How to travel somewhere new

One thing that I’ve been thinking about a lot lately, as I move to a new city (São Paulo) in a foreign country (Brazil, for the geographically challenged / lazy), and begin to prepare to explore the corners of my newly adopted country, is how one “takes on” a city – how one transitions from a cursory knowledge of major neighborhoods and a general sense of the geography / layout to a more nuanced, appreciative understanding of a city / place, and then how one goes about prioritizing what to highlight in the even that you’re pitted with showcasing this city to visitors (or yourself) or via writing.

In writing this post, I’ve been inspired by the new show Ugly Delicious, which does a fantastic job of explaining the often complex ways in which local cuisines and cultures have come to be. I was especially entranced by its episode contrasting New Orleans and Houston — Houston’s welcoming of its Vietnamese residents and their cuisine, versus New Orleans strict traditionalist and conformist view of cajun cuisine and culture (maybe a French thing…) I wanted to quickly do a thought exercise on how I would approach being a travel guide / writer, on how to unlock and demonstrate the intimacy and/or uniqueness of a place you’re either living in or visiting, using my personal experience of places I’ve visited in the past, and places I’ve had the good fortune to call home.

Looking at this system with fresh eyes and all written out on paper, it strikes me that it mirrors some of the advice often offered by motivation or ‘visioning’ experts in their talks or literature – start with the big picture, and break down into component parts that are more easily tackled over a shorter span of time. To me, this process seems to mirror the unseen and arduous steps behind painting a beautiful picture – the oftentimes unknown, but numerous steps that bridge an idea or image in your head to the final result.


Sketching with Pencil – Motivation

Considering the hypothesis that the places you’re living in or visiting is a place that you have some level of interest / motivation in being there, oftentimes the first step is to channel that motivation into a brainstorming exercise of sorts, unlocking what is special about this place, to you? What types of things will you be upset if you don’t get the chance to do while in this country / city / place?

Oftentimes, these motivations are surprisingly apparent, and can be jostled relatively quickly by asking yourself and/or your travel partner what their hopes and dreams are associated with this trip, and then prioritize which of these hopes and dreams are the types of things that can’t be missed / avoided. Once you get comfortable with the understanding that your time in any given place is finite, you can brainstorm the major things/places/activities that are truly important, which serves the role of your rough outline of your stay.


Going over it with Ink – Geography

No doubt one of the major determinants of one’s trip / experience is the geography of the place you’re exploring — is it highly compact and walkable, or is it more spread out and requiring of studied day planning to maximize your return (as is often the case). One trick that I’ve developed over time is the use of Google’s Maps feature to help me frame the relative placement of the “must sees/dos/eats” of a given city, which then allows me to break up sections of a given city into smaller, more manageable blocks.

This exercise also helps with the prioritization aspect of trip planning – is there a single attraction or restaurant that’s considerably distanced from the rest of the list? If so, knowing that you’ll likely be visiting at the expense of other items on your agenda can help you determine whether or not this is something you truly want to do. Even the best public transportation systems in the world can’t help you with an one-hour-each-way detour (even Tokyo’s notoriously efficient subway/rail system will take you a long time to get across the sprawling metropolis.)


Visualizing from the conceptual to the specific

Once you’ve identified your motivations, and have gained a strong sense of the geography of the place you’re visiting, you have enough pieces to begin assembling the jigsaw puzzle and its possible permutations to begin the physical act of “planning” your trip. I do this by drawing my own Calendar of the days / duration of the trip, with markers identifying any existing obligations. At a minimum, this includes arrival and departure flights, but oftentimes other commitments as well – plans you’ve already committed to, intra-trip flights, or reservations already made (more on this below.)

This act of visualizing the trip will quickly get you comfortable with the limitations that time oftentimes creates, as well as the idea that it will be truly impossible to do everything you want. From there, the challenge of seeing through your identified motivations becomes the mission. Sometimes, these facts, laid out, can restrict your timetable to the dates that will work to accomplish it all, and you can begin to “fill in the gaps” with the activities that you love, ideally mirroring the characteristics of the place you’re visiting.


