Plan a trip to Siena, the storied city in the heart of Tuscany, and a few must-do experiences come to mind: Witnessing the work of masters in the Pinacoteca Nazionale and visiting a nearby vineyard. Watching a horse race, however, might not feature in most people’s bucket list. But what a mistake that is. In fact, the Palio di Siena, comprised of two annual horse-racing events — one of which has taken place in Siena since the 13th century — marks one of the most important cultural events on Italy’s social calendar
Taking over the city’s main square, Piazza del Campo, on July 2 and August 16, the fiercely competitive occasion on each date sees a team from 10 of Siena’s city districts (known as contrade) come together to take on three laps of the square’s makeshift race course; the first horse (with or without its jockey, who rides bareback) to complete the course wins.
While the buzz of the city around each event is electric, Unforgettable Travel Company takes visitors under the skin of this time-honored event. In the days preceding the Palio, guests can experience a private visit to a jockey’s stables, where they will learn more about the rigorous training program and enjoy a private tour of Siena and its secrets, including a VIP visit to one of the 17 contrade for a behind-the-scenes look at the history of this special race. And then, the big day. Perched high above the chaos of the square below, Unforgettable Travel Company guests will view the race from a private balcony with prime views of the finish line, in the very location that Sienese elite have frequented for decades.
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This experience can exclusively be booked by Elite Traveler readers, directly with Unforgettable Travel Company with the code ‘ELITE.’ From $42,950 per person, based on two people travelling. Contact Graham Carter, Unforgettable Travel Company co-founder, graham@unforgettabletravelcompany.com, +1 646 921 2650, unforgettabletravel.com
Day 1: A Grand Arrival in Florence
“Arrive today into the one of the world’s most revered cities, Florence, to begin your Italian journey.”
Touchdown in Florence, where a private driver will take you to Four Seasons Hotel Firenze, your home for the next two nights. The elegant hotel is set in verdant private gardens with views over the grand Duomo. Spend the day settling into your suite before the itinerary kicks off in earnest tomorrow.
Day 2: Renaissance, Haute Couture and Gastronomy
“Step into Florence’s most iconic worlds — where Renaissance art, Michelin-starred cuisine and high fashion unfold in private moments crafted just for you. From exploring the hidden chambers of Palazzo Vecchio to an intimate encounter with the Emilio Pucci Heritage Hub, today is a celebration of Italian elegance in all its forms.”
Wake up bright and early for your first exclusive excursion: a private tour of Palazzo Vecchio. The 13th-century castle now acts as Florence’s Town Hall and hosts numerous historic artworks and artefacts (there’s rumor of a hidden Leonardo Da Vinci mural in its walls). A dedicated guide will share the building’s secrets.
Today’s lunch is hosted at the Michelin-starred Osteria Gucci by Massimo Bottura, a glamorous restaurant that melds Italian culinary tradition with international influence.
After lunch, it’s on to the Emilio Pucci Heritage Hub. A rare experience with private access to Palazzo Pucci, this visit includes a deep dive into the expansive Emilio Pucci archives, containing over 70 years of designs and rare pieces. Round off a memorable day in the birthplace of the Renaissance with a dinner at Palazzo Gondi – a privately owned mansion typically open to the public by appointment only.
Day 3: Tuscany’s Wine Country
“As you wind through the Tuscan hills, the landscape opens into a world of timeless charm — where storied vineyards and boutique wineries carry on generations of passion. Your visit to Capannelle, home of the famed 50&50, offers more than a tasting: it’s a journey into craftsmanship.”
Well rested after a second night at Four Seasons Hotel Firenze, make the short journey into the rolling Tuscan hills for a guided tour of the boutique Capannelle Winery, regarded for its signature 50&50 wine. Linger over a homemade lunch at the winery, served al fresco with views of the sweeping vineyards.
Suitably satiated, transfer to Rosewood Castiglion del Bosco, where you will be staying for the remainder of your trip. A sublime retreat in the middle of a 900-year-old estate, the sprawling hotel not only offers stylish suites imbued with a sense of classic Tuscan luxury but also incorporates a golf course, winery, cooking school and spa.
Day 3: A Day of Relaxation and Culinary Indulgence
“Relax today, spending time unwinding and mastering one of Italy’s gourmet classics.”
Today is all about indulging in the copious amenities and experiences at Rosewood Castiglion del Bosco. Spend the morning preparing your lunch with an authentic pizza-making class at the La Canonica Cooking School, including a tour of the neighboring organic kitchen garden.
In the afternoon, make your way to the spa for a relaxing treatment, followed by a stint in the sauna and a dip in the lavender-fringed outdoor swimming pool. As the sun sets, indulge in a pre-dinner alfresco spritz or a local wine.
Day 4: Immersed in the Spirit of the Palio
“Be a part of the time-honoured preparations for the Palio today, heading behind the scenes to witness the ceremony and traditions involved in advance of the main event.”
On the day before the Palio di Siena, you are invited to be a part of the time-honored preparations. The day begins with an exclusive visit to one of the Contrada headquarters, churches and stables, where the horses and their jockeys are preparing. You will also be presented with a traditional Contrada silk foulard to take home as a memento of your stay.
After lunch at a local Sienese restaurant, head to a historic apartment with prime views over the Provo Generale – the rehearsal race for tomorrow’s main event. Rounding off the day is a propitiatory dinner in one of the Contradas – an exclusive pre-race celebration. A private guide will accompany you throughout the day to share insider knowledge and stories.
Palio di Siena
First held in the 13th century, Palio di Siena is a horse race held twice a year in the Tuscan city of Siena. It takes place in the Piazza del Campo, the city’s central square, which is transformed into a packed dirt racetrack. Seventeen horses, each representing one of the city’s neighborhoods — called contrade — race bareback around the square in a thrilling contest that lasts just over a minute. But the Palio is far more than a race; it’s a deep-rooted civic ritual that stirs fierce pride, rivalry and tradition among the Sienese.
Each of Siena’s 17 contrade has its own emblem, colors, church and loyal following. The race is preceded by days of elaborate ritual: horses are blessed in churches, the jockeys are assigned by lottery and the city stages a grand historical procession called the Corteo Storico. The rivalries between contrade are intense and emotional — centuries old and deeply felt. Once the race begins, strategy and interference are part of the game; rules are few, and alliances or betrayals are not uncommon. Winning brings immense honor to the contrada, celebrated with feasts and parades.
The Palio race is short — just three laps of the Piazza del Campo — but it’s packed with drama. The track is tight and uneven, and horses often crash or lose their jockeys mid-race. Yet even a riderless horse can still win, as long as it crosses the finish line first. The prize is the drappellone, a hand-painted silk banner that becomes a symbol of glory for the winning contrada. Tens of thousands of people gather in the square to watch, and the atmosphere is electric.
Day 5: The Thrill of the Palio
“This is it: the day of the Palio. The streets of Siena buzz with excitement as adrenaline builds to the race itself.”
The main event: The first of 2026’s two Palio di Siena races is held on July 2, and you have a VIP ticket. A full-day private guide will once again join you for the day, escorting you as you witness the sacred blessing of a horse and attend the historical Parade at the Duomo.
You’ll have the opportunity to view the race itself from a grand palace overlooking the Piazza del Campo, all in the company of a legendary jockey who will regale you with tales of their time racing. Race completed and winner crowned, it’s off to a post-race celebration dinner at an elegant restaurant in the Piazza del Campo.
Day 6: A Memorable Goodbye
“It’s time to say goodbye after a memorable week in Italy.”
After six days in Italy, it’s time for a private transfer back to Florence Airport – memories of a remarkable trip firmly in tow.
