SIENA, ITALY: A COMPLETE TRAVEL GUIDE TO TUSCANY’S MEDIEVAL CITY
Florence and Siena are often pitted against one another when it comes to travel in Tuscany. Both are amazing, but so many visitors only have time for one. Most opt for Florence because it’s so beloved and famous, but I prefer the medieval beauty of Siena’s walled city. A stroll through the maze of contradas is like a step into another era, and there’s so much to love – the soaring views of the Duomo, the infectious vibes of the Piazza del Campo and pasta that rivals Rome as the best in Italy. Below is my complete travel guide to Siena including the best places to visit, historical sites, hotels, best Siena viewpoints, restaurants, wine bars, Siena photo locations, travel tips and more.
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The most sweeping view of Siena. OUTFIT DETAILS: Aerie dress linked here.
SIENA TRAVEL TIPS
- WHAT IS A CONTRADA? – A contrada is one of the 17 historic neighborhoods within Siena. Most of the contrade are named after animals or mythical creatures including Chiocciola (snail), Drago (dragon), Leocorno (unicorn) and Tartuca (tortoise).
- CURRENCY – The official currency of Italy is the Euro. While most places take credit card, it’s always handy to have some cash on hand for smaller purchases.
- STAYING CONNECTED – Almost all hotels and restaurants have free wi-fi available to guests, but for connection 24/7 download an e-SIM for your cell phone.
- OFFLINE GOOGLE MAP – Download an offline Google map of Siena to help navigate the city in the event you have no wi-fi or have trouble connecting to cell service.
The Duomo in Siena might be my favorite in all of Italy.
WHEN TO VISIT SIENA
- APRIL, MAY, SEPTEMBER, OCTOBER – Shoulder season is the best time of the year in Siena. Crowds can’t be avoided, but it won’t be as busy as summer, temperatures are more manageable and hotel prices are a bit more reasonable.
- JUNE-AUGUST – Summer is the busiest time of the year throughout Italy. Make all reservations well in advance.
- NOVEMBER-MARCH – Hotel prices are more affordable in low season when crowds thin out, but you risk cold and rainy weather this time of the year.
Grotta Santa Catarina is one of my favorite restaurants in Siena.
HOW MANY DAYS IN SIENA
TWO DAYS. It’s ideal to dedicate two full days to Siena. This is enough time to explore the city at a relaxed pace, visit the historical sites and eat at all of the best restaurants. Note that Siena has some of the best pasta in all of Italy, so the longer the stay, the more restaurants to try.
The bustling Piazza del Campo is the vibrant heart of Siena.
PLACES TO VISIT IN SIENA
BASILICA OF SAN DOMENICO
This 13th century basilica made from brick is an iconic landmark in Siena. It can be seen from the surrounding Tuscan countryside thanks to its perch on a hilltop within the medieval city walls. Also known as the Basilica Cateriniana, the Gothic cathedral is home to a very special relic: the mummified severed head of Saint Catherine, as well as her thumb.
BAPTISTERY OF SAN GIOVANNI
The exquisite facade of the Baptistery of San Giovanni sits on a square by the same name behind the apse of the Duomo. Similar to the Siena Duomo, the exterior is designed with the signature pattern of black and white stripes. The Baptistery dates back to the 14th century, an artistic treasure filled with a baptismal font, ornate sculptures and stunning frescoes.
MEDICI FORTRESS
The imposing red brick walls of the Medici Fortress are located just outside Siena’s historic centre. It dates back to the 16th century, originally for military use and served as a political prison. It’s now used as a public space where visitors can enjoy walking paths, views of the city and summer concerts.
PALAZZO CHIGI-SARACINI
Siena is home to several dazzling palazzos, and the curved facade of Palazzo Chigi-Saracini is one of the prettiest. The 12th century palace now houses the Accademia Musicale Chigiana, but can still be visited as part of a guided tour group. The palazzo is home to an impressive art collection, historical library, sculptures, antiques, loggias, decorative frescoes and a beautiful Renaissance courtyard featuring an ancient well.
PALAZZO PUBBLICO
Of all the palazzos in Siena, this is one of the most grand. It sits in the heart of the city on the Palazzo del Campo and serves as both City Hall and the location of the Museo Civico. Most notable is the palazzo’s soaring Torre del Mangia, one of the tallest medieval towers in Italy, made of red brick and white stone travertine. The 14th century open air brick courtyard and its vaulted archways is equally stunning.
PALAZZO SALIMBENI
Palazzo Salimbeni sits anchored by a sculpture of the Italian economist Sallustio Bandini. The palazzo was constructed in the 14th century, and sits directly next to Palazzo Spannocchi and Palazzo Tantucci. Today the palace is the headquarters of the one of the world’s oldest banks, Monte dei Paschi di Siena.
PIAZZA DEL CAMPO
Piazza del Campo is the beating heart of Siena. Shaped like a seashell, the bustling medieval piazza is lined with outdoor cafes and wine bars that look out onto the square. It’s a popular gathering place where people sit on the sloped bricks to eat gelato, sunbathe, picnic and people watch. The views of the Palazzo Pubblico and Torre del Mangia from the piazza offer a fabulous setting for evening aptertivo.
SANCTUARY OF SAINT CATHERINE
This 14th century religious complex was the birthplace of Saint Catherine. The sanctuary is an incredibly serene space where visitors can explore the interconnected chapels, inner courtyards and oratories.
