The insider's guide to booking holidays

How to avoid unnecessary holiday headaches through proper planning

Marcus Webb – Virgin Money Living Mentor

by Marcus Webb | Independent Money Mentor

Editor of Delayed Gratification and independent journalist

Holidays should be fun-filled and provide happy memories to last a lifetime. Unfortunately, it doesn’t always work out that way. If you book a dodgy hotel or end up on a never-ending tour with a bus-load of other tourists, your holiday glow can be extinguished in a second. Never fear! This insider guide covers every stage of your trip, so you can travel like a pro from start to finish.


The best way to navigate the labyrinthine network of airlines and routes is to use a travel fare aggregator such as Skyscanner to find the cheapest option. But do be aware that the cheapest option isn’t necessarily the best one – look out for lengthy stopovers, second-rate airlines, dodgy bucket shops (look for the ATOL code to know you’re protected) and, in many cases, outrageously indirect routings. While your wallet may thank you for flying four hours in the wrong direction, the environment almost certainly won’t.


Most people leave buying their insurance until the very last moment. Rookie mistake. Get yourself covered ASAP. That way you’re protected should anything go wrong in advance of your trip, such as a cancellation or a medical issue. Also look at multi-trip insurance – if you’re going away several times over a year it should work out cheaper.

Ground transportation

Nothing ruins a holiday like a missed flight, an experience that’s made even more frustrating when it isn’t your fault. Trains get delayed, vehicles get stuck in traffic and airport buses get so full that the driver won’t let you on. If you book your airport transport early, not only will you get the best prices, but you won’t be left on the side of the road when the busy bus leaves the stop. Trains are usually more expensive (if you’re travelling to Gatwick or Heathrow consider the various non-Express options) but they’re not always faster, and while cabs are pricey for solo travellers they often work out cheaper than public transport if you’re in a small group.

Hotels lists 1,282,229 hotels on its website, meaning it would take 3,512 years to stay at all of them if you changed hotel every night. In other words, the choice is unimaginably, overwhelmingly vast. So where to stay? While there’s value in TripAdvisor reviews, you shouldn’t place all your faith in their algorithm – plenty of perfectly good hotels don’t rise to the top of their lists. The trick is to know exactly what you’re after, and to keep whittling down the menu of options in the sidebar (gym, jacuzzi, pets allowed, aircon, free wifi, room service) until you hit a manageable number.


Car hire firms make big money from the various add-ons – child seats, additional drivers, sat-nav, and obscurely worded insurance policies for car parts you never knew existed – and you’re likely to face a hard sell at the collection desk. Consider the alternatives ahead of time: most airlines won’t count child seats as part of your luggage allowance, your credit card might cover your insurance and a data roaming package on your phone is probably cheaper than hiring a sat-nav and will get you from A to B with the bonus of letting you check your newsfeeds too (not while driving, of course). When you’ve chosen your vehicle, read the small print carefully and inspect the car thoroughly, taking photos on your phone. Also, if you’re picking up your car towards the end of the day then don’t rush – if they’ve run out of the class of car you’ve booked they’re obligated to upgrade you to a plusher vehicle for free.


Guided tours can be an efficient way of seeing many things quickly without having to worry about driving, planning or making decisions. But a bad tour can feel like a hostage situation – an entire day with this lousy guide on this lousy bus with these lousy people, and there’s no way to escape unless you’re willing to walk back to your accommodation. It’s best to ask lots of questions before booking – who’s the guide, how big is the group, where’s lunch being eaten? For a low-key alternative, sites such as Vayable and Airbnb (through its ‘Experiences’ section) pair tourists with locals for intimate, highly personalised insider tours.

Before making financial decisions always do research, or talk to a financial adviser. Views are those of our mentors and customers and do not constitute financial advice.