I am one of those annoying travelers that plan everything to the last detail. Every itinerary I put together has a 20 - 30 minute provision for the things that can and often do go wrong. But from the time I was about 25-years old I've had a no rules trip put together to get lost and enjoy a country, city or town.
This tradition all started when around my 25th year of life, after spending eight months saving, begging and borrowing my dad's frequent flyer points (jetsetting is in the blood) my co-conspirator -- boyfriend at the time -- and I broke up.
It would be easy to make myself come across as the victim who got her heart broken. The only thing worse than ending a relationship on the brink of a big trip is being left at the altar. But then boyfriend and I decided that we were no longer close enough or in the mood to waste a two month long trip in Milan hanging about each other. So that was that. He got refunds on his ticket and used his half of the trip money to buy a bike.
I, on the other hand went on the trip anyway. I spent the first two weeks doing the usual: went to the Ambrosiana Library, went to the Leonardo da Vinci Museum, I even drank from the many fountains around the city. Yes, that's the most touristy thing I have ever done, going to buildings and looking at sites. Those places are still among the most beautiful I've seen.
On the third week my mum emailed me telling me how proud they were that I picked myself up and that I didn't let the end of that relationship destroy me. I spent that day in bed. I spent the next in a cafe down the street from where I was staying drinking coffee, eating and people watching. Then I spent the next two in bed.
It was around the end of the third week when I woke up with a fire in me; I took all my traveling info, a journal, some money and I headed out. I took a packed tramcar and sat there for what seemed like a couple of hours. I didn't have a plan or a destination in mind. I got off with the other last passenger and proceeded to follow her into a small street -- think the changing seasons scene in Notting Hill. I was in a market in a small neighbourhood.
I spent the whole day busking in the sun with beautiful and kind people. Ate what the cook called peasant dishes, joined street dancers and to my great glee I found a vintage Chanel wallet.
All in all getting lost made that the best holiday of my life because from that day on I spent my days and nights exploring the real Milan as recommended by the locals.
My only word of caution would be to stay safe by keeping a map handy, keeping your travel documents and cameras safe and keeping a number for where you are staying on you.
Go on, get lost.