How to plan a trip with friends without ruining a friendship

My past experiences booking travel with friends have ranged from straightforward to hopeless. At times entire itineraries have been aborted with me left questioning whether it is possible to plan a trip with friends without ruining a friendship.

I’ve seen the organisation of several trips fail quite spectacularly including the three times groups of friends have attempted to organise sail tours in Croatia via Facebook. Planning a trip with friends is especially hard when everyone has their own opinions on what dates to go, which operator to go with and what the budget should be. People added random friends to the group, others left due to lack of interest and there was no grasp on how many people were seriously interested in attending until suddenly, a deposit was due and the ringleader was scrambling to obtain order.

I’m currently in the midst of planning a rapid multi-destination summer trip in Europe with my London-based bestie Renee. Now I believe I have the right tools in place to successfully plan a trip with friends without ruining a friendship.

Be flexible on where you’re going and when

Initially our intention was a New Years break somewhere between Wellington and London. But we both had limited amounts of annual leave available and  flights were extortionate for at least one of us wherever we went.

Even with accommodation on offer in Hong Kong it made sense to wait six months, take a longer break, and for one of us to travel further.

Each of us wrote a list of cities we wanted to go to, parallels were drawn, destinations narrowed down and a route was found.

plan a trip with friends without drama

Get commitment early on when you plan a trip with friends

In this case I had to book return flights to Europe from New Zealand so I was all in. I booked these at the same time Renee started booking our transport around Europe.

If your friends tend to be a bit flakey I recommend agreeing a date at which people are either in or out. Collecting a non-refundable ‘deposit’ amount before booking so people are less inclined to bail and leave others with unexpected additional costs is also worth considering.

Determine budgets and non-negotiables up front

Budgets vary between people and it’s important to understand what everyone expects to spend on flights, accommodation and attractions. Research what the full trip will cost before bookings are made so everyone is aware upfront to prevent upsets and awkwardness later.

In terms of travel non-negotiables, for me a hotel has to have decent WiFi, for others it might be AirCon, free parking or breakfast.

plan a trip without ruining a friendship

Document what’s been booked in Google Docs (or similar) for version control

Renee started an excel document with dates and locations for us to populate booking information for transport and accommodation in as we went. With the number of cities we’re visiting it’d be a disaster without it.

It’s all very well having a spreadsheet but emailing it back and forward as we booked things soon resulted in version control issues.

I converted it to a Google Doc so we had a single, live document and we could both have visibility.

Assign jobs but have someone organised overseeing things

It’s a massive and financially challenging task for one person to take responsibility for booking an entire trip.

If you’re splitting the booking of flights, accommodation, transport and activities among a group it still pays to have someone organised keeping an eye on everything.

I’m quite happy to sit back and let someone else take the lead when it comes to organising a holiday. A small payoff such as first choice in bed or roommate might provide enough of an incentive someone to take on this role.

Have you got any additional tips to plan a trip with friends? Any dramatic stories of past experiences planning a group trip?

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18 Comments

  1. stephaniestraveldiary
    May 16, 2017 / 6:10 am

    Great tips!
    x

  2. Megan
    March 5, 2017 / 9:00 am

    I can’t agree more with get commitment early! It can be harder with a road trip (which I ran into issues with) but we sort of anticipated it and made it work! Awesome post!

    • March 5, 2017 / 2:42 pm

      Roadies can be a commitment challenge for all sorts of reasons, well done for making it work and thanks for your comment!

      • Megan
        March 6, 2017 / 6:28 am

        Yes! We kind of figured she would bail because she did on a trip a few years before, but it was still super fun!

  3. March 5, 2017 / 2:50 am

    I think it’s important to discuss WHAT you will do on the trip and how to accommodate different travel styles!

    • March 5, 2017 / 2:41 pm

      Yes working out WHAT we will do on the trip be the next step! We’re both pretty keen on foodie experiences. I like to have not too much planned that you’re running from one thing to the next, some down time and time out alone when required is a must.

  4. March 4, 2017 / 7:18 pm

    This is such a great point!

  5. Jean Bean
    March 4, 2017 / 3:47 pm

    Oh I usually avoid traveling with friends for the above issues! It just seems to create more hassles then not.

    • March 4, 2017 / 4:20 pm

      Oh no sounds as though you’ve had some rough experiences Jean! Travelling solo, with a tour group or with a partner (once you’ve travelled together before and are aware of each others habits and requirements) each of course have their own sets of pros and cons.

  6. Jess Mizzi
    March 4, 2017 / 3:06 pm

    Great tips! Travelling with friends is definitely make or break. I have a rule that if you didn’t contribute to planning, you’re not allowed to complain or whinge if it’s not to your liking on arrival (everyone is of course invited to contribute). The other thing is money when you’re away. Have you heard of the app Splitwise? It’s a lifesaver! Sounds like you and Renee are on the same wavelength and on track for an awesome trip!

    • March 4, 2017 / 3:39 pm

      Thanks Jess! ‘No complaining or whinging’ is a great rule I will keep in mind for the future. I hadn’t actually heard of Splitwise but a quick Google suggests it would be handy for local trips with friends. Does it get complicated when there are multiple currencies involved?

      • Jess Mizzi
        March 4, 2017 / 3:57 pm

        I’ve always used it my default currency. It is easy to switch the currency in the settings so I don’t think it would be all that messy.

  7. Karlie V
    March 2, 2017 / 5:56 pm

    I’ve always found it hard to travel with friends, but usually it turns out well. I do think that beforehand it’s important to talk about expectations since often those are what clash on a trip, but if you talk about them before, everyone has a better idea of what they want out of it.

    • March 2, 2017 / 9:04 pm

      I agree Karlie that taking about expectations beforehand is key. In one or two previous cases I’ve made the mistake of assuming all will be fine and there’s no need to raise such a conversation only for something surprising to arise later.

      • Karlie V
        March 3, 2017 / 2:33 pm

        Yes, I had this happen on a recent trip, too. I had the idea in my head that if my friend and I wanted to do something different, we had the freedom to part ways for a few hours or a day. She, however, wanted to stick together the entire time and it led to some uncomfortable discussion during the trip.