For my first year wedding anniversary a few years ago, we did a road trip across the UK. We started down south then up to Scotland before looping around and heading back down the other side. We only booked our accommodations a few days ahead so we could decide whether to stay somewhere for longer than our loose plan or shorter as we felt it. We also stayed at our first (and probably only) 5 star hotel that felt as big as our flat at that time. Was lovely and the only thing that would have made it better and even more memorable would be if I could've brought our pooch with us. Sitting beside a mountain stream, legs dipped in the ice cold water, blunts going around and the three of us breaking into songs. The fact that apart from travel tickets, we had nothing planned and just did whatever we felt like. That was special. One of my favorite memories is meeting an acquaintance of an acquaintance for literally 1 minute in Sydney. When I told him that i'd be visiting Melbourne, he said he'd show me around as he's from there. Unfortunately his flight back was delayed. Figured it was the end of that, but he ended up having a friend show me around instead, and through that friend I met some amazing people and ended up having the greatest day of my month long trip. Ended up feeling like this random group of people were lifelong friends.
The time I spent in Tokyo early this year. One night I stumbled upon a sake bar next to my hotel, and I was making small-talk with the owner/bartender. After a few minutes, it clicked for both of us, we knew each other already! In 2013, I went to a sake bar on the far west side of town and got friendly with the bartender. That night he gave me his business card and I took a photo of us. In 2016, out of all the bars in Tokyo, I found him again at his brand new self-owned shop in the northeast side of town, by pure dumb luck. We were so utterly stunned, that he, his partner, my newlywed wife, and I shared a bottle of his best sake, on the house!