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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.
4-star hotel
One the largest hotels in the historical center!
5-star deluxe hotel
Ever wanted to live like royalty? The Continental is Grand in every sense. You're guaranteed a luxurious and memorable stay.
Boutique
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 1 review

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!

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
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