When I was growing up, my family took many vacations to a wide variety of places, but our travels rarely featured just my brother, our mom and me. Instead, we frequently brought along friends and other family members which always made our adventures so much more fun and memorable.
Deciding to vacation with friends, however, is not something to take on lightly. Luckily for me, I have friends who make perfect travel buddies. A few years ago, two couples who are dear friends and I decided we love spending time together so much that we should start traveling together. Now, with several trips under our belts—to Maine, the Southeast U.S., the Baltics, and the Pacific Northwest—we’ve figured out some specific ways to minimize miscommunication and maximize fun.
As you plan for upcoming vacations with family or friends, here are some Pro Tips for helping trips go smoothly and creating experiences that bring people even closer together.
Pro Tip #1: Choose a team captain for each trip.
One thing I’ve learned in my lifetime of traveling is that every vacation needs a main trip planner. Of course everyone can, and should, pitch in, but the trip tends to run more smoothly if one person is checking boxes on a master list. I’ve almost always played the role of the main trip planner—which I love to do—but with this special group of friends, I found the freedom to give up the reins, starting with our trip to Boston. I got to sit back, let someone else do the planning (and driving), relax, and enjoy the ride. Pure bliss.
Pro Tip #2: Invite everyone to contribute to a “must see/must do” list.
When dreaming about an upcoming vacation, everyone has their own idea of what the trip will entail. Avoid conflicts and post-trip disappointment (and possibly resentment) by sharing what you really want to see and do while the trip is in the planning process. Then, as a group, decide what the itinerary will be. Keep in mind, however, that vacationing together doesn’t mean spending every moment together. Going off on your own is always an option, and this is especially easy when you take cruises together. With a multitude of excursions and on-board activities, this is a great way to spend the day doing your own thing and still catch up with your travel mates for dinner and evening activities.
Pro Tip #3: Make room in the trip to play to the group’s strengths and interests.
One of the couples in our quintet are runners, so when thinking about where (and when) to travel, we kept in mind their dream race locations. They wanted to run the 10K of the Whistler Half Marathon, so we built a trip to Vancouver. The remaining three of us, however, are terrible cheerleaders, so as our friends awoke pre-dawn to get to the starting line, we slept in. It was all part of the agreed-upon plan (see Pro Tip #2)! The three of us were all about being there at the finish line, of course, because that was just about brunch time. And all five of us are always ready to eat (we loved La Cantina Urban Tacos)!
Pro Tip #4: If someone can’t make it, don’t let the trip fall apart (if you can help it).
On our first trip together, the portmanteau “Danica” (Danny and Monica) and “Braimy” (Brian and Amy) were born. On our second trip together, Danica couldn’t get away, so it was just Braimy and I, and my eldest daughter who had just graduated from college. In order to still include them, we enlarged, printed and laminated a photo of our missing friends (inspired by the famous “Flat Stanley” school project). We carried it with us everywhere, taking photos of “Flat Danica” in front of everything from the Czar’s throne at the State Hermitage Museum in Saint Petersburg, Russia to the deckchairs of our Holland America cruise ship. We got many strange looks—and even an offer to purchase them, which of course we politely declined—but it gave the trip a fun twist and our friends got to experience the trip even though they weren’t there in person.
Pro Tip #5: Figure out where the group falls within key travel criteria.
Danica, Braimy and I were all pretty savvy travelers who had been to a lot of places around the world, and had similar levels of creature-comfort expectations. We all shared a philosophy that down-to-earth, real experiences beat out Michelin-rated restaurants and five-star hotels anytime. But what about your group of friends or family members? Do you see eye to eye on food, activities, hotels, budget?. Does your group like fancy schmancy, roughing it, or somewhere in between? Are they picky or adventurous? Are you and your travel buddies on the same page when spending money on activities? Following Pro Tip #2 will help determine some of these criteria, but it might take some gentle team leadership (Pro Tip #1) to identify common ground.
Pro Tip #6: Consider the personalities of everyone in the group.
How do the members of your group handle adversity when things don’t go perfectly? There’s always room for things to go wrong, and you don’t want to be in the middle of who-knows-where with people who look at misadventures as problems rather than opportunities. Even the best of friends do not always make good traveling partners. Think about how your companions like to travel and make sure you’re all on the same page as far as expectations, as well as how to deal with it when things don’t go exactly as planned.
Pro Tip #7: Consider the adventure of a road trip instead of flying to your destination.
On our first trip—and each of the trips that followed—we planned at least some long-distance driving as part of the itinerary. That gave us lots of opportunities for car games, playlists and comedy one-upmanship. Planning trips that include some of the most beautiful and scenic locales in the United States didn’t hurt either. Seeing America from a car is such an adventure, from the majestic mountains of Acadia National Park in Maine to the Spanish moss-covered trees of South Carolina to the Capilano Suspension Bridge Park in British Columbia, Canada. You miss so much by flying instead of driving to your destination.
Pro Tip #8: Get that next trip on the calendar by figuring out a fun way to decide where to go.
Life comes at you fast when you get back from vacation, so while you’re on one trip together, start dreaming and talking about the next one. On our first trip, this is exactly what Danny, Monica, Brian, Amy and I did. We agreed to try and travel together once a year, and that we would alternate between U.S. and international destinations. To pick our next adventure, we decided to do a playoff bracket, and the Baltics won handily. Other ideas: pick a location out of a hat, play destination BINGO, or even throw a dart at a world map! No matter how you choose, don’t let the momentum of your current trip get away without making plans for the future.
Pro Tip #9: Cherish your friends and make memories that will last a lifetime.
Life is short. Each of our trips brought my four friends and me closer together and deepened our love for one another. Who knew that trip to Canada in 2017 would end up being our last trip together? Not us, that’s for sure. But life slowly creeped in, and our schedules fell out of sync. Then in 2019, Danny was diagnosed with brain cancer and we knew we’d never travel together again, at least not in the same way. He passed away recently, and the remaining four of us came together in Richmond, VA to celebrate his life and wish him Godspeed until we all meet again. After the ceremony, my heart was overjoyed to hear Monica ask, “Where are we going next?” because I knew that while things were changing, Danny would always be with us in spirit. Of this, I am sure. Because in the end, the ultimate trip you take with close friends is your commitment to travel through life together, come what may.
