Travelling with Friends

by Josh Adventure
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Travelling with your best mates? This can be one of the most rewarding or one of the most devastating decisions for your trip. Everyone’s travel style is different. Everyone’s expectations vary.

The “Best” You

When a friend invites you out to catch up over dinner, grab a hike, or have a drink at the local pub, they are the “best” version of themselves. And, so are you. You know that you only have to be out for a few hours and can laugh and live in the moment. You can stick it out until you part ways, and maybe give yourself a bit of space for a few weeks without causing a scene.

Travelling together, you’ll be seeing each other at all of the ups and downs of your day. Travel isn’t always easy and fun. It can expensive, stressful, and at times disappointing. I firmly believe you don’t truly know someone until you see them at their worst or when they come to you in a time of need. Travel can be a very unwelcome looking glass. Always do a five day trip with someone in advance to test the waters.

Expect Conflict

You’re going to spend more than you anticipated. Something isn’t going to go to plan. You’ll be more tired and irritable than you thought. Maybe one of you will fall sick, while the other wants to keep rushing out experiencing things on the adventure. Maybe you discover the person that you’re travelling with has had a crush on you, when you thought it was platonic. The potential for conflict is limitless.

Communicate Like a Pro

Polite communication is absolutely key. I’ve tried various methods to “get through” trips in the past when things haven’t gone to plan. I’ve stayed silent. I’ve gotten angry. I’ve passive aggressively tried to hint away from behavior I wasn’t keen on. Be direct, flexible, and polite. Always. Never stay silent and trudge through the day allowing your blood to boil. The number one key to effective troubleshooting is to explain how you feel, and propose a solution.

A great example is you’ve just spent sixteen hours together on the plane. You’re tired. Your friend has been chatting non-stop and wants to hit the streets as soon as you check-out of the hotel and grab drinks to meet locals. You know you’re only here once, but you also know yourself. Avoid at all costs phrases like “Why are you being like this?”, “I’m sorry if this…”, Fine.”, “Sure, if that’s what you want.” Always try to avoid directly attacking your travel buddy and calmly explain how you feel, and make a suggestion.

Learning to Communicate in Fijian

Instead of tagging along with your friend above and bringing the energy down, and maybe being more irritable than you’d like, say “I’m feeling really beat today, and not super social. Head on out without me, and I’ll join you tomorrow. I want to hear a good story when you get back!”

Be Decisive and Learn How to Say “No”

Travel requires constant decision making. Don’t keep biting your tongue if you’re not enjoying something. Don’t say yes to experiences that don’t interest you. You’ll regret spending excessive amounts of time and money on things you’re not enjoying. It is not your job to entertain each other. Not loving the idea of doing something? Make light of the situation by saying something like: “More ruins, eh? I’m going to have to buy you an Indiana Jones hat when we get back. I’m feeling more of the food tour tomorrow instead. What time would your tour end? Let’s meet up later in the day and grab dinner?”

Feeling too beat and just want a casual day back at the hotel in the pool? Make sure your buddy doesn’t feel guilty about leaving you behind, and tell them to go rock it out there and take some wicked photos! It is very important to remove that sense that they’ve let you down or irritated you and that you need time apart. It’s a wise move to plan time in advance for time apart from one another.

Vieques Mosquito Bay Bioluminescent Tour in Puerto Rico

Travel Styles

Make sure your travel styles are compatible! If you find yourself with one of these bad type combos, suggest that you two split up for some and meet up later to share stories. Don’t avoid each other entirely, but don’t let someone else hold you back from a trip that belongs to both of you. Just because you came together, doesn’t mean you have to do everything together.

The Big Spenders vs The Big Regretters. Maybe your buddy is on a really tight budget and wants to check out all the freebie and low cost attractions. They don’t want to overspend, but see you wanting to experience some more extreme features, and begrudgingly splurge anyway. Or worse, they complain about the $5 entry to the botanical garden when you’re already spending $150 each per night on a hotel. They’ve spent big on the trip and checked their credit card. They now feel like they have to constantly sacrifice and just “get by” before more financial doom incurs. Even spending the tiniest amount on something makes them feel choked unless it’s something that feels absolutely essential.

Canada Meets New Zealand, Round 2!

The Partier vs The Culture Addict. Maybe your travel buddy is just out to party, party, party! They don’t seem to care about the culture side, but that’s completely your jam. Maybe they’ve got a girlfriend back home, and you’ve had to watch them flirt and maybe even cheat day in and day out. You’re seeing an entirely different unexpected side to them.

They wake up at 11am the next morning after crashing at 3am after a night at the bars. You want to see the Giant’s Causeway and miss the lines, and you’ve just spent the last four hours waiting for them to wake up. Keep your judgements to yourself. It is their decision, their life, and their own consequences later.

SOLUTION: “Damn, I haven’t partied like you since college! I’m super pumped for the tour tomorrow. I’m going to head down to the lobby for 9am. Come join if you’re interested!”

The Winger vs The Plan-o-Holic. Maybe your buddy is super slow mover or a winging-it type, and you’re a plan-o-holic. You’ve gotta be at the museum by 10, the food tour at 1pm, and at the viewpoint by sunset. It all has to go according to schedule, or it will domino and the day will fall apart. Your attitude towards planning stresses the hell out of your buddy, and their seeming lack of care to your masterplan drives you nuts!

Karmakamet Diner in Thailand. Super gourmet!

The Foodie vs The Hungry Man. You’re hungry. You don’t care what you eat. But, your travel buddy is on a strict diet, is a fussy eater, or will only eat at the most elite and experiencing-making expensive restaurants.

SOLUTION: Stop booking meals together, and both bring snacks for your day separately. There’s tons of other things you can do. Or, if they’re the pickier eater and you’re more easy going, ask them to choose a restaurant the day before.

The Complainer vs The Memory Maker. These are the most soul-sucking type to travel with. They leave home and already readying themselves for disappointment. They get a sick sense of enjoyment of feeling “better” than a situation and constantly puking out their negative vibes verbally. They can’t seem to see it, but to you, it’s making you wonder if they’d rather be at home.

SOLUTION: Learn to reprogram their brain. Don’t acknowledge their complaint, and immediately make your own positive comment about the situation.

Getting Downtime at Xcaret, Mexico

The Doubter vs The Adventurer. You both made these awesome plans and talked a big game. Now, you’re on day one and they’re starting to change their mind about what they want to do. Constantly down-scaling activities and attractions. Questioning decisions that were made months ago on where to stay.

SOLUTION: “I’m still really looking forward to going to the river tomorrow for the air boating tour. And, if you’re feeling more like exploring on your own today, that’s completely cool.”


Above all else, just get a good night’s sleep! It will make everyone less irritable and more ready to conquer the trials and tribulations of tomorrow.

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1 comment

Paurian June 16, 2020 - 8:04 am

This reminds me of a modern-day Philip Greenspun travel blog (who won the webby award years ago). Nicer layout, and just as insightful, playful and fun to read. Thanks for sharing!


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