Evocative Siena

By Rebecca Toy  

Just a short train ride from Florence, THIS TUSCAN CITY is an intimate introduction to the iconic region

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Imagine a labyrinth of narrow cobblestone lanes climbing up, up, up a picturesque hillside, snaking between quaint, Gothic, near-millennia-old buildings to reach the pinnacle structure lording over a historic Italian village. A hilltop cathedral is a masterpiece of intricately detailed architecture with its own maze of soaring arched ceilings donning frescos by artists none other than Donatello and Michelangelo. This is Siena, a town that has remained medieval in size and tradition.

Familiarity comes easily here—nods from recognizable faces in door frames along routes that quickly become muscle memory. Then suddenly, at the turn of a corner—an arresting fresh view where the street drops and tiled villas pierced by cathedral towers stretch out into a neon blue twilight.  

This is the enduring allure of Siena—disarming visitors with the ease of small-town rhythms before stunning them with aesthetic glories that stack up against the city’s historic rival, Florence. An hour from its famous and often overrun neighbor, Siena makes a laid-back alternative base and gateway to Tuscany. 

It’s easy to tackle the condensed city’s Duomo, famous Piazza del Campo and pinacotecas (art galleries) before hopping on to the next destination. But stop here. Soak it in. The rich cultural heritage beckons.

Photo Courtesy of Comune Di Siena

The Soul of Siena 

The secret to Siena’s civic spirit and livable center hides in plain sight. “There’s much more of that sense of community because it’s a small town filled with 17 villages that we call contrade,” says Anna Piperato, Siena & Italy Tours owner, professor and Lupa contrada member. Each centuries-old contrada has fanciful names and symbols (She-Wolf, Unicorn, Snail, Dragon) and bestows pride and identity. “If you come for only three hours, you’re not going to feel it,” says Piperato. 

The amalgamation of this cultural pride—with Catholic revelry, of course—is the Palio of Siena, a famous, centuries-old horse race. But this is no ordinary state-fair-style event. It’s a four-day affair that happens twice yearly—in July and August. Laced with rich formal dress, a rainbow of contrada flags waving and rousing contrada songs bouncing off the walls, the event culminates with more than 50,000 people wedged into the center of the piazza to witness the 60 to 90 intense seconds of thundering hooves of ten horses wildly racing around the perimeter in an attempt not to win, but simply to prevent a rival contrada racer from winning.

Photos Courtesy of Comune Di Siena

Year-round, each contrada makes up the city’s heart with traditions, deep community connections, hidden social clubs, rivalries and celebrations. Piperato recommends visiting the contrada museums and churches with local guides who can get you behind the scenes–even into the contrada social clubs. “All of them are beautiful. Yes, even our rivals’!” Piperato says. 

Photo Courtesy of Comune Di Siena

Art Immersion  

Like any Italian destination worth its salt, Siena has striking art and architecture packed into its spaces like an overstuffed attic. In 2024, the renowned Duomo is offering a new view. For the first time in history, guests can access the rafters with the Porta del Cielo (Gate of Heaven) tour and see the floor-to-ceiling artistry. 

Another limited experience goes from the heights of the city to its depths. This hidden tour takes you into the Bottini di Siena, the ingenious ancient underground aqueducts that feed the city’s copious fountains. Piperato warns that it is tough to get tickets, but with enough planning, you could get lucky. Visit Siena Official coordinates these exclusive adventures. 

Specialized tours will take you from reveling in works of art to creating them. Siena Experience Italian Hub offers artisan introductions and ceramics labs for families. Make sure to join its tour of artist Marco Caratelli’s 14th-century studio. You’ll learn the historical techniques to work in gold-ground medieval painting, creating your own work using plaster, clay, gold and egg tempura. 

Photo Courtesy of Comune Di Siena

Photo Courtesy of Molly Lee Greenblat

Tasting Tuscany 

It’s as easy to find a tour of the iconic countryside that fits your culinary desires as it is to enjoy a glass of Chianti. Consider devoting a day to relaxing at a farm that counts Jack Nicklaus and Michael Jordan as fans: Tenuta Casanova. Owners Silvano and Rita Cis stepped away from corporate life to rebuild a property once owned by the Vatican. The family enjoys sharing their authentic culture and making new friends on their restored farm, which mirrors one from the 16th century. “People live the same lives here, day by day,” Silvano Cis says.

Less than an hour from Siena, Tenuta Casanova offers three experiences. The most popular is the lunch featuring samples of its namesake wine, olive oil and balsamic vinaigrette, which are unavailable in stores. For those wanting to jump into the kitchen, a local chef guides a small-group cooking class through 12 recipes over seven hours, savoring results throughout the day—book at least three months in advance for this memorable experience.

“Tenuta Casanova is a magical place because of its beauty and the family,” says Molly Lee Greenblatt of Denver, who visited in the summer of 2023. “The family is as beautiful as the scenery. The organic winery, with its emphasis on high-quality and curated ingredients, is impressive.”

Photo Courtesy of Molly Lee Greenblat

Two years ago, the family added an exclusive dinner experience limited to just one party on the entire farm. The sparkling light of the Tuscan sunset is a striking backdrop for this spectacular gourmet dinner with authentic Tuscan recipes. 

“You will see something that is not so common here,” Silvano Cis says. “People will cancel the rest of the tour and stay at the farm all day for quiet moments.” And the proof is in the return rate; over the last decade, at least half the farm’s bookings are repeat visitors. 

Taste Tuscan Treasures Without Leaving Home 

If you can’t make it to Siena soon, Silvano and Rita Cis will bring the delights of Tenuta Casanova to you—virtually. Organize a private tasting for your family and friends, and they will mail you the farm’s wine, extra virgin olive oil and balsamic vinaigrette for only a nominal shipping fee. The engaging couple will walk you through a complete and technical tasting while sharing stories of the Siena countryside. Book your virtual tasting at

Photos Courtesy of Italy Unfiltered

Harvesting Oil 

October hosts a hallowed Tuscan tradition. Olive harvest dominates the countryside as families bring in the fruits of their trees to fill their jars for the year. “This is a chance to understand how the whole community in Siena comes together to harvest this precious oil,” says Deb Larsen, co-owner of Italy Unfiltered with her Sienese husband, Massi Mori. “It’s a part of the yearly cycle: a stake in the ground and a defining moment. Fall is here!”

Beginning October 16, 2024, and running for the next month, depending on the harvest, guests can add the olive oil mill to their sightseeing or tasting tours. The locally owned mill hosts families in two-hour increments around the clock, bringing olives in buckets for processing into coveted oil ready for the jars. Not a drop goes to commercial sales; this is the families’ supplies for the year–or until it’s gone.

The experience, best booked at least five months in advance, includes education and a tasting fresh off the press. “You’ve never had anything fresher in your life,” Larsen says. “We take it right off the spigot and pour it on the bread.”

Visit Siena Official

Siena & Italy Tours

Siena Experience Italian Hub

Tenuta Casanova

Italy Unfiltered