How to make a complicated travel itinerary without going crazy

After exams ended during my semester abroad, a few friends and I set out on a speedy tour of the English Peak and Lake Districts. They had made most of the plans, so I just tagged along. We never stayed too long in one town; we bounced around to different cities every other day in order to squeeze everything we wanted to see into the space of a week. The many train and bus rides and hotel check-ins and hauling all our luggage around with us got a little chaotic at times, but I loved the nomadic feeling of waking up to an unfamiliar landscape every morning, long journeys through the countryside, and seeing so much in a small amount of time.

Stanage Edge, The Peak District, England
Stanage Edge, The Peak District

When I returned to the UK for a solo trip over the Christmas holidays a few months later, I wanted to accomplish the same thing. I planned out an itinerary that took me from the southwest corner of England up through Wales to Edinburgh, Scotland and then back to London—with plenty of stops along the way. Fitting all of those locations in and figuring out transportation between them took a number of stressful planning sessions, but that meant that once I was in the UK, everything was already taken care of.

On vacation, I will easily watch TV all day or just wander aimlessly around a city if I don’t have a solid plan. That’s why an itinerary is important for me. When I spend hundreds of dollars and many hours on a plane to get to Europe, I want to make the absolute most of my time there and see as many places as possible. I put in a lot of time on the front end of a trip Googling and reading reviews on the best sights to see, places to visit, and things to do. I plan constant movement so that I can see a lot and don’t have too much downtime in any one place.

Making an itinerary requires a lot of time and organization, especially when there are many places that you want to visit in a short period. Here are my recommended steps for building a daily plan for your trip so that when you go, you can hit everywhere on your list without any loose ends to worry about.

1) Make a list of the places you want to go

This is the fun part! Start this step when a trip is just a seed of an idea in your mind. Write down everywhere that, in an ideal world, you would go while you’re on this trip.

When I decided I was going back to England for a few weeks, I knew I wanted to see the places I hadn’t gotten to when I was studying abroad there. I made a long list (a page and a half) of places around the UK that I had heard of and wanted to see.

This step might require some research. For example, I knew I wanted to explore more of Wales, but I had no idea what the main sights were in Wales or which towns were the best to visit, so I had to look around for information. I relied on reviews, blogs, and other sources I found online to decide which destinations in Wales were top priorities for me, writing down everywhere that looked beautiful or interesting.

2) Categorize your list

Now is the time to narrow down that great big wonderful list a bit. Take a look at the map and see where all the things are in proximity to each other. If there are a bunch of locations in a particular area, then it makes sense to hit those locations and get rid of some of the outliers. For example, I would have loved to go to the North Pennines, but since most of the places on my list were either in southeastern England or Wales, I knew that the timing wouldn’t work out to make a detour to the Pennines (sadly).

Another way that you can narrow down your options is by starring the ones that are most important to you. I had heard amazing things about Cornwall and north Wales, which was why I chose those over some places in central or northern England.

This is also the time to decide where you want to spend the most time. Do you want to visit a LOT of different sites/towns, or is it more important to you to spend a few days getting to know each place you go?

I had been to both Cardiff and Edinburgh before, briefly, and I wanted to spend more time there, so I dedicated not quite a full week to each. When you are visiting places you’ve never been, it is harder to say which ones you will want more time in. I tend to spend short amounts of time in new places so I can explore them quickly and move on to the next location. It usually takes me about a day to see a city in the UK (excluding the really major cities and any museums).

3) Bookend your trip

Assuming that you will have definitive start and end dates for your trip, you can begin planning your arrival and departure.

I started by looking at my work schedule and fitting my travel plans into the time that I was able to take off of work. Maybe you are limited by your school calendar or family commitments; some of my study abroad friends flew home just in time to start classes at their home university again.

I also based my trip around the cost of flights for the days I would arrive and leave.

Having set dates helps you plan everything else. Knowing when I would arrive in London and when I needed to be back there to catch my flight home gave my trip structure.

If you are able to be more flexible with your dates and are not sure where to begin, spend some time thinking about how long you want to spend in each of the places you would like to visit. Add up the number of days you decide on (it adds up pretty quickly!) and you have the length of your trip.

4) Create a general timeline

Start with the bookends, since you absolutely know where you will be on those days, and work towards the middle.

