How to plan your vacation: Figuring out where to stay, how to get around, how to see what you want to see, and how to pack what you need.
This guide is helpful for any kind of travel to a destination where you will be staying for more than one night, whether it’s for business or pleasure.
Finding the right location to spend the night can make a huge difference in what you get out of your trip. Finding out how to get to and from the places you want to visit, before you are standing on the corner with your phone in hand, will make a huge difference in how much you get to see and do, and your overall experience and outcome from your trip.
Why you should plan your vacation
With a little bit of planning and preparation, you can save time and even some money, at your location. When I say that you should plan your vacation I don’t mean the usual planning in order to get things to work out between work, the kid’s school schedule, and your significant other.
I’m talking about beginning when you know that you want to go somewhere and, when the dates are set, the transport and the accommodation is in place, you continue to plan your vacation by finding the fastest way to get from a to b. You will need to do this anyway. Why waste time at your location when you can do it in front of your computer on a rainy Sunday?
Start planning before you make decisions
If I read about someplace that I want to go, I usually add this place to one of my Google maps. When we start to discuss what to do on our next vacation I’ll check to see if I have a map of the area we are discussing.
How to find the perfect place to stay
Finding the right accommodation is about more than just good beds and free wifi. It does not matter if you are staying in a hotel or booking an apartment using Airbnb. Location is really important. Staying close to the places you want to see and public transportation makes it so much more convenient.
Start with Google Maps
Start with creating your very own Google map of the city you are visiting. Go to mymaps.google.com to place your first point of interest. This could be a shop you want to visit, a restaurant you have been recommended, or anything really.
I will sometimes start a map like this even before I have concrete plans on when I’m going on this trip. I will then gather places I find in magazines and online. This way, I’m halfway in my planning by the time I’m buying the plane tickets.
As you keep on gathering information, you will start to see a pattern in where your places are located. When the time has come to look for a place to stay you should look at something that is conveniently located close to where you want to go.
When looking for a location, you should consider the distance to public transportation to the places you want to see. Sometimes, moving your accommodation just a few blocks can mean that you will not have to change between different modes of transportation every day.
Read the reviews
I’m often surprised by the number of people who will choose a place to stay for a week based only on ratings. By reading the reviews, you will see what people are saying about the place, both positive and negative. Someone might give a place a bad rating because they could not bring their pets inside. For most people, this will not be a problem.
See if the owner/manager answers the complaint. I have seen a negative review turn into a positive thing because of the response from the owner. Check multiple booking sites if in doubt. Don’t forget to use the map-view function to see if you have the same definition of “walking distance” as the hotel manager.
A note about Airbnb
Renting an apartment can sometimes be a better option than staying at a hotel. You have more flexibility and generally more room for your stuff. I think it has to be more than five years since my wife and I booked a hotel for a vacation.
We have stayed in Airbnb or similar apartments in Berlin, New York, Oslo, New Orleans, Copenhagen, Tokyo, and London. For our upcoming trips to DC and Tallinn (Estonia), we have booked Airbnb again. We have never had a single negative experience. I think this is because we are reading the reviews, both on the apartments and the hosts.
We always book entire apartments and end up enjoying staying in a spacious apartment for less than the cost of a hotel. You will have to make breakfast yourself, but you can sleep as long as you want to.
How to get around in an unfamiliar place
Proximity to public transportation can make or break your stay. Let’s say you are staying in a city and are planning to use underground transportation. You find that the place you want to stay at is just across the street from an underground station, thinking that this is a perfect location.
Upon arriving, it is clear that for most of what you have planned, you will have to take the underground one stop, then having to change to another line. In cases like this, I would be willing to pay more to stay at a location more conveniently placed. In other words: Try to find the most practical mode of transportation and take this into account when choosing where to stay.
Downloading local transport apps can make getting around a lot easier. However, there is one app that I find amazingly useful in cities across the world: Citymapper. What I like about this app is that not only does it work on both Android and iOS, it has a good web interface, making it easy to plan your vacation ahead of time.
I always find myself using TripAdvisor, both for finding attractions prior to the trip and for finding places to eat when we are at our destinations. In Tripadvisor you can save all the places you want to see, making it easy to find the information when you need it.
My preferred app for the complete itinerary is a combination of App in the Air and TripIt. You can read all about that in the below blog post.
The ultimate packing list
Now that you know what to see and where to stay, the time has come to do some packing. Don’t worry, I have made packing easy for you. All you need to know and the template for how to create a packing list in Todoist is presented in the blog post below.
What to do if you need to work during vacation?
In the ideal world, you would not have to work during vacation. But, as we all know, in the real world, you sometimes have to work – even if you don’t want to. In the below blog post, I have some tips on how to avoid or limit the amount of work during vacation, and how to handle it if you have to take a working-break.
How to make the return to work as smooth as possible
When you plan your vacation, you should also plan for how to get back into the daily hassle without feeling like you have hit a wall.