Typically, I'm a very structured traveler. I love planning, and I'm all about being prepared for the day's adventure. But years ago I found that the best way to experience Tuscany's Siena is to toss the itinerary aside and leave Lonely Planet behind. Instead, step out into the medieval city and let the labyrinth of alleyways, steep pathways and winding streets serve as a guide. Yes, the Duomo and Piazza del Campo should be a part of your Siena plans, but it'll be way more fun trying to find them without a map (it isn't difficult, I promise!). And for the more structured travelers I've included all of my favorite Siena spots below, as well as sightseeing tips, hotel suggestions and restaurant recommendations.
A stroll through the historic heart of Siena is like stepping back in time.
THINGS TO DO IN SIENA
CHURCH OF SAN DOMENICO
A 13th century basilica often overshadowed by the city's Duomo (Cathedral of Santa Maria Assunta), the Church of San Domenico sits at the northwest edge of the city. It's constructed entirely of brick, and its grandeur is best appreciated from the outside. The church can be seen rising above the rooftops from many viewpoints throughout the city. (LOCATION: Piazza San Domenico, Siena; HOURS: 7 AM-6:30 PM)
DUOMO DI SIENA
Duomo di Siena is an iconic black and white cathedral that sits on the Piazza del Duomo, the highest point in medieval Siena. The cathedral is a masterwork of Gothic architecture, and one of the few churches that boasts an interior more epic than its exterior. It's recommended to get tickets in advance, but we purchased ours the morning of our visit. There are a variety of Duomo ticketing options. A regular ticket includes access to the cathedral, cathedral crypt, cathedral museum, baptistery and Oratory of San Bernardino. There is a second ticket option that includes access to the Gate of Heaven via rooftop walkways that lead to one gnarly view overlooking the black and white church interior. Tickets for the Gate of Heaven are limited and must be booked for a specific time slot. (LOCATION: Piazza del Duomo, Siena; HOURS: Monday to Saturday 10:10 AM to 6 PM; Sunday 1:30 PM to 6 PM; PRICE: Depends on ticketing option and time of year)
ORTO DI PECCI
Orto di Pecci is a lush, green mirage that sits in the heart of Siena, just a short walk from the Piazza del Campo. Countryside views inside this pleasant, open park are a refreshing change from the narrow alleys and brick surroundings that pack Siena's medieval walls. Stroll through gardens, and say hello to the park residents that include goats, donkeys, peacocks and turkeys. (ADDRESS: Via Porta Giustizia, Siena; PRICE: Free)
PIAZZA DEL CAMPO
All roads lead to the Piazza del Campo, or so it seems. Even if it's not an itinerary item, most visitors end up on the vibrant square several times a day while in Siena. It's the social center of the city where cafes and al fresco dining surround a massive open brick plaza where both locals and tourists sit to enjoy the sun, wine and friends. An absolute must while in Siena - great for people watching. (ADDRESS: Il Campo, Siena)
TORRE DEL MANGIA
A 14th century medieval tower that sits on the Piazza del Campo. It's lovely to admire while seated on the square, or purchase a ticket and climb a narrow staircase to the top of the tower. (LOCATION: Pubblico Palace on the Piazza del Campo, Siena; HOURS: 10 AM to 6 PM; PRICE: 8 Euros)
The iconic Torre del Mangia on the Piazza del Campo.
A typical street in Siena with all the medieval feels.
The gorgeous Duomo sits perched above the surrounding medieval city.
That's me feasting on passion fruit gelato 24/7 at Gelato Nice.
WHERE TO EAT IN SIENA
Make sure to do as much eating as possible in Siena - for me, this was the best pasta in all of Italy.
CONSORZIO AGRARIO DI SIENA
A bustling food emporium with several sellers offering focaccia pizza, wines, butcher meat, cheese, pasta, desserts and more. (ADDRESS: Via Giuseppe Pianigiani, Siena; HOURS: Monday to Friday 8:30 AM to 1 PM and 3 PM to 6 PM)
There are loads of gelato options scattered throughout Siena's labyrinth of streets, but Gelato Nice is my favorite (mostly because they make passion fruit gelato, and they do it so well). (ADDRESS: Via di Pantaneto 152; HOURS: Weekdays 1 PM to 11 PM and Weekends 11 AM to 11:45 PM)
OSTERIA LA SOSTA
For meat eaters, this is a place to enjoy the specialty of Tuscany - rare Florentine steak. For non-meat eaters, the menu also has a variety of fresh pasta offerings. (ADDRESS: Via Pantaneto, 115, Siena; HOURS: 12:30 PM to 3 PM and 7 PM to 10:30 PM)
ANTICA OSTERIA DA DIVO
This might be my favorite restaurant in Italy. The space is completely atmospheric set in caves that were once part of an old church. Small rocky alcoves are filled with tables, and there is al fresco dining that lines the alley just across from the restaurant. The fresh pastas and sauces were absolutely delicious - I've seriously considered catching a flight back to Italy just to eat at Antica Osteria Da Divo again. (ADDRESS: Via Franciosa 25-29, 53100, 64; HOURS: 12 PM to 3 PM and 7:30 PM to 12 AM; Closed Mondays)
RISTORANTE SAN DOMENICO
Ristorate San Domenico is a great lunch stop for pasta with nice views of the Duomo. The bucatini with pomodoro sauce is particularly delicious. (ADDRESS: Via Camporegio, 17; HOURS: 11 AM to 11 PM)
Popular jazz bar owned by the renowned Osteria Le Logge, Un Tubo hosts live performances select nights of the week. (ADDRESS: Via del Porrione, 33; Hours 12 PM to 2:45 PM and 7 PM to 10:45 PM; Closed Sundays)
The city's incredible Duomo di Siena.
The Piazza del Campo is a central square surrounded by the city. It's where everyone goes to eat, drink and meet up with friends.
Piazza Salimbeni. One thing I love about Italy is that you can find great sculptures scattered throughout the city.
Such a treat to stay within Sienna's historic centre and wake up to these views.
Lost in the labyrinth of winding streets.
The view from the Gate of Heaven, a special Duomo ticket is required to access this part of the cathedral.
WHERE TO STAY
CERTOSA DI MAGGIANO
For travelers looking to escape the city walls at night, this former monastery is located just one mile from Siena's historic centre. Nestled in the Tuscan countryside, Certosa Di Maggiano houses just 17 rooms in an intimate setting that looks straight out of a classic Italian movie. (ADDRESS: Str. di Certosa, 82/86; PHONE:+39 0577 179 4006)
GRAND HOTEL CONTINENTAL SIENA
The only five-star option in the historic centre, the Grand Hotel Continental Siena is an upscale boutique property that sits in a 17th century palazzo. The location is ideal, surrounded by restaurants, cafes and shops, and just a few blocks away from the iconic Piazza del Campo. For a room with a view of the Duomo, guests should request to stay to the rear of the hotel. Like the city, the palazzo's decor is a step back in time with Tuscan terocatta floors, 17th century frescoes, vaulted ceilings and marble travertine. (ADDRESS: Via Banchi di Sopra, 85, Siena; PHONE: +39 0577 56011)
Visit the Duomo early - it's one of the most popular tourist attractions in the city!
Views over the city from atop the Duomo.
The interior pattern and design of Siena's Duomo is my favorite in Italy.