Tuscany Beyond Florence

June 2016
Photo set on Flickr

One can easily spend weeks in Tuscany and not see everything, a region blessed with historic hilltop villages, iconic landmarks, world-class vineyards and mesmeric landscapes. We had a week split between Montefollonico and a farm near San Gimignano and managed to visit (and in some cases revisit) the following places.


For those who doesn’t plan to hire a car, Siena makes a good home base for Tuscany. Granted, Siena does not process nearly the same amount of attractions as Florence, but this medieval hilltop town has a more inviting atmosphere. It is touristy though not nearly on its more famous neighbor’s level. And since most of them are day-trippers, Siena begins to quiet down by late afternoon.

For four centuries until 1555, Siena was an independent republic and a prominent rival to Florence until it was defeated by an alliance of Medici’s Florence and Spain in the Italian War of 1551–1559. The main plaza, Piazza Del Campo, is very photogenic, and I find Siena’s Duomo to be as impressive as Florence’s. Surrounded by centuries-old buildings, getting lost in Siena’s narrow alleys was more enjoyable than anything we did in Florence where the inescapable crowd made a simple walk a tiring and unsatisfying experience.

A local festival took place when we were at the top of Torre del Mangia, the clock tower at the main plaza. Drumbeats echoed through the entire town and the surrounding hills. When we got back to the ground, we followed the drumbeats and reached a gathering of paraders, each dressed in traditional clothing and holding either a flag or a drum. The drumbeats were deafening at such close range. We trailed the parade crowd and without prior planning reached the plaza where the bus from Florence dropped us off earlier in the day. The sky was getting dark, yet the parade showed no sign of slowing down.

San Gimignano

Many hilltop villages dot the landscape around Siena. We only had time for one and we went with San Gimignano because of the simple fact that it was the closest to where we were staying. Famous for its fourteen well-preserved medieval towers, San Gimignano was once a thriving stop along the Via Francigena pilgrimage route to Rome until Black Death wiped out half of its population. Neglected as backwater, San Gimignano saw little development over the next five centuries, which was the main reason why its towers remain intact while those in Florence and other cities were destroyed by war or urban renewal. After the unification of Italy, the town reemerged as a resort and artistic haven thanked to its unscathed historic core.

Besides its towers, San Gimignano is also renowned for its saffron and white wine Vernaccia di San Gimignano. We had our best meal in Tuscany at Ristorante Dorando, a member of Slow Food, and some decent gelato at Gelateria Dondoli. The town is quite touristy as it almost completely depends on tourism, but with plenty of decent restaurants it makes a fine if nonessential half-day stop.

I only took one photo — on Via Giacomo Matteotti close to the main car park where the entire town can be captured in one frame.


Pisa is mass tourism at its worst. Alright maybe that’s a little much — nothing can actually beat cruises — but it is right there near the bottom along with the likes of Time Square, Hollywood and Madame Tussauds. The real pity is, unlike those other tourist traps, Pisa’s Piazza dei Miracoli is an architectural gem that deserves anyone’s focus and time, but two factors make any visit a frustrating experience.

Without a doubt, Pisa was by far the ugliest town we came across in Tuscany and Umbria. The Leaning Tower is the only attraction in town and nothing else is there to divert the crowd. No matter your method of travel, whether you are traveling on your own or joining a tour, your impression of Pisa will invariably be the same as everyone else’s.

The majority of people has one goal in mind in Pisa — take a generic photo where they appear to be propping up the tower from collapsing. They leave. Then a new wave of people show up to do the exact same thing. Soon your perception will change — what’s standing in front of you is no longer a seven-century-old medieval masterpiece but one of the world’s tackiest photo background.

Even if you want to leave the scene as soon as you have taken your mandatory photo, at least go visit the Romanesque baptistery, the largest in Italy celebrated for its excellent acoustics.

