
Planning More Complex Travels: 8 Tips To Ease The Process
Usually I stay in the one place; exploring as much as I can find, and just doing day trips and tours. Lately though I’ve been changing it up and booking all sorts of trips – multi-cities, short last-minute city breaks and using local transport rather than just guided tours.
I was booking so many different trips at the same time that I totally lost track of what I’d booked for where. These plans were some of the most intricate travel plans I’ve ever compiled.
Of course, there are far more complex travels than what I planned, but sometimes it helps to take things right back to the basics.
Here are some of the things that helped me simplify things:
1: Find a destination that suits your budget

The ‘everywhere’ option is one of the most under-rated tools out there when you don’t have a specific destination in mind, particularly if you’re trying to stick to a budget.
If you know, for example, that you want to spend a week on a beach but don’t care where as long it’s warm and sunny, then this is an ideal time to use it.
Available on both Skyscanner and Kayak, adding ‘everywhere’ as your destination will show what routes are flown from your departure airport and will give you starting prices (or the option to search) on the dates you include.
I have used this before when I’ve just got fed up with life and want to go somewhere for a few days peace and quiet without spending a fortune. I’ve also used it when I don’t know which flight connections are available between destinations – instead of trawling through multiple airline route maps, this option does the work for me.
I've also recently discovered Kayak's 'Direct' search option, which lists all flight routes and airlines offering those routes from your selected departure airport. It also provides extra details such as flight time and seasonal availability. I actually discovered some direct flights I didn't even know about from my home base!
Using the 'everywhere' tool was especially helpful when I needed to be back in a specific city for a specific date, but needed to find a ‘go-between’ location to ensure my planned route fitted with those non-negotiable details. Otherwise, I would have either had to go back and change most of my already-planned route, or miss a rugby match I had tickets for.
2: Give yourself enough time to plan

If nothing else, my disastrous trip to Iceland taught me to have a rough idea of a variety of things available to do ahead of time. I know some people like it all to be a total surprise – and that’s totally cool.
But if you like a bit of planning to your travels, then having a rough idea of activities, sights to see, what’s in the vicinity etc will save you from wasting precious time while away looking up stuff to do, instead of just doing it.
I also discovered through my own travel plans, that where I thought I’d just hop on a few super sophisticated trains and it would all be sweet… well let’s just say my plans changed drastically multiple times. I even purchased a flight that a few weeks later, I had no use for because my destinations and dates had changed.
I spent around six months planning that particular (6-week) trip, and had to temporarily give up several times after my brain was fried with figuring out all the complexities involved. Thank heavens I started planning so far in advance, or half of it wouldn’t have been possible.
I also knew in advance that this trip would be different to any other travels I’ve done, so I was able to mentally prepare for that.
Making travel plans should be enjoyable, not stressful – so giving yourself time to research and plan everything will make your booking process a whole lot smoother.
Plus, who doesn’t love a good oul holiday countdown?!
3: Look at transport options first

I started with a rough plan of where I wanted to go and how long I wanted to stay in each place. I had wanted to use trains as much as I could, going from A to B.
I soon realised that it sometimes took multiple trains, buses and trams to follow through with those plans. By continually tweaking I was able to find, for example, a flight from place A to place C, and then I could grab a train and double back to place B afterwards.
Using a combination of transport options cut down on how complex my plans were, streamlining my actual travel to just one or two connections rather than 4+ connections per journey.
I used Rome2Rio quite a lot for my initial transport planning – but found that sometimes prices and routes differed slightly, so do check/book via the direct websites for the most accurate information.
Looking at transport options helped me to figure out which destinations were easily accessible from the destination I would be in at that time. Some cities are more readily connected than others, so I let this dictate the order of my plans and took it from there. Doing this made it so much easier to plan a sensible, and more importantly, realistic itinerary.
4: Check out things to see/do to help decide the length of your stay

It surprised me how well this actually worked. I was pretty set on my plans and dates, only to realise I was going to miss out on so much due to taking a shorter visit to a particular city – which is how the non-refundable flight I had purchased ended up no longer being needed.
So after looking at my other travel plans, I realised I would be staying longer in a place where there wasn’t much I was fussed on seeing, and scrimping on a place where I found tons of cool things.
By looking at what activities and things that I absolutely must do in each city, I was able to tweak my plans and spend more time in a place more suited to my interests.
5: Traveling can be physically and mentally tiring..

