Siena

A delicious Tuscan delight.

Siena is a UNESCO-listed treasure-trove and Tuscany's largest hilltop town. Legend has it that after Remus cofounded Rome, his sons founded Siena. There's no evidence to support this tale, but there's been a Roman trading post here since at least the time of Christ. The city's strategic position was strengthened with the development of the Via Francigena, the road which linked Paris and Rome.

In its heyday, Siena was a rival to Florence. Florence eventually got the upper hand under the leadership of the Medici family and Siena was incorporated into the territory of Florence. This rich legacy can be seen throughout the old town of Siena, with its palazzos, towers and churches. Probably the most significant expression of Siena's history is wrapped up in the Palio di Siena, as much a show of neighborhood pride as much as it is a bareback horse race, this pivotal event takes place in July and August every year.

Where to stay in Siena

With accommodation options ranging from a family-run 3-star farm-stay just outside of town, to a 5 star boutique hotel located in a 17th century palazzo, whatever kind of accommodations you're looking for, we've got it covered. Get in touch with us for a free travel consultation. Once we start preparing your customized itinerary we will present our recommended options for you to choose from.

Stylish Modern Hotel

Large hotel offering terrace bar with countryside views.

Historical Luxury Hotel

Ever wanted to live like royalty? The Continental is Grand in every sense. You're guaranteed a luxurious and memorable stay.

Charming Boutique Hotel

Enjoy the charm of a bygone era with all modern comforts, in an elegant mansion within walking distance to all amenities and attractions

Things to do in Siena

Hit the ground running in Siena with a private walking tour, or spend a day exploring Tuscany on a day trip to San Gimignano, Chianti, Val d’Orcia, Monteriggioni, and Montalcino (two of which are UNESCO listed, and all of which are memorable). When we send you your customized itinerary you will be able to choose additional excursions to include in your vacation package or consider adding later.

San Gimignano, Chianti & Montalcino Small Group Tour

Siena Private Walking Tour

Glowing Reviews from Our Guests

5.0 / 5

Average of our Guest's Ratings of our Siena vacation packages, based on 3 reviews

Linda, Robert, William & Carmen

Colorado

If you want a worry-free vacation, choose JayWay Travel. They go the "extra mile" to make your vacation so enjoyable and so memorable!

Year : 2019
Visited : Italy
Itinerary : Rome, Cruise, Rome, Siena, Florence, Lake Como
Rating :

5 / 5

Year : 2019
Visited : Italy
Itinerary : Rome, Cruise, Rome, Siena, Florence, Lake Como
Rating :

5 / 5

Julia & Kirk

Colorado

Love the friendly people you interact with either on the phone, or via email. The Guest Page is so easy to use with loads of great information. JayWay Travel makes it very easy to build a great completely customized vacation trip.

Year : 2019
Visited : Italy
Itinerary : Venice, Bologna, Milan, Levanto, Florence, Siena, Rome
Rating :

5 / 5

Year : 2019
Visited : Italy
Itinerary : Venice, Bologna, Milan, Levanto, Florence, Siena, Rome
Rating :

5 / 5

Jacqueline, Timothy & Lauren

Texas

JayWay Travel listened to our thoughts about the trip and customized the experience to be better than what we expected. I appreciate their ability to handle the detail planning to create a custom, hassle-free vacation with private transfers, beautiful local hotels and excellent dining recommendations. I also liked the comfort of having someone in the country I could call if there were questions or a change in plans. An overall excellent experience!

Year : 2018
Visited : Italy
Itinerary : Rome, Siena, Florence
Rating :

5 / 5

Year : 2018
Visited : Italy
Itinerary : Rome, Siena, Florence
Rating :

5 / 5

Frequently Asked Questions about travel to Siena

What are Siena's prices like?

A quick lunch with a drink costs around 25 euros. Museums and landmarks generally cost 10-20 euros. For a full dinner, budget at least 40 euros.

How can I get around Siena?

Siena's center is best explored on foot. Taxis are available, but cost about 20 EUR for two kilometers.

Is Siena safe?

Siena is safe, especially in the center, but pickpocketing can be a problem in crowded, touristy areas.

Does Siena have options for those with dietary restrictions?

Siena has increasingly more options for people with dietary restrictions and intolerances. Many places (such as Osteria il Ghibellino) offer gluten-free options. You can also find many vegetarian options in most restaurants, and places specializing in vegetarian/vegan dishes, such as Bio e Te.

How long should I stay in Siena?

We suggest spending around two nights in Siena, in order to being able to enjoy its cultural richness, plus a potential third night to make room for a day trip.