How To Plan a Large Group Trip: Lessons Learned for Less Stress

Planning a trip for one is something I’m an expert at. Two to four, no problem. But as I quickly found out when I hit the age for reunion getaways, stag and hen parties, and big birthdays, planning a large-group trip is a whole other world. One that I was initially pretty terrible at.

Travelling solo or with your partner is pretty easy-going; you know what you like, and there’s not much to balance. But when there are 10, 20 or more different palates to feed, wallets to please and a whole lot of other needs, it becomes a fine balancing act – especially if you need to keep travel costs low – a balancing act that I now know can fall apart if you overlook the key initial planning steps. 

Now with a few of these more complex trips (both domestic and abroad) under my belt, I’m feeling more confident. Here are some mistakes I learned from that will help you plan that big group trip without the learning curve. 

Getting Started: Smooth Comms, Individual Needs and The First Spreadsheet 

Communication

Honest, clear and concise. That’s the recipe for smooth sailing going forward. The more you know about the group – especially if you’re organising a surprise trip for a mate and you don’t know everyone attending – the fewer problems are on the horizon. Emails will be important for things like payments, but my first suggestion is to start with a fast-response channel. A WhatsApp group is ideal. If it’s a surprise trip, get the bride, groom, or birthday celebrant to start the group and add everyone they want to join; then they can leave, and you can get to work.

My preference for WhatsApp isn’t just that it’s fast; it’s the polls feature. If you’re working with a large group, this can give you a concise, quick and non-time-consuming way (let’s be honest, no one wants another group chat) to ask the quick-fire important questions: budget range, home or away, how long, rough dates. The more honest and detailed the questions are (word them so no one feels awkward ticking money boxes, etc.), the less likely you’ll see dropouts around those dates. With those answers, you can start filling in the blanks. 

The rough dates should be the first things you poll. The sooner you start planning a large-group trip (ideally a year in advance), the more likely you’ll be to settle on dates that work for everyone. Also keep in mind seasonality and costs at this point. A birthday might be a fixed date, but a stag or hen do can be flexible, and if it’s, say, a September wedding, shifting the date back to June (before the school holidays) rather than late, expensive August might be the only way certain attendees can afford to join.

The Spreadsheet

While I’m usually on a whim when flying solo, I’m a sucker for a spreadsheet when planning more complicated itineraries. And let’s be honest, even if it’s just a weekend getaway, managing a large group is complicated. Setting up a spreadsheet and giving everyone access is a way to capture all the details that you can’t in a poll.

Here you can add a template in the top row for people to follow and capture the likes of: full legal names (aka, what’s on the passport), preferences on room share (and with who) or solo supplement, where they are coming from and local airport, if they can drive (and are happy to go abroad), and anything else that’s important or relevant to your likely destination. 

First Hurdle: Where, What (Works) & How

Keep an Open Mind

This is going to be the heavy lifting. The more work and preplanning you do at this stage, the easier everything will become down the line. You soon realise your job isn’t just pulling together a trip and an itinerary; it’s initially managing expectations, liaising between a group of people (some you may not know), and reading between the lines to understand if someone’s “I can try and make it work” actually means “this isn’t financially possible for me”. 

Remember: your job is to make the trip as fun as possible for everyone, and if that means trading destinations (if it’s not pre-set for a specific event or reason) so it’s more accessible to others, then do it. It’s better to have the gang together and relaxed than a trip that only works for half of you, leading to people dropping off or resentment at the destination. No one is going to cry over Crete or Corfu, but if there are no convenient flights to either, they might just not make it. 

Consider How Everyone Can Get There

With all the above compiled into a spreadsheet, you can start to work out a shortlist of where. Of course, if it’s for a specific event, this decision has already been made for you. But if it’s of your choice – say you’re planning a surprise stag or hen party – then picking the destination is the first step (though having a plan B or C, in case the accommodation or travel makes A impossible, is wise). This is also when you might need to make some hard decisions, especially if the person you are celebrating has expressed a preference for a place, but the spreadsheet and comms aren’t aligned. Destination dupes or more affordable alternatives should always be considered. 

Research where you’re thinking of going and if it’s easy to reach for everyone, not just those living in a major airline hub such as London. If you’re heading to Europe from the UK, see which destinations are served by many regional airlines; that way, pals from Edinburgh, Manchester and Bristol might be able to get a budget Ryanair flight too and not need to pay double to get to London first. Look at flight times and how regular the schedule is for these flights: if you know it’s a weekend trip, it’s no use if flights are only on Tuesdays.

