BootsnAll Travel Network

The San Gimignano and Chianti tour – Italy

The smaller towns and countryside of Tuscany are impossible to visit without a car. So I had booked a day tour with a company called Tuscan Escapes. What I wanted was simple: pick up in Sienna, a tour of San Gimignano, some wine tasting, some sightseeing (which I was leaving up to their judgment), and drop off in Cortona (which was our next destination).

Milo came to pick us up at 9:30 in Sienna – nice guy, very relaxed and pleasant. I knew we would have a good time with him. We drove though the countryside and he gave us some history on the region: the historical rivalry between Florence and Siena, the alignment of some of the towns in this rivalry, the history of the Palio and the resulting divisiveness of Sienese life where identification is with the neighborhood (or “contrade”) over anything else – Milo is from Bologna and says he wouldn’t be able to live in Siena, he just wouldn’t be accepted.

Our first stop was Monteriggioni, a small fortress town built on a hill by the Sienese as a front line in their wars with Florence. The town looks out over a valley (which Milo says used to be a swamp) across which San Gimignano lies on another far away hill (San Gimignano was aligned with Florence).

Our next stop, half an hour later, was San Gimignano. The town is famous for the towers built by its wealthiest citizens as symbols of their power – there used to be 72 towers in the town, only 14 are still standing. San Gimignano is also on the Via Francigena, the ancient road used by pilgrims linking England to Rome.

(below; San Gimignano’s skyline)

One thing I love about Italy are all the towers. I love climbing towers and seeing a place from its highest point. The Torre Grossa doesn’t look so high looking up from the piazza – but the views from the top were really impressive. Maybe it’s just because the weather suddenly cleared up for me, but the views from the top of Torre Grossa were actually the nicest that I had seen to date; the piazza seemed deceptively far below, the people like ants. And the views of the countryside were great. The town was very nice but the highlight for me was climbing that tower.

(The tower from the piazza)

After San Gimignano, we drove into the Chianti hills (really beautiful – would love to do some hiking here), the heart of the Chianti region and stopped in a few of the small towns; Castellina in Chianti and Radda in Chianti. Medieval little towns with towers, old buildings, and tunnels. This area is the heart of the Chianti Classico – only wines from this area can have the Chianti Classico label (the black rooster).

(below: Milo with the black rooster label)

Driving up higher into the hills we stopped at the Casamonte farm for some wine tasting. It’s beautiful estate where they not only produce their own Chianti Classico wines, but also Olive Oil and pork (from Sinta Senese pigs – rare pigs that they breed). We were given a tour of the facilities, including the meat lockers, and were really impressed (I was, lissette not so much – she’s a vegetarian so meat hanging from hooks isn’t so much of a turn-on for her).

Then we had the wine tasting. And that led to my fuck up.

I can’t say I’ve ever been a fan of Chianti Classico, I like my wines more round bodied and bold and so far on this trip I’ve bought mostly Super Tuscan wines – wines including Sangiovese grapes but also mixed with Cabernet Sauvignon and Merlot in varying degrees. Chianti Classicos have a minimum of 80% Sangiovese grape which can be a little harsh. As Milo said, you have a Chianti Classico with food but a Super Tuscan you can just sit around a fire and drink.

So I wasn’t expecting anything that I would love. In fact I was blown away by the wines I had at Casamonte. So much so that I ordered a case for shipment to Montreal. The reason that I can’t describe the wine a bit better is that; 1) I can’t remember exactly what it tasted like and 2) I’m still waiting to take possession of the wine. My advice: never, never import wine into this fucking province. I’ve had over a month of run-around from DHL, then Canada Customs, then the SAQ (Société des alcools du Québec). I’ve had to go to DHL’s offices at the airport to pick up manifests, have had to send same to the SAQ. Then I had to pay $350 in fines to the SAQ for an import permit (on $570 worth of wine). I should be receiving the permit in the mail the next few days. Then I have to go back to the airport to get the permit stamped by Canada Customs, then finally, back to DHL who will, hopefully, finally, let me walk away with my case of wine. The most expensive case of wine I’ve ever fucking bought.

So please, if someone ever tells you “no problem, we ship all over Canada and the United States”, say thanks but no thanks.

(below: Casamonte farmhouse)

After Casamonte, we visited another winery close to the town of Gaiole in Chianti. The winery was actually on the grounds of a large castle which we were given a tour of; below are photos of underground tunnels and a small theatre (dating from the 14th century) within the castle. We were happy to see all this – unfortunately the wine wasn’t anything special (we bought a token 3 bottles but that was mainly as thanks for the castle tour).

That was the end of the official tour. Milo then drove us to Cortona (about an hour out of his way) and dropped us off at the hotel. We really enjoyed the tour, lots of fun and very informative. And Milo was great. It was expensive (400 Euros – ouch!) but I figured that if our time is money that it was worth it. We didn’t have to drag our bags around train stations or worry about anything, everything was taken care off. If only I hadn’t bought that wine…

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