A ONCE IN A LIFETIME Palio experience
From the first rituals to the final race, a journey into the soul of the Palio di Siena, guided by those who know it from within.
JULY PALIO EXPERIENCE - WEEK 1 PROGRAM
ARRIVAL: Settle in at leisure
10:00 – TOUR OF SIENA, Afternoon at Leisure
Explore Siena, one of Italy’s most beautiful medieval cities and a UNESCO World Heritage site—rich in art, history, and timeless Tuscan tradition.
Your private guide will lead you through Siena, starting at Basilica of San Domenico, home to the relic of Saint Catherine of Siena. Strolling through the picturesque contrade, you’ll arrive at the shell-shaped Piazza del Campo—one of the world’s most beautiful squares—where the legendary Palio di Siena takes place each summer. With your Sienese guide, you’ll uncover the stories and traditions that make this city so uniquely alive.
During your tour, you’ll stop at a renowned local bakery to taste Ricciarelli—soft, delicate, and deeply rooted in Sienese tradition.
The experience ends in Piazza del Duomo, where the breathtaking marble façade of the Siena Cathedral awaits. Along the way, your guide will take you off the beaten path, revealing the city through a true local’s eyes.
10:00 – TOUR OF THE CHIANTI REGION, Duration: 6 hrs.
Set in the heart of Chianti, this landscape of sunlit vineyards, rolling hills, and timeless villages is more than a destination—it’s a way of living, shaped by centuries of winemaking tradition. Here, every glass tells a story of culture, passion, and place.
Follow winding country roads through hills lined with Sangiovese vines, where soil rich in clay and limestone gives Chianti wines their unmistakable character. From the bold structure of Chianti Classico to the elegance of Chianti Rufina, you’ll learn to recognize the nuances that define each expression.
VISIT OF CANTINE ANTINORI
Visit a private wine estate and cellar, enjoy a guided tasting paired with Tuscan cuisine
This winery is an architectural masterpiece, a place where tradition and innovation coexist in perfect harmony, it was built entirely with local materials—terracotta, wood, and natural tones that reflect a deep respect for the Tuscan landscape and the family’s centuries-old bond with the land, dating back to the 1400s.
Carved into the hillside and almost invisible from the outside, the cellar is both fascinating and highly innovative: designed for gravity-flow vinification, it naturally maintains a constant temperature of 14°C year-round, eliminating the need for heating or cooling and ensuring ideal conditions for wine production and aging.
From its panoramic terrace, the estate overlooks the rolling Chianti countryside, with vineyards planted with Sangiovese and other historic varietals—an authentic tribute to the beauty and heritage of this land.
10:00 – TOUR OF FLORENCE, Duration: 3 hrs.
Discover the timeless beauty of Florence with a private guide on a cultural stroll through its most iconic landmarks.
Begin in Piazza del Duomo, the vibrant heart of the city, home to the magnificent Cathedral of Santa Maria del Fiore, crowned by Filippo Brunelleschi’s extraordinary dome, alongside Giotto’s Campanile and the Florence Baptistery.
Continue to Piazza della Signoria, then explore the lively Mercato del Porcellino—don’t forget to touch the famous boar for good luck—before ending at the iconic Ponte Vecchio, lined with historic goldsmith shops.
Includes private guide and skip-the-line tickets to Brunelleschi’s Dome
14:30 – VISIT UFFIZI AND ACCADMIA, Duration: 3 hrs.
Step into Florence, the celebrated birthplace of the Renaissance, where art lives in every corner. With your expert private guide, enjoy a cltural journey through Italian artistic excellence, exploring two of the country’s most iconic museums.
Begin at the Uffizi Galleries, a masterpiece in itself, with nearly one hundred rooms showcasing works by Giotto, Sandro Botticelli, Leonardo da Vinci, Raphael, Michelangelo, and Titian—a living journey through the history of art.
