Giro d'Chianti
May 8 1999

Distance: 70 miles/113 kms
Elevation: 5,990 feet/1,826 meters
Difficulty: 6/10
Scenery: 8/10;
Route: San Gimignano-Poggibonsi-Castellina-Radda-
Volpaia-Panzano-Greve-Panzano-Castellina-Poggibonsi-
San Gimignano

I woke up quite late (9:30AM) the morning after yesterday’s late ride to Volterra. I dragged myself out of bed and rode the 600 meters to San Gimignano’s south gate for a cappuccino. It was a Saturday morning, and San Gimignano was still reasonably crowd-free. I wanted to escape before the tide brings in the usual flock of day-tourists to this gorgeous city. I hurriedly finished my recommended daily caffeine allowance, went next door for a banana for the road, took out the map to orient myself, then pointed Erasmus southeast for Poggibonsi, my port of entry to the fabled Chianti region of Tuscany.

Ah, Chianti en Toscana. Less than 20 kilometers from Florence. Home to Hannibal Lecter’s favorite dinner wine. The name alone (Chianti, not Hannibal Lecter, silly) evokes visions of sun-drenched vineyards, majestic hilltop settlements and miles and miles of quiet undulating roads. The maestro loved the place, so did Elaine (if you have to ask, then you’re not a Seinfeld fan; not that there’s anything wrong with that, provided you stay master of your own domain).

(Above: Along Via Chianti, just outside Poggibonsi)

And perhaps I would love Chianti too, if I could only get to the darned place. Following a quick 11-kilometer ride from San Gimignano (of which distance seven kilometers were downhill) I had fallen into the bewildering maze of nondescript busy streets that was Poggibonsi. After 20 minutes of dutifully following all the "Castellina in Chianti" signs, I kept finding myself only one or two streets from where I had been before, much like being in one of those English-style garden mazes, sans the charm. So there I was, feeling as trapped as a lepidopteric insect in a Venus flytrap, or a dim-witted hamster spinning round and round. Eventually I stumbled into an ordinary-looking uphill residential road that turned out to be none other than Via di Chianti, the SS429, my yellow brick road. The effort in trying to find the way was well worth it; a couple of miles out of Poggibonsi, I was transported into a completely different world. The landscape opened up, motor traffic and concrete structures faded away to be replaced by medieval stone houses and neatly arrayed shoulder-high grapevines basking in the sun.

(Above: On the SS429 headed for Castellina)

Poggibonsi is less than 400 feet above sea level while most of Chianti lies between 1,000-2,000 feet. From Poggibonsi, I had to climb steadily to for 1,000 feet or so to gain the necessary altitude. But the SS429 was quite smooth, and its grade not too severe (perhaps between 4-6%). As I mentioned previously, traffic on this part of Chianti was not bad; this fact plus the beautiful scenery made for an interesting, though not very strenuous, riding (this uphill being near the start). But if fact, on my way back several hours later I realized this road was ALL uphill from Poggibonsi to Castellina (17.5 kms., or about 11 miles).

(Below: Part of the uphill before the drop to Castellina)

Castellina, situated on a ridge that divides the Elsa, Arbia and Pesa valleys, announced itself from the the summit of a short, but steep, uphill. The place was expectedly quaint, though I got the sense that the tourists outnumbered the locals by at least 2:1, with American and German accents predominating. The town center was not much more than a pretty church, a 100-meter stretch of souvenir and wine shops, and a handful of tourist-oriented eating establishments. Because of its location, Castellina had the misfortune of being on the Firenze-Siena warpath and much of the centro (fortress, walls, etc.) shows this.

(Above: The "castel" in Castellina)

Owing to my late start, it was time for lunch by the time I reached Castellina, so I had a balanced meal comprising a banana and a Coke. The nice thing about cycling in Tuscany is that the towns, and hence the fuel supplies, are neatly spaced 10 miles apart, so one need not worry about running out of water or food.

(Above: Castellina's main street)

Last Updated: June 12, 1999