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How I Travel Plan: Travel Planning Tips

How I Travel Plan: Travel Planning Tips

Planning your travel itinerary can be the most nerve-racking part of any trip. It means you actually have to choose what you’re going to do – and, more importantly, what you’re going to leave out.

In three weeks, I’m heading to Singapore to visit my mom. I’m a big planner so I’ve been making lists for a few months now.

If there’s a site that comes up when you google “things to do in Singapore”, I’ve definitely read it.

Since I love planning and I get overwhelmed really easily, learning how to plan a travel itinerary was essential.

Without them, I showed up in London almost paralyzed by choice and ignorant of so many brilliant things to do in the city.

Planning a travel itinerary has saved me more times than I can count.

Since they’re something I think is incredibly vital for any traveller – especially a solo traveller – I want to share how I plan out a trip itinerary so you can confidently create your own.


Tips on How To Plan a Travel Itinerary

Step 1: Find Things to Do

how to plan travel itinerary
Photo from Unsplash.

I’m going to skip the whole process of deciding where to go, as that’s another post unto itself.

Instead, we’re going to skip to the first actual step of planning a travel itinerary: choosing things to do.

Now this step does vary from place to place. Some locations, like London or Singapore, are really well-known and there are thousands of resources to find information. Others, like the Toronto Beaches Neighbourhood (because yes, I even make itineraries for day trips), as less well-known and have less information.

Either way, my favourite ways to find things to do will yield enough for your itinerary. They’ve gotten me around Europe, across New Zealand, and even through Toronto with complete itineraries for all of my adventures.

Use these tried and true methods to plan things to do for your travel itinerary.


1. Google

This seems super obvious, right? Google “what to do in X” and you’ll find literally days worth of suggestions to occupy you.

But who wants to spend days sorting through dozens of articles that just repeat each other?

Avoid time wasters by following this simple formula:

  • Look through posts on page 1 & 2
  • Refine your search by the time of year. Look through pages 1 & 2.
  • Refine your search by the kind of travel you do (i.e. solo travel). Look through pages 1 & 2.
  • Refine your search by “hidden”, “unknown”, “obscure”, or “unique” thing to do. Look through pages 1 & 2.

That sounds like a lot to read, but trust me it isn’t. You’ll find a few articles that are the same across different search terms and some that you can tell from the description aren’t going to be helpful.

A bonus tip I always use: check out Wikipedia. It’s usually one of the first results but people skip it because it’s not a travel blog.

Forget what your fourth grade English teacher said and use Wikipedia as a source!

The notable history and attractions sections will give you some good background info to help you figure out what interests you.

Maybe that walking tour of the Hussites that you were going to skip is a must do because you found the history so fascinating. Or maybe it’ll reiterate what you’ve already found.



2. Tourism Boards

Tourism boards are a wealth of information. They describe the city, its attractions, the food scene, tips for visitors and where to stay.

Since tourism boards are run by someone from the place you’re going to, the information is really tailored. It also includes deals on ticket prices and info on the weather.

It’s worthwhile to click through the tourism site for events happening when you’re visiting, ticket deals and hidden wonders in the city.

Not sure how to find the tourism board for your destination? Google “X tourism board” and it should be one of the first few searches.

I always use tourism boards to find out what the area is most known for and what they pride themselves on. Sometimes you’ll even find cool bonuses, like the recipe for Austrian Potato Salad that I got off of the Austria tourism board site.


3. Travel Blogs

What kind of travel blogger would I be if I didn’t tell you to go to travel blogs?

Honestly, travel blogs are my main guide for planning trips. I check out travel bloggers I love who I know have similar interests or travel styles to me. Even though I love some bloggers, I don’t use their guides because we aren’t into the same stuff.

Find 3 travel bloggers that you feel have a similar travel style to you and see if they have helpful guides on your destination. Being similar to the blogger will help you connect with their experience and make it more likely that you’ll enjoy what they recommend.

Travel blogs are my favourite source for off the beaten path sights and activities on my travels. I never would have known about the Kutná Hora Bone Church without Nomadic Matt. How would I have survived without seeing the bone chandelier??

If you’re looking for comprehensive travel itineraries, check out my guides to travels around the world. I offer a Complete Guide to New Zealand – with bonus tips and tricks you won’t find anywhere else. See if we have similar styles by following some of day trip itineraries to places like Stratford Upon Avon or Zurich.

The best part about using travel bloggers to plan a travel itinerary? We love questions!

Comment on our itineraries, send us an email, or find us on social media to get some additional insights on your destination. I’m always happy to answer any questions you may have (even on how to plan a travel itinerary).


4. Ask People You Know

Since I’m a well-known travel addict and blogger in my circles, people constantly ask me for trip advice. I love sharing what thrilled me about a place or things worth avoiding to save some money.

It’s one of the reasons I run this blog!

