Everyone dreams about fleeing from work to vacation with friends, but few people can predict how swiftly that experience can spiral into mayhem. A person who seems totally relaxed in daily life can suddenly feel passive and lazy when it comes to planning an itinerary, while a shopaholic gal pal might drive you batty with her insistence that you visit every Hermes store in Paris in pursuit of the elusive Birkin bag. Three days into the trip, you start telling yourself that you’ve made a terrible mistake. Halfway through the journey, at least two people have stopped talking to each other. By the end, you consider ditching the entire crew, lest they drive you into a murderous rampage.
Don’t get us wrong – vacationing with friends can be extremely rewarding. But getting along on the road can take as much thought and preparation as the itinerary itself. So before booking that plane ticket, consider the following, lest you and your friends end up booting each other off the island, Survivor-style:
Reminder: It’s not about whether there are too many or too little people in the group
It’s about whether that number is right. Here’s what works:
Two: Awesome. You’ll get along splendidly as you’re probably already close enough to weather any storms.
Four: This is also convenient, as it’s easy to share a hotel room or split into pairs if there are two separate itineraries on a particular day.
Five: Not only is it easy to split, but someone can always be a tie-breaker on days when the whole group wants to be together, but can’t decide on what to do.
Six: A little risky and there are a lot of personalities involved, but in a group this big, there’s bound to be at least one other person who sees things your way. Plus, if you’re traveling to London, six is the perfect number for splitting a cab.
Here’s what may spell disaster:
Three: It’s easy for two people to agree on an activity. But three? At some point, you or someone else will feel like a third wheel. And leaving the other two alone to go off by yourself can come off as petty and awkward. Plus, if the hotel only has two beds in a room, you’ll have to take turns over who sleeps on the extra cot.
Seven and above: Yeah, NO. Have fun getting seats at a restaurant!
Decide how to prioritise your spending
People always ask each other how much money they’re willing to spend. That is the wrong question. Everyone can budget S$3000 each, but what happens when half the group wants to spend more money on the hotel than on food, while the other half wants to live in a dingy hostel so that they can indulge in Michelin-starred dining every night?
Our recommendation: If you’re traveling with more than two people, stay at a lower-end inn or a short-term vacation rental. You’ll have your own bedroom and bathroom, but you’ll save money for other activities – because really, how much time will you spend in the hotel? The only exception is if you’re doing one of those villa deals in Bali, because trust us, those cabins on stilts are totally worth it.
Travel with people who live as dangerously (or as safely) as you do
There are some friends who insist on carrying their money in hidden fanny packs, who don’t go out after 9 PM, and who will not eat anything outside of a restaurant in fear of food poisoning. Then there are other friends who are down to hitchhike all over South America, who will sleep in the Paris train station to save on lodging fees, and who will go to underground parties in Eastern Europe because a stranger invited them. Make sure you and your friends see eye-to-eye on precautions.
Our recommendation: Haven’t seen Hostel or Taken? Rent both of those right now and then tell us how you feel about accepting propositions from strangers.
“Are we planning this or are we winging it?”
Some of the best buddy comedies play on the drama that ensues when a Type A personality is forced into the wild with a Type B personality. But in real life, it’s not so hilarious. Are your friends the type who plan every single day, down to the hour, on Excel spreadsheets? Or are they the type who decide the night before (or even on the spot) what to do and where to eat?
Our recommendation: Plan two or three things per day, but don’t do set hours on when to take a break, how long to spend at each place, and so forth. Otherwise, you’ll just feel disappointed if you didn’t accomplish everything on your list.
Shopping, sightseeing, or partying?
Trust us, in a group of five, at least one person’s going to get annoyed the fifth time you take everyone on a detour to Harrods in London from some air-conditioned shopping. And let’s not even get started about what happens when your friends miss the tour you booked because they couldn’t wake up in time after spending the previous night clubbing.
Our recommendation: First, you should really go with a group of friends who enjoy the same things you do. Second, don’t make a fuss when you’re bored. Refrain from acting entitled to a day doing what YOU want to do just because you spent all of one evening following the others around. Simply show some gratitude that you’re exploring a new place with great company, and the others will be more inclined to oblige you.
Don’t be selfish – always ask what other people want to eat, and when
How many meals are you eating a day? How much money do you want to spend per meal? Are you all open to street food? Is hoarding croissants from the hotel breakfast buffet a lunch option? Is anyone gluten-free, lactose intolerant, or vegetarian? You don’t need to answer all of these questions prior to going on your trip, but if you’re the only one in the group with special needs (be it an intolerance or extreme pickiness) prepare yourself mentally and research alternative dining options, in case you need to stop by one for a quick bite.
Our recommendation: Have everyone request at least one restaurant or one type of cuisine for the trip, so that everyone gets a chance to eat what they want at least once. And always carry some snacks in your purse (we can guarantee that the group will delay lunch on at least one occasion because they got caught up spending an extra half our swimming with the dolphins, or whatever).
Sightseeing style: Hit up a lot of places in a short amount of time, or spend a longer time in less places?
How ambitious are the people in your group? Would they rather pack six European cities into six days, or spend three days in two cities? The upside of going with less people is that it’ll be easier to agree on a method, so if you’re going with a big group, make sure everyone sees eye-to-eye.
Our recommendation: Savor the place! It’ll take more than five minutes at each landmark to really soak in the landscape. Don’t worry about missing out on a couple of sights -- when it comes to making memories, it’s better to fully enjoy a few things, than to get just a glimpse of plenty.
Decide ahead of time how you’re going to handle transportation
During a recent vacation in Europe, we hauled our 20kg luggage on the Paris Metro, the Tube, and UK National Rail while shuttling between cities. In the summer. And in train stations with no escalators. While it wasn’t easy, we and our friends appreciated the money we save by not taking cabs – but of course, not everyone would prioritise their funds in the same way.
Our recommendation: It won’t kill you to haul your luggage down a flight of stairs to save a few bucks. But if you’re the one who recommends the cheap-o method of forgoing cabs, make sure everyone has fair warning – and be prepared to help your less-fit friends haul their stuff when they’re clearly suffering.