The best trips I have ever taken in my life have all been with my best friend Sarra. We are entirely compatible travelers: we’re both cool with hostels, walking at a snail’s pace, and eating McDonald’s three times a day, if need be. We like our days to be scheduled in a loose sense, and we don’t put a lot of pressure on ourselves to see and do everything. In short, we have the same traveling philosophy—relax, relax, relax—and therefore our relationship has endured many shared vacations and weekend getaways. But here’s the thing: before we take a trip together, we always spend some time going over our traveling expectations. That ensures there are no unpleasant surprises or major disappointments along the way, and we can spend our trip doing exactly what we should be: having fun.
In order to avoid ruining both your vacation and your relationship, make sure you ask your traveling partner the following eight questions before you book your trip:
1. “What’s your budget?”
I mean, duh. If your friend’s budget has a comma in it and yours doesn’t, the two of you should definitely not be traveling together. But assuming your overall budgets align, there are a few other monetary questions you should ask your partner prior to setting off. How much of her budget does your friend intend to put toward transportation? How much does she plan to spend on accommodations? On shopping? On food? Find out before you book anything together.
2. “How do you feel about eating fast food and street meat?”
This one sounds kind of silly, but it’s actually important. If you’re a foodie, you’ll likely want to spend a lot of time checking out the local restaurant scene. If your traveling partner is a a “street meat and hit the road” kind of girl, the two of you are going to run into some problems. You should always talk about your dining expectations before you travel with someone new.
3. “Do you plan on sticking to a schedule, or are you a ‘go with the flow’ kind of person?”
Nothing is more frustrating than traveling with a “scheduler” when you’re a “go with the flow” fan, and vice versa. Talk to your friend about your scheduling expectations (or lack thereof) before you two hit the road.
4. “What’s the one thing you really want to do while we’re on vacation?”
Talking about the things you’re most excited to see and do will ensure that neither you nor your friend go home feeling disappointed.
5. “Do you plan on spending some time on your own, or do you expect us to stick together throughout the trip?”
This one is key, because if two travelers don’t agree about “trip togetherness,” chances are good that someone will walk away from the situation feeling offended or hurt. If you know that you’re going to need some alone time during the trip, make sure you communicate that to your friend prior to setting off. That way, she won’t feel shocked or upset when you decide to spend an afternoon or two exploring on your own.
6. “Are you an ‘early to bed, early to rise’ traveler, or do you plan on partying and sleeping in?”
Nothing will ruin a holiday faster than two travelers who disagree about going out and sleeping in. Make sure you’re both on the same page about how you plan to spend your nights and mornings before you leave.
7. “Do you have any major traveling deal-breakers that I should know about?”
Maybe you can’t handle crowds, or you get seasick easily, or you would rather die than spend an entire day at a museum. Whatever it is, you and your partner should know each other’s comfort zones and deal-breakers before the two of you begin your trip.
8. “What’s your overall goal for the trip?”
If your goal is to relax and your friend’s is to sight-see, there’s a good chance that you’re going to disagree a lot during your trip. Save yourselves the trouble and discuss your overall goals for your vacation before you leave.