Apparently, I have a problem. I have been told by multiple people, including my spouse, that I am booking our travel plans way too far into the future. We are losing spontaneity and somewhat confining us; possibly resulting in missed adventures and lost meetups with friends and family. I understand those criticisms and do feel a bit of that, but I would like to defend myself. I have reasons for booking far in advance and I am not sure I really want to change. Although, I usually listen to my wife…. I will to try to justify my actions in this post.
We play the credit card game and like to pay for our long haul flights with points. My wife also really like business class flights so we are always trying to find a way to get out of economy seats when we are flying over oceans. This takes some planning and understanding of each airlines schedule in order to hit the best deals. For example, we typically spend the fall in Europe after a couple of months of summer in our home in Seattle. In 2026, we would like to start in Helsinki, Finland and travel through the Baltic countries and Poland. There is a direct flight from Seattle to Helsinki on Finnair that we really want to be in Business Class. I can transfer credit card points to British Airways Avios points and then can transfer those Avios to Finnair to book this flight. I learned that Finnair releases their seats, including 2 business class seats, 361 days before the flight. Award Travel seats are extremely limited, so if we really need to grab those as soon as we can. I will be on Finnair’s site on the seat release date to make sure we get those business seats, or at least some premium economy seats.
This isn’t always the case with long distance flights. Sometimes, we can be much more flexible and just look for seats to any city in Europe or Asia. If I find a great deal then we can design our trip around the flights. Sometimes this takes a few months of searching everyday but usually I can find something that works. The best time time find these deals is still 9 to 12 months away. Last year, we knew we wanted to start the year in Southeast Asia after our Christmas in Seattle. We don’t have a direct flight to Southeast Asia from Seattle so we need to fly through Seoul, Tokyo or Taipei. After several weeks of searching I couldn’t find reasonable business class flights, but I did find some economy award travel. In March of 2024, I used our points to book Seattle to Seoul on January 1st, 2025 and then Seoul to Taipei on January 3rd. We were able to spend a couple of days in Seoul, and then a week in Taipei before we headed on to start sour Southeast Asia trip in the Philippines. It worked out just fine. It was great to be crossing oceans almost free, but we needed to be booking many months in advance in order to ensure those award travel deals.
When I search for these deals 3-4 months out, I am not seeing much. Many airlines do have sales and some can be some excellent deals closer in, but I don’t want to risk it for long haul flights. Alaska Airlines has regular sales on their flights just a few months out, but they don’t always include the flights from Seattle to Mexico or Hawaii. For shorter flights I tend to be a lot more patient. For short flights between cities in Europe, America or Asia, I am booking from 2 to 12 months out. I will wait for the deal to come if I am just talking about $150 flights. We don’t feel the need to be in a first class seat if the flight is only 2 hours long.
So, I think I have the proper logic when looking at flights, but why am I booking lodging 7 to 12 months in advance? The first reason is that I only book cancellable hotels and Airbnb’s. When searching, I always set my filters to “Cancellable“. We actually don’t cancel very often, but I can’t risk losing the money from multiple stays if we need to return home for some reason, or want to change our plans. Things can happen and we want the flexibility to be able to get back to Seattle without worrying about losing tons of money.
I also believe that we get the best Airbnb’s and hotels when we are booking 7 to 10 months out. There are many places that have limited inventory and I want to make sure that we are searching when there are the most units available. I have heard many stories about nightmare Airbnb situations and the hosts can’t or are unwilling to fix. We have had great luck with Airbnb’s and think part of that is because we book so far out. We are getting the ones with the best reviews and in the best locations. If I wait until our stay is 3-4 months away, the selection is certainly narrowed quite a bit. Booking far out also lets us find some fantastic deals. Some Airbnb’s are still usually priced at the owner’s discretion so we sometimes end up with some amazing places for less than market rate. Those places are usually gone when looking 3-6 months out. When we are looking in high cost of living cities like London or Paris, I want to make sure we are booking right after we have booked our airfare.