The physical effort of actually traveling from one place to another can be more tiring than we think - even more so if it requires long journey times or multiple legs!
Particularly for those of us who battle with long-Covid fatigue.
I didn’t expect just how fatigued I would be lugging my two backpacks around from place to place, especially as I added more souvenirs to the pile.
And the endless cycle of packing and unpacking. Ugh. That got real annoying, reaaaaaal quick.
Even sleeping on the journey to new places, I found that by the time I arrived and got checked in, unpacked what I needed, sometimes had a fatigue-nap, freshened up and headed out – I was already so exhausted on my first day in a new city that I sometimes struggled to find the energy to completely immerse myself into the experience.
If I was to do the same itinerary/route again, I would give myself the day of traveling/arriving to a new city as a ‘rest day’. This way I could either explore a little bit at a slower pace, or spend the day resting up without exhausting myself so much that I struggle to keep up the next day.
6: Foreign fees

You don’t even need to ask how I know, but it can be so easy to quickly rack up non-Sterling/foreign fees when using your usual bank cards.
Even non-travel credit cards can charge fees and it would surprise you how quickly your 30p fee here, £2 fee there can add up.
I first tried the Pre-Paid Post Office Currency Card in 2019 in NYC and it was fab – just zap my card and no foreign transaction fees to deal with when I’m back home!
It currently allows 22 currencies to be held, can hold multiple currencies at any given time, and is easy to top-up and manage through a user-friendly app.
I used it throughout my 6-week Europe trip and definitely saved myself an absolute fortune by not having to pay the non-Sterling fees my own bank charges.
However, there are fees that may be applicable, as well as daily withdrawal and topping-up limits, so do always check the current terms and conditions carefully.
7: Local transport versus guided tours

I have started to dip my toes into getting out there and exploring more locally, rather than just always booking guided tours.
I found a particularly big difference when checking out if I could save some pennies by taking local transport from Gdańsk to Malbork Castle instead of paying over a hundred quid for the convenience of tour bus transport.
Which option is better is dependent on several factors as I also explained, but I tried to use this process much more on my 6-week trip.
I found that as I embraced transport options that I don’t get to use at home (think trams, cross-country trains etc), my confidence in trying and figuring out new things grew.
A good example was when I was looking at the multitude of Annecy tours from Geneva, but then decided I would actually prefer to dander through it at my own pace with my camera. For a little under £20, I could do just that – a quick look on FlixBus showed me that Annecy was less than an hour away from Geneva.
I found that by using a combination of local transports and guided tours, I had a more locally-immersed experience, rather than just being the ‘tourist on holiday’ who sticks to the easy ways.
8: Be flexible

Yeah, when I say I was continually tweaking and making changes – I mean even when I was actually on the trip too.
Certain parts of my trip were non-negotiable due to date-limited transport options, timing limitations for tours because of my continuous arrivals/departures, as well as rugby matches I was attending. These were the main reasons why I had 95% of my 6-week itinerary planned and booked prior to starting it.
But for those who won’t be so restricted on non-negotiables, being flexible would work particularly well when tip #5 hits you unexpectedly, but you don’t want to miss out on any of your plans.
I had also booked transport for early morning/afternoon arrivals where possible with the intention of maximising my first day in each new location. Turns out, this wasn’t always a good idea..
Arriving into Geneva at 8am with no check-in until 2pm didn’t bode well specifically because I arrived into an endless downpour of rain after a thunderstorm.
I was also exhausted and feeling in severe need of freshening up, so I ended up just spending my morning/afternoon shopping for toiletries then hanging out in the local pub (yeah, that bit was just awful.. ahem).
Next time, unless tickets sold out quickly or there was a limited schedule, I would just wait until the morning of/night before to book train or bus tickets.
Doing this, along with the extra travel day, would offer the flexibility to manage the realities of continuous traveling without having to sacrifice your plans while there.
Of course, everyone has their own travel style and their own limits, but anyone who has traveled post-Covid knows how chaotic it can be with last-minute changes etc.
Hopefully these tips will go some way in helping you to organize your more complex travel plans so that the actual trip goes smoothly!