Traveling Well With Others

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Vacationing is my happy place! I love to travel, so much so that I would venture to say that I need to vacation regularly in order to stay sane. And nothing makes me happier than sharing my travel bliss with my very favorite people. The first time my husband saw Times Square or the Las Vegas strip all lit up at night, I was right at his side taking in his overwhelmed joy and fascinated awe as if they were my own. To me, the magic is only magic if you’re sharing it.

My husband’s first trip to New York City

However, every well-intentioned vacationer learns the difficult lesson that no matter how much you love your friends and family, not everyone travels the same! I learned this lesson as a Spring Breaker in my early 20’s. I had a lot of friends, I was dating somebody who had a lot of friends, so we decided to travel with all of our friends: his, mine, and some of theirs. What could go wrong?! Well, by the end of the week, I wasn’t really speaking to anyone else on the trip, and the dating break-up happened not too long after. I wore myself out trying to plan with and for very different groups of people, didn’t factor my own (or anyone else’s) wants or needs into the trip very well, and ended up unable to just relax and let the good times roll.

Since then, I’ve managed to take many wonderful vacations ranging from traveling with people I barely knew, to one or two close friends, to up to a dozen mixed family and friends. Here are some of the essentials I’ve found for traveling well with others:

Know your fellow travelers

For every moment of excitement I have in planning a vacation, my husband has a moment of anxiety. After all, excitement and anxiety are essentially the same emotion. The only difference is whether we express it in the positive or the negative, right? Inevitably, two weeks before every vacation, his anxiety peaks and he decides not to go. In the beginning of our relationship, I would panic, scream that everything was already paid for, not talk to him for a day, and try to figure out what the heck to do until he calmed down enough to get back on the travel wagon. Now, I know him. I expect this. So, I stay calm, quietly remind him that everything is already paid for, and try to find ways to turn his anxiety into its happy sister excitement. For him, this means helping him learning about the area, showing him the money shots from travel blogs, filling him with enough information to make the unknown seem a little more known. For him, feeling secure means having a slight lay of the land. I think most people can relate to that.

I say all this because it is equally important for you to know your fellow travelers and know their interests and limitations. Nothing kills the vibe on a trip quicker than misaligned travelers in the same group. So, think carefully about where you want to go, what sorts of things you’ll want to do there, and who would be a good fit for those things. Consider what your fellow travelers like and don’t like, what makes them uncomfortable, and what opens them up to really enjoying themselves.


My mom likes to travel as much as I do. That said, she is much more of a “tourist” than I am. She likes to travel the beaten path, do lots of souvenir shopping, and ask lots of questions. Under the right circumstances, this can make for a perfect trip for us both! My favorite example, I asked her to come to New York City for a job interview with me back in 2000. I was a nervous wreck, so I needed her support. Neither of us had ever been to New York, so we decided to make a weekend of it – in true tourist form. We got on the double-decker bus, took in all the sites, and had an absolute blast! As it turns out, the double-decker bus is now my “go to” favorite for touring with anyone I take to the city for the first time. It’s the perfect way to see everything on your own schedule, because the busses travel a loop of the landmarks on a 20 minute schedule. So you can stay on the bus if you aren’t interested in something, hop off the bus at the sites you want to explore in more depth, and hop back on whenever you’re done at a particular place.

I’m sure you didn’t come to be the awesome person that you are by only surrounding yourself with like-minded people. If you’ve been accumulating friends and family over the course of your life, you’ve probably got a mix of folks you love who are similar to you in some ways, but very different in others. If you’re going to travel with them, you have to be open to doing some of their things in exchange for wanting them to do some of your things. If you approach the compromise with an open mind, you’ll get the best travel benefit of all – the chance to really learn about yourself and others by seeing and trying new things. By being open to my mom’s style of travel, I’ve discovered a favorite travel method that is a huge hit with everyone I’ve shared it with since.

Roll with the punches

Flexibility is also crucial in travel, because unexpected things happen. My husband and I did a destination wedding at Sandals Grande Antigua , and I knew my luggage might get lost. So I carried on the one thing I couldn’t replace when I got there – my dress. Sure enough, my luggage got lost. But, I had my dress, I bought a new swim suit at the resort, and I enjoyed myself until everything else showed up the next day. You can’t control most of the factors at play when you travel, but you can always control your reaction. You can have a basic contingency plan for bumps, and consciously choose not waste your vacation energy stressing over things you can’t control.

A great example that I’ve seen in my own husband was on our last big family vacation. We booked a cruise to several Eastern Caribbean destinations, leaving from Miami. As our ship set sail, the Captain came on to announce that a hurricane was threatening our would-be destinations. We were heading to the Western Caribbean instead, and a new itinerary would be delivered to our rooms later that evening. I’ve told you how my husband needs a lay of the land to feel comfortable. He had read about our stops, looked at the pictures, and we had at least a vague game plan of what we would do at each stop. We were comfortable with those stops. Now we had no idea where we would be stopping in the morning, or what there would be to do there. We didn’t even have affordable Wi-Fi to read about these places once we figured out what they were. I expected a full on freak out from my husband, but I was wrong! Maybe it was the fact that we were already out in the middle of the ocean, with no real viable option for turning back. Maybe it was the fact that “vacation mode” had already kicked in, so we were already relaxing on our balcony watching the waves with a cocktail in hand. Whatever it was, my husband took the news in stride. We found out what we could as information was delivered. We talked to other knowledgeable travelers and staff on the ship, at every opportunity we had, to get recommendations for things to do, and we had a great time!

