Travelling in a group with friends
We’ve all heard of that infamous getaway that somehow made it out of the group chat, only for friendships to come back on life support. Turns out, squeezing 6 different personalities into 1 itinerary isn’t always the recipe for a relaxing time – and we get it. To help you keep the good vibes going, we’ve put together a guide to travelling in a group with friends, including apps that’ll save you from travel mistakes, tips for handling drama, and the subtle red flags you defo don’t wanna ignore.
Table of Contents
- Travelling in a group with friends
- What’s it like travelling with friends?
- Useful apps to download when travelling in a group
- – For splitting costs –
- 1. Splitwise
- 2. Settle Up
- – For itinerary planning –
- 3. Wanderlog
- 4. Google Maps
- – For making group decisions –
- 5. WhatsApp/Telegram
- – For fun & memories –
- 6. POV
- 7. 1 Second Everyday
- How to avoid travel drama during group travel
- Red flags when travelling in a group to look out for
- What to prepare for group trips
What’s it like travelling with friends?
Some people love the freedom of solo travel – no need to wait for anyone, no drama, and you get to do whatever you want, whenever you want. But most of us start spiralling the moment we have to eat alone or take a selfie with our phone propped up on a water bottle.
If the thought of asking a stranger to help take a photo gives you the ick, then travelling with friends might just be more your thing. You’ll never have to eat alone, there’s someone to hype you up during photoshoots, it’s generally safer, and splitting the costs is always a win for the wallet.
Of course, it’s not always sunshine and rainbows. Decision fatigue is real when you’re choosing between 5 cafes for brunch, and money matters can get awkward when someone suddenly develops amnesia during bill-splitting time. There’ll also be times when you just want to chill, but someone else is already shaking you awake at 6am for a sunrise hike.
Don’t let the chaos scare you off, though – with a little teamwork, clear communication, and the occasional compromise, the trip doesn’t have to end in tears and unfollows. It can still be the core memory you hoped for.
Useful apps to download when travelling in a group
– For splitting costs –
1. Splitwise
Free expense-splitting tool that does all the calculations
Image credit: Splitwise
Universal experience: sitting at a restaurant table post-meal, trying to figure out who owes what, and ending up more confused than when you started. Splitwise (App Store | Google Play) is a free expense-splitting app that does all the math for you, so there’s no need to whip out calculators.
Image credit: Splitwise
It’s one of the more popular apps out there for a reason. All you have to do is get everyone on the trip to download the app and join your group. Then, start adding expenses in any currency as you go. The app tracks everything and tells each person exactly how much they owe and to whom. Tap “settle up” once the money has changed hands.
Screenshot from: Splitwise
Pro tip: Splitwise recently introduced a new update that limits how many expenses you can add at a time. We tried it out and got hit with a 10-second cooldown timer after 2 entries. Slightly annoying, but not enough to derail your trip. The trick is to make your friend input the next expense.
Alternatively, consider upgrading to the Pro version at $29.98/year for your first year, then $59.98/year after that for unlimited entries.
2. Settle Up
Split group expenses without having everybody download the app
Image credit: Settle Up
The thought of forcing all your friends to download yet another app sounds like a headache, but Settle Up (App Store | Google Play) doesn’t require everyone to sign up – only 1 person needs to download it and set things up. So if you’re the planner of the group trip, AKA the person who made the itinerary and purchased the travel insurance, you might as well add this to your to-do list.
Once you’ve downloaded the app, create a group, add everyone’s names, and start tracking daily expenses. Settle Up will do the rest, like crunching the numbers and letting you know exactly who owes what to whom.
Image credit: Settle Up
Share the group link with your friends, and they’ll be able to view the breakdown on their browser without downloading the app.
It’s free, but you’ll get the occasional ad – we got 1 after entering 3 expenses. Not a dealbreaker, but for an ad-free experience, go Premium for $5.98/month or $28.98/year. Or just activate it during travel season and cancel it after.
– For itinerary planning –
3. Wanderlog
User-friendly & comes with an in-app map for easy planning
Image credit: Wanderlog
Wanderlog (App Store | Google Play) is a sleek, all-in-one travel planner that makes it ridiculously easy to organise your trip. You’ll get to build and share detailed itineraries, plot everything out on an in-app map, and even access your plans offline – all without paying a cent.
Image credit: Wanderlog
The app pulls info directly from Google, so when you key in a location, it auto-fills the deets like opening hours, addresses, and reviews. No more hopping between tabs or copy-pasting links into your group chat. It also lets you manage and split expenses within the app, which is great news for those who would rather not deal with yet another download just to track who owes what.
Image credit: Wanderlog
While the offline maps are a Pro feature, the free version still lets you view your itinerary on the go. There’s also a paid upgrade from $18.90 that gives you extras like route optimisation and Google Maps export – it’s handy for overachievers, but TBH, the free version already covers most travel needs.
4. Google Maps
Completely free to use with a comprehensive map coverage
We all use Google Maps to get from Point A to B, but it’s also a great itinerary planning tool that’s completely free. Beyond just navigation, it also lets you pin and save places you want to visit, colour-code them into neat little categories, and view everything at a glance on 1 map. It also gives you real-time traffic updates and reviews of attractions, so you’ll know if that “hidden gem” is actually worth the detour.
