How To Travel With Friends

Barbara: Since Deb and I and the boys just got back from our amazing trip to Costa Rica, I thought it might be fun to start a convo about traveling with friends. I mean, let’s face it: it’s one of those adventures that sounds appealing in theory, but often ends in quasi-comic disaster. We’ve all heard the stories of a group of friends heading off together to some distant land, only to find their dreams of sun-dappled rest, smart cocktails, and scintillating conversation suddenly morph into nightmares of personality clashes, mismatched expectations, and money mayhem.

First off, I will say this: Phil and I and Deb and Colin make EXCELLENT travel partners. When the kids were younger, we traveled together over several years to ski in Panorama, BC. My memories of those trips just burst with giddy laughter, silly game-playing, and sassy cocktail hours. 

2005: Zoolander was the movie theme for our first shared Panorama trip:
sun and wind whipped, that's right, we're supermodels... 

And the boys? Brandishing "Le Tigre" and "Blue Steel", of course.

So we knew going in that Costa Rica wouldn’t be ruined by unexpected conflict.

But why do we travel so well together? I’m afraid mutual love and admiration are not enough when you’re in close quarters. But here’s what does work:

1.     Let things slide. Go in with a come-what-may attitude and you will evade a LOT of conflict. This is rule #1 for very good reason!

2.     That said, do some planning ahead. Compromise is 9/10s of the law of travel. Like this:

3.     Agree on how to deal with money matters ahead of time. We split any bills we received (asking the server to accommodate this at the start of our meals) to avoid that clunky “my turn, your turn” quandary. We also agreed on how much we would tip. It may feel a bit awkward at first, but believe me, it’s way less awkward than suddenly realizing you hate those ungrateful-heathens-formerly-known-as-friends for taking such blatant advantage of you or for being such social idjits. Not that this has ever happened to us, but this seems to be the number one complaint in those nightmare-traveling-with-friends scenarios.

4.     Agree on what you’re going to do to some degree. Some people look forward to spending the week just lying on the beach, some prefer exploring and shopping, some a mix of both. If you plan ahead, even just a little, you can avoid the frustration of either being that guy who’s always bored and disappointed or listening to that guy who’s always bored and disappointed. The best part of this preemptive plan is that some of the divides occur within a couple, so now individuals can potentially enjoy more cake whilst also having it as people split off in diverse groups to do what most appeals to them. This rule applies to traveling with your kids too, btw. When we go on hot-weather holidays as a family, Stefanie and I prefer beach, book, and snorkeling, while Phil and Michele go for the diving. Not only does splitting the group allow for everyone’s tastes to be satisfied, but it gives you great re-cap talks at the end of the day over vacation dinner.

5.     Waiting for others can be a pain. It’s okay to agree to disagree about what time to get up, or eat a meal, or get a drink. This is everyone’s holiday. We would often let happenstance guide us in a “we’re sure we’ll bump into you at some point” kind of way. Even amongst the couples themselves. Phil might decide he wants to sit by the pool instead of waiting in the room while I shower and “beautify”. Deb and Colin might decide they want to get up early and sit by the lodge fire instead of waiting for us to get our sweet asses out of bed. That kind of thing.

6.     And last but not least—and this comes NOT from personal experience, but from sharing a resort week with guests and kinda getting to know them from afar—but try, please please try, not to bicker. Bickering is so … ugly. It sounds petty and feels irritating. It’s not the Muzak you want in the soundtrack of your trip. Every resort trip we’ve ever taken has included some version of the Bicker McBickersons. I don’t how they do it, but they manage to suck the light from the very equatorial sun itself. While these aren’t my own friends, I’ve felt sad and empathetic for the poor sods forced to travel with them. If you can’t say anything without bickering, don’t say….yadda yadda.

Now it’s your turn. Any great tips (and/or tales) to add to this list???

Deb: Barb, I think you pretty much covered it. All the potentially awkward things were taken care of and that left it open for relaxing, easy travel.

I do hate the deciding what time breakfast is on a trip, though. I love it, of course, when there is something planned and we can all meet an hour or so before said event to eat and chat with anticipation. But on the non-scheduled days, I love just saying, “See you at breakfast.” That way the early birds can go down for coffee and meet the later birds when they arrive. We did this on our trip and it was perfect. If one couple had eaten they would join the other for a second or third cuppa. No one felt pressure.

The only thing I do not enjoy on a trip—and we only had to endure it once (LOL)—is shopping with boys. Boys. Shopping. No. Now, in fairness, Phil is not too bad because at least he was interested in maybe getting himself something, although he did say, “Why are you girls going to the closest shop first? Why not do this shop at the end???”  Oh Phil. Poor well-intentioned Phil. The answer is that we must “scout”, boys! We must know what is nearest the hotel. In this case, the shop right outside the gates at The Harmony had all the treasures we could hope for. Had we not “scouted”, we would have spent our budgets before we even landed there. Rookie mistake, Phil, rookie mistake.

However, and I say this with love ... compared to my husband, Phil is one of the Sex and the City girls when it comes to shopping. My husband abhors shopping. Bless him.  And the beauty of him is, he does not try to hide it. We went into a very chic men’s shop and Phil looked around at a few things. Colin stood outside. When I poked my head out the door, this is how the convo went:

Me (holding up stunning simple gorgeous fabric T-shirt): “Honey, I am going to buy you this shirt!”

Him: “I don’t want it, thanks. I already have a shirt.”

And so it goes.