How I Plan Big Trips

Let’s Go Away For A While

Today we are going to look at how planning a big trip! I go away about 3 times a year for leisure (more if we include work) and the number one reason I’m able to afford to do this is forward planning. For me, travel is a big luxury and one I work very hard to be able to do. Before we get into it, I want to just be clear on what I mean about a “big trip” as that’s hardly a scientific term!

Obviously, there’s lots of different types of travel; travel with friends, romantic getaways, press trips, going somewhere for/with work, family holidays, and last-minute cheapo breaks (RIP £5 Ryanair sales). And then there are my favourite kinds of adventuring: the Big Trips! Long planned out holidays to places you’ve been longing to visit! For me, a Big Trip has a few key factors:

  • Leaving your current continent and therefore normally involving a long haul flight.
  • Having a duration of 12+ days.
  • Either alone or with a partner/close friend (i.e. rather than family/a big group).
  • Be somewhere new to you that you’ve had a big desire to visit!

So, that’s normally what a big trip looks like to me. I’d classify my first Big Trip as New York with a friend when I was 16, and since finishing university I’ve gone on roughly one Big Trip per year. Some examples of those kinds of trips I’ve taken since I’ve been blogging (i.e. you may have read about them) would be my USA trip in 2014, Ryan and me in New York, our recent Cuba trip, and my previous trip to Japan.


So step 1 is choosing a destination. This part never gets hard for me because the list of places I’d like to explore could fill a book! Currently on my “Big Trip” list is Las Vegas, Indonesia, Brazil and Florida.
Once you’ve got a dream destination, start gathering info! To me, this looks like checking guide books out of the library, making a Pinterest board of images and guides, and bookmarking any blog posts on the area.

I usually do a search of Google and Bloglovin, plus if I remember reading about a certain place on somebody else’s blog I’ll dig that up too and bookmark it! Something I also do is make a google map of the area. I also have one layer for animals and one layer for vegan places and then the other layers are dependent on place (so, my Japan map has a “temple” layer whereas Helsinki had a “Tove and Moomin” layer which later became a blog guide). The benefit of this is you’ll discover what areas you’ll want to spend most time in. This will also help later with actually planning the trip out!

When To Go & Flights

Hopefully, in reading and learning about the place, you’ll have a good idea of when you want to go. For example, for my previous trip to Japan, we wanted to go late March-April so we could catch the cherry blossoms, whereas with New York in 2016 we very specifically wanted to be there for Christmas! I tend to note down any specific festivals or national holidays as I read about them, and then come back to that later. For quite a while my trip to Helsinki was going to be in June so we could catch the midsummer festivals… this didn’t end up working out, but if you find a specific thing you want to visit for then at least note that down. Don’t forget to take seasons into account here as well. Depending where you’re off to, you want to make sure you’re avoiding rainy season, cyclone weather and so on! I’m always shocked at the amount of people I see visiting Mauritius for Christmas aka MONSOON SEASON.

Once you know theoretically *when* you’d like to go, you can start looking for flights. I normally don’t book the flights on the spot, but the minute I’m interested in somewhere I will start monitoring the flights. My Japan flights for my current trip were £180 (a record low for me) and about £400 last time (it can get up to £850+ for hanami season). For Christmas 2016 in New York we paid £280 return which is not bad- it can get up to £1400+ at the exact same time of year. I’m going to do a separate post on cheap flights at some point because it’s become a bit of a personal sport for me.

Accommodation and Must-Dos

Next up is to actually start planning out the trip. Note that you haven’t booked anything yet! Again, hopefully, in your reading up on the place, a few things have started to jump out at you. Put these all in your documents and start roughly dividing that up into days. This has been a gamechanger for me in terms of making the most of the time I get on holiday. Holiday’s are expensive in both money spent to go and time lost from work (especially if you’re freelance!) and making the most of every single day is something I’m much better at now than when I was younger. For example, with Cuba I knew we would want at least two days in Trinidad and that it would take about half a day to get there- so I marked off four days to get to and from Trinidad on our hypothetical itinerary. I also knew I wanted to stay in a Casa Particulare (government run Air BnB system where you stay with a local family). In this way your trip will start to shape up and hopefully, you’ll get a rough idea of how long you’d like to go- between 10-14 days seemed good for Cuba (we ended up going for 12).

It’s also good to look back at your map here (if you made one) and see if there are any general areas you can mark down as somewhere to visit. For Helsinki, we were staying pretty central but I marked off a day for Kallio (this turned into two days when we there) and a day at Linnanmaki, the theme park.