Second Step: Where to Stay – Rooms, Villa or Other?

Room Blocks and Group Rates: Best for City Breaks 

The first annoyance you’ll encounter when trying to book a group trip, especially if you need more than nine rooms (be sure to have checked and decided at the spreadsheet stage who is happy to twin-share, and who prefers to pay more for private), is figuring out what’s available and how much it will cost.

If you’re travelling to the USA and some other countries, there are more platforms and options for scanning larger group bookings. Depending on where you’re heading, using a hotel room block service for large groups (this one is mainly USA-focused, but has started to expand to cover Europe) can be the quickest way to both price up the trip and put a hold on the number of rooms you need. Then you’ve got however long it takes to get everyone’s buy-in and agreement.

If the destination you’re considering isn’t listed on such platforms, don’t be afraid to email hotels directly to request group rate quotes. There are always different rates available behind the scenes for these cases, same as there are for media rates. Big companies like TravelLodge in the UK or Hilton globally have departments for this, while independent properties can sometimes be more flexible. At this stage, the key things you want to know are a) the confirmation and cancellation policies and b) if everyone can pay directly and individually for their rooms – this is preferred, to save you the expense. That said, I have in the past booked all rooms on my credit card just to have it secured, but only if the cancellation policy suited me. 

Large Property Rentals: Best for Beach or Nature Escapes

The alternative to hotel rooms, if the destination suits it, is a large villa or property where everyone can stay together. This might actually be the preferred option if your pre-planning has revealed it would suit better because there are kids joining, etc. Key considerations here include how the rooms are split and whether they are fairly evenly in terms of comfort (is there a weird 4-bed bunk room that no one will want to stay in?) and, again, the cancellation policy. Somewhere can seem like a really great price when divided by 16, but once three people drop out, the new per-person split is above the original budget. As such, aim to save a bit if you can here to give you that buffer.

I took this approach when organising a recent friend’s hen getaway in southwest England and booked a farmhouse Airbnb. Luckily, the owners were so nice and understanding that when a couple dropped out, they agreed to reduce the overall fee so no one had to pay extra. Legends. The added bonus of this kind of property is that you can also reduce some food and drink costs. Doing a bulk supermarket delivery order for breakfast items, snacks, drinks and perhaps even lunch bits means everyone can help out and eases the pressure of booking so many restaurants. Trust me, something will go over budget, and every penny helps.

Forward Thinking: Getting Around on The Ground

Transfers or Cars

Next to tick off on the planning and budget list is how you’ll manage getting around on the ground. If it’s a city break, easy stuff. For everything else, it’s a numbers game. The size of your group will dictate the best solution, as will whether everyone’s arriving together or at different times.

If it’s going to be a boozy, sunny villa kinda holiday, booking transfers or airport taxis for the group is best. Or you might suggest people take an Uber in smaller groups when they arrive and work out the costs together, as it’s less admin for you.

If it’s a more active trip with day trips and outings on the agenda, consider suggesting that people buddy up into groups of four (refer to your ‘driving’ and ‘coming from’ columns on the spreadsheet). The bonus of this over a large people mover – and trust me on this, it’s usually a pain in more ways than one – is that each car can usually have a second driver for free, and when it’s time to go somewhere, no one is left herding cats into a van as smaller groups can go when they want. It also means the two designated drivers of one big vehicle aren’t the only ones who can do supermarket runs.

As Few Taxis as Possible 

Taxis can become an annoyance to you as an organiser, especially with a large group. When I organised a big trip to Ibiza (elsewhere in Spain is usually a more solid option, as there are main regional budget flights) a few years ago, this was my biggest stress: it’s hard to pre-book for huge numbers of people far in advance, and splitting and factoring in the costs into the proposed budgets is also complicated and variable. Hopefully, if it’s the kind of trip when people aren’t going to be sober at night and heading out is an important part of the trip, you’ve booked somewhere to stay near the nightlife. 

Now, with point one, two and three considered, you can really whittle down which destinations, accommodation and transport options would work, and have a rough budget for each. Time for another poll in the WhatsApp group with 3-5 options. Send a concise one-page FAQ summary (WhatsApp also lets you send PDFs) of the travel options and your research to avoid the chat becoming a spam of back-and-forth Q&As. Check guides on websites like Numbeo to get a rough idea of how much meals and other extras will cost; that way, people can estimate how much extra cash they will need to budget for. 

