San Gimignano – How to Spend a Day in this Tuscan Hill Town

December, 2018

Thinking of visiting Tuscany? Then the little Italian hill town of San Gimignano needs to top your list.  This makes for an easy day trip from Florence.  There is no direct bus, so you will need to stop at Poggibonsi and change buses.  The Florence to Poggibonsi bus is #131 taking approximately 50 minutes and the Poggibonsi to San Gimignano is #130 and is another 20 minutes of travel time.  

As San Gimignano comes into view, you will realize there is something magical about this Tuscan town on top of a hill.  In the skyline, you will see 14 of the original 72 towers still standing as the bus makes its way up the hill to this quaint, charming and unassuming town. 

From town, you will overlook the marvelous Tuscan countryside, adorning the enchanting vistas.  For the best views, you will want to climb the 177 feet Torre Grossa.  This medieval structure was built in 1310 (let that sink in for a minute) and it is the tallest tower in town.  The climb is worth the effort to soak in the Tuscan sun kissing the tiled terracotta rooftops and rolling countryside below you. 

I think it is always best to simply stroll around exploring the streets and alleys easily getting swept away in the beauty and the culture.  It is our favorite way to spend a day.  Come stroll back in time with me as I highlight the top things in San Gimignano.  

After taking in the views from the tower, check out the Palazzo Comunale.  Now a museum, this former palace, showcases paintings from the 13-17th centuries.  As you tour from room to room you can admire the beautiful frescoes.  

Piazza del Duomo – This is the main square in town, which still bustles with activity well into dusk.  It is a unique trapezoid shape with a slope encompassing three important medieval structures.  On the north side, you will find the Torri Gemelle dei Salvucci, opposing the Palazzo Nuovo del Potesta and of course, the Torre Grossa.  However, the most imposing is the Collegiata, the church, which sits atop a stairway.  If you are in town on a Thursday, enjoy the market where you can wonder the stalls sampling local fruit and delicacies.  

Piazza della Cisterna – A popular square where you will find a water cistern in the centre built in 1273.  This piazza is enclosed by medieval towers and noble homes and is cited as the most beautiful and famous of piazzas in San Gimignano.  It’s shaped like an inverted triangle with sloping paved brick, connecting to the Piazza del Duomo with an open passageway.  Surrounding this square, you will find cafes, boutique shops and the best gelateria in town.  You can’t miss it as there is always a line and it’s known for its creative flavours infused with sparkling wine.  Gelato and sparkling wine, wow, Italy that is brilliant.  

Make your way down Via San Giovanni to browse the shops filled with leather goods, handcrafted jewelry, ceramics and pottery.  You will also find food specialty shops offering cheeses, truffles and wild boar cured meats.  Looking for some artisanal leather goods, then peruse the Mela House.  Looking to sample the gamey wild boar?  You will find it in the specialty shops with shop owners offering samples and on menus everywhere.  Just as a glass of Chianti is all things Tuscan, so is this delicacy.  

La Rocca di Montestaffoli – Just pass the Duomo you will find a path that offers a gentle walk uphill to the highlight of our visit to San Gimignano.  You will find roving musicians playing classical tunes, artists painting or actors performing along the way.  You will eventually reach the ruins of a 14th century fortress above the town.  Don’t anticipate a huge fortress, but it is a picturesque ruin offering stunning views of the towers rising from the town centre.  Climb the 30 steps to the top of one of the fort’s ruined towers, where you can soak in the best view of San Gimignano, encircled by the vine-covered hillsides.  This is the perfect spot to indulge in a picnic under the lovely olive groves sharing some salami and cheese on a baguette.  Tuscany is known for Chianti, but San Gimignano is known for Vernaccia.  Since the Renaissance, it has been considered one of Italy’s finest white wines.  It is a bright white wine with crisp citrus flavour offering a slightly bitter note on the finish.  Many of the enotecas that line the medieval streets offer a glass to go, which would be the perfect pairing to your picnic.   La Rocca Wine Museum is located in this fortress where you can learn more about this local wine and even head to the tasting bar, offering endless tasting options. 

Museum of Torture – This was a unique experience.  Just as the name suggests, you will find a grisly collection of historical torture techniques used in the medieval times.  This museum is not for the faint-hearted as you will be exposed to the very dark parts of our collective human nature.  The museum contains more than 100 instruments of death including the guillotine, the Iron Maiden, the Hanging Cage, the Head Crusher and the Rack, to name a few.  All of sudden your sun-drenched Tuscan dream day quickly turns into a nightmare when you enter this museum. 

While wandering the encircling 13th century walled city of old towers, your afternoon aperitivo leads you to an umbrella starring out at the gorgeous Tuscan landscape.  The sun is shining, you sit down on the outdoor patio to enjoy the views at the most glorious Italian, Mediterranean Wine Bar, Divornum.  You order the most delicious shareable platters with a flight of white wine and a flight of red, savouring every sip and bite!

Explore San Gimignano into the evening as the streets become relatively empty where the cobblestone and arched alleyways glow with a warm hue.  As dusk falls around the towers, this romantic Tuscan town is now yours to savour.  Smart travelers, unlike us this trip, will stay overnight.  We stayed late into the evening, but an overnight stay would offer that feeling you were dreaming about when envisioning the romantic Tuscan charm.  I already have Case Irene with AirBnB on my list for when we visit again!