I had a return flight and a key waiting in a lockbox in Lisbon. That was the entirety of my preparation. No accommodation booked beyond night one, no tours reserved, no restaurant list. It turned out to be the best travel decision I’ve made in years.
Lisbon takes care of you if you let it
The first morning I got completely lost in Alfama and ended up at a tiny tasca where an old man was playing guitar and singing fado to an audience of four, one of whom was asleep. I ordered coffee and stayed for two hours. That kind of thing doesn’t happen when you’re rushing to your 10am walking tour. The trams are slow and crowded and I loved every ride. The miradouros are the city’s real meeting places — locals, visitors, everyone watching the light change over the Tagus.
The Algarve surprised me
I expected beaches and crowds. I got sea caves. I rented a kayak in Lagos for 15 euros and spent a whole morning paddling into grottos where the water was this impossible shade of green and the light came in through holes in the cliff ceiling. There was nobody else inside. Just the sound of water and my paddle and the acoustics doing something I couldn’t fully explain.
Go slower than you think you should
Most people give Lisbon two days then rush south. Stay four. Stay five. The city keeps showing you new things as long as you’re willing to walk and get lost and sit somewhere for longer than feels strictly productive. That’s the whole point of being there.