multi-destination, multi-destination travel, travel planning

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 visiting various destinations in a short time. If that sounds overwhelming to you, don’t worry. I got your back! Multi-destination travel planning is fun and easy.

This post will help you get started even if you’re planning on going to one destination. Travel planning doesn’t have to be difficult, and I’m going to show you just how easy it can be.

Affiliate DisclosureThis post contains affiliate links. If you make a purchase through these links, I may earn a commission. This doesn’t affect your purchases or any fees you may pay for the product or service. Read more in my DISCLAIMER.

Why choose multi-destination travel

Unless you are a full-time traveller, you probably have a 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, many European adventures and an extensive tour of Italy. Each trip had different location stops, variables, and timing, but they all shared the same planning elements.

What makes 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

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. If you’re starting to get into multi-destination planning, a good trip planner might be the thing for you. Now, let’s look at the more detailed elements that go into the planning.

Choose your destination

Quite often, choosing your destination is the most fun part of travel planning. It’s even more fun during multi-destination planning. We usually try to pick one place that we 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 reasonably close. At this point, we are deciding on the location before we choose the order.

If you’re enjoying this, you might like 10 Awesome reasons to visit Italy!

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 see, 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 trip.

It’s essential to pick an anchor designation to lay 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. If you’re planning only to visit one place, you’ll still need that anchor location when you’re exploring.

Decide on the duration

How much time you have available is also a huge variable. We usually planned our multi-destination 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 more challenging to fly between continents than 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 distance and cost perspectives.  A lot of our multi-destination trips have involved Europe. If you stay only in one country and want to visit other cities, the same idea applies.


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 unwelcome delay to our vacation. I have made it my mission to find direct flights.

multi-destination, multi-destination travel, travel planning
multi travel planning can be fun

Depending on the time of the year, flights’ availability, especially direct ones, might be limited. It helps to narrow down your options to get there and back. Return flights are as important, especially if you fly from a different location than where you started. Sometimes it’s cheaper to book a return flight from other destinations. However, sometimes it’s cheaper to buy one ticket there and then a separate ticket home. Make sure you check out both options to maximize your savings.

This is precisely how we found ourselves in Amsterdam a 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. I ended up loving it, even if we ended up there by chance.

Time vs cost

Transportation plays a vital role in the whole time vs cost argument. While I am a massive 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 more affordable flights if you opt for one or two stops, but that can add quite a bit of time to your journey. Again, this might not be an issue depending on how much time you have.

multi-destination, multi-destination travel, travel planning
travel planning made easy so that you can enjoy Amsterdam

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 the train or driving would have taken about eight. We chose a 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 getting to the airport and waiting to board. It was also a cheaper option. Determining the availability of flights can also dictate where you go and for how long.

Organization is key

When it comes to multi-destination planning, being organized is critical. 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 helpful for counting days, noting important holidays and weekends. Or you can buy an organizer with templates already there.

This is also one of the times when the 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 a few years ago, there wasn’t much info available. We stopped 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 many companies 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 flights, hotels and other transportation. This is great for providing alerts and ensuring you have the info handy. As a backup, I print a copy of the whole itinerary in order of the stops. This is a good, old-school backup when your phone dies or there is no Internet connection. I’ve recently come across an app called Tripcase, which allows you to input all the travel info into one place. I can’t wait to try it out on my next adventure.

Leave room for errors

The thing about travel, especially one that involves multi-destination stops, 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 several things. While annoying, understanding what you are entitled to will make the situation a little easier.

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 crucial to find a solution. There was a time where I accidentally booked our flight from Zagreb to Dubrovnik when I needed to fly the other way. Another time I booked our hotel in Paris for one night while we stayed 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 backup of your electronic or printed booking, it will make it easier to smooth out the problem. Not all places have the same rules or technology we are used to.

Trip planner checklist

Sometimes the simplest things are forgotten. Ensuring your passport is valid would be the most obvious thing. It shocks me whenever someone gets outraged that they can’t board a plane because of their expired passport. I have no words.

Visas (whether you need one or not), currency and electricity converters are 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.


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 worrying about seeking medical help. It can 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 multi-destination travel planning

We’ve looked at the elements that go into travel planning a multi-destination trip. Another aspect of that is 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 going 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.


There will be a range of lodging options in most places you will travel to. 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 a 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 a hotel transfer and that your room will be available if you arrive late.


How to get around different destinations also involves planning. Each location on your multi-destination tip might have a different transportation network with various rules. Generally, when we’re in big cities, we don’t rent cars, and getting around by walking is sufficient. However, most places will have transit passes that can become quite handy when getting around for several days.  Some even include airport transfers.

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 to use while visiting. It might also be cheaper than buying a transit pass, mainly if you’re sticking to touristy places on the route.

Fine line between overdoing multi-destination travel

Multi-destination travel planning can be fun and will lead to a fantastic experience. However, there is a fine line that can quickly turn this into a nightmare. Here are some things you might want 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 a 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. You should consider these things 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 we’re constantly on the move. Airplanes, buses, ferries and even people can make us sick. It’s also easier to get sick when you’re tired, so taking it easy is 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. It was so hot on our last Euro trip that we were running out of clean clothes. Thinking ahead, I brought a small detergent bottle, 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 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 you have at home. Or they are not in a language you are familiar with. I experienced that first hand, trying to find a hair conditioner in Germany. It took a while.

Other ways to enjoy multi-destination travel

If you’re not quite ready for planning your multi-destination trip or just can’t be bothered, there are a 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.

Multi-destination travel – 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-destination travel planning? Or are you more into one location at a time? Let me know!

Similar Posts