It helps to create a calendar with a section for each day of your trip. Where will you be? Which town will you stay overnight in? This timeline isn’t set in stone, so if you get all the way from the ends to the middle and you’ve run out of room for some of the places you want to go, you can rethink.

Remember that a chunk of time on some days will be dedicated to transportation.

Pro-tip #1:

I usually plan about four days for a major city, one to two days for a regular city or town (if there’s nice hiking or wilderness to explore nearby, I go for the two days), and half a day for a tourist site.

5) Treat each destination as its own unit

Now it’s time for more in-depth planning for each of your destinations. Start with the first destination. When you get off the airplane or the train, where will you go? What time will you arrive, and will you need accommodation for the night? Go from there and determine all the details for each place you are visiting, one by one. This part takes the longest, and you will likely have a lot of tabs open on your computer as you compare public transportation times and costs, hostels and hotels, and opening hours.

You can start booking things like accommodation at this stage, but it is sometimes safer to wait until you have confirmed things like train times and so on for the entire trip so you know for sure you don’t need to make any last minute changes.

Make sure you know:

  • How and when you are getting to each place (By car? Bus? Train? Does public transportation go there? How long does the journey take, and what time will you get there?). The main resource I use is the bus tab of Google Maps.
  • Where you will stay at night
  • Does your arrival time match up with reception hours at your accommodation?
  • Where will your luggage go? Can you check in at your accommodation right away when you arrive, or is check-in later in the day? If so, do they have luggage storage?
  • If you are planning to visit a museum or other site or to attend an event, are there tickets available for the day you will be there? What are the opening hours?
  • How and when you are departing
  • If you are departing after check-out time for your accommodation, can you store your luggage there for the day?

Pro-tip #2:

When I’m traveling between cities, I find out which one has cheaper accommodation and try to adjust my itinerary to spend more nights there. Sometimes that means taking an evening train after a day of sightseeing and arriving in the new city for the night.

Pro-tip #3:

Sometimes you might have a situation where you are leaving a city in the morning, traveling to a day trip destination for the day, and then going on to a new city for the night. I have done this a few times and am usually surprised to realize that I am getting off the train with all my luggage and now I have to carry it around with me all day. To avoid this, see if the tourist site you are visiting has luggage storage or if you can pay for a locker at the train station or elsewhere. Alternatively, pack light!

Pro-tip #4:

I travel exclusively by public transportation, and often when visiting more remote areas I have found it can be very difficult to get around in a reasonable amount of time without a car. That’s why it’s important to carefully research train and bus timetables. On several occasions I wanted to visit different tourist locations only to discover that it would take almost a full day to get there by bus. I had to restructure that part of my trip and either find somewhere else to go or lengthen my time at another location.

6) Make bookings

Again, go place by place to make sure you don’t miss anything.

Definitely book accommodation ahead of time. I would also recommend booking long train or bus trips so you can get the best price (day-of tickets might end up being more expensive).

Book tickets for things like events or museums if there is a reason to do so. Reasons might include:

  • The site tends to have long lines
  • It’s cheaper to buy tickets online or in advance
  • Tickets might run out if you wait

You don’t want to feel stressed or be trying to buy a ticket on your phone while you’re traveling. But if the site or event is something you can just walk up and buy a ticket to, then I would recommend doing that because it allows you a little more flexibility if you decide you don’t want to go.

On my last trip, I booked every last train ticket for each day trip. I kind of regret doing that because shorter train journeys tend not to vary as much in price if you buy them day-of, and the fact that I had them already made me feel very locked in. If I didn’t use them, the money would be wasted.

Sometimes I forgot that I was the only one in charge of my trip. I felt like I owed it to myself to follow my carefully planned itinerary. But if you want to spontaneously go somewhere or do something else, it is 100% your decision. No one will be upset if you don’t end up using a ticket that you bought.

Pro-tip #5:

Create an email folder for your trip where you can keep all emailed tickets and confirmations in one place.

Pro-tip #6:

Make sure that you print out or download copies of any ticket that you will need to present. Downloading a ticket to a mobile device is better than just keeping it in an email or something, in case you can’t access wifi or data when you need it.

7) Create your finalized itinerary

Lastly, list out transportation times, the name and address of your accommodation, and your plans for each day. Carry this itinerary with you on your trip so you can refer to it whenever needed.

Enjoy your trip!

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