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There's nothing worse than a friend who cheaps out on a hotel bill but buys $500 shoes the next day — and the resentment that can come with it. Making sure you both have the same budget and spending priorities before your departure is crucial.
If your budget is higher, seeing your friend stress out over costs and exchange rates the whole time will not only depress, but annoy you. Likewise, if you’re on a tight budget and traveling with a spender, you’ll either go into debt trying to keep up or feel like a total charity case.
Both scenarios suck, so don’t beat around the bush when it comes to budget expectations. Be realistic when you talk about what you can afford and don't feel pressured to increase your spending limit just to make it work.
You want to wake up early, walk for hours, and explore new sites, but your friend wants to sleep in, order room service, and take cabs everywhere. Don’t wait until you arrive at your destination to find out that you have very different ideas about what makes the perfect vacation.
Either your hopes and expectations for the trip are more or less the same or you both happily agree to compromise beforehand. Just be sure that any compromises are genuine: I once traveled with a friend who begrudgingly agreed to do the things I wanted (even though she didn't really want to) — and it was torture. Experiencing an exciting new place with a friend who's visibly reluctant really sucks the joy out of it.
If your friend is the type of person who doesn't like to try new foods or activities or hates mingling with new people, there's a good chance he or she will be a complete Debbie Downer. The best part of traveling is going outside of your comfort zone and experiencing things you'd never do at home, so planning a trip with a friend who always says “Yes!” to life is so important.
I once did the most incredible road trip through Sicily with a friend, and we constantly encouraged each other to go big or go home. Embracing that outlook led us to make the best food discoveries, have life-changing conversations with amazing strangers, and generally encouraged us to divert from our itinerary whenever the moment called for it.
If you're a chill and happy-go-lucky gal (in which case, let's be friends!) and your friend is the type who easily gets offended or rattled, expect those differences to be infinitely magnified when you get lost, encounter rude taxi drivers, or have a bad experience in a hotel or restaurant.
You're on vacation; you should be able to relax without walking on eggshells. It's great to have yin and yang friendships in everyday life, but it’s smarter to travel with friends whose general disposition melds nicely with your own. And if you’re the overly sensitive one (no judgment!), consider a solo or all-inclusive getaway.
Here’s the bottom line: If you want things to run smoothly, make sure that you adore being together all the time, every second of the day, or you both appreciate having a little alone time. If you're not on the same page about that, one — or both — of you is going to wind up feeling annoyed, frustrated, and resentful.
I've traveled with groups of friends where one didn't understand the point of going on a trip together if we were going to split up at all and another couldn't stand to constantly be around other people. Suffice to say, by the fifth day there were tears, angry words exchanged, and unbearable tension.
The moral of the story? Talk about it (and everything else) openly and honestly before you make any concrete plans — and if you get the feeling that something is off, trust your gut and consider finding someone else to travel with.