How I Travel Plan: Travel Planning Tips

How I Travel Plan: Travel Planning Tips

In three weeks, I am heading to Singapore to crash my mom’s work trip.

Over the last few weeks, I’ve begun planning my conquest of the city (sorry, I’ve been listening to A LOT of history podcasts recently).

I’m a big planner. Always have been. I love making lists and overthinking absolutely everything. So, for me, planning is vital for any trip I go on.

Travel itineraries help you avoid missing out on amazing experiences during your holidays. They keep you from getting overwhelmed when you arrive and give you a sense of guidance.

Without a travel plan, I’d be totally lost when I travel.

I want to share how I plan out a trip itinerary so you can feel confident creating your own!


Finding Things to Do

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

Besides, this time I didn’t get to pick the place. I wanted to visit my mom while she’s closer to my part of the world, and that happened to be while she’s in Singapore. (I’m definitely not complaining!)

The step is to planning a trip is figuring out what to do during your stay. I have a number of tried and true methods to find great tips that won’t take you days.

Here are my favourite spots to find out what to do in new places:


  • Google

I basically begin by googling “What to do in X,” which brings up way too many results to go through. Who wants to spend days sorting through dozens of articles that just repeat each other?

I limit my search to places I know will have good information.

To start, I head to Wikipedia to check out notable history and attractions. This is great for finding extra background info and seeing what a city is known for.

Afterwards, I head back to my search.

I never go beyond the first two pages of Google. I look for companies I know and trust, like CN Traveler or The Culture Trip.

If you have the time, search for “unknown,” “hidden,” or “obscure” things to do in the place you’re visiting. The first page of results alone can give you some unique tips.


  • 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 tourist 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.


  • 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 look at travel bloggers I love who have similar interests or travel styles to me. Being similar to the blogger will connect you with their experience and make it more likely that you’ll enjoy what they recommend. Otherwise, any suggested itineraries or stories will be about as helpful as Wikipedia.

Travel blogs have been a great source for out of the way sights or day trips on my journeys. I wouldn’t have known about the Kutná Hora Bone Church if it wasn’t for Nomadic Matt. How could I survive without seeing a bone chandelier?!

If you’re looking to do a specific type of trip, like hiking or travelling with kids, it’s vital to find a blogger in that niche. They’ll offer more helpful tips with a focus on what you are looking for from your destination.

Travel bloggers tend to be open to questions about locations. Comment on their post or send them a message to get some additional insights on your destination.


  • Poll People You Know

Since I’ve travelled so much, people constantly ask me for advice on their trips. I love sharing what thrilled me about a place or things to avoid so they have a better trip. It’s one of the reasons I run this blog!

To this day, I still ask everyone around me for travel tips if they’ve been to a destination I’m going to (or want to go to).

Getting personal experiences can lead to amazing finds. If someone has visited recently, their information can be more valuable than a blogger who went there years ago.


  • Tours

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 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.

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.

I don’t often book tours since I have been travelling with tighter budgets lately. Instead, I always try to go on a free walking tour early into my trip. Then you get access to a local full of tips and facts to help you out during your time in the city. This may alter your itinerary when you get to your destination, but that’s ok!


Make a List

All that information needs to be organized somehow. As a list addict, I highly recommend make a list (or three or four!).

After almost an hour of searching, I had written four pages of notes on things I want to do in Singapore. That was just during a lull at the office!

I could never remember all that stuff without writing it down.

Make sure to jot down your impressions of each activity beside it so you can easily see what excited you. This is especially important if you aren’t doing all of your planning on the same day.

I also use my list as a ranking system. Attractions get a star for each time they are mentioned in my sources. The more stars, the more popular the place.

Popularity doesn’t mean I’ll visit, but it can be helpful to know!

Try to take a break from your list after writing it down. Walk away for a day or two and see what still sticks in your mind. If you’re still excited about it, then do it!


Making an Itinerary

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.

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 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.


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

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


Plan Backups

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 for four hours.

Backups are great to have as a safety.

I try to vary what is on my 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 easily carry it around.


Research Restaurants

Tasting new cultures through their cuisine is one of my favourite parts of travel.

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).


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.

Pick one thing you each 100% want to do during your trip. Make time for both/all of those activities as best you can, then work on filling in the extra time with activities you all enjoy.


Be Prepared to Throw Out Your Itinerary

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 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.)


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.


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!




50 thoughts on “How I Travel Plan: Travel Planning Tips”

  • I agree that research and planning are important but there are also times when you just need to go with the flow and do something you didn’t plan. I’ve had some of my best travel experiences that way!