Then continue to the Accademia Gallery, where Michelangelo’s iconic David stands in silent, breathtaking power.
Includes private guide and skip-the-line access to both museums (passport required).
ENJOY GUILD SIENA, our pool, our restaurant, the Michael’s bar and the cool breeze in our 4 hectare forest.
FROM 09:00 – TO EVENING, Piazza del Campo, Siena
In the heart of Siena, experience the extraordinary intensity of the Palio di Siena—a centuries-old rivalry between the city’s contrade, brought to life in two electrifying races each year. Every contrada competes with its own horse and jockey, turning the city into a stage of passion, pride, and emotion.
Enjoy the Palio from privileged vantage points—private terraces, elegant apartments, or exclusive windows overlooking Piazza del Campo—for a truly intimate and comfortable experience.
Beyond the race, immerse yourself in its rituals: attend the Tratta (horse allocation), witness the Prove (trial races), join a traditional contrada dinner, and experience the moving blessing of horse and jockey. For a deeper perspective, you may even follow the event alongside a former jockey.
Every detail is tailored to you, creating a deeply personal and unforgettable journey into one of Italy’s most powerful living traditions.
09.00 – LA TRATTA , the selection and assignment of the horses.
Around 9:00 AM, the Tratta begins—one of the most decisive moments of the Palio di Siena—when horses are tested and assigned to the ten competing contrade. After veterinary checks, they run trial laps in Piazza del Campo to assess their suitability for the track.
By early afternoon, following the Captains’ selection, each horse is paired with a contrada by lottery—an irreversible match that ignites raw emotion. In that instant, joy erupts or disappointment cuts deep: contradaioli celebrate, tease rivals, argue, sometimes even clash—because here, fortune is never neutral, and every draw feels like destiny.
That evening, the first trial (Prova) takes place, as horses and jockeys begin to test the track. These runs are less about winning and more about preparation, strategy, and preserving energy for the final race.
Includes reserved places in a private Palazzo on Piazza del Campo to participate to the Palio from a privileged view point.
FROM 09:00 – TO THE AFTERNOON – THE TRIALS, Piazza del Campo, Siena
From 9:00 AM, the Seconda Prova (second trial) takes place, with horses entering the canape in reverse order from the previous evening. Later that day, the Terza Prova (third trial) unfolds, this time following the official order established during the horse assignment —b ringing increasing intensity as strategies begin to take shape: horse vs. horse, traditionally contrasting contrade trying to find alliances with friendly ones.
The heart of the game starts here, as emotions get progressively more intense.
JULY PALIO EXPERIENCE - WEEK 2 PROGRAM
FINAL REHEARSAL AND DINNER IN THE CONTRADA, h. 20.30 historic center, Siena
On the following day, the ritual of the Palio di Siena deepens, blending spectacle, strategy, and community.
In the morning (9:00 AM), the Quarta Prova takes place, with horses entering the canape in reverse order from the previous evening. That night comes the Prova Generale, the final full rehearsal before the race—announced by the firing of the mortaretto and preceded by the dramatic mounted charge of the Carabinieri.
After the trial, the city transforms. In each competing contrada, long communal tables fill the streets for the Cena della Prova Generale: hundreds gather—residents, leaders, guests—around the jockey, sharing food, songs, speeches, and hopes of victory. Later, behind the scenes, Captains and their lieutenants meet with allied contrade, forging quiet agreements and strategies that may shape the outcome of the race.
To join a contrada dinner is to step into the soul of Siena: long tables, traditional dishes, songs rising in unison, playful teasing between rivals, and an atmosphere charged with belonging. It’s pure, joyful togetherness—where strangers become part of something deeply shared.
PALIO DAY, Piazza del Campo, Siena
On the morning of the race, at 7:45 AM, a solemn Eucharistic celebration—the Messa del Fantino—is held at the chapel of the Palazzo Comunale, led by the Archbishop of Siena in the presence of the Captains and jockeys of the competing contrade.
