My guide to boss travel: Step 1 – Deciding where to go, and when

First step – are you ready?

Dream a little dream – there will be much more on dreaming in Step 3 of the series, but you can’t have a plan without a dream. Maybe you already know where you want to go. Maybe you’ve got a friend living someplace wonderful. Maybe you haven’t been able to move past the simple thought, ‘I want to travel’. All good!

It may seem obvious but you do need to have a general idea of where you want to visit so you can figure out how many days you want to spend in each place. Fire up Google Maps (more on my love affair with Google Maps in Step 3), and see which cities, regions and countries speak to you.

  • Two words: Off Season. Travelling at less popular times of year can be a very rewarding experience. Think Venice in January. Scotland in early April. Budapest in the run-up to Christmas.
  • A good rule of thumb: spend at least 2 or 3 nights in each city you plan to visit. That way you get to sleep in the same bed for more than one night and you can enjoy at least one full day without arriving or departing from somewhere.
  • Consider reverse engineering your trip. Rather than thinking about a destination, have a look at offers and deals from your home airport and make a snap decision. So it’s not on your bucket list? You might have an even more wonderful time without being weighed down by a lifetime of preconceptions and cultural references.
  • Research the best timing for purchasing flights. Someone once patronised me at a party for booking flights from Toronto to London six months in advance. It’s not adorable, it’s what we hoi polloi do to scoop up the best deals. Having said that, the cheap flight game rules change constantly and it’s worth seeking out current trends and tips. Late last summer, I snapped up cheap flights from London to Toronto for October, so the six month rule doesn’t always apply. Skyscanner is a great starting point. If specific dates aren’t important, try doing your search with their handy ‘whole month’ option – you will be able to see at a glance which days (and months) have the cheapest tickets. Skyscanner also published a fantastic article back in January 2017: 6 secrets of finding the best low cost flights. Have I mentioned I love Skyscanner?
  • Consider flying ‘open-jaw’: fly home from a different airport than you flew into.
  • It’s best to buy your UK rail tickets for popular destinations up to 12 weeks in advance, and save even more by committing to specific train times. The Man in Seat 61 knows everything about getting around the UK and the rest of Europe on rail. Listen to him.
  • Rail stations in the UK and Europe usually have lockers or ‘left luggage’ services to store your bags. Perfect for those smaller cities that don’t warrant an overnight visit. We once visited York, a small, compact city, for about three hours in the middle of our rail trip from Leeds to Edinburgh and used Left Baggage. I’ll provide more detail about what to do with storing your bags in Step 4, but it’s worth a brief mention at this point, when you’re figuring out your rough itinerary.
  • Don’t forget about travel agents. Some people think they’re dying breed, but they know what they are doing and have tricks and contacts that you can’t even imagine. Use them, especially if your multi-city itinerary is getting a little intense, it’s a special occasion like your honeymoon or a milestone, or it’s adventure travel. Even if they charge you a fee, which not all of them do, it will be worth it.
  • Research your chosen destinations to find out what events might be taking place. Do you avoid festivals? Do you run enthusiastically towards festivals? Good hotel rooms and restaurant reservations will always be harder to come by during busy times. And even if you don’t care about that particular event or festival, anyone who IS there to check it out will annoy you and make everything busier. And yet, you’ll be the one in their way.
  • This may sound stupid – but – you have a valid passport, right?

Previous posts in this series
My guide to boss travel: Introduction 

Upcoming posts in this series – published on Fridays 
My guide to boss travel: Step 2 – Who’s joining you?
My guide to boss travel: Step 3 – Time to dream
My guide to boss travel: Step 4 – Sorting out the boring stuff
My guide to boss travel: Step 5 – In transit
My guide to boss travel: Step 6 – Your trip, your way


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