Two of central Tuscany’s most popular visits are to Siena and San Gimignano. Both are walled cities with unique landmarks including San Gimignano’s towers and Siena’s striped cathedral and famous town square. Both are also cities that peaked during the middle ages and which eventually came under Florentine control during the Renaissance.

While we could easily spend more than a day in each city, especially Siena, we dropped in on San Gimignano in the morning and went onto Siena for lunch and the afternoon (it also probably works just as well to visit Siena first and then San Gimignano). It’s roughly one hour’s drive between the two landmarks but I’d allocate an extra half hour for parking.

Both San Gimignano and Siena were badly impacted by the Black Plague in 1348 that wiped out two-thirds of the population. The cities never recovered to their heights prior to the plague and gradually declined from then on. As it stands now, San Gimignano is mainly a “museum city” with few residents. The city is noticeable for a prolific number of tall towers attributed to a building boom during the middle ages when the city’s nobility tried to outdo each other.

I enjoy roaming around San Gimignano without really going into any particular site or museum. It’s also quite nice to walk around the city walls from where there are views of the surrounding valley. Because we had scheduled lunch in Siena, we only stayed for an hour in San Gimignano itself. I think ideally for first time visitors, around two hours is better.

Siena is a university town these days for the most part. The city is best known for its twice yearly horse race, the Palio, that converts the main square, the Piazza del Campo, into a race track. On the day that we visited last May (2014), they were holding a special ceremony to celebrate the town’s public service providers. So unfortunately, I yet again failed to climb to the top of the tower as they closed the area to visitors after lunch. This has turned into  multi-decade endeavour for me (should have climbed it on my first visit in 1994). Maybe one day I’ll come for the Palio and actually stay in the city a few days so that I can finally get to the top of this tower. I think it’ll be a great view from up above of the Piazza del Campo and the burnished Sienese rooftops.

My favourite cathedral in Italy is actually Siena’s Duomo. While Florence’s Duomo and the Vatican’s St. Peter’s Basilica are better known, I think Siena’s Duomo is particularly photogenic. It may be because it’s not too big and thus, a more comfortable place to visit, but it’s also because of its distinct stripes, amazing mosaic floor, impressive pulpit and the ceiling of the Piccolomini Library.

Being one of Tuscany’s main cities, Siena has some great places to eat. Since we were visiting on a Sunday, options were more limited but Osteria da Divo was open and served up a good steak and pasta. The restaurant is charming, with some colourful art work adorning the walls of its cave-like rooms.

For something quick, really good cold cuts and cheese are available in Siena. The area is also known for the Cinta Senese (aka Tuscan Pig).  This is a black pig with a white band around its upper torso making the pig look like its wearing dark trousers. Cinta Senese salami is well worth a try. Pizzicheria de Miccoli is possibly the city’s best known salumeria. The store is well marked by a boar’s head at the entrance. We bought lots of various types of salami and cheese to bring back with us.

Like many of Tuscany’s historic sites, we had to park outside the historical city walls. I’d recommend doing a bit of planning ahead of time to figure out which parking area is most convenient to where you want to go. For us, we chose to park in the public lot closest to the restaurant in Siena as we were running late for lunch (otherwise, it can be a long walk across the town). For San Gimignano, it was simply trying to find parking anywhere.

Osteria da Divo website: http://www.osteriadadivo.it/eng/chi-siamo.htm

Pizzicheria de Miccoli unofficial facebook page: https://www.facebook.com/pages/Pizzicheria-De-Miccoli/153860551313998