kasiawrites – travel blog

Multi-destination travel planning made easy

Ever since I’ve started to see the world, I’ve been addicted to multi-destination travel. I came to that realization after someone asked me about planning such trips. Practically every trip I have done has involved elements of visiting various destinations in a short period of time. If that sounds overwhelming to you, don’t worry. I got your back! Multi-destination travel planning is fun and easy.

blogging travel map

Always in trip planning mode

Why choose multi-destination travel

Unless you are a full-time traveller, you probably have set amount of vacation days to use each year. This was us for pretty much most of our  adult lives. We had between two to three weeks of vacation that we could take and wanted to make the best of it. Choosing multi-destinations – by that I mean different cities and countries not out-of-town trips – made the most sense.

Travel planning has always been my favourite activity and I enjoy every part of it. Next to actual travel, that is. To date, some of our multi-destination trips included a seven-day drive around Iceland, a number of European adventures and an extensive tour of Italy. Each trip had different location stops, variables and timing, but they all shared the same elements of planning.

What gives multi-destination travel so appealing?

  • You get to see more places in a shorter amount of time
  • It’s more cost-effective when compared to visiting each place on separate trips
  • Your travel planning skills will be challenged and tested
  • It will be an adventure
  • You won’t be bored

Ready for adventure

Travel planning basics

So we have established that visiting multiple destinations is good for you. It is also a great way to discover new places. Now, let’s take a look at the more detailed elements that go into the planning. If you’re just starting to get into multi-destination planning, a good trip planner might be the thing for you.


Quite often this is the most fun part. We normally try to pick one place that we really want to visit. That can be a country or a specific city. Once you have that anchor, it’s easier to decide what other places you’d like to visit that are fairly close. At this point, we are deciding on the location before we choose the order.

For example, when we decided to visit Croatia, we knew it was our anchor for the rest of the trip. We had to choose what part of the country we wanted to visit, which also helped with the rest of the locations. While visiting Portugal, we had the same dilemma, but we needed that anchor to organize the rest of the trip.


It’s important to pick an anchor designation as it lays out the rest of the trip. Everything else is a variable, but the anchor stays the same. This will allow you to pick other places based on location and the ease of getting there.


How much time you have available is also a huge variable. We normally planned our trips around existing public holidays and weekends, which allowed us more time away. Creative planning takes a bit more figuring out, but the time gained is a pretty good reward.

The amount of time you have available can also decide the distance between destinations. For example, it would be a lot more challenging to fly between continents than it is within one. It’s not impossible, but you will have to consider the time spent getting from point A to B and the cost.

Europe is particularly easy to get around from both the distance and cost perspectives.  A lot of our trips have involved this continent.

multi-destination travel planning


No travel planning can be complete without the transportation part. As we are based in Canada having a direct flight to anywhere in Europe is always a bonus. This is especially crucial when time is of the essence. The flight is already long enough and having an additional layover adds unwelcomed delay to our vacation. I have made it my mission to find direct flights.


Depending on the time of the year, the availability of flights, especially direct ones, might be limited. It really helps to narrow down your options to get there and back. Return flights are as important, especially if you are flying from a different location than where you started.

This is exactly how we found ourselves in Amsterdam few years ago. While we wanted to visit Amsterdam at some point, it wasn’t high on the list. However, it was one of the few direct flights from Toronto during our trip so we booked it. Ended up loving it even if we ended up there by chance.

Time vs cost

Transportation is largely tied in with the whole time vs cost argument. While I am a huge fan of sweet deals, sometimes the cheapest isn’t always the best. The average flight from Toronto to anywhere in Europe is between seven to ten hours direct. Sure, you can find cheaper flights if you opt for one or two stops, but that can add quite a bit of time to your journey. Again, depending on how much time you have, this might not be an issue.


However, for me, flying to Europe means a loss of at least half a day. To add a stop or two would make that trip close to 24 hours. If you have two weeks of vacation, spending extra time flying might not be worth it. This was also the case for flying from Dubrovnik to Zagreb. The flight was less than two hours while train or driving would have taken about eight. We chose shorter time and the convenience of a quick flight.

There are times when flying isn’t the quickest option. When going from Lisbon to Porto, we opted for the train. While the ride was longer than the flight, we saved time by not having to get to the airport and wait to board. It was also a cheaper option. Determining the availability of flights can also dictate where you go and for how long.

travel planning


When it comes to multi-destination planning, organization it key. The need to coordinate so many different elements needs to be done well. Fortunately, there are many tools to aid you with that. I usually start with an old-fashioned calendar which is useful for counting days, noting important holidays and weekends. Or you can just buy an organizer with templates already there.