Screenshot from: Google My Maps
Need to plot out your whole journey? Google My Maps is a more detailed version that lets you customise routes, add waypoints, and share the map with your travel buddies so everyone stays on the same page.
– For making group decisions –
5. WhatsApp/Telegram
Create polls for voting purposes
You probably already have 1 or both of these apps on your phone, but they’re not just for spamming memes and stalking blue ticks. WhatsApp (App Store | Google Play) and Telegram (App Store | Google Play) actually let you create polls in group chats, great for when your travel group can’t decide on anything.
Screenshot from: Telegram
Use them to settle major debates like which country to go to, what time to book that flight, or whether it’s vibes over value when picking a hotel. You can even get into the petty but necessary stuff, like whether latecomers deserve a grace period or a passive-aggressive glare.
You won’t have to screenshot every opinion and manually tally responses like it’s 2008. Just send a poll, let the people vote, and move on. Group trips run smoother when decisions don’t end in “up to you lah”.
– For fun & memories –
6. POV
Digital disposable camera for film-like photos
Image credit: POV
If you love the aesthetic of film photos but not the stress of carrying a fragile camera around, try POV (App Store | Google Play). It’s a digital disposable camera app that adds a retro touch to your group trip snaps. And yes, the photos come with a delay for that authentic film experience.
Image credit: POV
Only 1 person needs to download the app and generate a QR code. Your friends can scan it to join the album, then start snapping pics from their own POV. You get to decide how many shots each person gets, and the gallery will only be revealed after a customisable waiting time. No peeking allowed till then, which makes looking back at the photos even more satisfying.
It’s also a lifesaver for mixed-brand friend groups – everything’s in 1 shared album, no matter what phone you use.
7. 1 Second Everyday
Stitch snippets from your trip into a video diary
Image credit: 1 Second Everyday
1 Second Everyday (App Store | Google Play) lets you upload 1-second clips from each day of the month, then stitches them into a video diary, even if you have zero editing skills or don’t know anything about fancy transitions.
It’s great for remembering the little moments that don’t make it to the group chat. And when the post-trip blues start getting a bit much, hit play and relive the memories.
How to avoid travel drama during group travel
Even with an arsenal of apps, it’s inevitable that disagreements arise. After all, we’re only human (channelling Christina Perri with a dramatic stare out the plane window).
Here’s how to avoid turning your holiday into a soft launch of a friendship breakup.
Have candid money talks before the trip
Nothing kills the fun faster than someone gasping at dinner prices or ghosting when it’s time to split the bill. That’s why it’s so important to have the money talk before the trip, even if it feels a bit awkward.
Be upfront about your spending comfort zone, and ask the group what they’re okay with. Are we ballin’ on a budget? Street food or fancy omakase? It’s not about shaming anyone, but more of setting expectations so no one’s caught off guard mid-trip.
Once everyone’s on the same page, you’ll avoid paggro moments and enjoy the holiday without financial tension lurking in the group chat.
It also helps to sort out things like how much cash to carry. Are you going to pool a group stash, or is it every man for himself?
Assign roles for each friend
Instead of having everyone Googling directions at the same time, assign each person a role like it’s a group project.
- The Navigator: lives on Google Maps and knows which bus to take, how many stops, and where to transfer.
- The Treasurer: keeps track of everything and logs it into the expense-splitting app so no one goes home broke or bitter.
- The Timekeeper: not just a human alarm clock – also picks people off the bed, watches the time during pit stops, and gives countdowns so you don’t miss flights or reservations.
- The Admin: handles bookings, reservations, and screenshots every confirmation email like a pro.
- The Vibes Manager: the most underrated role – whips out snacks during meltdowns, plays the right tunes when everyone’s grumpy, and cracks jokes at just the right moment.
Don’t force togetherness
Newsflash: just because you’re travelling as a group doesn’t mean you need to be glued together 24/7. Understand that different people have different interests, so it’s perfectly fine to split up for activities.
Suggest a simple plan, like doing your own thing in the day, then regrouping for dinner or hangouts later. You’ll avoid unnecessary tension and have more stories to share.
This also means you don’t have to cram everyone’s wishlist into 1 chaotic itinerary. Less stress, more freedom, and no one has to suffer through activities they’re secretly not into. It’s a holiday, not a hostage situation.
Schedule downtime
There’s always that friend who wants to carpe diem from dawn till dusk – but not everyone’s idea of a good time involves sprinting from one place to another.
Sometimes, you just want to nua in the hotel room. That’s why it’s a must to slot in some proper free-and-easy time in your itinerary for naps, solo exploring, or just doing absolutely nothing.
Well-rested friends are less likely to snap over where to eat. It really makes a difference in keeping the group sane and the vibes immaculate.
Agree on a “post later, live now” pact
“Pics or it didn’t happen”, but if the group’s been stuck in the same pose for 20 minutes because someone needs 37 angles, mutiny is inevitable.
