Since I started traveling regularly in 2019, I’ve become increasingly interested in visiting as many countries in my lifetime as possible. Although my travel goals are unlimited, my PTO is very much limited so I’ve had to plan a few multi-destination trips in the past. The two main ones were a visit to Brussels, Belgium with a day trip to Paris, France and a trip split between Tokyo, Japan and Bali, Indonesia. Through these adventures, I learned a lot about the dos and don'ts of planning multi-destination travel. Keep reading for factors to consider, tips to make the most of your vacation, and mistakes to avoid. For reference, this is assuming your entire vacation will only be one or two weeks. Of course if you are doing month long tours, you have the ability to be much more flexible.
Know Your Travel Style/Goals
In my opinion, the most important things to consider when planning a multi-destination trip are your travel goals and your travel style. If your goal is to visit a lot of places in a little bit of time or if you are attempting to satisfy travel goals for multiple people at once, multi-destination trips may be a good option for you. However, if you only have a few destinations on your bucket list or have a lot of time to check destinations off of your bucket list, I would not recommend this type of planning because you could end up feeling like you missed out on something.
In the same manner, your travel style is super important when making travel plans. I think the best way to make the most of multi-destination trips is to be a bit of a planner and consistently on the go once you’ve reached your destinations because your time is limited. If your ideal vacation includes waking up at noon and just seeing where the day takes you (esp. if you could end up only doing at most one thing during any given day), splitting your time between multiple places probably won’t be the best idea.
How High on Your Travel Bucket List is the Destination?
When deciding which countries to split your time between, make sure to consider how high on your bucket list the locations are. I would not recommend picking multiple destinations high on your bucket list because I can almost guarantee you will feel like you have unfinished business. Instead, I would recommend choosing one high level and one low level or two low level locations. For example, if I could go back in time, I would have chosen Amsterdam (low level) instead of France (high level) for my day trip when I was visiting Belgium with my friend. Because I had so little time in Paris, which is at the top of my list, that trip felt very incomplete.
Pick Nearby Countries
I would also recommend choosing two locations close to each other (and preferably close to your home). For my Tokyo-Bali trip, the goal was to satisfy both my top travel goal and my roommate’s top goal at once. However, in doing that, we wasted a lot of valuable time simply flying. We flew about 18 hours to get to Tokyo, 7 hours to get to Bali, and at least 24 hours to get back to Tampa. We only had 9 days for the entire vacation and spent 2-3 days of it in transit (not to mention dealing with major jet lag). If you can, choose countries that will be closer to you and/or closer to each other and easy to navigate between the two. For example, European countries are around 10 hours from the U.S. and flying from country to country is typically really easy. There are also plenty of trains that travel between the countries (Brussels to Paris was only 3 hours by train). Caribbean islands are really close to both the U.S and to each other (sometimes boats/ferries provide easy transportation as well) and would also be good options for multi-destination trips. Google Maps will be your best friend here.
How Easy is it to Move Around the Destination?
Because you have limited time in each country, this is also going to be a major factor. An easily walkable city like Brussels is great for this type of trip because you can explore everything in a little bit of time. Although I only had 1 full day there, that part of the trip honestly felt complete. Even if you can’t necessarily walk around the city, pick a location where you can get to most of your interests in 30 minutes or less by either public transportation or car. If you only have 3 days but everything is an hour plus away, you will be limited as to what activities you can actually do (a mistake we made in Bali). I would also recommend picking an accommodation that is central to everything you intend to do (another mistake we made in Bali).
Google “How Much Time is Needed for ___”
Although, this answer is somewhat subjective, a quick google search could really help you get a general idea of if a destination will be good for quick trips. If an overwhelming majority says it takes a week to experience a location, I would recommend saving that place for when you have more time. If you need some suggestions, based on a quick search, Toronto probably requires 4 days, Brussels requires 1 or 2, Lisbon and Porto need about 2 each, and Venice can be done in 1-2 days.
Search for Itineraries Based on the Length of Your Stay
This is my go to when I know I’ll be short on time! Many travel bloggers write posts titled “1 day in Paris,” “3 days in Toronto,” “3 days in Aruba,” etc. that give you day by day itineraries for any destination. Oftentimes these posts will highlight 3-4 main activities per day, suggest restaurants to stop at in-between, and tell you how to get from spot to spot. They do the hard work for you!
Determine your Must Dos
It’s important to remember that you probably can’t do everything in every destination during these types of trips. Do your research ahead of time and pick the “must dos” for your trip. Plan the rest of your itinerary around these activities. Of course it's possible (and exciting) to fall in love with a city after a sneak peak on these trips and want to go back. But you don’t want to leave the location feeling like it was a waste because of the things you missed out on. If you return to a country, it should be because you want to, not necessarily because you have to simply due to poor planning (especially if your vacation budget is tight).
Take Advantage of Layovers
Layover can be a great (and inexpensive) way to add destinations to your overall trip! On our way back from Bali, we had a 7+ hour layover in Seoul, South Korea. South Korea was lower on my bucket list so I did not have plans to visit soon but since I would be there anyway, I decided to take advantage. Incheon International Airport actually offered a few free tours for people with long layovers. We participated in two tours, shopping in the city center and a casino visit at a resort. Many airports have locker areas to store carry-on luggage so feel free to head out and explore whatever city you are in (you can sleep on the plane later)! I guarantee it will be nicer than sitting in an airport for a whole day.
After reading this and thinking about how different the weather was in Bali and Tokyo, preparing appropriately for drastically different climates might be necessary for a reader who still intends to do something similar.
Such wonderful trip tips !! Never ever considered layovers as a bonus to the trip . One of my favorite reads so far