How to Choose a Travel Partner for an Unforgettable Road Trip

The right—or wrong—friend on a travel adventure can make or break the trip.

The Road Trip: is there any more iconic American way to travel? The open road, a great playlist and, of course, a buddy. It’s the latter, though — the travel companion — that can really affect the journey, for better or worse. That’s why it’s very important to consider who you want to bring along with you on your next road trip adventure.

I’ve had my share of road trips, including one that seemed like a dream of a plan. Three work friends – all full of fun – headed on a three-day hiatus from San Francisco to Napa. The weather was beautiful, we had a convertible, and a reservation at a destination restaurant. Maybe I should have been tipped off to the potential problems when one friend pressed to stay at a luxury resort and the other thought we could all share a room, which leads me to the first important road trip rule when it comes to friends.

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  • Consider finances.

Do you like to splurge on accommodations or go the budget route? I’m somewhere in between. I don’t want to break the bank, but camping, “motels” and room-sharing is not for me. I need a good bed too. On this particular trip, we compromised and chose a Hilton (not as luxe as one friend wanted, but not as low-budget as the other preferred). I ended up sharing a room with the penny-pincher (separate beds) but felt a little resentful about it. Not a great scenario.

The trip had some other snafus as well. One friend doesn’t drink – not a problem at all, or so we thought. In fact, since we were visiting wineries in Napa, we had a dedicated sober driver. What we didn’t consider, though, was that our sober friend might start to get antsy and bored as the pair of us sampled wine, got tipsy, and felt perfectly content wiling away a couple of hours at tasting rooms. After a few winery visits, she became noticeably irritated — not surprisingly — and we ended up cutting the tastings short. The moral here?

  • What is your agenda, and does your travel companion’s sync with it? 

My friend and I assumed that a trip to Napa meant mostly wine-tasting (an easy mistake, right?), but our other friend would have preferred more variety. While there should always be some element of surprise and spontaneity on a road trip, it’s still critical to have at least a general sense of what your plans are—so everyone has a good time.

Mealtime was tough too. One friend is a vegetarian with other dietary restrictions, while two of us eat anything. Fortunately, Napa had a pretty good mix of options, but some of the restaurants I was really looking forward to weren’t aligned with her diet. I used to be a restaurant critic for a newspaper, and can plan an entire vacation around dining, so I was pretty bummed to jettison a couple of places I’d been longing to try, which brings me to the next road trip rule:

  • Don’t discount mealtime. 

Food is an integral part of travel — and the type of food and how much you want to spend can quickly become a sticking point with your road trip bud if you haven’t talked about it beforehand.

Another issue — a significant one — had to do with where we were in our lives. One friend was still grieving over the loss of a former partner while two of us were in happy marriages with children. As a good friend, I was there to listen to her, and she had a lot to get off her chest. That’s what friends are for — and I never would have brushed aside her feelings. However, I was looking for a good time — a weekend sans husband and kids to just blow off some steam, and that became very hard to do in her presence. It just didn’t feel ok to be too happy. Lesson?

  • Not only should you consider your travel partners’ unique personalities and quirks, but where you all are personally at the time. 

One person may be in healing mode, another in happy-go-lucky land and so on. Before you head off into the sunset together, consider your state of minds and whether they’re the right match for this particular road trip.

Road trips are meant to be a blast and shared with the right person (or people), they can be. That’s why the people with whom you embark on a travel adventure must be chosen carefully. Some friends lend themselves to rollicking escapades, others contemplative reflection. What do you need from the trip, and who will help you best accomplish it? Traveling truly is about exploration of place and self, and the people who we’re honored to bring along for the ride can make all the difference. Don’t just default to your “best” friend but consider what others have to offer. You may end up having the time of your life, experience a huge epiphany, or deepen a bond with someone you may not have otherwise. A travel adventure can be boisterous or meditative, or a little bit of both. It’s your choice, so choose well!




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