Typically, when I am taking a trip, the destination has a way of choosing itself. I do have a mental list of the top 3-5 destinations I would like to travel to soon, however that list likely won’t be the next places I actually travel. I try to knock off one ‘dream destination’ per year, but usually a destination is based on a single event. For example, this summer we went to Hamburg because I was able to get Taylor Swift tickets there, and this fall we are going to California because my husband is competing in a CrossFit competition.
Our 2024 dream destination trip was when we went to Iceland in February. For 2025 I think I might be lucky enough to get two, Morocco in Spring and Peru in Fall, but plans often have a way of changing!
I’m telling you this because when I research and plan my trips, often the destination is non-negotiable. We are going to that city/country/area anyway, so I plan the trip around that. Which means the dates are somewhat pre-determined as well. If I had my choice, I would not have gone to Europe in the middle of summer, but that’s how the cards fell this year!
However, when I do get to pick where and when I go, there are some factors I consider…
Destination, Duration, and When to Go
For me, duration is the leading factor when picking a destination. I’m not going to fly to Australia for a week, it’s just not worth the journey for me. If I have a week or less, I’m probably not leaving North America. Iceland was the exception to that, or maybe some Caribbean islands that happen to be owned by far away lands…
Two weeks, and I would travel to Europe, Africa, or Central/South America. Anywhere in Asia or Oceania I would want 3+ weeks. This is the main reason I have yet to go to Japan as I want to spend 3 weeks there and of course, vacation days are limited!
Once I know how long I can travel, I pick a place that I want to go. Sometimes that will easily choose when to go too. For example, I want to go to Chicago for St. Patrick’s Day, so we decided to go for 4 days in March. This satisfies the destination versus duration clause, and also given that St. Patrick’s Day is a fixed date, chooses when.
However, the decision when to go is not that easy all the time. The factors I consider are:
- High tourism season
- Severe weather possibilities
- Cost
- My personal schedule
High Tourism Season
I have an aversion to large crowds, and lines, and general overwhelming busyness. I’m sure I am not alone in that. I prefer to travel during what is often called “shoulder-season”. This would usually be the time just before or just after the “busy season”. I have heard a lot of people say that the shoulder season no longer exists, but I have not had any problems traveling during this time.
I believe it comes down to managing expectations. For example, we went to Venice, Italy in October, of course it was still a busy place, but it was nothing compared to summer or carnival season. Or, Disney tends to be a bit quieter in September, as people often won’t take their kids out of school at the beginning of the school year. Doesn’t mean you will walk on to the top attractions, but there will be less people than at Christmas when school is out.
When given the choice, I do try to avoid the high tourism season, which can vary depending on where you are heading. A quick Google search can answer when the high tourism season is for your intended destination.
Severe Weather Possibilities
There can be a valuable trade-off when traveling during times of statistically poor weather, such as better prices and fewer crowds. You should do some research to make sure that during these times the things you want to do are not closed though. Many extremely seasonal destinations essentially shut down in periods of slow tourism. We have several small towns near us that are like that.
When we traveled to Iceland earlier this year, we chose to go in a time of unpredictable weather. Because of this choice, we made decisions that we would not have made if traveling during other times. We normally would have rented a car and driven ourselves around. But because we were worried about severe winter weather, we decided to make a home base in Reykjavik and do organized tours instead. I knew their main road sometimes closes during bad weather and I really didn’t want to be stuck!
Other places in the world may have weather conditions worth avoiding, such as extreme rain, extreme heat/cold, or periods of very reduced daylight! Again, a Google search of your destination can reveal these things, it’s just worth considering.
Cost
Simple economics will tell you that increased demand often results in increased costs. That can be true with travel, but it can also mean that increases in demand also increases offerings. During the summer months, from approximately May to October, Condor offers a direct flight from my hometown to Frankfurt, Germany. This is because there is demand for the service. From November to April this flight isn’t available. It costs us more, and takes us longer to get to Germany (where my husband’s family lives) during these “off” months.
However, when demand is lower, things like hotel rooms, tours, admission, and food prices can be lower. Depending on where you are going, traveling during a season of lower demand can save you a lot of money.
My Personal Schedule
This factor, as the name suggests, is unique to me however I am sure you each have your own personal schedule!
One thing I have to consider is my work schedule. I am not able to take any time off during the first 7-ish business days of the month due to my job tasks. This is something I always have to be able to work around. I also only have 15 paid vacation days each year (I have been known to make the most of these in different ways, which you can read about here).
We also have a dog, so we need to make sure she will be able to be cared for while we are away, and of course the schedule of whomever I am traveling with matters too!
