Arriving in Tuscany (I suspect in any city here) can be quite scary for a single male traveler. What am I supposed to do! It’s not exactly cosmopolitan. Luckily I had a guide to my Tuscan adventures and a city that turned out to be charming…if you like that sort of thing.

First off, having lunch at a picnic table in the backyard of a local house, overlooking the Italian countryside is a pretty cool way to start a trip to any city. Cortona happens to be on the top of a rather large hill, completely surrounded by walls. It’s old as shit and you feel like you’ve gone back in time while you are there.

I suspect that the very thing that makes places like this attractive, are the very things that are going to destroy it in this age of globalization that we live in. That being said…my money is green. Dinner at Mario’s restaurant is like sitting in the chef and owner’s house. Having a true Italian lunch with tons of wine, 4 courses including pasta and grilled game, and people toasting all around you is just perfect (I am told you can’t go there if you aren’t with a local). Ate some fantastic Italian pizza (flat and crispy as hell), chilled with a bar owner who seemed to have very little interest in talking to me, and discussed the merits of fascism with the Marlborough man of Cortona.

This town is great, but without my companions, I would have left after a couple hours…

My second visit was just as good as the first. This time we spent an entire day exploring the local wineries. We went to some of the oldest wine cellars on earth (most from the Etruscan age). This was truly like going back in time, and some of those old oak barrels are bigger than houses. We also had “lunch”, which was really just the biggest bruscetta platter on earth, in a thousand year old wine cellar. It was a once in a lifetime experience. And of course, we truly had to have dinner at the new burger bar in the center of town (Beerbone). Cool spot, but the beef needs work (that being said, every country has their own tastes and this place seemed popular enough). Super nice people and lots of upside here me thinks.

Notes to self:

-If possible, visit one of the Olive Oil festivals. It’s like a miracle of delicious…and it’s free of all things.


Hotel Italia (Oct. 2013, June 2016)