February 14, 2026 | Amtrak Train
Staring moodily out of the train window, sun colorfully setting over the endlessly frozen Hudson River, I’m miserable. I’m on my way back from an overnight work trip to Albany, and it’s Saturday. It’s deep winter, the busiest work time of the year, and one of my closest friends had a life-threatening injury last weekend. The moments I remember that it’s Valentine’s Day I’m reminded of last summer’s heartbreak. I’m eager to be home in the city in a few hours so I can melt into my couch for the next few days.
I must have taken this train back and forth over 100 times over the last decade-plus of working in New York politics. The view is truly epic, and I don’t get bored of it, always opting for a river-side window seat for my hyper-productive laptop time. I sometimes spot bald eagles. Today’s chunky ice on the frozen river is a seasonal reminder that it’s busy season, which doesn’t really end until the summer.
For a minute, I’m reminded of just 6 weeks ago, when I was staring out another window at a different body of water, the weather and the stress levels infinitely better as I bade farewell to Puerto Viejo, Costa Rica. I took a mental snapshot of the tropical blue Caribbean shore peeking through the palm trees from the mini-bus, letting an epic trip sink in and relishing the last time the sun would touch my bare skin for months. I didn’t want to leave. And that told me something about the bigger impact of that trip, with something opening inside me as I anticipated the travels to come.
Another thing that happened this week was that I told my boss about my plans to take a work break of approximately 5 months starting in late July. I expressed a desire to return afterwards, knowing my job might look different, but also knowing there is no policy in place for sabbaticals and that it might not work out for me to come back; so if that’s the case, I will look for a new job in 2027. After 7 and a half years at this organization, it was a big decision. Usually I like my job; it pays me well, I have a lot of independence to work on things I want to work on, and it’s usually not too stressful. Still, I’m bored and tired, and I want to use my brain in a different way for a while.
Uncertainty is the worst, but somehow I’ve decided to be at peace with it. Because I’m going to spend 5 months traveling the world, indulging my whims and exploring wherever my heart leads me. I’m going to write about it and remember it forever. It’s going to be amazing and challenging and lonely and social and surprising. I’ve got a one-way plane ticket to Greece on July 29th, and we’ll see what happens from there. It’ll likely involve a lot of Southeast Asia.
Perhaps there’s some irony that it’s my current job and salary that is enabling me to do this. I’m firmly on the side that money can buy happiness.
Costa Rica was a 4-week trip, my longest yet, and was intended to serve as a test case for long-travel. I’d been considering this idea since last spring, when I hit a block of bad burnout from working and living through the Trump administration. I brokered a deal with myself, that I would not make any decisions until after this 28-day trip, in case I decided long-travel wasn’t for me. I’m honestly not surprised by my reaction. I loved the parts of the trip where I moved around a lot and was on a very-social group tour, and I loved the parts where I was mostly alone and working remotely from exciting locations. I stayed in touch with people at home and didn’t feel homesick, New York is simply a part of my identity. When I got back in early January, I started putting my plans into motion quickly.
Travel saves me. On a grand scale, and even today. I feel better than I did an hour ago. Because as I confront my unhappiness and jaded winter vibes this week, I look out the window to the future, imagining a time later this year when I’ll look at a sunset view over the water on the other side of the planet, and I will feel freedom and joy.
Tuesday, August 11, 2026 | Naxos to Milos Ferry
It’s been just six months since I wrote that last piece, trodden by misery and holding firm to a future I could envision of peace and freedom. Now, at just over a week and a half into my trip, I believe I have already found my sunset.
I spent a full week in Naxos, the largest of the Cycladic islands that only in the last several years really developed as a tourist destination. I’d been looking forward to my time there, anticipating how a week on the beach would chill me out and let me begin to process the transition. It was certainly a major contrast from my first days in Athens, where I was constantly moving and distracting myself.
The 5-hour ferry journey from Athens was a bit chaotic, with some moments of insanity as passengers squished together in the bumpy cargo hold with our luggage waiting for the doors to open. I easily found the bus station office in Chora and bought my paper ticket, managed to get on the appropriate unlabeled bus, and arrived to my accommodation smoothly in 20 minutes.