    • I agree. I think having a rough outline and knowing something of what you’re doing is really helpful – especially on tight trips. But I do love just wandering and seeing what happens.

  • What a useful post! I completely agree that you should never overbook yourself – the amount of things I’ve ended up cancelling because I was just too wiped to do them is ridiculous! I also definitely make sure to source out the best restaurants before visiting a place!

    • Yes restaurants are a great idea! I tend to find them night of depending on what I’m craving/where I’ve ended up. Not always a great idea when you haven’t planned to have the wifi to do that!

  • This is such a helpful guide . Being a solo female traveler I personally liked your advice to for travelling alone in India, so bold and true. If you can adapt, India is not so difficult to deal with.

  • Wonderful! well done, keep it up!
    This article is very helpful, so far I have always had difficulties for travel bloggers who are having a hard time marketing their blog

  • Travel itineraries help you feeling the regret after the travel when you miss visiting a place! It helps when you travel in big cities to get the city pass because it saves you a lot and it contains guide on what places to visit.

    • That’s a very good tip! I never use city passes because I don’t often want to go to enough places to make it worthwhile.

  • Good point about throwing away you plan!
    I used to plan trips very carefully, but the spontaneous trip I had two weeks ago was so awesome that I think everyone should travel without preparation at least once.

  • I love that we do the exact same thing with tours: I research them, and even watch youtube videos of various walking tours etc. just to see where they go and recreate it myself! You are a great travel planner and have such important tips here!

    • Thanks so much, Cate! I’ve never watched Youtube videos of tours but that’s an awesome idea! I used to use Google Earth to “walk the streets” of where I was going to (mostly because I was bored at uni).

  • Nice breakdown of how you plan for your trips. I actually use Trip Advisor to come up with things to do, but I always take the reviews with a grain of salt. The “don’t overbook yourself” is super important when we travel plan. Our kids get too tired when there are too many activities in one day.

    • Tripadvisor is a great resource. I honestly get overwhelmed by the options. Sometimes I check reviews of tours or places I’m debating going to for more info. Kids are definitely not made of energy – good that you take the time to let them rest!

  • I’m a big planner, too, and I think that often you save time and money and nerves on the spot. However, on my last trip I just sketched the route and the number of days I wanted to spend in some places – which for others would be major planning, for me, this is anarchy. It worked well and I didn’t feel like such a prisoner of myself.

  • We love it that you included the “don’t overplan” and “be prepared to throw out your itinerary” parts! Because truth be told, we’ve stopped planning too much. Of course it’s important to have hotels booked (and even that, it depends on where you go), and have enough cash, a valid passport and so on, but slow travel and spontaneity is much better. 🙂

    • Thanks, ladies! I love spontaneous travel, but I do tend to read about the place and then slowly I start internally planning :p I think it’s just how I am!

  • I like the way you plan your trips. Myself too plan itinerary before actually visiting the place but sometimes you got last minute deals and turned out worth doing in the end. In this case I prefer to be bit flexible. As you mentioned, you are indescisive that made you overplan the things.

  • I have a very similar process, our website is all about travel planning and personalizing itineraries! i just hope my customers do not read your last point and throw out my hard work, although I must say I do it myself sometimes!

  • It’s always interesting reading about how people plan their trips! We aren’t big planners, we usually have a couple things in mind and food we want to eat! Then we see how it goes and try to be open to what comes up. bit it’s good to have all sort of travelers! Have a great time in Sinagpore 🙂

  • great tips for planning the trip, for me the problem is that often our trips are spontaneous and then there is not much time for planning

    • Honestly, I don’t usually plan ahead very much. This planning can happen the morning I arrive in a new place or the night before – or even during!

  • A great guide to travel planning but I so agree with your point about being prepared to throw out your itinerary. I find that can be when all the best, most special and truly unique moments happen when you travel. You never know what awesome opportunities will come your way. Or it’s ok to change plans to have a chill day. Having a super packed itinerary can be pretty exhausting after all.

  • My goodness, this list makes me look lazy! You have every eventuality planned for! This is a great list for those who like to plan ahead with their trips!

    • I actually don’t plan a ton when I usually travel. A lot of this can happen within an hour lying on my hotel room bed!

  • wow, I travel for 3 years ald, but it is still a very useful post for me. everything is listed clearly. thank you so much for your sharing. keep doing<3

  • Not overbooking yourself is such a good thingto remember when traveling. Great tips, planning is so important to get the most out of a trip!


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