The fun part! You’d better believe that these days I’ve made a full on spreadsheet that I just insert figures into. I can pull up a chart right now with my DisneyWorld or Las Vegas budgets now. Knowledge is power…! There’s no way you’ll be able to plan out every single expense but at least getting down the rough estimates of stuff like accommodation and big chunks of money (ie visiting theme parks and attractions). You can easily look up costs for most things in advance.

This is important to do because otherwise, your spending can be so hard to guess. I would say be realistic here! For me, the budget isn’t about “what is the least possible amount I can spend” and more “what are the key things I want out of this trip”. My opinion has definitely changed- older me is much more likely to spend money eating out or visiting attractions than teen me would. For example, on my previous trips to New York I’ve travelled alone, made sandwiches at home and basically not eaten out. I think we’ve all had trips in our teens where you ended up cooking a pan of shitty pasta for the 8 people in your hostel room… fine if you’re 18 and on a budget of 3 euros a day but for a magical trip with your fiance that’s not quite the thing is it!

For my Christmas New York trip with Ryan, I knew in advance that we would want to try every vegan restaurant we could as the scene is so good. I literally googled the menu of some key restaurants and wrote down an estimate cost into my budget and came up with basically the same amount the flights cost us! We could have done the same thing I usually do (sandwiches at home etc) but it was Christmas, and our anniversary trip, and it was so much more fun eating out. So even though it cost more than I might have initially imagined, I was at least ready! It’s not necessarily about budgeting yourself into the ground but more being prepared for what you might need. I also don’t want to sound like a smug cunt here but it’s also been YEARS since I came home and had essentially bankrupted myself with overspending on a holiday… these days, I know what to expect and how much I’m likely to want spare for souvenirs and whatever. It means more saving in advance but less “oh my God NO” moments when I check my bank balance on the way home.

Booking The Flights

Okay! So at this point you know when you want to go and how long for, roughly how much it will cost you, and what you want to do whilst you’re out there. Now you’ve got your entire trip planned you can buy the flights to go there..! Sort of. So the benefit of knowing all the background for your trip is you can basically sit around, wait until you’ve got the funds (vital), and THEN… wait for flights to come up. I think I mentioned before that I’d been planning to go to Cuba for about three years. That’s three years I basically had my map, itinerary idea and budget just sat around (that trip went through four previous partners before Ryan lucked in). I didn’t want to spend more than £400 on flights but was struggling to find anything cheaper. At some point I met Ryan, that happened, and he wanted in on the trip, so I was now looking for two sets of flights for cheap.

When I found £330 return flights, it was obviously on budget but wasn’t for quite the time I’d originally planned to go. I knew from research it would still be a good time of year (and crucially we’d avoid rainy season). Plus, I knew if we booked the cheap flights when I found them (only about 5 months before we went), I knew how much extra I would need to save to be able to afford to the trip we wanted whilst out there, thanks to my budget. Obviously, if you’re on a good salary and money’s not as much of a concern, you might be able to just book stuff when it comes up and just spend when you’re out there. But for all you fellow penny-pinchers, having that plan is key. This ended up working out perfectly for Cuba – we had gorgeous sunny weather every day, had both been able to save enough to live like kings whilst we were there.

So, it might seem exhaustive to plan all that but honestly, I love it! Planning the holiday and knowing I’m setting myself up to be really well-prepared makes me happy. I like knowing I’m going to get the most out of a trip, and also knowing I’m not going to potentially bankrupt myself if I book something on a whim. How do you plan trips? In my next travel post, I’m going to go through exactly how I planned my current trip to Japan as basically all of them above went out of the window 😅


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  • Reply Denise

    That’s really a nice post about how to plan a big trip! It’s nice to plan for some particular happenings in a country, like the cherry blossom or Christmas. Planning tickets and a place to stay can be tricky, but you are doing all so well! Hope you go to the places you want and that you have a great week!

    January 30, 2018 at 3:48 pm
  • Reply Caitlin Teibloom

    Amazing post!! I’m bookmarking it and can’t wait for the flight post, too❤️

    January 31, 2018 at 3:36 am
  • Reply The Monday Project

    THIS IS SO HELPFUL! Thank you so much Laila, I’ve got to do a three week stint in Italy in June for university and definitely going to be using your post to plan!

    Kirsty | The Monday Project |

    January 31, 2018 at 11:19 am
  • Reply Laura

    i’ve never even been on something i’d classify as a ‘big trip’, but will come back to this post when i have the means to go on one, haha! but i do love planning trips, and do something similar to this on a smaller scale when i go somewhere. xx

    January 31, 2018 at 5:38 pm
  • Reply TAPEPARADE - How I Planned Two Months In Japan - TAPEPARADE

    […] Today we’re going to talk about how I actually planned this trip. I recently posted about how I plan big trips, and this current trip certainly counts as a big one, although I didn’t plan it in the same […]

    February 18, 2018 at 7:33 am
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