Siena and Southern Tuscany
May 10, 1999

Distance: 65 miles/105 kilometers
Elevation: 4,540 feet/1,384 meters (including 600-foot climb to San Gimignano)
Difficulty: 6/10
Scenery: 8/10;
Route: San Gimignano-Castel San Gimignano-Colle di Val d'Elsa-
Monterrigioni-Siena (then back)

 

It was 6:15, a very early Monday morning, when I started this ride, the last of four consecutive I was to do in Tuscany on this trip. In the last three days, I had ridden west (Volterra), northwest (Pisa and Lucca), and east (Chianti) from my base. My planned route for the day was an out-and-back route exploring the southern reaches of Tuscany, to Colle di Val d’Elsa, then Monteriggioni and finally to Siena, then hightail it back to San Gimignano. I had to start early because I needed to be back in San Gimignano by noon to make the check-out time.

 

Much of San Gimignano and the surrounding hills were still covered with fog when I started my ride, and visibility was restricted to no more than 10 meters, making the immediate descent both chilly and dangerous. The fog cover also made the descent somewhat of a disappointment; I was hoping to catch a good view of the renowned San Gimignano skyline from the south, but no such luck. The 12-kilometer mostly downhill stretch from San Gimignano to Castel San Gimignano would have been uncomfortably cold had the downhill not been interrupted by marked uphills that allowed my body o warm up. The whir of tractors—just about the only thing that escaped the fog’s stranglehold—told me that, even this early in the morning, a lot of the locals were already up and at it and hard at work in their pristine vineyards.


(Above and Below: Fog enveloped the road down to Castel San Gimignano)

My goggles fogged up; I had to take them off so I could see the road ahead. Even Erasmus gathered moisture beads on his frame—"Good for you…" I thought, "…now you know what sweating and being chilled feels like." (this was only Erasmus’ 6th ride out and yes, I do talk to my bike as if it were a living thing). It never ceases to amaze me though how much sound there is in nature even without man’s aggravating presence—now a lizard "tuck-koos" from up the trunk of some tree, now it’s the rustling through the bushes as some rodent scurries through the bushes as it hears my approach. I could see over my shoulder through my peripheral vision that the sun was out a few miles to the western valleys—it was just a matter of time before the fog in these hills burned off.

As I neared Castel San Gimignano, the road started going downhill again through a series of fun switchbacks that one does not quite expect in Tuscany. Castel San Gimignano’s church bells announced my arrival, tolling seven just as I got there.


(Above: Porta Nuova, the gateway to Colle Alta)

I turned left on to the A68 for the 7.5 km run to Colle di Val di Elsa. Motor traffic was non-existent this time of the day, and I quite enjoyed the undulating and switchbacking stretches although I can see very little but the road ahead. Soon I reached the outskirts of Colle, which at first looked depressing as I caught glimpses of it through the morning’s overcast. But Colle had a Jekyll-and-Hyde personality. The section up the hill, Colle Alta, comprised the old town, itself not much more than one principal street (Via del Castello) lined by wonderfully preserved medieval buildings. I found all of it exceptionally charming and attractive, more so because I got there at 7:15 in the morning and the place was literally empty of any activity.


(Above and Below: Via del Castello, Colle di Val d'Elsa)

It was a curvy descent to Colle Basso, the lower town, and I found myself suddenly having to fight for my share of the road against the many cars and trucks too concerned about getting to work in time to slow down and give me and my bike a break. This was enough to alert me that I am approaching an actual Tuscan working city, where residents do not just run souvenir shops or restaurants or otherwise cater to the multitude of tourists that swarm the area. The ride through lower Colle was living hell, for no fewer than three A roads converged in the town center. Worse yet, the motorway connecting Siena and Firenze ran nearby. I got so discombobulated by all this that I missed my turn for Monteriggioni.

I ended up on the N541 in San Marziale. I found a narrow road that would take me back, only to realize to my dismay that it, too, was busy with traffic from the N541 trying to get to the motorway. I had no choice but to join the motorized multitude--we shared the narrow road; I, on my way to Monteriggioni, and they, on their way to work. Work! Though I was notionally aware that it was Monday, I had not associated the day with working, I being on holiday. No wonder the cars on the road didn’t have that directionless, meandering motion typical of vehicles driven by sightseeing tourists I had been dodging all weekend. Far from it, Colle’s drivers meant business. Their cars had a determined forward movement about them. I even saw a jam-packed bus full of suits. I momentarily thought of the Hampstead to Pimlico 24 bus and its usual expectant queue of passengers at Agincourt and Mansfield. Usual queue minus one, that is. Perhaps to our mutual relief, our ways parted; I continued on while my motorized escort hopped on the motorway.

Just past the spot where the N2 and the motorway intersected, before the road started climbing, I saw, perched on a hill, an imposing set of walls, looking more intriguing as it stood mysteriously shrouded by a thin layer of slow-moving fog. I was approaching Monteriggioni, a formidable-looking citadel built by the Sienese in the 13th century and a place that was actually mentioned by Dante in the Divina Comedia. The place (I hesitate to call it a "town" since it was no more than a couple of hotels and 2-3 eating establishments along a 100-meter long main street) was situated on top of a hill reached via a short, but steep uphill detour from the N2 road to Siena. It was still early enough when I crossed the town gate to have a look see, but, like Colle Alta, the place was absolutely empty, almost eerily so. It was an inviting place to have breakfast, but since the temperature had not warmed up, I decided not to linger.


(Above: This picture just about captures most of Monterrigioni)

(Below: Romanesque church and Il Pozzo, Monterrigioni)

Last Updated: July 12, 1999