This is also one of the times when Internet is your best friend. You can pretty  much google any question and the chances of getting your answer are pretty high. When we planned our trip to Iceland few years ago, there wasn’t as much info available. We were stopping at a different location each night and needed to know what distance we could cover in the day, allowing for stops along the way.  Not being familiar with the area, language or geography was challenging. But there were lots of companies that did similar tours which gave me an idea of where to make the stops. I must say, we nailed it.

I have many apps on my phone for flight, hotels and other transportation. This is great for providing alerts and ensuring you have the info handy. As a back up, I print a copy of the whole itinerary in order of the stops. This is a good, old school, backup for when your phone dies or there is no Internet connection. Most recently, I’ve come across an app called Tripcase, which allows you to input all the travel info into one place. Can’t wait to try it out on my next adventure.

Room for errors

The thing about travel is that it can be unpredictable.  Flight delays, road closures, accidents and weather can all mess up the best laid plans. While inconvenient, it is a part of life. It pays to do your research and be informed of your rights. Quite often airlines will be required to compensate you for flight delays or cancellations. It can be monetary, food and/or lodging vouchers, or a combination of a number of things. While annoying, understanding what you are entitled to will make the situation a little easier.

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There are also things called human mistakes. I’ve made so many, but they all taught me something and fortunately, didn’t impact my travels too much. It’s easy to focus on the issue when it happens, but it’s important to find a solution. There was the time where I accidentally booked our flight from Zagreb to Dubrovnik when I actually needed to fly the other way. Another time I booked our hotel in Paris for one night while we were staying there for four. Looking back, these were trivial issues, but when they happened it was a huge deal. You learn to move on.

Another error that can put a dent in your travel planning can be caused by technology. You get to your hotel to realize your reservation is not there. If you have a back up of your booking, electronic or printed, it will make things easier to smooth out the problem. Not all places have the same rules or technology we are used to.

 Trip planner checklist

It might be obvious, but sometimes the simplest things are forgotten. Ensuring your passport is valid would be the most obvious thing. It shocks me every time when someone gets outraged that they can’t board a plane because their passport is expired. I literally have no words.

Visas (whether you need one or not), currency and electricity converters are some of the things you also need to consider. Do you need a SIM card? Cash? Should you get it ahead of time or on location? Every country might vary so don’t take things for granted. Find out before you go. I can’t stress this one enough.

Don’t waste your time looking for your passport and other important documents while you’re on the road


I personally never travel without insurance. Multi-destination travel has its own set of challenges that can be overcome with travel insurance. There are different types of insurance, based on your country of origin, your credit cards and services providers.

Having gotten sick while travelling, I can attest to the importance of not having to worry about seeking medical help. It can literally save your life. Travel insurance might also help with lost or stolen property, flights, car rentals and other things that can go wrong.

Things to consider while travel planning

We’ve looked at the elements that go into travel planning a multi-destination trip. Another element to that is actually planning your stay in each location. After all, how will you know how long is enough?


In my experience, you can see most European cities in a two-three days time frame. From organized tours, bus tours and available itineraries, this is enough time to give you a taste of the place.  Generally, I research what is there to see and do in a place before I go there. Having an idea of available attractions will help you decide how long you should stay.

Some places ask to purchase tickets ahead of time and doing so will give you guidance on how much time you have available. It won’t be possible to see everything in such a short time frame, so it’s super important to pick what you absolutely need to see vs what can be omitted.


In most places you will travel to, there will be a range of lodging option. From hotels, motels, bed and breakfasts, AirBnB and everything in between, the choices are better than ever before. For me, the decision often boils down to location and cost.

If I’m in a place for a short time, I want to see as much of it as I can. I don’t want to spend time on buses, subways and cabs. For that reason, I would pick location as my main requirement. As far as prices, I always compare hotels and private lodging. The winner for me will always be the most cost-effective place in a great location.

Another element to consider is your arrival time. When we visited Palermo, we were supposed to arrive around midnight. Due to delays we didn’t get to our place till 2 a.m. Our hosts were accommodating and there were no issues, but that might not always be the case. Always check if there is hotel transfer and that your room will be available if you arrive late.


How to get around different destinations also involves planning. Each location you visit might have a different transportation network that will have different rules. Generally when we’re in big cities we don’t rent cars. Getting around by walking is sufficient. However, most places will have transit passes for different amount of days that can become quite handy when getting around.  Some even include the airport transfer.

