Mark Twain once said, “I have found out that there ain’t no surer way to find out whether you like people or hate them than to travel with them.”
He got it right. That friend who always shows up late for things and laughs about it? Not so funny when you are running for a $1,500 flight. How about the one who always complains about having no money? They’re not lying; they literally can’t even pay for a $3 Bali cab ride.
But holidaying with friends can also be awesome. Just follow these tips to make sure you do it right.
Let’s start with the most taboo – money
The best way to holiday with friends is to set very clear expectations up front of who is paying for what. Splitting the bill evenly is fine, unless your friend is eating lobster, while you munch on a burger. Try using an app like Splitwise, which keeps a running total of who owes what. At the end of your trip, the app lets you settle up with your travel partners via PayPal. Download the iPhone version here and the Android version here.
Also, travel with friends who have the same attitude towards money as you do. If your friend wants to write down every cent on a budget, but you’re a spendthrift who lives it up, you could be heading for trouble. If you do like to budget and spend differently, consider staying at an all-inclusive resort so there are fewer transactions to worry about.

Choose friends who all get along
This may be easier said than done. Imagine you want to holiday with your best friend, but her significant other is a nightmare. No matter how much fun she is, you could end up at odds with her partner, which wouldn’t be great for anyone. Pick travel buddies with similar interests and values, and most importantly, who all get along. Pace is also important. Are you a sit-by-the-pool-and-do-nothing person? Holidaying with someone who likes to have every minute planned out is going to be exhausting if you thought you were there for a relaxing beach break. To avoid confrontation, be choosy from the get-go.
Give each other space…
Choose the right holiday, the right length of stay, and give everyone their own space when they need it. Cramming a group of friends into a single hotel room may seem like a great way to save money, but tension is sure to mount when everyone’s luggage and personal items start taking over the space. The savings aren’t worth losing friends over, so if you are sharing accommodation, consider adjoining rooms when available. Also think about spending some time apart. Not only will it let you enjoy things that your friend/s may not, but it’ll make for a fun evening when you’re back together with lots to share.

…But not too much space
You chose to holiday with your friends so don’t turn completely anti-social and close the door to your hotel room every night. Instead, unwind with a drink together, discuss tomorrow’s plans, or play a board game. Enjoy your time together, as holidays never last as long as you’d like them to.
Speak up, but also listen well
If you’re staunchly against a particular destination or activity, you owe it to yourself to speak up. This benefits everyone, as there’s nothing more frustrating than hearing criticism afterwards from someone who nodded along when plans were being made. That said, try to share your friend’s passions and interests, even if they aren’t necessarily yours. Keep an open mind to ideas that may not have originally appeared on your must-do list. If your travel companion is passionate about a place or activity, give it a try. You may be pleasantly surprised and going along will earn you the right to pick the next activity.

Clean up your own mess
Nobody wants to be cleaning up after other people on their hard-earned holiday. Or cooking each night. If you do have to do chores while you’re away, try to hash out people’s strengths and weaknesses and divide up the work fairly. Betty might be the best chef in town so let her cook, while you do the dishes. Just be sure to always pitch in and offer to help even if someone hasn’t asked you to. This is especially important when choosing villa or apartment life over a hotel.
Hold your tongue
Whether it’s a love of greasy fast food, questionable driving skills, or just sleeping late every day, you may discover that your travelling companion has some personal habits that you don’t like. This especially becomes an issue when families travel together. For example, why are your friend’s kids up all hours of the night when yours are in bed by 7:30pm? Did Sarah seriously put her kid in a timeout for throwing food at her sister? You couldn’t stop laughing. We all parent differently and what works for one family may not work for yours. On holiday, respect each other’s rules, routines, and values.

Use lifesavers, i.e. babysitters
If you are holidaying with kids, offer to babysit one night. A couple who goes out, has some drinks and a good meal comes back refreshed, happy and more pleasant to be around. Of course, there is always the chance that the favour will be returned 😉. Also, if possible, go out together as a group and leave the kids with a reliable sitter – many hotels offer the service – so you can enjoy just one night without changing a nappy or falling asleep reading to your child at 7pm.
Cast a vote
Finally, vote. Vote on activities, where to go, and where to sleep. Be flexible, be open, but do vote. Make an agreement that whatever wins gets the full support of the entire group. If you don’t think voting is going to work because of uneven distribution of power (i.e. your friend, a former debate-team star, has the ability to convince everyone he’s always right), then there’s always the amazing and accurate Magic 8 Ball 😉
No matter how well you think you know your friends, you don’t really know them until you’ve lived under the same roof for a bit. That’s when you find out that your sweet, loving bestie is really a neurotic clean freak and that her significant other’s boyish charm is only skin deep. The good news is if you can live with your friends’ challenging personality traits, chances are they can also live with your, ahem, little quirks.
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