Lisbon is one of Europe's most beautiful and most underrated cities. Seven hills, cobblestone streets, azulejo tiles on every corner, and a food scene that will quietly ruin you for everywhere else. October is its sweet spot. Warm enough to feel like Southern Europe, cool enough to run your best race.
I studied Portuguese in college, not because I had to, but because I fell in love with the language and couldn't stop. The culture, the history, the melancholy beauty of fado drifting out of an Alfama doorway at night. Lisbon has been on my list for a long time. This trip is personal.
Okay, but what do I actually get?
Edit 002 / Lisbon
Seven Days in Lisbon
Porto and the Douro Valley. Three nights. Tuesday October 13 through Friday October 16. Wine country, cobblestones, and one of Europe's most beautiful landscapes.
We board the scenic train from Lisbon to Porto. Three hours through the Portuguese countryside, arriving in one of Europe's most beautiful cities. Check in to a hand-picked boutique property in the heart of Porto, explore the riverfront Ribeira district, and let the city introduce itself over dinner and a glass of aged tawny port. Because obviously.
Morning run through Porto's neighborhoods. Along the Douro River, across the iconic Dom Luis Bridge at dawn, through Miragaia and the Ribeira. These are cobblestones worth running. The rest of the day is yours to explore. The port wine caves of Vila Nova de Gaia, the azulejo-covered Sao Bento train station, the Livraria Lello bookshop, the best francesinhas in the city.
We head east into the Douro Valley, one of the most breathtaking landscapes in the world. A UNESCO World Heritage Site of terraced vineyards cascading down to the river. We'll spend the day at small family-run quintas, taste wines that never make it outside Portugal, and linger over a long lunch with views that will stay with you for years.
Return to Lisbon by train for international flights, or depart from Porto directly. Or stay one more night if you can't bring yourself to leave. We completely understand. We're here for it.