It is easy to feel overwhelmed when first starting to plan a trip. There are so many things to figure out, and right now, many people have a harder time affording life in general. This is exactly the right time to stay committed to your travel plans, even if you have to think ahead a bit farther than you initially thought.
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To be an effective planner, you need to give yourself time to connect with what’s important to you. Before you dive into the logistics, you have to remember what you love, and why you want to take this trip. This helps you make good choices, but it also sets you up to enjoy the entire planning stage. For many people right now, travel may seem ridiculous. Maybe not even possible. Yet. That word yet is very important.
Parque de Merendas das Pedras Irmas, Sintra, Portugal
Start with a Feeling
Whenever you start thinking about how you’re going to accomplish a really big goal, if you’re anything like me, you get stuck almost immediately. There are three possibilities for this: overthinking from the fear of making the “wrong” decision, trying to control too much too soon, and not having clarity about what you actually want. The only way out of this trap is to stop the monkey mind before it derails your trip, before you’ve even looked up a single flight.
When you think about this trip, what are you looking forward to? For me, it might be sitting outside a café in Paris with an espresso, with time to watch people and no particular place I need to be. That’s what I want to keep in mind as I plan. When I think about sitting in that café, the feeling I get is one of excitement mixed with relaxation. I’m content to be right there, enjoying being somewhere new.
What Do You Want to Do on Your Trip?
Figuring out a destination can sometimes be as easy as remembering your bucket list. Other times, it could be determined by specific activities. Maybe you already know you want to go to Europe, whether it’s a new idea or a trip you previously had to postpone.
Alcoutim, Algarve, Portugal
But where? And when? I suggest considering less busy times of the year, but keep in mind that many people are on to that trick now. Stay true to what you want to do, but be flexible about when you go. Summer is still busy in Europe, and even spring can bring crowds, so traveling outside summer doesn’t necessarily mean crowd-free. Once you have narrowed down the continent, what do you really want to do when you are there? Is it art, history, and museums? Sports? Soccer, cycling, or ski racing? Or do you want to do physical activities: hiking, skiing, and biking? Chasing the Tour de France or walking the Camino de Santiago is just as valid as wanting to spend your time shopping and going to the Louvre. Maybe it’s both!
Start Comparing Flights Before You Set Your Dates
When you’re ready to move beyond recon, How to Know When You’re Ready to Book a Trip can help you think through that next step.
Once you have an idea of where you want to go, start looking at flights. I tend to get my flights set first, but I also now realize the game has changed. Most everything in travel is now targeted and dynamic. I try different browsers and also stay logged out to see whether the prices differ. Keep in mind that this is still recon, and we are not locking anything down yet. The old adage that it is cheaper to fly in off-peak travel windows is generally true, but individually, your previous choices and data may get in your way.
Alcántara, Lisboa, Portugal
São Pedro de Sintra
Misericórdia, Lisboa
I created the Bon Voyage books and planners to help keep all these possibilities in one place. You don’t need to have your trip figured out before you start using them. Begin with your ideas, compare your options, and add the details as you go.
I also look at Google Flights, Skyscanner, and individual airlines’ sites. As I compare different search engines and then check back as my plans continue to develop, I start to get a better idea of the real cost of airfare. At this stage, I am comparing options before considering my miles or member benefits.
Compare flight prices across a range of dates and nearby airports. Include baggage and other fees so you know what the trip will actually cost. I cover this in more detail in How to Play the Airlines’ Game and Win.
Look for Price Patterns, and Mind Your Technology
Once you start to see the price patterns, this is where a little flexibility can make a big difference. Try shifting your dates by just one or two days and notice what happens. Tuesday or Wednesday are considered to be the least expensive days to travel, but starting on a Saturday can sometimes be less expensive as well. I always start a search by being logged out of my account, and in “private window” mode for Brave, Safari, and Firefox. When you close all the private windows, the browser clears that session’s cookies and browsing history. Websites can still see your IP address.
Aviasales is another place to compare flights across airlines and booking sites while you’re figuring out where and when you might go.
A VPN can hide your IP address and make it appear that you’re in a different state or country. Unfortunately, some websites will just not let you in because they have ways of detecting VPNs. But I always try everything in the beginning and see where I land, no pun intended. I do this for rental cars and lodging with larger hotel chains, too.
Another thing I look into before traveling is how I’ll stay connected. Airalo offers travel eSIMs, so you can compare data plans for your destination before you go. Check that your phone is unlocked and supports eSIMs.
Belém, Lisboa
I discuss preparing for changes and cancellations in Force Majeure and Travel Insurance.
The biggest thing to remember is this: Right now, you might or might not be able to sketch out the whole trip. Keep a brief journal somewhere handy for you, and take notes on what you are learning. Things are more expensive. Pricing is now almost predatory and also concerning. The best thing to do is to keep up with what the industry is doing, and if you are really cost-conscious, getting good at and doing your own research can end up saving you a lot of money. Travel is important, however. Whatever is going on in your life, travel has a way of expanding your understanding of the world while keeping you engaged in wonder and in adventure. If you have to postpone a trip, that’s ok. Just don’t give up, and change the dates.
