From polling the group chat to finding the right insurance cover: five top tips every ‘chief holiday officer' lives by

The Guardian

a day ago

There are several flavours of traveller: those who simply like to grab their passport and go, and people who prefer to book a few key activities then let the rest of their holiday take care of itself. Then, there are the CHOs – or chief holiday officers – who like to squeeze the most out of every break by dedicating the run-up to the joy of careful planning.
For this type of traveller – often the planner of the family – getting the details exactly right is their superpower, and the journey (including all that delicious travel prep) is every bit as important as the destination. Those travelling alongside them can rely on their efforts – often with a sigh of relief – to make sure every holiday runs smoothly.
From sussing out the best time of year to travel and finding the perfect base from which to explore, to scouring reviews to find hidden gems and booking the best restaurants well in advance, these dedicated preppers do all the hard work so you don't have to.
If you've holidayed with a CHO, then congratulations: you likely enjoyed a stress-free break. And if you're the one who rates spreadsheets above sunscreen – even if you didn't realise it until right now – we're here to help you get even more out of your holiday prep.
From apps designed to get everyone on the same page, to holiday insurance with some handy extras, level up your holiday-planning game with our expert travel tips.
If you're planning a group trip – whether it's a bunch of friends getting together to celebrate your birthday or a multi-generational holiday featuring family members of all ages – it pays to use tech to smooth out any niggles.
It can feel awkward nagging everyone for the money they owe you for that boat trip you booked, but if you use an expense-splitting app, you can add in any spends and divide them among the group, so you don't have to initiate any tricky financial conversations. Bonus tip: if you use a credit card such as the Barclaycard Rewards card* to pay for those bookings, you can get cashback1 on eligible purchases, too.
Setting up a dedicated group chat and using polls to decide details such as when and where to eat can also reduce the likelihood of receiving complaints down the line.
*28.9% APR representative (variable). The approval of your application depends on your financial circumstances and borrowing history, so do the terms you may be offered. The interest rates may differ from those shown. T&Cs apply.
As CHO, you'll know how important it is to arrange comprehensive travel insurance that covers you for any eventuality as soon as your trip is booked. When you choose Barclays Travel Pack2 you can enjoy worldwide, multi-trip cover from £14.50 a month, so it's one less thing to worry about when it's time to book your next trip.
Named a Which? Best Buy in June 2024, Barclays Travel Pack features the kind of holiday-enhancing extras CHOs live for: think cover for lost bags and cancellations, as well as RAC breakdown cover across the UK and Europe for you and your partner; and six free airport lounge visits a year and a 24/7 digital concierge service with the Travel Plus Pack3 (for £22.50 a month) to help you access the exclusive events, restaurants and discounts that make holiday planning an adventure rather than a chore.
The secret to being a successful CHO isn't to create a super-rigid schedule – it's being organised enough to plan a great holiday while riding the wave of any setbacks that might come your way.
There are plenty of strategies you can employ to minimise potential disruption, including checking the government foreign travel advice page well in advance (your insurance may not cover you if you book somewhere holidaymakers are advised against travelling to) and making sure everyone's holiday jabs, passports and visas are valid and up-to-date.
When it comes to finances, booking your trip with an Atol- or Abta-protected provider on a credit card – preferably one with no transaction fees for spending abroad, such as a Barclaycard Rewards card* – offers extra protection for your purchases.
Finally, make sure you keep any essential details on hand, including contact details for your insurer and your Abta certificate, in case of emergencies.
*28.9% APR representative (variable). The approval of your application depends on your financial circumstances and borrowing history, so do the terms you may be offered. The interest rates may differ from those shown. T&Cs apply.
If you're used to being a CHO, letting go can be scary. But there are ways of delegating some of your holiday-planning tasks that will help ease the pressure while allowing you to stay in control. Allocating smaller jobs to other travellers – such as scouting out the best vegetarian restaurants in the area or comparing airport transfers – can help you focus on the bigger picture.
When you're looking at which accommodation/restaurant/boat trip to choose, make sure you check out the two- to four-star ratings too (not just the five-star ones) before booking. Keep in mind that if low-scoring reviews all mention similar problems, or the replies are dismissive or rude, it's a red flag you shouldn't ignore.
When you've spent hours of your own time organising a trip for other people, it can be frustrating when not everyone's equally keen on your choices. But giving the group some autonomy when it comes to your carefully planned activities can reduce friction, especially on a group holiday.
If some of you would like to spend the day on the beach while others want to hit the museums (as detailed on your colour-coded itinerary), lean into letting people do their own thing. Just make sure you choose one daily group activity, such as meeting up for dinner in the evening, so you can share stories of your perfectly planned adventures.
1 You'll earn cashback on new purchases that you make. You won't earn cashback on balance transfers, money transfers, cash withdrawals, buying currency, or any cash-like transactions you make such as money orders or wire transfers. It also doesn't include gaming related transactions such as gambling, betting and buying lottery tickets.
2 Terms, conditions, exclusions and eligibility criteria apply. You must have a Barclays current account, be 18 or over and hold this product for at least six months from the date of purchase – then you can cancel at any time.
3 Terms, conditions, exclusions and eligibility criteria apply. You must have a Barclays current account, be 18 or over and hold this product for at least six months from the date of purchase – then you can cancel at any time.
Find out more about Barclays Travel Packs and the Barclaycard Rewards card