To avoid becoming that friend, agree on some boundaries. Snap your pics in the first 10 minutes, then move on and actually enjoy the moment. No need to force everyone to stand around while you edit your IG story or pick the perfect caption – that can wait till you’re back at the hotel in your PJs.
Remind yourself, “it’s not that deep”
Missed the bus? A friend used your expensive shampoo without asking? Unless it’s life-threatening, tell yourself: “It’s not that deep.” The best stories always come from the dumbest travel hiccups anyway.
Red flags when travelling in a group to look out for
The “anything lah” friend
Image credit: @factmaniac via X
Remember the nostalgic drinks, Anything and Whatever? Cute. But when your friend turns into a real-life version of that, not so cute. You’ll spend 45 minutes crowding around Google Maps trying to pick a lunch spot because they refuse to choose, but also don’t like anything you suggest. Bonus points if they say “up to you all lah” and then still look upset the whole meal.
If this sounds like someone in your group, send this to them with love and maybe gently nudge them to, quite literally, pick anything next time.
The budget sabo kia
You all agreed on a budget trip, but this one suddenly wants expensive dinners, private tours, and luxury hotels. They may also say things like: “YOLO right?” and “I don’t mind topping up.” Sorry, you might not mind, but the rest of us didn’t budget for a bougie lifestyle on a tiny salary.
The MIA traveller
No message, no update – just poof. Then they reappear hours later, shocked and appalled that the group didn’t wait for them to go cafe hopping or catch the sunset.
Look, everyone deserves alone time. But at the very least, just drop a quick text in the chat. No one’s trying to track your every move, we just don’t want to file a missing person report in a foreign country.
The complainer
Too hot. Too cold. Too much walking. Too little to see. And the list goes on. This person somehow finds a way to complain about everything. The worst part is that their energy is contagious, and not in a good way.
Don’t be that person. Not every moment of a trip will be 5 stars, but constant complaining is how group trips turn sour real quick.
The drama magnet
Every small issue has the possibility to turn into World War III, and travelling with them feels like being in an episode of Keeping Up with the Kiasu-dians. Somehow, you’re always the unwilling co-star.
We’re all bound to have a moment or 2 on a trip, but if someone’s default mode is chaos, it might be time for a gentle intervention.
The oversleeper
Despite multiple alarms and wake-up calls, they cannot get out of bed. Missed the hike. Missed the ferry. Almost missed the flight. They’ve probably said: “5 more minutes please…” while the rest of the group stood outside the hotel room, silently plotting their revenge.
If you spotted yourself in any of the above, it’s okay – self-awareness is the first step. But if you have zero tolerance for chaos, may we suggest travelling solo, or accept that patience is a virtue. At the end of the day, no group trip is ever 100% smooth-sailing.
What to prepare for group trips
So you’ve picked your destination and mentally shortlisted which friend might cause drama. But before you jet off, don’t just wing it and hope for the best.
Besides the emotional prep, there are also actual travel essentials that’ll make travelling in a group smoother.
Universal travel adapter with multiple ports
Image credit: SC LEE via Amazon
Get yourself a travel adapter with multiple ports because someone is going to forget to bring their own. Choose one that comes with interchangeable plugs, supports worldwide voltage, and has USB or USB-C slots so your Android and Apple crew can live in harmony.
And if you’ve got multiple devices, you won’t have to play charging musical chairs every night.
Shop the LENCENT travel adapter (from $35.99).
Noise-cancelling headphones
Image credit: Sony Singapore
You’ll thank us when The Complainer starts going off for the nth time that day. Noise-cancelling headphones aren’t just for flights and noisy trains – they’re your personal bubble of serenity when the group chat starts becoming too loud IRL.
Go for a wireless, Bluetooth-compatible option for extra convenience.
Shop the Sony WH-1000XM5 noise-cancelling headphones ($151.31).
Travel-sized toiletry set
Image credit: Amazon
Everyone knows to bring a travel-sized toiletry set, but in a shared bathroom, those identical bottles are just asking for confusion.
Avoid “whose shampoo is that ah?” convos by getting a set with clear labels, or just slap on your own stickers. It’s the little things that keep the peace when you’re all trying to use the sink at the same time in a tiny Airbnb toilet.
Shop the Gravel travel bottles (from $23.60).
SIM card or eSIM
Plan ahead and ensure everyone has data upon landing to avoid bickering at the airport. Purchase a SIM card or eSIM online beforehand, and you’ll be able to access the internet and all your social media apps right away.
Shop SIM cards and eSIMs (price varies).
Travelling in a group doesn’t have to end badly
We hope this guide helps make your next group trip a whole lot smoother. Just remind yourself that give and take isn’t reserved for BTO-bound couples – it applies to friendships too.
But if you’ve done your part and the trip still flops, maybe it’s time to rethink your travel companions. Otherwise, go forth, have lots of fun, and come home with memories instead of trauma.
More travel tips:
- Countries with digital nomad visas
- New direct flights from Singapore
- Comparing budget airlines’ business class
Cover image adapted from: The Smart Local, 1 Second Everyday
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