How to take amazing trips for cheap
“Bye-bye New Jersey, I’ve become airborne.” - Chuck Berry (UBC Library Digitization Centre)
“If you don’t know where you’re going, any road will take you there.”
This memorable line comes from a charming, Grammy-nominated song called “Any Road”, off of George Harrison’s posthumous album, Brainwashed.
A similar idea appears in Lewis Carroll’s Alice’s Adventures in Wonderland:
"Would you tell me, please, which way I ought to go from here?"
"That depends a good deal on where you want to get to," said the Cat.
"I don't much care where—" said Alice.
"Then it doesn't matter which way you go," said the Cat.
"—so long as I get SOMEWHERE," Alice added as an explanation.
"Oh, you're sure to do that," said the Cat, "if you only walk long enough."
And this, my friends, is how I have planned my very best travel experiences — and many life experiences as well.
The Cheshire Cat and George Harrison are absolutely right. It’s only logical that if we have no particular destination in mind, there is no particular route we need to take. Indeed, we might already find ourselves exactly where we want to be.
It’s true that when we give ourselves constraints, we actually improve our ability to find creative solutions to problems. We’re giving ourselves a starting point that’s refined enough to prevent us from getting overwhelmed by the multitude of possibilities. However, when we’re stuck or finding our options limited, we can systematically relax the constraints. We can question each one of the assumptions that got us to where we are.
This is what makes it possible to discover joy and happiness without making dramatic changes to our lives. It can also allow us to plan some really great and surprisingly affordable vacations.
Even though travel is impossible right now, I’ve been thinking about it a lot. I know I’m not the only one; in fact, I received a question recently on this blog about how I go about planning a trip. Here, I want to share a bit about my approach. You might notice metaphorical resonances that can apply to solving any problem — or finding more satisfaction in life.
I begin by considering the non-negotiable constraints I have. Usually, these are related to time or money. It is best if all other constraints are suspended: Mode of travel, destination, and so on. I’m seeking new experiences and adventure as opposed to luxury, comfort, familiarity, and predictability.
With few constraints as to where, when, or how, I can use a tool like Google Flights to play around with the options. Tinkering with dates and destinations in various combinations, I can find unexpected deals.
For example, a few years ago, I found a flight from Boston to Paris for only $500 round trip — in the middle of July. All of the other flights from the U.S. to Europe were triple that price.
Once I find a desirable intercontinental flight at at desirable price, I have created a new constraint. But this need not limit me to just the destination city. From Paris, for instance, I might find a $26 flight to Dublin or Nice. I can keep playing around for awhile.
This additional tinkering is helpful to prevent a situation in which you have found a bargain on a flight only to spend $200 a night on hotels in an expensive city. There are so many other possibilities, from Airbnbs to hostels — so if you’re not finding what you’re looking for in one city, you can look somewhere else.
When I was planning a trip to Greece (a destination that was, itself, chosen as a result of a mysteriously half-priced flight), my exploration led me to the island of Santorini. All of the accommodations that faced the famous caldera and its incredible sunsets were $100+ per night. No thanks! So I found a little guest house on the opposite side of the island, away from the most popular tourist destinations, for only $35/night including breakfast. I would have to take the bus to go anywhere, but for me, that was fine. I saw sunrises in addition to sunsets and enjoyed a quieter experience among locals.
For someone else, such a holiday might have been terrible. But for me, things like buses and trains and ferries are part of the adventure. And if I can spend less on a given travel experience, I am able to travel more often. It’s well worth it for me.
I happen to enjoy the research that goes into a trip, and I’m comfortable with unknowns and uncertainty. If that wasn’t the case, I’d take a totally different approach. But going down the rabbit hole, to apply another Carroll metaphor, suits me well. I like my little itinerary spreadsheets and lists of ideas, and I don’t mind if I have to completely rework them (which I ended up having to do once when there was a death in the family). The ideation, preparation, and adaptation is part of the fun for me.
These days, I must accept the reality of Covid as a set of constraints that prevent me from going anywhere at all. However, even within that framework, I can see what is possible and build from there. I’m finding other ways to have new experiences. I’m making the most of what I can do within the restrictions I have. Along the way, I’m questioning the assumptions I’ve made up to this point that prevent me from going where I want to go in life, regardless of where I can or can’t travel.
If I really want to go to a resort in the Caribbean in the middle of February, well, I’ll probably end up paying full price. And if my only definition of success is to make a quarter million dollars a year as a doctor or lawyer, that’s a restricted path indeed. But there are so many other places we can go and experiences we can have — and so many roads that can lead us to places worth going. We can choose one, and if that doesn’t suit us, we can choose another.
If these explorations wind up taking us nowhere, we can appreciate being right where we are. You do save a lot of money that way.
