The Beginning – Boston

I picked up Joe late Wednesday night from Logan Airport, shocked he had only brought a 40L pack. I was struggling to fit everything into a 50L pack plus the daypack I was bringing. More shocking than anything, though, was that this trip was really happening! We had loosely formulated plans for the trip last July on the roof of the Ludlow Hotel during one of my trips to Etsy’s headquarters in Brooklyn. Close to a year later we were almost off. The trip was almost all we’d talked about since December, and especially since early January when I booked my flight from San Francisco to Boston, and we both booked our flights to Lisbon.

On the way back from the airport we managed to turn a 30 minute trip into an hour one. The follies of thinking you have Google Maps enabled when you don’t. We both laughed realizing how terrible we were at navigating streets we knew when we were about to head off into foreign lands where we really wouldn’t know where we were. Still, an early spring night in Massachusetts is as peaceful as they come, so the extra leg of the journey home was welcome as we drove through countless back roads near Concord.

My mom and dad were both awake when we arrived, and we chatted for a while about the trip. My mom, too was shocked at Joe’s minimalist pack, and Joe and I worked for a while trying to get my pack down to size. Still, I wasn’t ready to get rid of a second pair of pants, yet.

Early Thursday Joe and I ran some last minute errands around Concord. We drove back through the Middlesex circle a few times (for those unfamiliar, Middlesex = the high school where Joe and I met before going to the same college, Georgetown). We parked and walked out on the dock at Bateman’s Pond to take an appreciate moment of just how nice a day it was and how interesting it was to be back here 11 years after we first met and before our trip.

Thursday evening we packed up for the final time and headed into Logan after triple checking we had our passports. I said farewell to my parents and we headed through security, past that overwhelming smell of clam chowder at Legal Seafoods, and onto our gate.

From there, things were pretty seamless, and we landed in Portugal six hours laters, 12am EST, 5am local time.

Touch down in Lisbon

We arrived in Lisbon early Thursday morning, exhausted from the restless one or two hours of sleep we’d been able to get on the flight. We were meeting our Airbnb host at 8:30am to get the key to our apartment, so we waited for a couple hours in the airport. It was raining inside, but by 8am when we made our to the subway, the rain had stopped, and it ended up being a beautiful day.

Breathing in some of that sweet European air.

Our Airbnb was really perfect. Writing this after the fact, two weeks later, it’s clear how lucky we were with that apartment. It was right next to the train station in the Cais do Sodre neighborhood. It was four floors up, but the view was worth it. We had a sweeping view of the 25 de Abril bridge (you know what one that looks exactly like the Golden Gate because it was built by the same company and if it ain’t broke don’t fix it). We managed to get a few hours of sleep through the mixture of fatigue and excitement.

The view from our apartment later that day


The first day we went out and mostly did a good deal of walking around the city without particular goals or sights in mind. After waiting for a half hour to take the famous elevator up to the Bairro Alto, we learned they only take cash, which neither of us had. We made a mental memo to always have cash in the local currency (duh?), laughed, and went on our way. (We never did get to go in that elevator, though.)

Our apartment was right next to an “establishment” called TimeOut Market. Establishment is in quotes because I’ve never really seen a place like it before. It’s similar to a food court with a lot of really quality mini-restaurants with reasonably priced local dishes. A tourist’s dream.

Joe extremely happy to be eating local food and drinking beer.
These meals were gone in 60 seconds.

We headed out in the neighborhood towards a crowded street where we assumed we could find a good post-dinner beverage. We did a lap looking for a spot until we came to a bar with live music and we both knew immediately this was our spot. But, it was an Irish bar…in Lisbon. We figured we could patron a truly Portuguese establishment on following night, and followed the sound of an acoustic guitar.

We banged our Guinness pints on the tables for a solid two hours and pretended we knew the words to Whiskey in the Jar. It honestly could have been Temple Bar. People in there were wild.

Lisbon Day Two – Cascais and Benfica

Our first real day of the trip. Joe and I were both committed to learning some new things while traveling, and we set aside a few hours in the morning to focus on those activities.

Joe is starting in a stats program at Stanford in the fall, and he’s been learning programming in preparation for that program. As a software developer, I’m around to answer any questions. On my end, I’ve been playing guitar casually for a while, but haven’t invested the time necessary to break out of the intermediate level. As an accomplished guitarist, Joe has a lot to teach. It’s worked out well as a trading of skill sets. We’re both coming into the trip with a big interest in meditation, so we’re carving out time for that as well.

Hunting for breakfast

In the early afternoon we headed out for a day trip to Cascais, a smaller former fishing village turned vacation spot of the nobility. The thirty minute train ride was easy from the train station across the street, and we spent the day walking along the picturesque waterfront in this small seaside town.

After three or four hours of walking around, we decided to catch the train back to Lisbon. On the way we saw a large crowd gathered in front of a TV in a courtyard. It seemed like a particularly large gathering, but hey, Europeans love their football.

We arrived back at the apartment an hour later and were hanging out while people were going crazy with excitement outside. Wow these people love soccer, huh? We thought. All this for a normal game? Eventually it became clear this wasn’t a normal game, and it turns out Benfica, a Lisbon based team, had just won the league.

We decided to follow the groups of people clearly headed somewhere, and ended up and one of the main roundabouts in the city, surrounded by 200,000 people and countless flags and flares. The number of people was staggering and the celebration was incredible. Benfica has won the title for the last four years, but you’d think this was Boston in 2004 the way they were celebrating. We soaked in the moment, feeling extremely fortunate that this happened by chance on our second night in Lisbon.

They love flares here. Don’t worry, Mom, we stayed towards the edge of the crowd.
Pretending we’d actually watched the Benfica game earlier in the day.


After a few hours we pulled ourself away from the celebration and grabbed a late-night dinner before heading back to our place.