If you’re used to the services of Uber or Lyft, you might not find them in many other places. Different countries have their own set of rules for these types of services. It’s always better to check in advance.


One of my fave ways of seeing a new place is one of those hop-on, hop-off tours. It’s a great way to get the lay of the land, learn about the places you are visiting and get around the city. Most will have passes for up to three days which might be enough for you to use while visiting. It might also be cheaper than buying a transit pass, especially if you’re sticking to touristy places on the route.

Fine line between overdoing it

Multi-destination travel planning can be fun and will lead to an amazing experience. However, there is a fine line that can easily turn this into a nightmare. Here are some thing to consider in your planning to avoid crossing it.


What works for other people will not always work for you. Sure, we have done five cities in four different countries in couple of weeks, but it doesn’t mean you have to do as many or more. If you are comfortable doing three places then you should stick with that.

Some people don’t travel well so flying overnight and heading out on an excursion right away may not be for everyone. Maybe three days are not enough to see a city. These are definitely things that should consider before setting up an ambitious itinerary, especially if you are not used to moving every few days.


As much as I love travelling and checking out new places, sometimes it tires me out. I know when I am about to hit that point and make sure to take it easy. Sometimes it means sleeping in instead of getting up early to explore. Other times it can be a nap, doing laundry or simply enjoying the moment.

Wearing yourself out will not make your vacation fun. We all get tired, especially when you’re constantly on the move. Airplanes, buses, ferries and even people passing us by can make us sick. It’s also easier to get sick when you’re tired, so taking it easy is also vital.

Additional resources

I make it my mission not to overpack when I travel. Generally I do well, but there are times when what you have is not enough. On our last Euro trip, it was so hot that we were running out of clean clothes. Thinking ahead, I brought a small bottle of detergent thinking we could wash our stuff along the way. Unfortunately, we didn’t have that opportunity. So when we arrived in Porto, finding a laundry facility was our main priority.

Aside from laundry, it’s good to look into things you might need. I always bring with me a bag filled with various pills, creams and ointments for maladies that can potentially befall me while I travel. There were times when we forgot sunscreen or toothpaste. It’s always good to know where to get such things. Sometimes, they might not be in the same type of store as they are at home. Or they are not in a language you are familiar with. I experienced that first hand trying to find hair conditioner in Germany. It took a while.


Other ways to enjoy multi-destination travel

If you’re not quite ready for planning your own multi-destination trip, or just can’t be bothered, there are few ways you can still get a taste of it.

  • Cruises: Cruising can be a great way to see the world. Everything is pretty much planned for you.
  • Group tours: Another great way to visit multiple destinations while someone else does the planning.
  • Specialists: There are plenty of travel experts out there who can plan your entire trip for a fee.

Bringing it together

Multi-destination travel can be fun and it offers a great way to see the world. It can sharpen your research skills and challenge your mind. For me, it’s like trying to solve a problem and I’m good at it. 🙂

How about you? Do you enjoy multi-destiantion travel planning? Or are you more into one location at a time? Let me know!

Don’t miss future posts!


10 thoughts on “Multi-destination travel planning made easy

  1. Pingback: Are group travel tours for you? | kasiawrites - travel blog

  2. Semi At Beauty in Complexity

    [* Shield plugin marked this comment as “trash”. Reason: Failed GASP Bot Filter Test (checkbox) *]
    I enjoy multi-destination traveling, and wish I could do it now! Moreover, haven’t done Cruising yet, so next trip could be on cruise!

  3. runningtotravel

    Nice tips! As you mentioned, I’ve found there is definitely a fine line between trying to cram in as many places as possible and getting to actually enjoy the places where you’re going.

    1. kasiawrites Post author

      Absolutely! What’s the point? Cramming too many means you don’t really see a lot and you’re not likely to remember much.

  4. a mindful traveler

    We always choose multi-destination travel. Coming all the way from Australia, we tend to want to make the most of our holidays and spend a good amount of time overseas seeing as many places as possible, especially in Europe and the U.S. 😉

    1. kasiawrites Post author

      Exactly the same for us! Although I would love to make it to Australia some time soon 😀

      1. a mindful traveler

        You should definitely come down. Especially Christmas time as it’s Summer here and the days are glorious. If you’re ever here let me know. ❤️

      2. kasiawrites Post author

        I like the sound of that! Summer in December 🤗 It probably won’t be anytime soon, but will let you know for sure!

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