a nice mix of people from the U.S., as well as international travelers, which is something I didn’t quite expect—it was a nice surprise.

Do keep in mind that you are sleeping and staying with strangers, so always lock up your valuables — lockers are usually provided — and show caution if something doesn’t feel right.

I definitely met some memorable people and feel like the trip would not have been the same without these hostel visits.

Problem Solving on the Road

This isn’t the end of the world, and you probably won’t get robbed or kidnapped, but something unexpected might occur, and you might need to adapt on the fly. This happened to me a few times throughout my trip, and I was forced to alter my plans and adjust my schedule.

One of those situations occurred while I was visiting my uncle in Los Angeles. Toward the end of what had been a great visit, I started to come down with a sore throat. My tonsils were red and had started to swell; I was tired and feeling very weak. My uncle gladly offered to allow me to stay at his place for however long I needed.

I was lucky because I could stay with a close relative, but I was overall nervous because I was supposed to go to San Diego and then meet up with my friends in Palm Springs later that week.

On the recommendation of my mother, I got my throat checked out at a local Urgent Care — on Hollywood Boulevard no less — and it turned out I had strep throat. I got it treated, but chose to stay at my uncle’s house the rest of the week to recover. And I am so happy I did. I cannot imagine having to stay at a hostel or sleep in my car with strep throat.

Now, I got extremely lucky being able to stay at my uncle’s house. But this experience taught me to keep a separate pot of money stashed away in case of emergencies. Not only was the Urgent Care visit an out-of-pocket expense, but if I hadn’t been at my uncle’s, I would have at the very least forked over the money for a nice motel, hotel, or Airbnb.

If you get sick on a trip, you want to put yourself in the best possible environment to recover as soon as possible.

Also, you do need to be prepared to be flexible with your schedule.

After my uncle’s house, I was supposed to head down to San Diego before meeting my friends in Palm Springs. But because I was in no shape to travel, I stayed at my uncle’s house all week, then went to Palm Springs directly. I went to San Diego afterwards because I really didn’t want to miss it.

Palm Springs with friends. Photo courtesy of the author.

Another time I chose to adapt came toward the end of my trip. I had been planning to stop by Jacksonville, Florida on the way home and see one of my close friends who lived there.

But due to all of the shuffling around that happened from getting sick and a few other stops getting sidetracked, it turned out that he would be away both weekends I would be near Jacksonville. We both acknowledged that we would just have to catch up some other time.

Then I had another decision to make. I was in New Orleans at the time. It had been more than two months; I was tired and the travel was starting to get to me.

I could keep going to the southeastern part of the country. But now there was nothing I was dying to do there. Even though I did want to see the Carolinas and states like Georgia and Alabama, I knew I was ready to start wrapping things up. I left New Orleans, headed up north, and skipped the southeastern part of the country.

Sometimes, you just have to know when you’re spent and accept that you may not get to see everything.


But understand that you may be forced to travel alone if you really want to make it work. People have jobs, are in relationships, or may not have any interest in traveling with you. But that shouldn’t stop you from satisfying your itch.

Traveling alone is a great way to challenge yourself, broaden your horizons, meet new people, and try new experiences.

Follow these steps to make your solo road trip an unforgettable, independent experience without the loneliness:

  • Make a plan. Pick places that you want to go that have activities you want to do and sights you want to see. Go in with a purpose.
  • Try to visit a friend or relative every few weeks. Although it’s not hard to meet people, hanging out with a familiar face will be nice every so often.
  • If you can’t stop by friends or family throughout your trip, invite them out for a week or a weekend — something that is more manageable for their schedule.
  • Find hostels to stay at in major cities. They are cheap and a great way to meet people.
  • Don’t be afraid to change your schedule. If you’ve met a great group of people and are having a blast, stay a few extra days. If you are tired of a place, move on.
  • Know your limits. Sometimes you need a break or may just be ready to come home. It’s OK to know when it’s time.

Better Humans

Better Humans is a collection of the world's most trustworthy writing on human potential and self improvement by coaches, academics, and aggressive self-experimenters. Articles are based on deep personal experience, science, and research. No fluff, book reports, or listicles.

Bram Berkowitz

Written by

Full-time journalist and Content Strategy Lead at GoingVC writing about business, the economy, startup culture movies, sports and much more.

Better Humans

Better Humans is a collection of the world's most trustworthy writing on human potential and self improvement by coaches, academics, and aggressive self-experimenters. Articles are based on deep personal experience, science, and research. No fluff, book reports, or listicles.

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