The Great Italian Roadtrip / Twins Trips

Montalcino and San Gimignano, Tuscano Region, Italy

Monday, Oct 15, 2012 

Girls woke up at 8am and on the road by 10. Forecast of heavy rains. Only had 2 stops on the itinerary. That, as always, would change while on the move.

First stop was more of a ‘fly by.’ Monteriggioni is a small medieval hill town enclosed in a beautifully well-preserved wall with 14 towers. We snapped a couple of pics from outside the town. The sun was out but clouds were growing on the horizon so on to our next stop we sped.

Monteriggioni, Tuscany

Monteriggioni, Tuscany

Scenic Tuscany roadtrip

Scenic Tuscany roadtrip

Farm house

Farm house

Next on the list was San Gimignano (SG), ‘San Gimignano delle belle Torri’ or the city of the fine towers. This is also a well preserved medieval wall city in Tuscany.  So far it is second in ‘wow factor’ only to Cordona with a small catch.  Many of the cities we are visiting on this trip are off the beaten path of most tourists. Even in Mid October, bus after bus was bringing in umbrella toting tour guides each with a gaggle of followers waddling behind like little ducklings. This is a common finding on many of our travels, but we were still briefly shocked as we had already grown accustomed to a degree of solitude on this trip.  The spell of peaceful tranquility was briefly broken as we forced our stroller up and down the narrow alleys through the throngs.

Truly, tourists aside, San Gimignano is worth a visit.  These walled cities are just so charming and interesting.  The narrow streets twist and wind in haphazard fashion and the buildings mirror them in a Picassoesque style.  They remind me of my 2 year olds’ Lego creations. They are just stuck together seemingly without rhyme or reason.  On beholding this marvel, you are instantly transported to another place and time and can almost feel as though you are living, if but for a moment, in medieval Italy.

The rains hit us shortly after arriving in SG.  It continued to rain on and off. After lunch and a couple of hours of gloomy weather, it was clear we needed a change.  The girls needed some milk and a nap so we decided to drive south past Siena to Pienza and Montalcino.  It was labeled as a ‘scenic drive’ in our book and was in the opposite direction of the black clouds engulfing us in SG. What the hell? At worst it would be raining there, at best we’d find better weather and more of the Tuscan landscape to cherish. 

At this junction in the narrative I feel compelled to say a word about our girls.  My wife and I have taken many road trips in the past but have been stopped or slowed because of difficulties with the girls. I’m not sure exactly what changed or when, but they now sit contentedly in the back seat watching the world go by.  They sleep when they have to, eat and drink when they need to, sing or play with an occasional toy when they  want to.  There have been very few, very brief episodes of true crying.  In short, they are doing better than we could have hoped. It may simply be that they, newly facing forward in the car seats, are as mesmerized by the beautiful countryside as we are.  This is great as we have a ton more kilometers ahead. Game on.

We escaped the rains and clouds to find a beautiful, sunny afternoon south of Siena. The scenic drive was brilliant with endless vistas and ageless buildings dotting the countryside. I suspect Pienza is a lovely village of 2000 people and wonderfully kept ancient buildings, but we didn’t stay long enough to find out. While the drive had been sunny, some dark clouds were creeping in on the horizon. We decided to continue with the road trip and check out Montalcino before the weather found us with renewed fury.

Montalcino is another hilltop Tuscan city (yes, there is a theme here). It lacks the charm of Cortona and San Gimagnano, but it makes up for it with tranquility.  If you are into red wine, this is your place as the tasty “brunello di Montalcino” or simply “brunello” is grown and sold here by just about every open door in the city.  There are a couple of decent old churches and quaint piazzas with a fortress (now an enoteca) thrown in for good measure. There were NO tourists to speak of, but few amenities for those looking to do more than buy wine. The gods had found us again and were starting to pound us with whipping winds and increasing rain.  We decided to skip our planned dinner (we only found two restaurants in a short recon) and move on. 

It was the right decision. We drove home through near constant pounding rain that made travel slow. We stopped in Siena to hit a supermarket, grab some dinner, and then we drove home through the continued deluge. Despite the bad weather (and an itinerary without indoor backup plans) we had a great day. So much for having only 2 stops on the itinerary.

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