Where to Stay in Siena: Inside or Outside the City Walls?
Located in the heart of wine country, pretty Siena in Italy is a fairytale tourist destination. Perched on its hill, within towering Medieval walls, the city of Siena sits directly between Florence and Rome. This makes it an ideal hub for exploring the Tuscan countryside and Umbrian hilltowns.
I recently visited Siena during the world-renowned Palio, which is a bi-annual event featuring exhilarating bareback horse races, and I fell in love with the stunning views, excellent shopping, and of course, the Tuscan food and wine. It's truly a lovely place!
If you're considering a trip to this part of Italy (which you probably are if you're reading this), here are my suggestions of where to stay in Siena and how to enjoy this adorable city.
Quick Overview of Siena
The ancient Etruscan city of Siena is a time capsule of the Medieval world. It's famously divided into 17 contrade or neighborhoods. These tiny areas have their own banners, civic ordinances, and symbols – complete with allies and intense rivalries, which mostly come out during the world-renowned Palio horse race.
While the neighborhoods were once administrative and military sections, now they're a deeply ingrained part of the identity of Siena's citizens. Each contrade only consists of a few streets, and you'll seamlessly flow from one to the other, only noting the oddly modern (and slightly unattractive) wall lamps that distinguish each region. They're all within walking distance of the heart of the city – marked by the famous Piazza del Campo.
When it comes to where to stay in Siena, it's important to note that the city is very small. Home to 55,000 people, tightly packed in its towering walls, there's really not a bad place to stay.
Everywhere within the walls is a central location. That being the case, I'll break down my recommendations into three categories:
1. Stay Inside the Walls
For first-time visitors and young travelers, staying inside the walls is the best option. It's home to all the major sights and most of the luxury hotels. It's also the best choice if you're utilizing public transit to get around. As mentioned, the Historic Centre is walkable, and you can cover it all in a couple of hours.
Here are a few districts to consider.
Piazza del Campo: The area around Piazza del Campo is the heart of the city and the perfect spot for fun nights out. Full of charming restaurants and friendly bars, it also has a few boutique hotels, easy access to all tourist spots, and is the most vibrant area of Siena.
Aquila: This contrade is adjacent to Siena Cathedral and features plenty of trattoria. The Duomo square is also a popular spot for locals and tourists to enjoy gelato with a view.
Lupa: Lupa is a residential area a bit farther north. It is lined with casual bars and clothing boutiques and is the perfect place for fashionistas and those looking for quieter surroundings. There are also budget-friendly restaurants for lunch in this area.
Istrice: Next to Lupa, Istrice contains several walking paths, the Medicea Fortress, La Lizza Gardens, and more open space. It's a good spot for families within the walls.
2. Stay Outside the Walls
Now, you might be wondering why in the world you would go to Siena and stay outside the famous walls. Well… the magical thing about Tuscany and its hilltowns is the spectacular views, and Siena is actually best seen from outside the walls!
Just beyond the walls, you'll discover gorgeous Tuscan villas surrounded by Cyprus, lower accommodation prices, and fantastic views of towering Siena.
The relaxed neighborhoods are a great place for families, couples looking for romantic surroundings, or anyone traveling by car (as all of the city center is a limited traffic zone).
3. Countryside of Tuscany
As much as I love Siena, it's not the only great choice in the surrounding area. If you want a more rural setting, the town of Monteriggioni is just 20 minutes from Siena and offers lush wineries and quaint farmhouse bed & breakfasts. It's a great choice for couples or friend groups looking to explore the wineries of Tuscany.
Other nearby towns include Castelnuovo Berardenga and Buonconvento. Siena can be easily seen on a day trip, so if you're more interested in the Tuscan countryside, these are great options!
Where to Stay in Siena for First-Time Visitors: Inside the Walls
Quick Note: If you're traveling by car, you'll likely need to park in the lots outside the city walls.
For those who want to be in the heart of the action, here are my suggestions for the best hotels inside the walls. Remember, it doesn't much matter where you stay within the Historic Centre. It's all very walkable!
Luxury Option: Grand Hotel Continental Siena – Traditional 5-star hotel within a 17th-century building, 820 feet from Piazza del Campo.
Mid-range Option: Villa del Sole Siena – I love this hotel because of the location. From its breakfast terrace, you get an incredible panoramic view of Siena.
Budget Option: B&B San Francesco – This adorable bed and breakfast is located in a 15th-century structure just next to Bruco Fountain and is a great option for budget explorers.
What to Do in the Historic Centre of Siena
- Spend a night out bar hopping at the casual pubs of Piazza del Campo.