Even as a travel professional, I still ask people I know for tips to help me plan my travel itinerary. It can be friends, work colleagues or even friends of friends (one time very inopportunely in the middle of a night out, but I needed to know about Seville!).

Getting personal experiences can lead to amazing finds. Often friends will have visited more recently and know your specific interests to steer you towards certain activities. Their information can actually be more valuable than a blogger who visited years ago.

Plus, everyone loves an opportunity to talk about their travels – as I learned when I started Tripping Up, a comedy travel podcast. So even if you don’t get any new ideas of things to do, you’ll get a great conversation!

5. Check Tour Itineraries

This is my secret weapon for making an itinerary when I travel: I search tours in the area. Not to go on them, but to see what they feel is worth seeing.

Tour companies like Contiki or Intrepid that follow a path through the country offer basic information on their route. They do it to convince you to go on their tour, but I use their information for my own benefit.

I check out the main sites that seem to be worth visiting and how they travel between them. It can be a great way to find out what kind of transport is best between places or what is a must do in a certain city.

That’s how I found out about swimming with wild dolphins in Kaikoura in New Zealand.

Check out tour companies that specialize in the kind of trip you’re after. It wouldn’t make sense to look at expensive tour companies if you are budget travelling.

You can also look at the types of short tours places offer. They will show you what an area is most known for or what the locals like to highlight.

Airbnb Experiences run some great tours with locals running and preparing the tours. Take a look at them before planning what to focus on during your trip.


7. Take a Free Walking Tour

I don’t always book tours when I travel. I am usually travelling on a budget, so I avoid the extra expensive. Instead, I always take a free walking tour early into my trip. (Of course, free walking tours still cost some money but they’re much less expensive.)

A free walking tour is a great way to get local tips and facts that you can use during your travels.


Step 2: Make a List


how to plan travel itinerary
Photo from Unsplash

Now that you’ve gathered a ton of things to do, it’s time to organize it!

Take the first step towards writing out your travel itinerary by created a list. This is super informal. Just jot down everything you want to do: tours, places to see, places to eat, all of it!

You don’t need to weed anything out yet or do any actual planning so don’t limit yourself.

When I was planning my trip to Singapore, I had 4 pages of notes after under an hour of searching. That was just during a lull at the office!

I never would have remembered all that stuff without writing it down, which would have led to missing out on a lot in my 7 days in Singapore.

While you’re writing this mega list, use a quick code to rank items. I use a 3-point scale. An exclamation point means I’m excited about a place. A star shows how many times it was mentioned in sources (I give a star for each mention). A question mark means it’s lower on the list.

I usually end up skipping the question marks all together when I’m planning my travel itinerary because I end up with so many exclamation points.

Popularity isn’t a great indicator of whether or not a place is worth visiting, but it does show what’s more touristy. Sometimes I need a day away from the tourist traps, so I know the plan those activities for another day.

Try to take a break from your list after writing everything down. Walk away for a day or two. Then see what still sticks in your mind or what you’ve been telling other people about. If there are attractions that you can’t get out of your head, you know to prioritize them when you’re making your final itinerary.


Step 3: How to Plan a Travel Itinerary (with a template)

how to plan travel itinerary
Photo from Unsplash

Putting together an itinerary is one of my least favourite things to do. Because I’m INSANELY indecisive and this is a time when you have to make choices.

This is always the time I start regretting my flight choices and wish I had a million more days to spend in the place so I could see everything.

To combat this, I start small.

I always start by picking my top three things to do and fitting them into my schedule. That way, I make sure I’ll have time to do them.

These three things could be sights or activities the place is known for. Or they can could just be something relaxing I want to do, like getting a massage or seeing a movie. Remember that your itinerary can be whatever you want it to be!

Next, I pick one activity per day. If I’m away for a weekend, my top three things may be all that I put in my schedule. If I’m gone for a longer time, I fit in more. Sometimes, I even schedule two activities a day (when I’m certain there’s time).

That creates a schedule with huge gaps in it, but that’s how I leave it.

I recommend using pencil or a computer document for your itinerary, so it is changeable. Otherwise it may start to look crazy with pen scratched out or arrows drawn across pages as you get closer to your final itinerary.


Step 4: Don’t Overbook Yourself

It’s important that you don’t plan yourself into a frenzy for trips. Having every second allocated is exhausting. You’ll be tired just looking at that schedule!

Instead, try to hit your top items each day, but leave lots of empty space. That will allow you the freedom to change your mind, move things if the weather is bad or to wander aimlessly through the city.

Remember: you’re on vacation. You don’t need to sprint through the city and do absolutely everything there is to do.

Growing up in Toronto for over twenty years, I can easily say I haven’t done everything in the city. I have probably done like 10% of it. I was 24 before I even went hiking at the famous Scarborough Bluffs.

You aren’t going to be able to tackle everything on your weekend trip to your destination.

Focus on doing the things you really want to do and have fun!


Step 5: Plan Backups

women on top of rock outlook
Photo from Unsplash

I don’t just mean in case things go wrong. Backups can also be for when things go right and you have extra time or energy to do more.

