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Today is day 100 and another low-key computer day as promised. My news feed is full of shamrocks as expected, and I’m missing my Irish roots just a tad. However, there are things to do and work to get done and bills to pay and trips to plan. My afternoon was filled with harshly judging one Tuscan villa and hotel after another. Frowning as I’ve seen many do when they’re looking at those dating apps and flicking the phone in annoyance. I was looking for a place not far outside of Florence, vineyards preferred but views a must.

There are thousands of places to stay that are beautiful, but when you live here, you do get used to the aesthetics, and you know what is actually “the best” and when a place will be lackluster once you arrive. Again, this is all in my opinion, because I could be in the area in about 15 minutes and there are even more olive groves right up my street. This causes mayhem¬†when trying to choose a place for people coming to visit because my standards are technically snooty-high, but like a typical Italian, I want to find a way around paying for it.

To do that, you check Airbnb for the places just off the main pathways, or go directly to the hotel websites even after searching for them through an engine – then see if they have special offers for the time of your stay. Sometimes it’s a spa package, others come with dinner, excursions, and even cooking lessons at the more touristy spots. Also, a tip to note: Many places here would absolutely prefer you book directly through them and there is normally a discount. If you email, sometimes it’s even better.

So here I am scrolling straight through many places that are on Tuscany calendars and vetoing everything. How terrible of me. I showed four to my Mum and she loved them all. If I think about it, though, I’ve really just morphed my “normalness” because if you showed me any lakeside or ski-up cabin in New England right now, I’d be screaming at you to book it immediately.

I think we’re settling on somewhere near San Gimignano – (Pronunciation: San Jim-in-ya-no) because of a day spent there during 2010 – when I was studying abroad and Mum and I traveled half the country and back from Ascoli to see Tuscany for the first time. I was twenty-one. Both of us were in completely different phases of our lives, and if anyone had told either of us we’d be heading back there because it’s one of the closest towns to my house, well that would’ve just been silly. That day felt like it was a once-in-a-lifetime experience, and now, it’s as easy to do for me as some of you heading into Boston for the day.

I have to say, the panorama on the top of that hilltown has left me breathless in more ways than one on more than one occasion (it is a steep town – be prepared if you visit) – that view is incredible when you hit the top. When I was guiding day trips, I would let my group free and climb up to the fort, head to the back corner and sit in the open stone window in the wall. The green hills are lined and dotted with vines and olive trees and smoke rises from a few fires as the farmers burn the trimmed branches. No one would ever find me there – and I’d dangle one foot out over Tuscany and wonder how in the world did this ever become normal in my life.

It’ll be nice to go back – I haven’t been for a while. Rami and I normally seek out the towns where the laundry is still hung out on the street and the streets are full of kids and people that have lived there for generations. San Gimignano is too beautiful, and so many people want a piece of that, so they flock to it. But so much has happened in nine years since my Mum and I last stood looking out at those hills, and I think we need to get back up there and sit with a bottle of wine and talk about how crazy life is and the circles it takes us in. It seems like the perfect place.

Plus, I have been to so many towns around here, and they are all beautiful, but as I said; the towers, and the views, and the vineyards, and the saffron, and the little alleys full of window boxes full of flowers – it’s just plain gorgeous regardless of how many people flock to it by day – and by night, apparently most of them disappear, leaving the little town a little bit more like it should be. I can’t wait.




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