- Climb Torre del Mangia and visit the history museum at Palazzo Publico for an incredible view and a thorough dip into the culture and art of Siena.
- Shop the clothing boutiques or look for antiques in Lupa.
- Photograph all 17 contrade banners and lampstands.
- Visit the famously striped Siena Cathedral, making sure to pop in Piccolomini Library and the Museo del Duomo.
- Attend the famous Palio, a 17th-century horse race that occurs twice a year on July 2nd and August 16th. The months leading up to the Palio are filled with anticipation, special events, and contrade rivalry! Take a look here for more info on the Palio.
- Dive into the region's history at the National Museum of Etruscan Archaeology.
Where to Stay in Siena for Families: Outside the Walls
For families with children visiting Siena, staying outside the city walls offers more spacious accommodations, plus you get peaceful surroundings and easy access to both the historic center and the Tuscan countryside.
Consider one of the charming villas or family-friendly agriturismos for a relaxed and comfortable stay.
Luxury Option: Porta Tufi Luxury Apartment with Private Parking – High-end, modern apartment just outside the Porta Tufi gate to Siena, offering free on-site parking, large rooms, a private terrace, and air conditioning.
Mid-range Option: Villa il Borghetto – This 17-century remodeled villa is situated one mile outside the walls and offers fully furnished apartments with a traditional Tuscan style.
Budget Option: Borgo Grondai – Located on an old Tuscan farm, you'll get an epic view of the city from the outdoor salt-water swimming pool!
What to Do Outside the Walls
Take a day trip into Siena proper to explore the sights.
Go on a truffle hunting tour.
Tour Chianti Castle on a guided wine trip.
Walk the walls, photographing the ancient gates of Porta Romana and Porta Tufi.
Tour the 15th-century Basilica dell'Osservanza.
Where to Stay in Siena for Wine Lovers: The Countryside
Moving a bit farther out, the vineyards of Tuscany are ideal for nature and spa lovers. If you're looking for a vacation with no hassle, then you can't beat the small towns around Siena. The countryside of Tuscany is a place to “eat, drink, and be merry!”
Luxury Option: Pieve Aldina Relais & Châteaux – Situated in the town of Radda, in the nearby Chianti Region, Pieve Aldina is a 5-star hotel with an on-site bar, hammam, spa, pool, and shared lounge. Each room is large and decked out with all the amenities. One night here, and you'll feel like the king/queen of the castle!
Mid-range Option: B&B Pallazo a Merse – This lovely bed and breakfast is 12 miles from Siena in the town of Sovicille. It offers casual Tuscan style, outdoor gardens with a swimming pool, and a Continental breakfast.
BudgetOption: La Dogana – This air-conditioned vacation home is just 15 minutes to Siena by bus. It offers fast, free Wi-Fi, an interesting spiral staircase, and city views.
What to Do in the Countryside of Tuscany
If you decide to stay outside the city, your time is best spent with wine in hand. Wine tours in this region are fabulous and numerous! I personally enjoyed the Brunello Wine Tasting Experience at Montalcino.
Take a day trip to Florence, Pisa, or Perugia.
Explore the 12th-century Duomo in the charming town of San Gimignano.
Take a tour of Monteriggioni Castle, one of the most authentic and intact 13th-century castles in Italy.
Take in the view from the Crete Senesi Panoramic Viewpoint.
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Where to Stay in Siena – Frequently Asked Questions
☀️ Is it worth it to stay in Siena?
Staying in Siena is a good option for many travelers. It offers a small city vibe with a central location and easy access to Florence, Pisa, Cinque Terre, and the hilltowns of Umbria.
🛌 How many days should I spend in Siena?
You can knock out the major sights of Siena in two days. However, Siena is surrounded by some of the best vineyards and landscapes in Italy, and you can easily enjoy a week exploring this part of Tuscany.
👣 Is Siena a walkable city?
Siena is an extremely compact and walkable city. All of the major sights are located within the famous walls and can be reached by leisurely strolling on cobblestone streets.
Where to Stay in Siena – Final Words
Siena is a gem in the heart of Italy, filled with history, Chianti wine, and Medieval magic. When deciding where to stay in Siena, visitors from every genre of travel have ample options. From snug hotels within the towering walls to expansive Tuscan farms in the countryside, finding great rooms in Siena is thankfully pretty easy.
Due to its fantastic location, famous cathedral, and unequivocal charm, Siena is a very busy tourist destination. Make sure to book your hotel early because some of the best rooms do sell out, and their prices go up as you get closer to high season.
For more information on Tuscany, check out these articles on where to stay in Florence and Pisa!
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