SANTA MARIA DELLA SCALA
Formerly an old historic hospital, Santa Maria della Scala is now a museum located across from the Duomo. The reason to visit is the Hall of the Pilgrims, an incredible interior passageway that features an arched ceiling covered in 15th century frescoes.
SIENA DUOMO
The Siena Duomo is my favorite cathedral in all of Italy. The white, green and red marble facade is utterly exquisite with a striking interior design dripping in a black and white stripe pattern. The best views in and around the cathedral are part of the Porta del Cielo (Gate of Heaven) tour. It takes visitors up to the high level galleries for a sweeping perspective of the black and white nave, as well up to the soaring rooftops. Other notable sites to see in the Duomo include the Baptistery of San Giovanni, the Crypt, Facciatone and Piccolomini Library. This is the most popular tourist attraction in Siena, book tickets well in advance.
Hotel Certosa di Maggiano is a former monastery that has been converted into a luxury hotel, and it’s the prettiest place to stay in Siena.
WHERE TO STAY IN SIENA
For a simple, clean and moderately priced stay, Campo Regio Relais is the best option in Siena. It sits in a 16th century palace, and there are a mere six rooms. The location in the heart of the city is ideal, everything is walking distance from the property. Rooms aren’t particularly memorable, but it’s worth staying for the view from the hotel breakfast terrace that overlooks a sweeping panorama of the Siena.
Only one luxury hotel option sits within the Siena city walls, and it’s the Grand Hotel Continental. It occupies the 17th century Palazzo Gori Pannilini where guests can feel the grandeur of the palace’s storied past with opulent spaces that feature vaulted ceilings, original frescoes, Murano glass chandeliers, antiques and Travertine marble.
Hotel Certosa di Maggiano is located outside the city walls in a former monastery. It retains much of its historic roots with monastic features seamlessly woven into the luxury hotel space including incredible arched cloisters, a 14th century chapel, former monk cells and the incredible central cloister. The property houses just 17 rooms and suites, all completely unique to the monastery’s original design. Most rooms feature thick stone walls, antique furnishings, terracotta floors, vaulted ceilings and marble finishes. This is my favorite place to stay in Siena – it’s stunning.
Beautiful archways inside the grand Palazzo Pubblico.
BEST SIENA VIEWPOINTS
- ALBERGO BERNINI – Not a good hotel, but the view from the terrace is epic.
- CAMPO REGIO RELAIS – Amazing view of the city rooftops and Duomo from the breakfast terrace.
- HOTEL ATHENA ROOFTOP BAR – View of both the medieval city and the Tuscany landscape.
- HOTEL MINERVA – Panorama of the medieval city and its rooftops.
- I TETTI DI SIENA – Budget hotel with a spectacular terrace view.
- RISTORANTE SAN DOMENICO – View of the Siena Duomo and cityscape.
This medieval city is such a vibe.
BEST RESTAURANTS IN SIENA
- ALL’ORTO DE’PECCI – fresh pasta and meats
- CONSORZIO AGRARIO DI SIENA – supermarket to-go foods
- ORTO DE PECCI – fresh pasta
- OSTERIA CARROCCIO – fresh pasta
- OSTERIA LA SOSTA – fresh pasta
- OSTERIA PERMALICO – fresh pasta
- ENOTECA I TERZI – fresh pasta and meats
- GROTTA SANTA CATARINA – fresh pasta
- LA NAPOLETANA 2.0 – pizza
- PIZZERIA ALLE SCALETTE – pizza
- RISTORANTE PIER PETTINAIO – fresh pasta and meats
- SALEFINO – fresh pasta and meats
- ZEST WINE BAR – wine and vibe
I adore the black and white zebra pattern inside the Duomo.
SIENA GELATO SHOPS
- ANTICA CREMERIA
- CREME GELATERIA PASTICCERIA
- GELATERIA IL CAMERLENGO
- GELATERIA KOPAKABANA
- GELATERIA LA MANDORLA
- GELATERIA NICE
- GROM GELATO
- IL MASGALANO GELATERIA
- LA GELATERIA DEL 103
- LA VECCHIA LATTERIA
- VENCHI CIOCCOLATO E GELATO
The beautiful gardens of Hotel Certosa di Maggiano feel like a scene from Bridgerton.
GET AROUND SIENA
The historical center is a Zona a Traffico Limitato, an area that restricts most vehicles. Be prepared to explore Siena on foot and get lost in the maze of alleyways and cobbled streets.
All’Orto de’ Pecci is a tiny restaurant located in the park below the city, and food is phenomenal. Highly recommend the picci with tomato and garlic sauce – one of the best pastas I’ve had for a mere 11 euros.
Gelato for the win.
GET TO SIENA
- CAR – Siena is easy to reach by car as a day trip in Tuscany. Paid parking options within the city center include Il Campo Car Park, Santa Catarina Car Park, Il Duomo Car Park and Fortress Car Park. Or alternatively, Parcheggio Via Roma is walking distance to the city center.
- FLIGHT – The Amerigo Vespucci Airport (FLR) in Florence is a one-hour drive, and the closest airport to Siena. Alternatively, the Pisa International Airport (PSA) offers more flight options, but it’s a one-hour 45 minute drive from Siena.
- TRAIN – Stazione di Siena is the main train station in Siena. It’s located outside the city walls, and a bit of a walk to reach the historical center.
So much of the city is made of brick.
