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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Living for the little (and big things) that make life so fun, especially mistake deals and crazy last minute weekend mileage runs across the world. www.twitter.com/klatravel

4 Comments

  1. Marc

    April 7, 2015 at 3:45 pm

    Spot on! I think that those questions are key if you want your trip with someone to go smoothly!

  2. Marcelo

    April 7, 2015 at 5:00 pm

    I’d add one more thing, regarding transportation. If you’re traveling by road, who will drive? The others can sleep or at least one person needs to be awake? This should be agreed prior to departure. 😉

  3. Joey

    April 7, 2015 at 5:29 pm

    This list is great! For me, when I choose a travel companion to go somewhere new, the only requirement I have is that we stay at hotels that are clean and located in a safe neighborhood.
    As for miles/points redemptions, if it’s a hotel redemption, I don’t charge my friend anything since I would have used that same room anyway. If it’s for a flight, I’d charge them the taxes/fees but that’s it (will admit though that I’ve never had to do this.)
    If I am travelling with more than 4 friends, I’ll only go with them if it’s at an all-inclusive resort or on an organized tour or cruise. It’s my hard-earned vacation days too and last thing I need are unnecessary stressful arguments amongst friends about scheduling/restaurants/etc.

  4. P.L

    April 8, 2015 at 4:41 pm

    Really nice article. Very relate-able, and definitely important to discuss these issues beforehand! Good work!

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