10 things to deepen your experience of travel

I'm becoming too disenchanted with travel. Here's how I become a pilgrim instead of a tourist.

“God speed! Pilgrims Setting out for Canterbury” George Henry Boughton

One of the most common dating profile crimes is the statement “I like to travel.” It is one of the most vapid possible characteristics you can read in a bio on a dating site. It tells you exactly nothing about the person. “I like travel” truly means “I am willing to let you project your preferences upon me.”

I’ve become increasingly disenchanted with travel. I thought it was a way to open my mind, to bring myself out of my funk, to try new things and be delighted by the novelty of new cultures and the world. But lately, I’ve found travel to be unsatisfying. Some of it might be the form factor, where I can at most take a week to go explore a new place. Some of it might be the commercialization of travel experiences post-pandemic, where everything has become expensive. Some of it may be the feeling that travel is just supposed to be a brief moment of frenetic hedonism in between big blocks of drudgery. But the real reason I’ve become disenchanted with travel is that it does a poor job of teaching me something new. I am still myself in these places, and am still myself when I return. Serendipity has decreased while on these trips, as have the chances of running into something life changing along the way. I start the trip and end the trip right back where I’ve started, barely different.

Travel doesn’t need to take you somewhere different to be meaningful. Life changing journeys can still be loops. Even though Odysseus started and ended in Ithaca, his experiences along the way changed who he was. I am interested in making more travel experiences into life changing loops instead of boring tourist rambles.

I don’t want to be a tourist, I want to be a pilgrim. Here’s how:

1. Agnes Callard, the Case against Travel: I find this to be a flawed case against travel, but Agnes is an excellent philosopher. Agnes has a negative view on travel that rhymes with the view of my grouchy old great uncle who says “only do known things.” After a couple decades of traveling furiously (she is European and then moved to the US) Agnes’ commentary is really about the marginal value of tourist-like travel after one has already been fairly well traveled. It turns her argument into a bit of a watered-down toy, and it has a lot of contrived conclusions. Agnes says: “In the many great cities I have actually lived and worked in, I would never consider spending whole days walking. When you travel, you suspend your usual standards for what counts as a valuable use of time.” I disagree that this is a bad thing! You’re not trying to learn about the culture of your own city in a condensed way. Of course this activity seems absurd! Spending a whole day walking while in a new place is an attempt to compress a year’s worth of walks into one day. Agnes forgets that we might indulge in new activities in a new place in order to feel free. The more convincing case against travel, to me, is the economic case. Tourism is overwhelming Europe, travel is up more than ever, and public resources in those countries (transit, etc.) are crumbling under the weight of the load. Taxes and other means to make up for that strain are a lagging measure.

2. This is the rare excellent SNL skit. Ensure you set your expectations for travel correctly. A plane ticket is not Lexapro. “If you’re sad where you are, you will be the same sad in Italy. We can provide you with a wine tasting tour of Tuscany, but we cannot change why you drink” says the SNL skit.

3. Seek out Cathedrals: Gaudi’s Cathedral is stuck in my memory. When I went to Canterbury, it was attending evensong at the Anglican cathedral that remains close to my heart (I’m not religious!) Cathedrals are consecrated to create something sacred and transformative for large groups of people. They turn the mass of tourists into a sacred collective group. You feel buoyed by the crowd instead of stressed by their presence. There are many such cathedrals — a great concert hall, a grove of redwoods, an open sculpture garden — that can transform the disconnected herd into a collective. Visit a cathedral on every trip.

4. Read before visiting: One of the reasons that I loved London and the UK so much was that I had spent a lifetime reading books about the place. I had enough distance from any one specific book that I wasn’t close minded to my first-party experience. Every time I’d walk down a street, I’d think, “Oh so *this* is Bloomsbury Square? This is what it means to travel to Hampstead Heath? This is what Mayfair really looks like?” I freaked out when I realized that my apartment was right next door to Samuel Johnson’s. The difference between picturing things in my head and seeing them in reality was what heightened my observational powers. I made lots of Chanticleer the rooster jokes in Canterbury. I loved my experience visiting Dover because I recited the Matthew Arnold poem in my head the entire time. I think that I was better able to appreciate meaning in a place because I had done so much research.

5. Travel in order to do something with Locals: I am always surprised by how different my expat-American friends’ experience of Singapore is from my experience. It’s not enough to live in a country, you have to actively seek out local friends and experiences. And if you don’t have local friends? Tyler Cowen (the economist) recommends asking an older taxi driver for advice. When traveling in Nicaragua in the early 2000s, he asked the driver to take him to eat something delicious and typically Nicaraguan, for which he’d pay for both of their lunches and add on a $10 tip. I am not sure if Uber drivers would similarly oblige, but I could imagine finding local guides outside of the usual tourist traps that are willing to help. Cowen reports that finding older taxi drivers is the ideal profile because they’re seasoned and knowledgeable.

6. Travel with a thesis: My friend likes to anchor all of his travel by visiting a baseball game in every single place. Another friend is a chef, and can get private tours of specific restaurants fairly easily. And most oddly, another friend is a manufacturing person and likes to go visit factories in every location. I think if I ever get to go to Korea, I’d really want to visit a bunch of tech companies while I’m there to learn how they work. Traveling with a thesis gives you a chance to do your own comparative analysis in a subject where you already have depth.

7. My travel guide to London! I lived in London for 9 months and my family came to visit multiple times. Here’s the week itinerary in case you’re headed there. I thought that this itinerary reassured my family that I wasn’t going to ruin their visit with chaos while still leaving enough space for serendipity.

8. Here’s the same doc for Paris which includes a long list of places to find vintage clothing that I scrapbooked together from across the internet. My favorite place in Paris was actually a restaurant called Chez Janou, which felt intimate and familial — for dessert, they give you heaping scoops of chocolate mousse from a big communal cauldron. Despite having this list, I took a free approach to travel in France and Spain — I didn’t even book a hotel every night. I tried to embody the medieval pilgrim: they knew their final destination of Santiago de Compostela (for example) but they simply walked as far as they could that day, with little concern about where they’d stay for the night. I did the same thing. You will find a lot of little secret hideaways that way.

9. Recommended USA Hikes: The American cathedral is the national park. Here’s a list of recommended hikes from my former climate-loving colleagues who were avid hikers.

10. And here’s my document of Hawaii recs (Oahu and Big Island) — of which two are quite unique. 1) Secret big island spot for tiki drinks and the best sunset and 2) Oahu furikake bread that will blow your mind.