Tips for Traveling with Friends


Summer is officially under way, which means you’re probably day-dreaming of exotic locales and fruity cocktails with entirely too many garnishes. No? Just me?

Along with the standard vacation, I hope you’re also considering taking a little trip with friends. I’m lucky enough to have been able to make this type of getaway an annual tradition. And while I know that may not be realistic for everyone, I highly encourage you at least consider it if you happen to have an extra vacation day floating around.

But, like planning any other trip, traveling with friends comes with its own set of challenges. I’m coming up on my third go-around, so here are my tips for facing those challenges head on.


(1) Choose your [Travel] Squad Wisely

A good trip begins and ends with your travel companions. Even in the worst conditions (think travel delays and bad weather) can be turned around if you’re with the right people. Arriving at the best combination unfortunately might take time, but it’ll be worth it.

  • Start with a big group.
    A few years ago, I was lucky enough to take a couple of big road trips with large groups of women. If you were in a sorority or something similar, you probably had those experiences, too. Those can be really fun, but they can also be really informative. While there may be 10 or 20 people in your group, you will quickly figure out who you work well with, who you gravitate toward.
  • Don’t feel like you have to invite everyone.
    While I’m all for being kind to everyone, it’s just unrealistic to think you can (or should want to) be friends with everyone. And beyond that, not even everyone you’re friends with is going to be a good person for you to travel with. THAT’S OKAY! It will turn out better for everyone if you don’t force something.
  • Find the right combination of travel styles.
    I am admittedly an over-planner. My friend Liz, on the other hand loves throwing caution to the wind. Our third musketeer falls nicely in between, and is perfectly content either way. And together? The perfect combination. I make sure we have big things covered like places to stay and dining reservations for busier spots, but having Liz ensures that I don’t plan out every minute we’re together and having Erin there calms us all down when things don’t go as planned.


(2) Agree on a Location TOGETHER

In deciding on each of our destinations, there are obviously a lot of practical factors like cost and travel options. But beyond that, everyone has places they went to visit and others that have zero interest in. Have no fear! Even if it takes going through a long list of places, it IS possible to all agree on one – provided everyone is willing to compromise. And if none of you will bend, draw straws and plan to visit them all!


(3) Make Lists

Once you decide on a place, the planning can begin! It’s completely normal for every person in your group to have different priorities for the trip. Have everyone rank their lists and combine them. Then all you have to do is go down the list – all the 1’s, then all the 2’s, and so on. Everyone will get to do at least a few things on their list and no one will feel gypped. On a related note, be willing to go your separate ways if need be. On a recent trip to Miami, one of us got a massage, while another one swam in the ocean, while another lounged by the pool. No one said you have to spend every minute of the trip together!


Now, GO HAVE FUN! Traveling with groups can always be a little stressful, but remember that you’re there to enjoy yourself and spend quality time with people you care about. Once you find your travel buddies, decide on a place, and prioritize your activities, just enjoy yourself.

Speaking of, I feel a mid-year getaway coming on…


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