Bistecca alla Fiorentina

Forget about pasta and pizza — in Tuscany Bistecca alla Fiorentina rules. This local variation of porterhouse uses one of the oldest, tallest and heaviest breeds of cattle — the Chianina, one of two indigenous beef breeds of Italy. Haven’t heard of it? While the Chianina breed is exported to other countries, unlike Angus or Wagyu there is very little marketing around Chianina that’s not raised in Italy, and there are only less than 50,000 registered heads in its native country, the majority of them in Tuscany and Umbria. They are fed on grass, slaughtered at 16-18 months once they reach 650–700 kg and almost all consumed locally.

While there are restaurants in most towns that serve this dish, it is generally cheaper outside of Florence or Siena. We chose La Taverna di Vagliagli in Vagliagli, 30 min north of Siena in the heart of Chianti. Served at cold rare traditionally, the thickly cut steak was grilled over wood for about 4 min on each side and 5 min on its bone. Seasoning was kept to a little salt and pepper along with a generous dose of olive oil. The flavor was subtle because the meat was so raw, but the texture was firmer than the typical grain-fed beef. Cold rare was too raw for me — I learned about the local culinary culture more than how much I really enjoyed the meal. The bill for four was €100 including 16 oz of beef, some starters and a glass of Chianti.

Crete Senesi

South of Siena along SS 438 from Taverne D’arbia to San Giovanni d’Asso is a hilly area referred as Crete Senesi. The soil in this area is heavy in clay and gives the landscape a distinguished grey and brown tone compared to the greenery of Chianti or Val d’Orcia. Along with the latter this is where most of the classic Tuscan landscape photos are taken.

We drove along SS 438 to Asciano, onward to SP 451 to Monte Oliveto Maggiore, then back north to Siena on the same route. I personally find Crete Senesi’s scenery to be a little more diverse than Val d’Orcia’s due to its wider range of colors.

Val d’Orcia

Travelers are always at nature’s mercy and our luck ran out during our two days in Val d’Orcia. Rain poured incessantly aside from a brief respite of morning sunshine on the first day. Not only did the weather fail to cooperate, nothing much went according to plan. The Benedictine monks at Sant’Antimo Abbey were AWOL. Restaurants closed their doors because of heavy rain. Supermarkets ran out of stock on basically everything. We even experienced an afternoon of hail that might have damaged some of the prized Sangiovese vines in the area.

The landscape, especially the stretch between San Quirico d’Orcia and Montalcino, was photogenic, though not demonstrably superior to Crete Senesi’s. I am definitely biased from what I had endured, but unless you are a big Brunello di Montalcino fan I would suggest sticking to the area around Siena for more choices of activities and sights.


Not many people had heard of the little town of Corsignano, located in the middle of Val d’Orcia, before a certain poet with a particular interest in erotica was elected pope in 1458. Aeneas Silvius Piccolomini, born in this humble town in 1405, ruled as Pius II for six years. His reign resulted in only two accomplishments — the only autobiography ever written by a reigning pope and completely rebuilding his hometown into his papal summer retreat and renaming it Pienza. He sure did spend most of his energy on securing his own legacy, but he would always be known first and foremost for his passion of pornographic poetry.

Enlisted the help of the Florentine architect Bernardo Gambarelli, Pius II’s vision of his “ideal town” incorporated Renaissance humanist elements like civic engagement and the revival of arts and philosophy of classic antiquity. What looks like a typical Italian Renaissance town to us was in fact a pioneering attempt back in Pius II’s days. After enduring the Middle Ages’ centuries of chaos, urban planning was a novel concept at the time and it quickly spread to other parts of Italy and subsequently much of Europe.

Pienza’s main sights such as the Duomo and Piccolomini Palace congregate at Piazza Pio II. We didn’t go inside of any of the sights, but we found Pienza to be a pleasant town to stock up on food and take a casual stroll along its one main road where all the shops were located.


2 thoughts on “Tuscany Beyond Florence

  1. Great site! Your posts are interesting and the pictures very cool too. Check out our California wine country blog.

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