My guide to boss travel: Step 2 – Who’s joining you?

Choose your travel mates wisely. No pressure, but this one is right up there with budget concerns as the biggest maker or breaker of a great trip. You want someone to laugh with, be at your side when outlandish things happen, keep an eye on each other, decipher directions, and finish off each other’s drinks.

Don’t travel with friends if you’re wildly incompatible. It will end in tears. Yours, or theirs. Trust me. Bojack Horseman should never travel anywhere with Mr. Peanutbutter.

Ok! You’ve chosen good mates, with similar

  • travel sensibilities
  • budgets
  • likes/dislikes
  • priorities

Even still… you want to keep those friendships, relationships and trip memories beautiful.

  • Build in little breaks from each other. Make sure everyone knows in advance if you need time on your own and that it’s not personal. On one trip, my friend and I agreed to part ways between 4 and 6 each afternoon to chill and get ready for dinner.
  • Morning larks can travel with night owls, as long as you realize you’re not going to spend the whole day or evening together.
  • For the love of all that is holy, if someone tells you they aren’t a morning person, believe them and leave them alone until they’re ready to face their day.
  • Give everyone a task they’ll like doing. Who is best at navigating? Who has a knack for finding great restaurants? Who’s calm under pressure? Who picks up languages easily? Who is outgoing and likes to ask questions? Who’s good at math?
  • Have a system for communicating – Facebook Messenger and What’sApp both work on wifi and you can have as many group chats as you want.
  • Before your trip, meet up a few times as a group to plan together and get psyched together.
  • Are you doing a group trip where you’ll only meet the rest of the group once you’re actually there? You’ll have to strike a balance between being polite and friendly, and making sure you get downtime, especially if being ‘on’ around new people makes you tired. There’s nothing wrong with calmly telling someone that you’re going to sit something out, or catch up on your reading.

Travelling as a couple can have its own special rewards (hotel sex in a new city!) but it can have its own challenges too. Here’s one of my bona fide little tricks that dumbfounds baristas with its simple brilliance:

My husband likes to sleep in, no matter where he is. I burst out of bed early, filled with excitement for the city I’m in, and very, very hungry. That’s a marital spat brewing, right there.

This is how we’ve solved it:

I get up, shower and dress, and make sure he’s awake as I head out for a cup of tea and a pastry. He gets ready in his own time, I have breakfast #1, check my phone and make a plan for the day (and nail down our second breakfast location). On my way out of the cafe, I buy him a takeaway coffee. By the time I return to the hotel, he’s awake, showered, dressed and ready for that coffee. Marital bliss achieved.

Previous posts in this series
My guide to boss travel: Introduction
My guide to boss travel: Step 1 – Deciding where to go, and when

Upcoming posts in this series – published on Fridays 
My guide to boss travel: Step 3 – Time to dream
My guide to boss travel: Step 4 – Sorting out the boring stuff
My guide to boss travel: Step 5 – In transit
My guide to boss travel: Step 6 – Your trip, your way


8 thoughts on “My guide to boss travel: Step 2 – Who’s joining you?

  1. PIcking a travel companion is key to a good adventure. But I’ve had to take vacations with strangers and go on road trips with people I tolerated at best, and some of those trips were fun despite the differences, because of the travel, I think. Travel really does bring people together. Love your guide, big fan. The Wordsmith

  2. All true, but I’ve also had dull trips with indecisive people, and truly maddening experiences when people have had consistently bad attitudes. Especially when time and money are short, I’m not the type to take chances. Once bitten, twice shy maybe? I think travel amplifies everything, sometimes for the good, sometimes for the bad.

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