Travel Tips

7 Questions to Ask Before You Book a Trip With Friends

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Ever had a friendship or relationship dissolve during a trip? Your best friend may not be your best travel partner! So before you wind up halfway across the country or the world regretting your choices, discuss the questions below. Doesn’t mean you can’t compromise, but if you’re both compromising on everything, you might be better off traveling alone…

1. Do you want to relax or cram everything in?
This is key — there’s nothing wrong with wanting to spend all your time on the go unless the other person dreams of long days soaking in sun by the pool. So have a frank conversation about what you each want to get out of the trip. And take it even further by defining what you each mean by “relaxing” 🙂

2. What is your budget?
You might be compatible in all things except price. Candidly discuss financial constraints so arguments don’t come up during the trip like when one person wants to take a taxi everywhere and others prefer public transportation.

3. Night owl or early bird?
I love early morning breakfast buffets and seeing a city before it wakes up. That means I also tend to be in bed before 10AM. If you live for the nightlife every evening, I’m probably not a good choice!

4. What does it mean to “sightsee”?
Talk through your styles — is someone a by-the-travel-book enthusiast or do they prefer to wander coming upon things by chance? Do you like to see everything in a museum or skim through focusing on a few sections? Is a tour group something to be abhorred or sought? Is shopping the best way to get a feel for a city?

5. What do you like to splurge on?
You’ve already discussed budget, but there’s always a little extra splurging on vacation. Does that take the form of nicer restaurants? Helicopter tours? A better hotel room? Spa treatments?

6. Do you like to capture every moment on film?
This may seem like a small thing, but if you wind up spending an extra 15-30 minutes at every destination taking the perfect picture of video, it can get tiresome. In the same way I’m sure my friends and family are a little tired of me yelling “don’t eat anything yet!” every time I want to photograph our food at a restaurant. This shouldn’t be a dealbreaker, but set limits beforehand to avoid bad feeling on the trip.

7. Are you comfortable doing some activities on your own?
In my opinion, this is the most important question, and can resolve many of the differences above. If you both are comfortable with some independent activities, one person can take a helicopter ride to hike a summit while the other person indulges in a full day spa treatment. 🙂

And a bonus question for miles and points enthusiasts:

How will someone be compensated for using their points and miles?
Unfortunately many people consider points and miles “free,” but chances are someone has spent many hours and dollars applying for credit cards, maximizing bonuses, etc. So while you’re happy to use them it shouldn’t be assumed that they won’t factor into the cost of the trip.

What do you consider to be the most important part of choosing a good travel companion?

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