Ten Nights, Four Cities, Countless Memories
I cried before I even left. In my laundry room, folding shirts into a carry-on I refused to check, it hit me: I was finally doing this. My grandma’s death made me think about what I would regret if I were on my own deathbed. For years I’d said I wanted to try solo travel and never did. This time I stopped saying it and booked it — ten nights, four cities — because now was the time.
No souvenirs. Just memories.
Lisbon — Where It All Began
Lisbon gave me perfect weather and the best possible start.
Night one I walked into the bar at The Late Birds for a dinner tip and met Dave, a flight attendant from Rockford on a long holiday. He didn’t just suggest a place — he came with me. We picked a fish and watched it get deboned at the table.
The next morning I met Samuel, the hotel bartender, for breakfast at Dear Breakfast. We spent the day walking — gardens, overlooks, sand art by the river, coffee stops. We passed the site of a recent tram crash, flowers still covering the sidewalk. It was sad, and it stuck with me. That evening we had dinner, and I ordered chicken — simple, tender, perfectly seasoned.
At night I made it to Bairro Alto. The bars were too small for the crowds, so everyone just spilled into the cobblestone streets, drinking and laughing outside. It felt odd and alive at the same time.
The next day Samuel met me again for a scenic lunch — croquettes, sangria, and a view.
That afternoon was the highlight: out on the water under sail for the first time. After years on powerboats in Chicago, this felt completely different — slower, quieter, the boat leaning into the wind as the city slipped back. Everything narrowed to just the water and the pull of the sails.
After the sail, I had dinner again with Dave. Lisbon showed me early: solo didn’t mean alone.
Porto — Fire, Bridges, and the Valley
I arrived in Porto at São Bento Station, stepping into walls covered in blue-and-white tile murals. It felt like the city was welcoming me with its history.
That first afternoon I went down to Ribeira for the Seven Bridges boat ride. From the river, Porto looked held together by granite and arches. I sat after with vinho verde and tremoços while street musicians played “Billie Jean” and “Stand By Me.” On the way to dinner, a fire dancer spun under the arches — the silver lining, since the sausage and ham I ordered that night were dry and forgettable.
The next day I took the train into the Douro Valley, riding a 1940s carriage by the window. The light was clean, the river kept sliding past, and the rhythm of the tracks did the rest.
In Pinhão I had octopus for lunch, then took a short boat ride — same water, new angle, hills cradling the view.
The ride back to Porto stayed beautiful the whole way — steady, soothing, unforgettable.
On my last day I visited Livraria Lello, all carved wood and the famous red staircase.
Before leaving, I ate a greasy bifana at the counter — quick, perfect, exactly right.
Barcelona — Loud, Bright, and Personal
Night one I ate solo at Casa Jaime — simple and good — then went straight to Arena. Loud, packed, lights everywhere. I stayed late and let it be big.
Sunday started at Ciudad Condal. Being a party of one helped — I slipped onto a bar stool. Scallops, croquettes, short rib, tomato burrata, and crema catalana with sangria. Rooftop time after. That night was Churros con Chocolate, the Sunday disco. In the middle of it, Grindr pinged. Saurabh messaged, we met outside, walked a while, and grabbed a late snack.
Monday I explored while Saurabh worked — Gothic Quarter alleys, Plaça de Catalunya, Parc de la Ciutadella — then into Sagrada Família.
That evening we met at Fever for a drink and then my birthday dinner at Gresco. We split a bottle, laughed through the meal, and finished with churros dipped in chocolate. Simple and thoughtful — it landed.
Unexpected connection, right when I needed it.
Tuesday I nearly left my crossbody in the terminal after I’d boarded. A flight attendant helped me get it back. Instant cardio; lesson learned.
Amsterdam — A Gentle Landing
By the time I reached Amsterdam, I was ready to slow down. Jordaan was the right choice — canals, bikes, quiet streets that let me breathe. My first night I tried for dinner at De Belhamel but couldn’t get in, so I ended up at a pub nearby — a meal, a beer, a quiet start.
Next morning: canal cruise with Those Dam Boat Guys, then Winkel 43 for apple pie, a coffeeshop joint, and a long walk with an audiobook.
That evening I did get into De Belhamel. The room glowed, the food landed, and it was the right ending.
On the walk back I passed the Homomonument by Westerkerk. I put on “Fade Into You” and kept walking, canals lit with rippling light. The city was hushed, and it felt like a sigh.
What I’m Keeping
I liked who I was on this trip — curious, motivated, more comfortable in one-on-one connections than in crowds. I learned to sit still, in plazas and on trains, and let moments happen without rushing through them.
It was about people: Dave, Samuel, Saurabh. And messages from home that landed like gifts: “you deserve this.”
Lisbon gave me a first sail and nights where the streets themselves were the bar. Porto gave me blue tiles, fire, beans, octopus, and a train ride I’ll never forget. Barcelona gave me scallops, crema catalana, disco, Gothic streets, and a birthday dinner planned by someone who barely knew me but cared enough to make it special. Amsterdam gave me canals, pie, a coffeeshop haze, escargot, and a quiet walk past granite triangles under the night sky.
If the question was what I’d regret not doing, here’s the answer: this. Ten nights, four cities, countless memories.
I didn’t take this trip to prove anything to anyone else. I took it because I knew if I kept waiting, I might never do it. Loss has a way of showing you how short the window is.
What I found wasn’t just new places — it was a braver version of myself. ❤️