Naxos’s 20,000 year-round residents are spread across Chora, the main town by the port, and its many tiny mountain villages. I got an intro to the island from the bus: beach clubs and tavernas line small towns along the west coast of the island, getting quieter the farther south you go from the port. People ride around the narrow streets in small cars, ATVs, and scooters, interspersed with giant public buses that seem too large for the narrow roads.
I stayed at Maragas Camping, a well-known resort-type accommodation with rooms, RVs, and tent options right on the beach just south of the popular Agia Anna and Agia Propikos beach towns. Someone told me that years ago this was the only development in the area, and in recent years some more hotels and restaurants have sprung up. The vibe is European beach bum family chill. I stayed in two separate hotel rooms (because the cheaper room was booked up), both with lovely outdoor porches and just across the road from the most perfect beach.
As I finally stepped onto the beach that evening, sun still high in the sky, I immediately felt my shoulders relax. Turquoise and cerulean colors blend together under cloudless, breezy skies, the island of Paros in the smiling in the distance and blocking the waves from getting too big. The water is cool and salty, crystal clear. Some areas with perfect sandy bottom; some with rocks and fish swimming around. Beach chairs and tables are 20 euros for the day, and someone will bring you drinks or food if you want. The beach days have since blended together. It never rains. It is always 80 and sunny and breezy and not too humid. The vibe remains relaxed, nightlife a seeming afterthought and something I didn’t notice except for a few posters on the street. Naxos seems to be a place to settle into the sun, letting it tire your muscles and settle your mind.
I had plenty of time for a few excursions. First, a day trip of the island, where I saw tiny mountain villages and more secluded beach towns with an excellent guide, Thanos, who shared many Greek myths and Naxian sites. Historic highlights included seeing the ruins of the Temple of Demeter and a 2500-year-old massive statue of Dionysus, which was abandoned due to a crack and left to gather dust on the mountainside.
One reason I was drawn to Naxos was the ability to hike Mount Zas. I was struggling to find a guided hiking tour and didn’t really want to worry about pacing myself with a group, so I managed to self-guide myself. Zas, or Zeus mountain, is the tallest spot in the Cyclades island chain at 1003 meters tall. According to Greek mythology, it is the place where Zeus grew up, brought there by his mother who wanted to protect him from his father, the titan Kronos, who wanted to eat him. The adventure entailed navigating 2 buses that didn’t come often, allowing me a long transfer in Chora to check out the Temple of Apollo portara/gate landmark.
The hike itself wasn’t difficult – 15 minutes up a road from the bus stop, 3 hours out and back with lots of stops – mostly because the top half was soooo windy. It was incredibly beautiful with 360 degree views of the island, its mountains and deep blue waters in the distance. I also passed some goats on the trail. But oof, that wind. I found myself yelling “not today, Zeus!” as the wind threatened to knock me over and stop my ascent. After the hike, I had to walk almost an hour down a road with no shoulder or shade to reach the closest town of Filoti in order to avoid waiting hours in the middle of nowhere for the next bus. It was frustrating and mentally challenging, but I made it to an amazing taverna and refueled for the bus ride back.
And I took a full day boat trip around Naxos and stopping in the perfect paradise island of Koufonisia, a small nearby island where I stayed for 2 nights the last time I was in Greece. The water is a unique bright turquoise color and it felt magical. It was a very fun day with some friendly travelers (a solo guy just out of college wanting to work in law enforcement in Nevada; an outgoing group from Montana; a French family) and lots of jumping into the water and swimming into a cave.
Otherwise, I spent a lot of time walking around the beach in either direction; and lots of time eating delicious food at chill tavernas overlooking the beach. I did some lovely beach yoga classes. I passed a nude beach section just off the walking path, and was a little shocked at everything I saw, not knowing where to look. I got to see many perfect sunsets. Naxos is lovely and really has it all: beach relaxation, local cuisine, historic sightseeing, hiking, and a touch of island glamor.
One night I found a little rocky hill with a tiny white church at the top overlooking the water. I was on a walk back for the night but then stopped myself, realizing it was a perfect sunset spot, and who cares if it was 20 minutes away? I could just sit on a rock, read or stare into space. Some other people were doing the same. I thought of that feeling back in February, and realized with some surprise that I had made it to my sunset. The feeling I craved of pure joy and freedom wasn’t totally there yet; I was still a little restless and adjusting, but I knew those feelings were coming. Nothing now standing in my way.