Once I have decided on when and where, it’s time to actually start planning! The thing that I usually book before anything else is not what you might expect…
Where to Stay
I don’t know if this is “normal” but for almost every trip, I always book accommodations first. I like knowing exactly where I will be staying, and where I stay is important to me. I DO NOT use AirBnB, I am a hotel person, or I would stay in hostels in a private room (I’d consider a dorm if traveling with a friend). I like my hotel to be very centrally located to the city center, or for whatever reason I am traveling. If I’m going to Disneyland, I want to be close enough to walk. If I’m going to a concert I want to be decently handy to the venue. I prefer to walk places when I travel, so I want to be close to the attractions. Of course, in large places you will have to travel some, but I think you know what I mean.
In cities with good transit, I look for subway stops and what lines are convenient for it. In places like NYC, London, Paris, etc. I like to be within walking distance of two stops with different lines. I find this makes traveling around really easy and cost efficient.
I know for some where they stay is just a room to sleep in, but for me location is so important, and I book this first. The airport isn’t going anywhere, and there are always flights!
I book 90% of my accommodations through agoda.com. With my recent interest in loyalty programs, this may be subject to change, but here is 3 reasons I really like doing it this way:
- Agoda lets you make a reservation that doesn’t charge your card until about a week prior to your stay. This is ideal for me as I sometimes book accommodations and then change my mind about the trip. I don’t need to wait for any refunds
- I can almost always book accommodations that have a free refund up until a few days before my stay starts. This combined with the first reason means every vacation whim I have I can book a room
- When I book on my computer I also get Honey Gold from this site. I usually get a few hundred dollars in Amazon or Kobo gift cards each year just from booking my accommodations
Where Are All the Places I Will Actually Go
Sometimes this is relevant, and sometimes you have a single destination. When I am starting a multi-city trip, and only have one place that we need to be in, I will usually add a stop before or after.
We went to Hamburg for the Taylor Swift concert, but I knew I wasn’t going to spend all my time in Hamburg, so I pulled up a map and looked at what was close to there. The way my husband and I travel is generally I will pick 3-4 options and he will choose one. Based on knowing we will be in Hamburg, we decided to add Amsterdam and Brussels onto the itinerary.
For longer trips this is a very typical way I will plan additional destinations, just looking at the map and seeing where it looks easy to get to. I usually verify this with a site (and they also have an app) I like called Rome 2 Rio, which shows you ways to get from point A to point B and how long each will take. Just because a place is close, doesn’t always mean it will be that convenient to travel between them. I always double check.
Finding Things To Do
With the simple logistics out of the way, I get to the fun part – what are we going to do there! I do this by creating a spreadsheet, like a good accountant!
Here is an example of what that would look like once the trip is basically done being planned:
I write them as if I am talking out plans or thoughts directly to my husband, which of course makes the notes a bit longer. But, it’s a great place to organize hotels, addresses, tours and times, reservations, and confirmation numbers all in one place. I will note if we have prepaid or if we need to pay there. What the cost is, and I sometimes write notes on how to get there in case we are traveling without internet access.
When in the early stages of a trip planning, it looks a lot less fleshed out. I usually start by creating a line for each day we are there, adding in where we will stay and looking up flight options. Then I will start doing some googling to see what there is to do in places. I like to look at a good mix of tourism sites, Trip Advisor or Lonely Planet style sites, Viator or Get Your Guide tour options, and blogs written by people just like me! Off to the side I will make a list of ideas, places I want to see, restaurants I want to eat at, tickets to shows or theme parks, or whatever else I want to do. Then I start assigning days to things. For example if I want to get tickets to a show, that is usually at a fixed time, so I will place that into a certain day. Then, find a restaurant close to the venue and make a dinner reservation. Or, I will map out some destinations and make a morning of sightseeing some things that are close together to improve efficiency on getting around to them.
As the trip gets closer and more details get fine-tuned, I can usually tell exactly what I will be doing each day. I’ve made decisions on what I would like to do based on researching everything that is available to do, and I’ve done my best to make it the most enjoyable and efficient way to do these things. I can understand this style of planning might be a huge turnoff to many. My husband would absolutely hate to make this type of plan. But he really enjoys having it when we are away. Of course, how packed of a schedule you make, and things you choose to add to it are entirely personal choices, but I find having this plan ensures I don’t end up missing out on something I would have really wanted to see if I knew about it.
Another great side effect of this type of planning is that I know for the most part what I will be doing each day, so I can decide what I want to wear each day. This makes for extremely easy packing! Rarely do I put something in my bag that doesn’t get worn and I can usually travel for pretty long trips with just a carry on bag.
Booking flights
This is typically the next thing I will do once I have made a rough draft of my planning spreadsheet. I have already researched my flights (and often set a Google price alert on them) so I know if the price has increased or decreased. I may check flights using points at this time as well to make sure I am getting a price I am comfortable with. I typically book flights between 3-6 months out. Once the flights are booked, I start buying tickets or tours and making reservations at restaurants right after from the initial plans I have made.
At this point, the trip planning spreadsheet is pretty much complete! I really enjoy making these plans and doing the research for trips. If there was a way to make it my job it would be the best job in the world!
Please let me know if you have any questions at all about this!!
Jess xx
