My guide to boss travel: Step 3 – Time to dream

This is when you can start having a little more fun. Let out that breath you didn’t know you were holding in while you were buying your plane tickets. Let your imagination run riot, like the little girl in the bottom right corner of this photo about to run up that hill.

  • Before you even think about googling your destination or cracking open that city guidebook, close your eyes and think about what you’d like to do. Write everything down – sites, food, drinks, shopping. These are your must-dos. Ask your travel mates to do the same thing. Now you can look at travel guides and round out your list.
  •  ‘Star’ points of interest in Google Maps. You’ll need a Google account for this one, and in my opinion it’s worth it, for this functionality alone. Google Maps is a wondrous thing, but even more so when you take advantage of all its handy features. Directions are provided for driving, transit, walking (and cycling and flights); great for judging distances between two points.
  • But take it one step further and start ‘starring’ everything you want to visit – restaurants, museums, attractions, anything that has an address, really. You’ll get the bird’s eye view on your computer, so even if you don’t have a smartphone it’s worth it to determine where everything is and get a sense of where you’ll be spending your time. But with a smartphone it becomes a truly potent tool for transforming your trip planning. And even if you turn off your data and use only wifi on your trip, the maps can be downloaded into your phone and used offline. You’ll have a bit less functionality – oh how I rely on that live blue dot to tell me where I am – and less information will appear for each item, but it’s still better for navigating than anything else I’ve ever used. ‘Past You’ is the best travel guide and personal assistant that ‘Travel You’ could possibly have.
    York Google Maps
    Desktop version – map of York


  • Not a bad idea at this juncture to find out which days different sites and attractions might be closed, especially outdoor markets. Google Maps can help you there too, providing the website address, hours of operation and peer reviews.
  • Grab a calendar – online, paper-based – whatever you’re more comfortable with, and start figuring out the internal itinerary of your trip. Are you travelling from city to city? Or are you going base yourself in one place that’s also handy for day trips? Or a combination of the two?
  • Find a hotel that is convenient to something – the rail station you arrive at, the part of town where you plan to spend the most time, or perhaps something more affordable that’s a bit further out but quieter and near excellent transit. Trawl through TripAdvisor, scan the reviews, and find a good blend of affordable and location. Do this as soon as possible after you’ve booked your flights – this is another area where the early bird truly does get the worm. I’m not trying to make you panic. I use most of the time, and start by booking a good place that doesn’t ask for any money up front. That becomes my ‘safety hotel’. It might end up being my final choice too, but at least now I know I’m not homeless on that leg of the trip while I spend more time looking for a great deal. Also, consider Airbnb too, especially if you’re staying in the same place for a few nights.
  • Learn key phrases in the language of your destination. ‘Hello. Please. Thank you. I would like a glass of red wine, please. How much does that cost? Where is the toilet? Can we please have the bill? I will not buy this record, it is scratched.’
  • Bone up on history or fill yourself with anticipation with films, TV or books. Visiting Paris is cool. Visiting Paris is even cooler when you walk past a statue of Henri IV and remember that he’s the well-loved ‘Good King Henry’ who came up with the phrase ‘a chicken in every pot’. Don’t be the guy who didn’t know what Ellis Island was (or represented) when he cruised past it on the Staten Island Ferry.
  • If you don’t already know, find out what will make the best souvenirs, or the best shopping a city is known for – sometimes clichés are clichés for a reason. Think leather goods from Italy, perfume from Paris, whisky from Scotland. More ideas here.
  • Ask people for recommendations. But don’t feel like you have to actually follow their advice. If something sounds good, star the place right away. I usually whisk out my phone on the spot so that I don’t forget and can confirm that I’ve found the right place.
  • Ruthlessly cut anyone out of your life who tries to guilt trip you if you didn’t make it to that nice restaurant they told you about.
  • My favourite resources are a combination of books and websites. I can’t possibly list them all here, but I owe a lot of smooth, happy travel to Rick Steves, The Guardian’s Holiday Guides and Lonely Planet for dreaming and planning. I seek out and watch any travel show with Richard Ayoade or Anthony Bourdain in it.
  • Adjust your trip’s internal itinerary if you haven’t locked down your hotel dates and rail tickets… is Paris taking up more days than Amsterdam? Now’s the time to sort that out.


Previous posts in this series
My guide to boss travel: Introduction
My guide to boss travel: Step 1 – Deciding where to go, and when
My guide to boss travel: Step 2 – Who’s joining you?

Upcoming posts in this series – published on Fridays 
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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