Shortly after, at 9:00 AM, the Provaccia takes place—a light, almost symbolic trial where horses are spared and tension quietly builds. Following it, Captains and jockeys gather at City Hall for the official registration and the presentation of the racing silks—after this moment, no changes are allowed.
In the early afternoon, the city holds its breath for one of the most moving rituals: the blessing of horse and jockey in each contrada’s oratory, sealed with the priest’s powerful words—“Go, and return victorious.”
By late afternoon, the historic parade departs from Piazza del Duomo, winding its way to Piazza del Campo. As the drappellone is raised and the final flag performance unfolds, anticipation reaches its peak—then, suddenly, the race begins.
ENJOY GUILD SIENA, our pool, our restaurant, the Michael’s bar and the cool breeze in our 4 hectare forest.
VINTAGE CAR RIDE OF CHIANTI, Pick up at 08.00 – duration: 5 hrs.
Leave behind the cultural buzz of Tuscany’s cities and embrace the quiet beauty of Chianti with a stylish ride in a vintage car. Whether aboard a classic Fiat 500 or similar, sit back as your driver guides you through rolling hills and timeless landscapes.
Wind along scenic roads lined with stone farmhouses, vineyards, olive groves, Romanesque churches, and medieval castles—traces of a history shaped by rivalries between Florence and Siena. Every turn reveals a view worth a pause.
Includes private vintage car with driver and panoramic tour of the Chianti countryside. (Please note: vintage cars registered before 1976 may not be equipped with seatbelts, in accordance with Italian law.)
GOLFING IN TUSCANY, Pick up at 10.00 – duration: 8 hrs.
Soar above the rolling hills of Chianti on a breathtaking hot air balloon flight, discovering Tuscany from an entirely new perspective. As you rise gently into the morning sky, the world below unfolds into a tapestry of vineyards, medieval villages, and castles bathed in soft, golden light.
Drift silently over this timeless landscape, where every view feels like a painting and every moment invites stillness, wonder, and unforgettable beauty.
Includes private hot air balloon flight, breakfast, and round-trip transfer by private car. (Flight subject to weather conditions.)
BALLOONING ABOVE THE CHIANTI HILLS, Start up at 05.00 a.m.
Soar above the rolling hills of Chianti on a breathtaking hot air balloon flight, discovering Tuscany from an entirely new perspective. As you rise gently into the morning sky, the world below unfolds into a tapestry of vineyards, medieval villages, and castles bathed in soft, golden light.
Drift silently over this timeless landscape, where every view feels like a painting and every moment invites stillness, wonder, and unforgettable beauty.
Includes private hot air balloon flight, breakfast, and round-trip transfer by private car. (Flight subject to weather conditions.)
TRAVEL ARRANGEMENTS SPECIFIC FOR EACH GUEST, Pick up at Guild Siena
As your time at Guild Siena comes to a close, you leave with Tuscany in your eyes—its light, its landscapes, its quiet beauty now part of you.
In your heart, you carry the warmth of the Guild Way: thoughtful care, shared moments, and the feeling of truly belonging. And with it, new friendships—genuine connections to be nurtured long after you return home.
And perhaps, above all, you leave with a quiet, certain dream: to come back soon.
AN ALL INCLUSIVE OFFER, SO THAT YOU CAN LET GO, ENJOY AND LIVE LIKE AN ITALIAN
The Guild Way Hospitality approach,
an English speaking guest ambassador as your point of reference for every need,
all of the above activities and excursions
the security of having medical assistance at hand, if necessary
In superior suite for up to 2 people:
living room with fitted and equipped kitchenette bedroom with king-size bed,
working area, private wi-fi and A/C, en-suite bathroom and large walk in closet
Food and beverage included: breakfast, lunch and dinner @ GUILD SIENA
If you book before the end of may,
15% discount
on the whole amount of your booking.