Heading to central Italy this year? Check out this 3 day itinerary, Siena and beyond, which is all about showcasing the joys of one of the country’s undisputed stunners: A Tuscan hill town that’s now a designated UNESCO World Heritage Site, no less.
Over the course of 72 hours, it will run through the highlights and hidden secrets of the great town. You’ll begin with a whirlwind tour of the most important historic relics and palazzos, starting the ball rolling with the eye-watering points of interest that string around the bustling Piazza del Campo. From there, you’ll break out to some of the lesser known contrade (historic neighborhoods) to see great citadels and dine in family trattoria.
We’ve planned our 3 day itinerary, Siena and beyond, so that it can be completed at any time in the year, no matter if it’s the balmy days of midsummer or the chilly months of midwinter. However, we would say that it’s probably not a good idea to come when the famous Palio di Siena is happening. That’s in July and then again in August and turns the streets into a mass of bodies and people. It will be hard to get around and almost impossible to give the sights the time they deserve.
The top 3 day itinerary Siena hotels – where to stay for this trip?
There are PLENTY of hotels in Siena. Don’t worry about that. This city is up there with the bucket-list draws of the boot. Okay, so it might not hit the headlines like Florence or Rome, but it still magnetizes millions of people each year with the promise of its honey-hued palaces and redbrick belltowers, not to mention the iconic Palio race.
For our itinerary, you’ll want to base yourself somewhere near the center of the town. That could be anywhere in the Aquila, Torre, or Istrice areas, which are all within walking distance of the Piazza del Campo (where we start on day one). Here are a few specific hotel recommendations:
- Casatorre dei Leoni Dimora Storica ($$$) – This exquisite hotel occupies a centuries-old palace and has really spacious suites suited to couples.
- B&B Governo dei Nove ($$-$$$) – A very nicely done up boutique hotel with stylish touches, neatly placed up the hill and away from the baying tourist crowds of the Siena center.
- Palazzetto Rosso – Art Hotel ($$-$$$) – Channeling the age-old Gothic features of the building it’s in, this hotel offers quirky, kitschy rooms, some with amazing views of the old town skyline.
Day 1 – The historic beauty of Siena
There’s only one place to kick-start our 3 day itinerary: Siena city center. To get right into the middle of that, go from your hotel to the Piazza del Campo. You can grab an espresso and a pastry on the way if you don’t have breakfast included in the cost of your hotel – you’ll need the energy since there’s lots of walking to be done!
Arrived at Piazza del Campo? Good. Welcome to the beating heart of Siena. This vast public space is nothing short of legendary all around the globe. It’s hailed for its unique urban plan and array of gorgeous architecture. Take it in. You’ll spend the morning here hopping between the palaces and monuments.
First up: Palazzo Pubblico. This is the dominating structure that fringes the southern end of the square. Built way back in the late 1290s, it was the seat of the government of the powerful Republic of Siena, which once made it one of the most important buildings in all Europe, no less. Appreciate the exterior for a moment. It’s picked out with beautiful marblework and redbrick. Inside, enter the Museo Civico (tickets are €10 or $9 per adult) to see acclaimed frescos from the Middle Ages.
The next adventure will take you up the soaring spire of the Torre del Mangia. It’s another €10 to get to the top but boy is it worth it! You’ll be climbing a veritable icon of Siena as a whole, to a lookout point some 102 meters up. From there, you can survey the winelands of Chianti to the north and the jagged Arezzo hills to the east.
Return to ground level for lunch and make for Il Bargello on Via di Città. It’s two minutes’ walk from the Campo and is a chance to taste real Tuscan food – expect truffle tagliatelle and hearty meat ragus, cheese platters and rich red wines.
Eating there also puts you in a great place for the afternoon’s adventuring, which takes you up the Via del Capitano to the Piazza del Duomo. The trip there is fun. It can be a one minute walk if you like but there are loads of distractions in the form of local art galleries and souvenir shops, so take half an hour over it. The finish point is a sighting of the wonderful Duomo di Siena from the 13th century. Grab a Spritz at the Osteria del Gusto wine bar to finish off the day there in style.
Day 2 – Tread the unexplored contrada
Now you’ve seen the trodden main parts of the town, it’s time to stray a little more off track. That’s why we set aside day two for seeing the other contrade (neighborhoods) of old Siena. There are about three or four that we think are worthy of note, which we’ll tackle in turn one by one. It’s worth knowing at this point that the locals in Siena take the divisions between various historic areas very seriously. They determine the loyalties of people during the annual Palio race, after all!
Start in the Selva area. This was once a weaver district but is now primarily known for the Duomo. You saw that last night, so push through onto Via Franciosa and Piazza San Giovanni to encounter the local craft shops and tiny cafés (there are one or two that are lovely for a morning espresso). Soon, you’ll pass into the Civetta area, one of the largest historic neighborhoods. Once a shoemaker’s quarter, it’s now centered on lovely Piazza Tolomei.
North of that is Giraffa, a part of town famed for its affluent residents. The south side of it is quiet and empty, but Via del Rossi has places like Piripi Pizza Urban Food that are perfect for a casual lunch on the street side. Giraffa hits a zenith at its eastern end with the Basilica of Saint Francis, a Gothic church from the 14th-century.
Bruco district takes over from there, rolling down two picturesque streets to the Porta Ovile, one of the town’s ancient gates. From there, climb again into the heart of Istrice. This is one of the larger contrada of Siena and a top place to finish your day since there are lovely parks and adjoining aperitivo stops. If there’s something on the box office, head into the Fortezza Medicea to see an open-air show (they run throughout the summer months).
Day 3 – Beyond Siena
You can’t come to this jaw-dropping corner of central Italy and not head out to explore the countryside. So, for this portion of our 3 day itinerary, Siena and beyond, we go beyond. Our recommendation? Rent a car. Trains and buses are okay here, but they simply cannot get you to the hill towns and hot springs that we think you should see.
In the morning, drive north towards San Gimignano. The trip there will take you through one of the wilder parts of the region. If it’s hot, you can pitstop at the Parco Fluviale Alta Val D’Elsa, where a turquoise river gushes through pine woods to reveal a series of idyllic swimming spots in the forests. If not, push onto San Gimignano itself, park up below the old town, and walk in.
Cue one of the most celebrated historic villages in the country. A UNESCO World Heritage Site in its own right, this one dates all the way back the age of the Etruscans (that’s before even the Romans, don’t you know?). It’s anchored on Piazza della Cisterna, where Gothic palaces and the looming Torre Grossa keep watch. It’s a great place to people watch, drink an espresso, and feel truly immersed in history.
For the afternoon of your final day in the Siena region, we think you should drive south of the city itself. From San Gimignano, it’s roughly 1.5 hours to the beginning of the legendary Val d’Orcia, which starts with the also-UNESCO-tagged town of Pienza. Stop there to witness the handsome Palazzo Piccolomini and a great duomo. But don’t stay too long…
Driving through the valley as the evening light sets in is a joy you’ll never forget. We’d take the harder country roads via Monticchiello and Contignano, down all the way to Radicofani. There are lookout points en route that let you stop and survey sweeping fields of wheat dancing in the breeze and the sun setting over silhouetted cypress trees. It really is quintessential Tuscany. To finish, how about a soothing bath in the hot springs at Bagni San Filippo?