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.

Our 2019 trip brought some new things as we stayed a lot longer this time.

We stayed on a mountain overlooking lake Trasimeno. Beautiful area. We drove all around from that home base but one of the cool spots on the lake was Passignano where they have a nice market and you can also take a short ferry to Isla Maggiore. Not the most exciting place on earth but it’s pretty neat to see a place that is so isolated and has like 10 residents…not sure what is interesting about doilies though!

Tuoro was right down from out house and it’s charming.

Umbertide was not as close but their Wednesday market was fun and the town is cool enough…limited dining options though.

Perugia is worth a visit. Cool little town. Once you finally find parking and walk up it has a main drag along a ridge line so it’s very flat up there (humongous hills before you get to the ridge). We found an awesome pizza place directly in front of the cathedral on a side street.

Multipuciano is like Perugia really, but in this case the highlight is always the walk through the Ricci winery and their hundreds of years old casks and thousands of years old caves and rooms. Pienza is a cool town nearby as well with tons of Pecorino shops, their specialty. A cool main road for shopping etc.

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)

Hotel Italia (July 2019)