Simple tools for planning a great trip


Ben Harvey is an ace journalist; a dry, insightful and funny columnist; and the brilliant host of the Up Late videocast on But when it comes to planning a vacation, he’s a bit surly. He is planning a driving holiday next June and July to the UK and Ireland, and the emails are starting to pour in.

“And that?”

“What about that?”

If it goes south to Western Australia I get a slew of them so for this trip I’m expecting a long line full of hooks that will stretch pretty much across the North Sea .

I already had the list of things that he and his partner Grace “def 100 percent wanna do”:

  • England Lakes District and Leeds tour (for historical reasons).
  • Scotland “Some kind of whiskey experience and maybe fly fishing somewhere in a stream and playing St Andrews.”
  • Ireland See the Cliffs of Moher.

Seeing how Harvs, one of the most talented people I’ve ever worked with, is struggling with this (and asking for a little help), it seems logical that others are too, so here’s a approach to start planning a great trip. . .

Camera iconLeeds Castle (in the Kent and Surrey region). Credit: Visit Brittany


The way to start planning is to plan a start. And then a middle and an end. (For us travel writers, planning a trip is like planning a story — and, indeed, a good trip is an unfolding story.)

In Ben’s scenario, to visit the North of England, Scotland and a bit of Ireland:

  • I would fly Perth – Dubai/Doha – Heathrow (Emirates or Qatar)
  • Spend a few days in London (?)
  • Hire a one-way car and take a pretty route to Leeds.
  • (Or ditch London and fly Perth – Dubai/Doha – Manchester, which is much easier.
  • Include the Lake District for sure. I’d bet on three nights there, hanging out.
  • Drive to Scotland – easy whiskey to make in Edinburgh, and Edinburgh generally remains a good base.
  • Drop off the rental car one way.
  • Fly from Edinburgh to Shannon – Ryanair flies direct, but it’s an adventure sport.
  • Car rental at Shannon Airport (one way rental to Dublin).
  • Drive from Shannon Airport to the Cliffs of Moher and other sites in the area.
  • Explore a bit of the west coast.
  • Finish in Dublin (270km from the cliffs, just to give an idea of ​​distances) and drop off the car.
  • Fly Dublin – Dubai/Doha – Perth (Emirates and Qatar both fly from Dublin).

…even writing it down like that, we immediately have a structure – a plan – although a plan that can be changed, a schedule added, places removed, etc.

Edinburgh's Old Town is a good place for a food walking tour.
Camera iconEdinburgh’s Old Town is a good place for a food walking tour. Credit: Steve McKenna


There are all sorts of ways to plan, of course – from an app on your phone to a calendar on the wall at home or a whiteboard, which everyone on the road can see and add notes to. (Be sure not to use permanent markers.)

For apps, take a look at the free TripIt, which is pretty easy to use. You forward your confirmation emails and the app creates a travel schedule. It’ll tell you where you need to be and when, from flights to car rentals, to hotel and restaurant reservations. It will do just about anything most travelers would want, but its premium version, TripIt Pro, is subscription-based and costs $77.99 per year but adds features like real-time flight alerts.

There are plenty of planning apps to look at like Tripsy and Wanderlog. Or just start a Word document on your computer. Put the dates on the left and start writing down the things you want to do and figuring out how much time you need at each location.

More experienced computer users can start an Excel spreadsheet.

Or just wander into Officeworks and get an A5 notepad for a few bucks and start making lists and sketching timelines, places, and experiences you want to include.

Like Harvs, there will be “defs” (translation: places you absolutely want to go) and, I guess, those that are “poss” or “prob” or just maybe.

Looking over the quays in the city of Dublin, Ireland in the early evening.
Camera iconLooking over the quays in the city of Dublin, Ireland in the early evening. Credit: David Soanes Photography/Getty Images


I just want to go back to the previous item of planning tools. If you’re traveling with other people, I think it’s really important to make sure all the planning is ‘public’. If it’s just the two of you, the whiteboard in the kitchen could be a brilliant idea. If it’s a large group of cyclists, it’s a bit more complex, but it’s important to have regular updates.

There is nothing worse than a person who plans, books, commits. . . then, along the track, someone else says, ‘I think we should stay longer in Edinburgh’, or ‘wouldn’t it be good to go to Skye too’. It’s a nightmare scenario. (I saw Harvs ignite on a gloomy day and wouldn’t want to go back.)