So, if I am booking airfares and lodging really far out, what if I have a need to cancel a trip. I book flights with credit cards that include travel insurance. I book cancellable Airbnb’s and hotels almost all the time. I supplement that with Travel insurance with TravelGuard which also gets us additional coverages for trip cancellation and interruption, medical expense and evacuation, and lost or delayed baggage. I think I have most situations covered.
What I am really missing by booking so early is flexibility and spontaneity. What if I really like a place and want to stay longer, then it is difficult to change plans even though things are cancellable. On travel days, we like to ask ourselves if we are ready to move on. The answer is almost always “Yes!”. We are ready to see new things. We like to stay in places 5-10 days and it is really easy to see most places in a couple of days. We can always come back for a longer stay if we really enjoy it. Some day, we will choose to slow down our travel but now we are happy with our current structure. We like weeklong stays but we will throw in a one month stay once in a while to rest up a bit. We have been staying on a beach in Mexico for several weeks at a time and next year we are going to include a month in Brisbane, Australia. Those long stays are typically off the platforms like Airbnb, so it can be harder to cancel.
The other flexibility issue is meeting friends are family on the road. What if someone wants to come join us on their vacation? We really like traveling with other people, but if I am booking airfare 10-12 months out then it can be difficult to convince people to accept our scheduled travel plans when they are only thinking 6 months out. This doesn’t really happen much to us…. and talking to other nomads, it doesn’t really happen that much for them. We want people to want to travel with us but we need to accept reality. Some people don’t share our love of traveling. Even if they do, it is difficult to match schedules with our friends and family that have jobs. It is much more difficult to make plans to be together for a week on an island in Thailand when it takes multiple flights to get there. We have met up with friends in Greece, my brother in Costa Rica, and our kids in Mexico. We are going to be traveling on our second trip with Meg’s brother and sister-in-law in Spain. We can make it work, but it takes a lot more planning and coordination. If someone asks us to join them in Hawaii in a couple of months…. it would be rather difficult if we are in Lithuania.
One thing that I have to mention is that both Meg and I used to be project managers. We like schedules and planning, and I don’t think that will go away. I enjoy looking at our Tripit app, or Miro, our online travel schedule whiteboard. It is fun to see all the different cool places we will see in the next year. When, we were working, I always had to have a vacation booked to look forward to. When we finished a vacation, I was ready to plan a new one. Now I always have multiple new places to stay on our calendar and it makes me happy to know the future of traveling in the next 12 months. Traveling can be stressful and these plans make me have less stress.
One of the common themes that comes up with we meet with other nomads is that “Everyone has a different way to nomad”. Everyone should be happy with their own style of traveling. Some people are happy staying 3 months in each location. Some people prefer hotels. Some people like cruises. Some people prefer house sitting. We are traveling like we want to travel, and I like the safety and structure of having a set plan months (ok, usually close to a year) in advance. We know people that don’t know their destination next week or month and are perfectly fine with that. I can see how that flexibility would be enjoyable…. but it isn’t for me. Meg and I will continue to have conversations about our booking timing, but I enjoy our traveling style right now*, and she is very happy when we book a trans-ocean flight in business class. Even though I booked it 361 days before the flight.
* Meg appreciates the rationale to book flights farther in advance, to best use our miles for good deals. That said, she gets rather annoyed that we’re pretty locked in a year ahead, pretty much always. And that we don’t have really any spontaneity in our travel. This conversation occurs regularly 🙂
Still finding our footing as we’re finishing up our first year but we (aka I) also book close to a year out for long haul flights and 6-9 months for accommodations for many of the reasons you listed.
I’m with you on this one Bill. I’m just plain happier knowing where we’re going to be, and paying a small premium for 100% cancellable bookings. In 2026, we’re trying the Star Alliance Round-the-World business class airline ticket, which actually requires planning a full itinerary (although it’s pretty easy to make changes after the first leg has been completed). Fortunately, since hubby is neither the spontaneous type nor the least bit interested in the work pf making plans, all’s good!