SIENA

Siena feels authentic and lived in. The historic center is a UNESCO World Heritage Site and has looked more or less the same since the 13th century. The Piazza del Campo, the iconic shell shaped square at the center of the city, is one of the best places to sit in the world. Just go there and stay a while. The Duomo, the black and white striped Gothic cathedral that towers over the city, is worth the walk up the hill on its own. But the thing that really sets Siena apart is the Palio, a bareback horse race that the city's 17 neighborhoods have been competing in since medieval times. It is taken seriously in a way that is hard to convey. You won't be there for the race but each neighborhood has its own banner and colors and they hang all over the city year round. Once you start noticing them you can't stop. The whole city moves slow and means it. It's a very good place to be.

Tutto (Everything Else)

  • There are a lot of options in and around Siena. These are the ones we'd point you toward.

     

    Hotel Certosa di Maggiano — A converted monastery from the 14th century sitting just outside the city walls. Walled garden, pool, very few rooms. Quiet in the best possible way.

    Villa Ermelina — A well decorated Sienese villa just outside the center. Personal service, a lot of charm, and none of the fuss.

    Grand Hotel Continental — Dead center in Siena on the Banchi di Sopra. Frescoed ceilings, a grand old lobby, and everything walkable from the front door.

    Airbnb or VRBO — There are some beautiful villas and apartments available in and around Siena, especially in the countryside. Worth looking if you want more space or want to split something with another family or group.

  • From Florence — The most straightforward. Direct Trenitalia Regionale trains from Santa Maria Novella to Siena run regularly and take about 1.5 hours. Book in advance if you're traveling on a Friday.

    From Rome — No direct train to Siena exists, so you have two options. Take a Frecciarossa from Roma Termini to Firenze Santa Maria Novella, then connect to a Regionale to Siena, about 3.5 hours total. Or if you want to drive, the route from Rome through the Val d'Orcia is a very good excuse to rent a car.

    From Milan — Take a Frecciarossa from Milano Centrale to Firenze Santa Maria Novella, about 2 hours, then connect to a Regionale to Siena for another 1.5. Budget about 4 hours total. Book the high speed leg in advance.

  • Vico D'Arbia is about 10 minutes from central Siena by car. Parking on site will be limited, so if you're staying at one of the three recommended hotels there will be a shuttle from downtown Siena. Check back later for more details on the shuttle.

  • Montepulciano — 65km, about 1 hour

    A medieval hill town famous for its Vino Nobile. The main street climbs steeply through the town and is lined with wine shops and little cafes. Go into at least one cellar and taste before you buy. The views from the top over the Val d'Orcia are worth the walk alone.

    Montalcino — 40km, about 45 minutes

    Brunello di Montalcino is one of Italy's great wines and this is where it comes from. The town is small and easy to walk. The fortress at the top has a wine bar inside it, which feels exactly right. Pair it with a stop at a winery while you're down there.

    Val d'Orcia — 30km, about 35 minutes

    The rolling hills, winding roads, and cypress lined lanes you've seen in every Tuscany photo. Drive through it slowly, stop constantly, and don't have anywhere to be.

    Pienza — 52km, about 1 hour

    A small, almost perfectly preserved Renaissance town built on a hilltop in the Val d'Orcia. Famous for its pecorino, which you can buy directly from the little shops along the main street. Easy to do in a half day and pairs well with a stop in Montalcino on the same drive.

  • Castello di Brolio — 20km, about 25 minutes

    One of the most storied estates in Chianti Classico, owned by the Ricasoli family for nearly 900 years. The baron who owned it in the 19th century essentially invented the modern Chianti formula and later became Prime Minister of Italy. The castle grounds are open to visit, the views over the Sienese hills are staggering, and the cellar tours with tastings are worth booking in advance.

    Fattoria dei Barbi — 45km, about 55 minutes (just outside Montalcino)

    One of the most respected Brunello estates in the region, run by a family with roots here going back to 1352. The cellar holds vintages going back to 1892 and the tour through the aging rooms is genuinely impressive. They also have a taverna on site, which makes it an easy full afternoon.

  • Osteria Le Logge — Where we're having our welcome drinks and one of the best restaurants in Siena. The space used to be a pharmacy and provisions shop and the original floor-to-ceiling wooden cabinets are still there. Beautiful interior, serious wine list, very good Tuscan cooking. Worth booking for dinner on another night if you can get a table.

    Bar Margherita — Le Logge's bar, right on the Piazza del Campo, which is a UNESCO World Heritage Site and one of the great medieval squares in the world. Order something, stay longer than you planned.

    La Taverna di San Giuseppe — Underground stone dining room just off the Campo. Great pasta, good wine, ideal for a long dinner. Book ahead.

    Piazza del Campo — Not a restaurant but sit here and drink something at some point. It's one of the best squares in the world and it's right there.

  • If you want to rent a car, you'll need an International Driving Permit alongside your US license. AAA does them same day for about $20. Worth it.