7 unique things to do in Siena

by Andrea Gambaro  |  Published May 11, 2018

Wine, truffles, culinary innovation, the world-famous horse race and the celebrated Tuscan countryside. Our list of unique things to do while in Siena includes all that and more.

Torre del Mangia is one of Italy’s highest ancient towers (Photo: alex via Flickr)

Siena is the quintessential medieval city, a feast of architectural wonders, Gothic gems, narrow streets bustling with artisanal shops, and an enviable food and wine culture. Start your visit from the famous Piazza del Campo, shell-shaped and watched over by the tower of Palazzo Pubblico. Twice a year, the square comes alive with the centuries-old Palio di Siena, a horse race between the city’s contrade (wards). Each of them has its own museum, church, fountain and customs, so that you’ll have plenty to explore. A few escapes from the city will be on your list too, to discover the marvels of the surrounding countryside.

Discover the Palio di Siena

The history of the Palio, Siena’s famous horse race, goes back centuries. Twice a year, on July 2 and August 16, the 17 contrade that form the city race in the shell-shaped Piazza del Campo, keeping alive a local folklore that remains essentially true to its ancient origins. As the spirit of the Palio permeates the city all year long, a themed tour is a great way to experience it. Demetra‘s tour starts in Piazza del Campo and includes all the significant locations related to the Palio, such as the Duomo, the church of Santa Maria in Provenzano, and a contrada. While learning all about the history of the Palio, there will be also time for local snacks and drinks.

Meeting point – Piazza del Campo, Siena 53100

The Palio in full gallop (Photo: Janus Kinase via Flickr)

Go on a wine-themed day trip

While in Siena, a day trip to explore the indulgent wine culture of the surrounding regions is always a good idea. Grape Tours takes small groups of people (max eight) around the Tuscan countryside, reaching the wine regions of San Gimignano, Montalcino, Montepulciano and Chianti. Opt for San Gimignano if you’re looking for white wines, while the other destinations are mainly about reds. Each tour includes two family-owned wineries, tasting sessions, a visit to the local village, and typical food specialties at lunchtime. Tours are guaranteed to run with just two people.

Meeting point – Piazza San Domenico (by the church), Siena 53100

A typical sight during a wine tour (Photo: Grape Tours)

Dine with the chefs at Particolare di Siena

Just outside the historic centre, Particolare di Siena seeks to tell the story of Siena through innovative cuisine. An obsessive selection of local and seasonal produce is key to the restaurant’s philosophy, which results in a modern menu designed to make each ingredient stand out. The ambience is no less ambitious, bringing together different spaces each conveying its own soul and character. The ‘Chef Table’ is an exclusive dining experience in a separate lounge that faces the open kitchen, where you’ll enjoy a customized menu while watching the chefs at work (advance booking required).

Via Baldassarre Peruzzi 26, Siena 53100

The chefs won’t mind you watching (Photo: Particolare di Siena)

Explore the countryside on a vintage Vespa

Is there a more romantic way of winding up and down the Tuscan slopes than on a 1960s Vespa? Based in Montepulciano, Vintage Tours is a rental company and tour operator that provides motorcycles and cars from the 1960s, 1970s and 1980s, adding more flavour to your tour of the hills around Siena. Whether you’ll decide to tour with them or on your own, Vintage Tours will give you advice on what itineraries to follow and what attractions to look for. Renting a car or a motorbike will grant you discounts at the country house Le Stringaie, also located in Montepulciano.

Piazza dell’Amicizia 3, Bivio di San Biagio, Montepulciano (Siena), 53045

Enjoy the ride, but make sure not to end up on the motorway! (Photo: Domenico Cammarano)

Be initiated into the secrets of Siena

With Siena Bike Tour, you can cycle around the city and explore it in a different way. One of the most intriguing tours they offer is ‘Mysterious Siena’. Far from being the usual guided walk about witches and ghost stories, this tour is an insightful account of riddles hidden in history, streets and buildings. Touching on esoterism, religion, alchemy, masonry, Templars and the Holy Grail, Mysterious Siena presents the city in a very particular light. It is only one of the cycling tours offered by Siena Bike Tour.

Meeting point to be arranged

Not all is as it seems with Mysterious Siena (Photo: Paolo Ricci)

Make your stay a relaxing retreat

Located a half-an-hour drive away from Siena, Le Logge di Sopra is an ideal choice if you want a relaxing immersion in Tuscan country life. This family-run bed and breakfast lies in the heart of the Crete Senesi along the panoramic Lauretana Road, in close proximity to the thermal waters of Rapolano Terme. Housed in a 16th-century farmhouse recently restored, Le Logge di Sopra features a beautiful garden, a swimming pool and a solarium blessed with a vast and spectacular view. Both rooms and apartments are available, providing your stay with a warm, rustic and stylish touch.

438 Lauretana (km. 13+100), Asciano (Siena) 53041

Logge di Sopra is housed in a 16th-century farmhouse (Photo: Le Logge di Sopra)

Follow the scent of the truffle

Alessandro Pellegrini opened Siena Tartufi after 15 years of experience as a truffle hunter. He describes his shop in the heart of Siena as ‘small and delightful’, just like the product it promotes. In addition to fresh truffles, you’ll find all sort of products flavoured with it, such as oil, honey, beer, patés and much more. Alessandro also organises hunting tours in the woods around Siena, in the company of his faithful truffle dogs Pepita and Moka. He promises to make you experience the unique excitement of truffle hunting, the fruit of which will make for a special souvenir from Siena.

Vicolo dei Pollaioli 6/8, Siena 53100

Alessandro, Moka and the truffles (Photo: Siena Tartufi)