The best thing you can do when the unexpected strikes on your vacation is to do your best under the circumstances. Before you go, identify any must-haves and figure out how you’re going to ensure that are with you for the long haul. For everything else, have an idea of where you might get it, what you might do, and how you might do it. But be willing to adjust as the circumstances change. The time you have on vacation is short, so enjoy yourself and step back from trying to control everything and plan too much.

Know how much planning to do

Putting together what I’ve said about my mom and my husband, there are several truths that apply to traveling with them both. Since they both appreciate the known and the familiar (though for different reasons), I plan accordingly. We need to have airport transportation arranged at our destination. Arriving in a strange place and not knowing how we’ll get to our hotel won’t work for either of them. We need to plan our activities with reputable, commercially identifiable companies. Hopping into an unmarked “cab” with a stranger and winging it is not going to work for either of them. If we are going the local route, it needs to be with a local, who we trust, and who can guide us to things we will enjoy and answer our questions. Remembering these things about my travel companions and planning accordingly avoids a lot of unnecessary angst for us all. We can all relax and enjoy each other and the ride without  fretting the details.

Along the same lines, I have friends who are a little less extroverted than I am. So, I know going in that they will want to do some “big crowd” activities, but then will also need substantial quiet time to recover. If your group are explorers, don’t over-book them with a pre-arranged itinerary. If they are planners, don’t get there and have nothing booked ahead of time. Put your knowledge of the others in your group to work. Don’t forget it when you get excited and started planning. Talk about expectations before hand, and try to strike the right balance of planned activities and free time to do things that pop up, so that everyone in the group goes in feeling good about the trip.

The End Result

The end result of taking the time to be a mindful travel companion is having a great trip! I’ve had a great trip with an old friend who brought along another friend I had never met. Our mutual friend thought about our personalities and interests enough beforehand to correctly guess that we would want to do the same things and would get along well. We literally met in the airport boarding our plane and have considered ourselves friends since.

The best, most magical trip of my life was to Italy and Greece with my brother and some of our friends who are pretty diverse in age and interests. None of it would have worked without us making the effort to be good travel mates to each other. We were wise enough to take a tour that allowed us to see the popular sites, with plenty of free time built in to focus on our individual interests or have alone time. That was key, because everyone’s focus was different. I like literature, so I wanted to spend time at sites with literary significance. My brother likes to people watch and socialize. One of our friends really likes high-end shopping. Another couple were really into art and architectural history.  The only interest we shared without fail was eating, so we always ate together! It was a great way to come back together and share the highlights of our day. Everyone’s needs were met and we all had a great time. It was exactly the opposite of my college Spring Break experience.

I have to end this post by giving a shout out to my brother, who is the ideal travel buddy. He is the example of everything to do and be to make for the perfect travel experience. He is compromising, up for anything, and always a good sport (not to mention he’s charming and lots of fun!). He is an adventurer by nature, but he will spend just as much time shopping and viewing landmarks as he will daring you to try new foods or to try an adventure sport. He’s willing to go with a plan to accommodate others in the group, or go on a completely unplanned adventure when the opportunity presents itself. Most importantly, when he senses that the vibe is off, he goes out of his way to tap into whatever will bring out the best in people and put them at ease. As a result, every trip I take with him brings us closer as siblings, allows us to learn so much about other people, places, and ourselves, and truly have an amazing time together! On my 32nd birthday, he and I stood in St. Marks Square, spinning around like little kids, completely marveling in the fact that we were there – living out a dream. Those magical moments are what it’s all about! I hope my experiences help you to maximize your own vacation magic.

Me and my brother in Venice on my 32nd birthday


Author: Rachelle

Rachelle Dodson is a 40something mom & lawyer. She lives in Lexington, Ky with her daughter Delanie and dog Bentley.

10 thoughts on “Traveling Well With Others”

  1. Nice post Rachelle. I would love to travel more but I don’t have any idea how to even plan trips like these. Sounds like you have had some great experiences with lots of different people. And your brother is adorable!

    1. He is a gem, Shannon! I will try to come up with a good post about how to plan trips and use travel agents. Thanks for reaching out!

  2. Thanks for the travel advice Rachelle! I have been on a couple of bad trips due to all of the issues you listed. Super inspirational to read how you dealt with it all. It’s true, you have to take in account who you’re traveling with. I will definitely keep that in mind going forward. Keep it up! 🙂

    1. Thanks for the love! Like you, I think I might eventually want to write fiction, so I started with writing about things I know and love. Let’s hope the blogging adventure leads us both somewhere awesome!

  3. We are definitely cousins. Planning a trip to Aruba. Let me know if you want to go. I Love To Travel. For me, Big Boy, and Big Girl rules apply. We allow folks pitch in some ideas in the pot for things to do on the trip. Those that want to go, go. Those that don’t, see you when we get back. You grown, and you know how to find your way around just like me. I don’t babysit grown folks.

    Rule two, the ones that don’t get with the program don’t get invited to the next trip. I spend my money to have fun, not deal with Primae Donnas. 🙂

    1. Have an awesome time in Aruba! Post lots of pics! I think we are planning for Costa Rica this year. Grown folks rules always apply – Amen!

    1. Thanks for reading and I’m glad you enjoyed it! I struggled with the length, so I will definitely work on finding the right amount of content for one post.

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