Pulling Together the Itinerary: Less is More (and Teamwork Talks)

Delegate

By this point, you might feel like the trip is your baby and that you need to control every aspect. But getting buy-in from other attendees at this point, now that the major details are out of the way, can make your life easier and help get everyone excited and involved.

Ask in the chat if someone would like to be in charge of picking and booking different restaurants for lunches or dinners. Ask who is a dab hand in the kitchen and wants to be in charge of breakfast spreads or getting in the book for aperitivo. Someone might jump at the chance to look up beach bars and clubs or plan the driving route for an afternoon outing. Make a rough sketch of every day and what needs to be organised, and then, hopefully, you can delegate much of the on-the-ground planning, so your focus can be on making sure the grand picture goes smoothly. 

Less Is Often More

I’ve been to a few jam-packed pre-wedding parties where the itinerary was so intense that no one even wanted to go clubbing at the end of the day, and beach holidays where there was no time to just chill. Icebreakers or activities at the start of the trip, when everyone has energy and might be meeting for the first time, are great, but so is bonding time, whether it’s just chilling at the villa with a beer by the pool or down the pub playing some card games.

Not every minute of the trip needs to be filled, and with a large group, where everything usually takes longer – being served in a restaurant, all the taxis turning up, getting ready if there aren’t a huge number of bathrooms – those buffer times will really come in handy. 

Everything Doesn’t Need to be For Everyone  

If it’s a two-day getaway, then sure, plan for the group to always be together. But if you’re on a one-week holiday, make it clear to people which activities are optional and which you’d prefer everyone to attend, such as the big birthday dinner. People have different energy levels, needs and wants – and, perhaps most importantly, they are giving up their annual leave and their money to take a vacation, so they deserve to indulge some of their own whims. 

A totally free day for every four days is a good ratio in my opinion. Similarly, understanding that a couple might want a romantic date night, or that if there’s a family joining, they might want to make memories with the kids on their own time. The added bonus is that it brings the pre-trip proposed per-person cost down, as these days it’s up to individuals what they do and how much they spend.

Avoiding Awkward Conversations: Splitting Costs & Managing Expenses

What Everyone Should Book Themselves 

This is always a potential nightmare. Fronting people’s payments because they need to pay in instalments or being out of pocket with someone you might not personally know is not good (and for the latter, I really think it’s fine to ask the person you are surprising to step in with their friends if needed). As such, you ideally want to pay yourself as little as you need to, and instead have people pay directly.

Everyone should book their own flights. That’s an easy one. Ideally, if you’ve used a room block service or have individual hotel rooms, everyone should again pay their own costs directly (though you’ll want to keep an eye on it and stay in touch with the property to know who has and hasn’t, to be aware of potential drop-outs). If it needs to be – and I’ve done this before when it’s a villa or Airbnb, and it’s required – put it on your credit card to get points, but only if you know everyone will come through or the cancellation policy allows. At a minimum, if doing this, ask everyone to put up a deposit. 

What Needs to be Pooled or Paid Individually When Away

For everything else, decide the approach based on the above. Transfers aren’t too expensive, so it can be a one-time purchase everyone pays you back for. If people are getting cars in groups of four, ask them to sort it out between them. For activities organised by different people, they can be responsible for raising the money – this is another benefit of delegating: you aren’t fronting all the costs, nor are you the only one with skin in the game or the sole “money talker” in the group.

Don’t Shy Away From Money Chats on WhatsApp

Lastly, you’ll likely want a kitty or to use a travel app like Splitwise. However, be very upfront with the group about what the kitty will cover: will it just be for taxis, breakfast stuff for the house, and other miscellaneous costs? Or will it be for meals (because they are set-priced) and for stocking up the fridge with booze? The latter can become more complicated if there are those with champagne tastes and those who are sober, or you know someone always orders the lobster.

Pre-trip is the time to be honest and gracious, and to face those potentially awkward conversations as the host before you travel. You don’t want anyone to feel the costs aren’t fair or representative, and it’s much better to approach it sober months ahead than in a drunken last-night resentment debate. Make life as easy for yourself and everyone else, and you’ll have a fab trip. 

The most important thing is you also enjoy the fruits of your labour. Or, book yourself a package holiday and leave the heavy lifting to someone else – there’s really no shame in going for the easy route.