Adding the Color – Culture, food, shopping, etc.

For me, food is often the most important aspect of my trip once you’ve rounded out the “must sees / dos,” but this can be expanded to shopping, drinking, or just generally, “culture.” What’s evocative of the area? Are there particular cuisines or dishes that are woven into the fabric of the place you’re visiting, that you would be remiss if you didn’t try (or at least try an authentic version of?) I try to be fairly relaxed and open minded when it comes to trips, but one thing that I can’t abide by is a wasted meal – a visit to a nearby, oftentimes middling and/or expensive restaurant chosen for its proximity, its convenience, the fact that it’s the only place still open at 4PM for lunch (or 11PM for dinner). With a little bit of planning, this horror can be avoided altogether, leaving only delicious meals and interesting and worthy flavors for your precious time and finite stomachs.

My initial step for finding the best food in a given area is to ask locals, and/or predecessors who have experienced the location before you. This will oftentimes weed out the tourist traps, the places that were deemed important once upon a time and have become ubiquitous, and with small exception are usually mediocre and overcrowded (think Sachertorte in Vienna, Pats & Geno’s in Philly, or any one of countless places in New York City.)

If you don’t know any locals, or don’t feel comfortable asking friends of friends (or friends of friends of friends – it’s been done), then scouring the internet can be a helpful next step. I tend towards message boards like Reddit, which are normally populated by locals happy to help out and ensure that visitors get it right. Unfortunately, Trip Advisor can be hit or miss – it’s become so ubiquitous for travelers to popular destinations that it often leads to overcrowded and expensive restaurants (which oftentimes become overcrowded and expensive due to Trip Advisor).

Once you’ve completed your list of interesting and indicative restaurants, you can proceed onto juxtaposing this with the “reality” of these places which can help further fill out your grid – most notably location, reservations required (is it the type of place that requires reservations a year in advance, or a reservation at all?), your budget (can you afford it?), hours and ambiance (is it a lunch place? Only open at night? Requires a dinner jacket?), and then plot out the surviving options on your map to plot against the prioritized activities / places previously identified.

Note that while I used food as the example here, food can be replaced by whatever cultural activity you particularly fancy and/or is indicative of the culture you’re in – shopping, drinking, art galleries, etc. To demonstrate that this method can actually be accomplished, I’m attaching my Japan trip map, which was compiled in advance of a solo trip taken in late 2016. While I definitely didn’t do close to everything listed on this map, each location identified had an inspiration or rationale behind it, and allowed me to maximize my visit to specific regions / neighborhoods of the city / country.

While I definitely think that Google could improve the functionality and ease of use of its custom maps (business idea?), I like how easy it is to share with others and be constantly iterated upon, reflecting the ever-changing nature of the place you’re visiting.


A brief word on serendipity / chance

Before anyone reads this and gets too carried away with their own color-coded, meticulously planned to the hour trip of their own, one word that I’d like to impress is chance. One of the mottos that I live by is maximizing serendipity – the belief that incredible things happen through chance and serendipity, but only if you actively take steps to put yourself in the best position possible (i.e., the right neighborhood / environment / people), and leave yourself open to the serendipitous occasion if it presents itself.

This is oftentimes accomplished by ensuring that you allow yourself to let your innate curiosity guide your actions and not constrain yourself to much by the limits of a timetable or set plan. To me, this is one of the essential elements of any trip, and the one that’s almost certain to result in the most stories and memories that will endure for years to come. Ultimately, your senses are your best guide – if you see, smell, or hear something that piques your curiosity and seems compelling, seek it out!

I’m definitely still learning how to best mix impulse with planning, the idea that a place or experience can be different than you imagined, conceived, or planned, and the ability to remain open to the broader environment and the experiences therein, even if it means staying up a couple extra hours and imperiling your plans for the next day. This is a muscle that I hope to continue to train and harness, and feel blessed to be able to indulge in my life. Hopefully I’ll be able to report back with some of these stories / experiences / sights in the future, with less stuffy words and more beautiful photos.

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