I always have a list of extra activities on my phone when I travel. That way, if my museum tour is shorter than I expected or I feel like seeing more, I have instant options for what to do with myself.

It’s also great to have if things don’t go as planned. When I was in Istanbul, I was glad I had the backup of visiting the underground cisterns when I found out the Blue Mosque was closed. Otherwise, I would have had to hunt for WIFI to come up with other options. Or I would have slunk back to my hotel and napped while dreaming of hot air ballooning in Cappadocia.

Backups are great to have as a safety.

I try to vary what is on my back up list so I have a range of options. I always have a few indoor activities in case the weather is bad (museums and galleries are great for this!), as well as one or two hikes in case I have a high energy moment.

Be careful: it’s easy to get overexcited and make your backups list ten pages long. Try to keep it to three activities per day of your trip so it is not too large. Keeping the list on your phone or an accessible piece of paper is important so you can have it on hand when you need it.


Step 6: Research Restaurants

how to plan travel itinerary
Photo from Unsplash

I’m sure you’ve been wondering how to plan a travel itinerary that includes food. It’s a huge part of travel!

Tasting new cultures through their cuisine is one of my favourite things about exploring.

Before I head to a new place, I google “Must try food in X.” This gives me a sense of the native cuisine and things to keep an eye out for. (Check out my What to Eat in Canada post if you’re planning a trip to the Great White North!)

I also search for some places to actually try the food. That’s the best way to ensure you’ll find the dishes you really want to try.

My list of restaurants becomes a section of my backups list, because I don’t like being restricted by where to eat or when. It would suck to be required to eat pavlova on a night that you don’t feel like dessert.

Instead, I use my list as a guide in case I’m stumped on where to find food.

Occasionally, I’ll specifically work a restaurant into my itinerary. This is usually only when you need a reservation or if the meal is an event (like high tea in London). Or when I know the restaurant is right next to wherever my last excursion of the day is.


Step 7: Compromise with your Travel Companion(s)

This isn’t a step I usually need, since I travel solo 90% of the time. I basically never have to compromise (a great pro of solo travel!).

Since I’m going to Singapore with my mom, I can’t actually pick everything we are going to do. My itinerary has to reflect her plans as well.

In Singapore, I’ll be alone all day to do my own thing, so our “compromises” are more about saving activities until her time off.

If you’re travelling with other people, make sure to have a conversation about what you want out of the trip. If someone wants to go on a hiking holiday while someone else wants to shop the entire time, you’re going to have a problem. Compromises will be needed.

It’s better to make these compromises ahead of time so you’re not surprised when you get there.

I recommend both creating rough travel itineraries with your top 1 to 3 items (depending on the length of the trip), then finding ways to fit in other activities around those.


Step 8: Be Prepared to Throw Out Your Itinerary

plane window view of sunset
Photo from Unsplash

After all that planning, you’re probably terrified by this step. But sometimes this will happen!

Being okay with changing your plans will help you enjoy your trip.

Sometimes the changes will be out of your control: like terrible weather or unknown national holidays. Other times, you’ll discover that you want something different from your trip than you’d initially thought. Maybe you found a suburb you’d rather spend time in than the city, or your feet are too sore to continue your hiking holiday.

That’s okay!

Trips don’t always go as planned, which is part of the fun. Being rigid won’t allow you to enjoy the experiences you can have in a location.

If the weather is bad or you get sick (like I always seem to), just remember that you can go back to that destination. Doing what you need to do to have a good time now is more important than focusing on what you weren’t able to do.

(Granted, if you’re sick, you’re allowed to be a bit salty about not getting to do what you’d planned. Complaining when you’re sick is one of the few joys you’ll have.)


Learning How to Plan a Travel Itinerary is a Process

Those are the steps I’ve followed for the past few years when I’ve travelled. Sometimes the planning has happened the day I arrive in the city. Other times, I’ll be prepped a month beforehand with scrawled notes and open computer tabs ready for my adventure.

It can be a lot of work if you don’t enjoy research and learning about places the way that I do.

Try to find something fun in the process: even if it’s just looking at cool pictures or finding clichés in the articles you’re reading.

Use the planning as a way to get excited for your trip.


Free Travel Itinerary Template

Still struggling to plan a travel itinerary? Use this free 7-day travel itinerary template to help you!

It comes complete with a back up section and room for lots of extras!

This is the kind of itinerary I use when I travel and it’s gotten me to over 29 countries.


Still Not Sure How to Plan a Travel Itinerary – Or Just Don’t Want To?

If you don’t feel like doing all that work, travel bloggers have pre-set itineraries, like my Toronto Winter Weekend Itinerary. Google is full of bloggers’ preplanned trips that you can take advantage of for free!

Want a more personal touch? Contact me for a quote on my travel planning services. I will plan your entire trip (itinerary, backups and all), so you don’t have to!

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