• Jessica White

Siena, Italy: The medieval city that stole my heart

I recently returned from a trip to Italy, a country I have visited multiple times but just keeps calling me back for more. I spent the week exploring and learning about the country with my favorite Italian tour partner, IC Bellagio – taking in every sight, smell and taste of amazing Italia. We buzzed through Rome on vintage Vespas, met Florentine artists and artisans, and sipped Venetian cocktails on the Grand Canal.

This trip I got to visit somewhere I had never been: the medieval city of Siena. And I have to say, Siena took me by surprise.

She charmed me with her fascinating history, passion for her longstanding traditions, and cobblestone alleys. She wooed me with her ancient wine cellars, friendly locals, and culinary delights around every corner. After a day in Siena, I was head over heels in love.

Since returning to the States, I cannot stop thinking about this magical city.

I think Siena is worth the visit on your next trip to Italy – and here are 5 reasons why:

1. A fascinating living history

No one values lifelong loyalty like the Sienese. Since the medieval ages, the city of Siena has been separated into distinct “contrade” or districts. There are 17 contrade in total, each represented by an animal or symbol (for example the Eagle, Unicorn, and Giraffe). Symbols of the contrade, whether it be flags or mosaics, are seen throughout the city – and they are not an ancient legend but a part of daily life. Being a part of a contrade is akin to being a part of a tight-knit family. It is a lifelong commitment you are baptized into and as important to Sienese identity as their family name.

From social life, to celebrations, and even marriages – your contrade is taken into account (even one of the initial questions on first dates!). The many stories, alliances, and rivalries among the groups go back hundreds of years. My questions on the topic were endless, and met by the patient locals with detailed responses and genuine smiles. Having a local guide show you around and bring the history to life is a MUST to truly appreciate this special place.

2. A great home base for Tuscany

Lovers of food and wine dream about the Italian countryside of Tuscany. Siena is right there in the heart of Tuscany and just a stone’s throw from the wine region of Chianti. It is also only one hour away from Florence so easy to fit into many Italy itineraries. With Siena as a home base, you can explore all the wonderful things Tuscany has to offer. I know some of the best wine experts and drivers in the region who can take you around and make sure you see and do all you want to do in the region, no matter if you have one day or four!

3. An ancient (not so) secret tradition

Those in the know might have heard of the Palio di Siena. The Palio is a famous horserace dating back to the 14th century that occurs twice a year right in the main square of Siena. Each of the 17 districts puts forth a jockey for the race that is accompanied by dinners, parades and an intense air of competition. The contrade can and will go to extreme lengths to ensure a win. To win the Palio is the biggest achievement and honor for a contrade, and followed by storming the church by song and celebrations lasting months.

Very few tourists attend this local and unadvertised event, so to get to witness a Palio is an extraordinary and rare bucket-list item. It is not easy, so if you want to go, you want to plan years in advance and ensure you have locals to help you along the way.

4. A glimpse into the life of Italian nobility

The place to stay in Siena is no question the Grand Hotel Continental. Once a palace built by Pope Alexander VII as a wedding gift for his niece, this historic hotel is adorned with the most impressive frescos, rich woods, and lush fabrics. In a prime location, with a delightful restaurant, ancient wine cellar and gorgeous suites – it is the perfect place to rest your head while in Siena.

I highly recommend staying on the noble floors, where the noble family once lived. The ceilings are 18 ft. tall with the original frescos, so you truly feel like you have stepped into an Italian royal’s bedroom. Opening your windows to a view across the rooftops of Siena, while listening to the church bells toll, makes you truly feel like you have been transported in time. As a preferred partner, I will make sure you receive one of my favorite suites and also VIP perks during your stay.

5. And of course, the food!

The most popular Sienese treat is panaforte, a scrumptious sweet made with honey, nuts, spices and fruit that you can find all around town. The second one to try is ricciarelli which are almond-flavored cookies that are light and delicious. There are lots of wonderful places to eat, but two specific favorite restaurants to check out are Osteria Castelvecchio and Osteria Le Logge. Make sure to come with an appetite on your visit to Siena!

My sister used to live in Florence and she always speaks of the City of Lilies as one of her favorite places in the world, but I have to say, as much as I love Florence, my heart absolutely lies with Florence’s southern rival, the beautiful, one and only Siena.

Dying to go to Italy?

Italy has so much to offer with ancient cities, mouthwatering cuisine, charming villages, breathtaking scenery, and so much more. I recommend Italy as a particularly great option for first-timers to Europe, foodies, winos, families or couples celebrating something special, however I would definitely argue Italy has something for everyone. I would love to help plan your version of the perfect Italy vacation. Reach out to me at to get started!

#sienaitaly #italiantravel #luxurytravel #traveladvisor #luxuryitaly #italy #siena

  • Black LinkedIn Icon

Jessica White Travel is an independent affiliate of Brownell Travel, a Virtuoso Member.
©2018 by Jessica White Travel.