Keep the planning “open” and get everyone on board or “sign off” before booking.


Once you’ve committed to the duration of the trip (start and end dates) and fairly committed to what you want to do, my next step would be to lock in the flights.

Once you have these bookends in place, you can pretty much “wiggle in between.”


If you are planning a driving holiday, like Harvs, then you are looking for a car. In many places, it’s much easier and more affordable than here to get a car rental for a day – in his case, pick it up in London and drop it off in Edinburgh, for example.

A specialist whiskey shop on Edinburgh's Royal Mile.
Camera iconA specialist whiskey shop on Edinburgh’s Royal Mile. Credit: Ken Jack/Corbis via Getty Images


OKAY. So for the big international flight out of Perth we have an arrival date and a departure date. Definitely look for accommodation for the first two or three nights, so you can find your feet. You will know where you are heading next and do the same there.

Some travelers will like a bit of flexibility, others will want everything locked down. But I think the important thing is to set up the key elements of hosting. Some booking sites will allow you to book and pay while you are there; most have very reasonable cancellation deadlines, with no penalties, so you can ‘reserve’ seats well in advance. But it’s very important to keep a log of it all (in your app, on your Word document, on the whiteboard, or those sheets of paper). Don’t lose sight – record everything as you plan – or it will turn into a big mess.


Harvs is on a road trip, so transportation is quite easy. But there is a domestic flight to consider, from Edinburgh to Shannon (if he wants to get closer to the Cliffs of Moher) or Dublin, if he wants to return. Both are good ideas, but I think now I’d do a big loop from Dublin, because it’s easier with the rental car, and he and Grace will still want to drive around the country a bit. There’s no rush to buy these flights right away – and I’d be a bit hesitant as the travel dates might change a bit. But keep domestic flights or flights between countries in Europe, for example, in your sights, to book early.

If you plan to use trains, for example in Europe in general or specific places like Switzerland or the UK, start researching their rail passes. For example, there are many Eurail passes, and now you have a clear enough idea of ​​your route to determine which will give value or if it is worth it. The same is true with BritPass, which offers passes for the whole of the UK, or just for England, London Plus, the South West and Scotland.

Emerald Isle Campaign.  cliffs of moher
Camera iconEmerald Isle campaign. cliffs of moher Credit: Goss Vitali/Goss Vitali


Hey, planning is coming, isn’t it. I can already feel that we are all relaxing, now that we have the “bones” of the trip in place. If you want to incorporate a coach tour or a river cruise, you will of course have already incorporated an important element like this into your dates. But also think of “small circuits”. For example, there are very good tours of the Lake District. Joining a small-group tour for, say, three days might be right for you. But don’t worry about things like hop-on hop-off buses. All of this can happen later, or when you are there.


Another idea is to consider getting an international bank card, with a number of currencies, so you can start charging specific currencies to use when the exchange rate is good. For example, you could have done well in recent weeks loading UK pounds. (It’s a gamble, of course, because rates can go either way.)


You will soon be at the “fine detail” stage. If Harv’s is wandering around on a dark night, he’s likely to stumble upon the whiskey experiences in Edinburgh. So there’s not much to fix that – but fun to start looking at what’s on offer.

Details like playing a round of golf at St Andrews or other courses require more thought and planning. Start now. You can always approach them and find out about the possibilities, even if it’s too early to book. (But, again, write it all down.)

Experiences like trout fishing in a Scottish stream (yes, good luck and let me know how it goes, Harvs) will require a little more research and booking sooner. After getting the main structure in place, it’s something to dig into sooner rather than later – especially since I’m sure Grace will enjoy the ‘day off’.


Well, I hope things are going a little better for you too. If you’re tackling a big journey along these lines, setting up the big structure, the small structure, and then filling in the gaps, you should get there without too much heartache or hassle. But hey, you don’t have Ben Harvey in one ear all day. . .

PS: As it is a private holiday, but pushed me to this story, I emailed Ben Harvey to make sure he was comfortable with me posting it. He simply replied, “Yes, of course. But you gotta take the p**s right. Tell them I’m the cheapest man on earth, so I’ll be home in Scotland.

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