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7 Days

Join us to experience the most exciting horse race that no one has ever heard of!

Experience the Palio, a week-long cultural event culminating in a thrilling horse race in the square of the charming city of Siena. Here, you’ll witness one of the most fascinating and complex cultures on the planet. You’ll marvel at the colorful outdoor light fixtures that line the contrada…or neighborhoods, the huge vibrant banners that hang over the streets, and enthusiastic neighborhood parades, complete with flag-tossing, drum beating, and passionate singing. The Palio is a 500 year old social, political, historical and religious event that pits neighborhood against neighborhood in an ancient rivalry, and truly defines life in Siena.

You will stay in the midst of all of this excitement for several days to wander and experience one of the most vibrant cultures in all of Europe. Best of all, you will witness the most amazing race you’ve ever seen. You’ll visit one of the contrada that is running the race, visit their museum, attend their private pre-race dinner, hang out with them, and cheer “our” horse on in the race! Once you understand the significance of the contrada and the constant daily influence of the Palio, the spirit of Siena will come alive, and you’ll feel like a part of it all!

From the emotion-laden Drawing of the Horses, to the dinner, parades, practices, and pageantry…it all leads up to a wild 3-lap race that is the culmination of the year for the people of Siena. We’ll be immersed in the excitement, and cheering our contrada on from the comfort of our private apartment (with food and wine, of course) overlooking the square, complete with huge balconies for a viewpoint that can’t be beat!

During the week we’ll also manage to get out into the lovely Tuscan countryside to visit some vineyards, taste some wine, learn how to cook Tuscan-style, and have plenty of free time to explore on our own. We generally only have 12 people on our Palio extravaganza, drop us a line if you’re interested.

Tour Dates & Pricing

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Day 1 - The Medieval City of Siena

Your Italian adventure starts this afternoon at our meeting point in a private room off the lobby of our hotel in the medieval city of Siena. (You'll be provided with detailed arrival and departure instructions to help you coordinate your flights and travel.) When you combine the history of Siena with the current traditions of its inhabitants, you'll find that Siena is arguably one of the most fascinating, one of the most unique, and one of the most vibrant cultures in all of Europe! The Senese have kept alive the customs of their ancestors, and in fact live it every day.

You’ll grab a drink with your group, then meet your private Siena guide and sit down to a short presentation about the Palio. Afterwards your guide will lead you on a walking tour of the city, explaining all of the history and customs of this amazing place. Of course the tour will be mainly focused on the contrada (neighborhoods) and their preparations for the upcoming Palio. As you explore the city you'll marvel at the huge span of history represented in its architecture, from the Romans to the Renaissance to the Goths, Siena is a landscape of all the civilizations that have dominated here.

Tonight we’ll have an excellent dinner at one of our favorite local out-of-the-way ristorante. Tuscan cuisine, like all Italian regions, reflects the best of the local area. Fresh pasta is prevalent, along with salami, prosciutto, chicken, beef, and pork, with nearly everything organic and free-range, which has always been the natural way for Italians. Of course you'll find some of the world's best olive oils here, along with tomatoes, peppers and melanzane that are bursting with flavor. And the cheeses of this region are legendary, with literally dozens of varieties running the gamut from fresh and creamy to aged and robust...truly an epicurean's heaven! Italian wines need no introduction...during your time in Italy with us you'll be introduced to some exquisite wines that can be found nowhere else, from marvelous honest farmhouse productions to wines from some of the top estates in the world, and everything in-between.

Day 2 - Drawing of the Horses

After breakfast today you’ll have the morning free to explore the city. At midday we’ll gather to walk down to the main square of the town, the stunning Piazza del Campo, for the second-most important event of the week…the wild, wooly and always exciting...drawing of the horses!

This is where the contrada find out if they have a fast horse or a slow horse, and from this point they have to find and hire their jockey (who are mercenaries, highly paid but fundamentally unfaithful, and often bribed…or even kidnapped) and decide on a strategy. The most important thing in LIFE for a Senese is to win the palio…but the SECOND most important thing is to prevent your ancient enemy contrada from winning…so from this point plots are hatched, alliances are formed, and reformed…double-deals are considered…money is exchanged or promised (sometimes in the tens or even hundreds of thousands of dollars)…and all manner of dirty tricks are planned in order to win…or force your enemy to NOT win….the Palio. There is no “second place” in the Palio….there is only the winner and all the losers!
Make no mistake, this is not a game to the Sienese…it is a deadly serious way of life. The race itself is just a culmination of a year of plotting and scheming.

Later this afternoon the first trial run of the horses takes place in the campo. This will be the chance to see all of the horses and jockeys as they start to get a feel for each other and the track. The excitement builds…

Tonight we’ll have a private wine tasting of some renowned vintages at Federico’s…a sommelier and one of our long-time Siena contacts and friends.

Day 3 - San Gimignano

After breakfast this morning we head north and west through the ancient heart of the Etruscan lands to one of our favorite local family farms. Luigi and Silvia, along with their two sons farm tend olive groves, vineyards, fields and forest. They are pioneers of Tuscan organic and biodynamic farming. The farm's vineyards produce delicate white Vernaccia wine, a local specialty, along with several styles of robust Chianti, Chianti Classico and Super Tuscans. They also produce one of our favorite Tuscan olive oils, which along with the other farm products will figure prominently in our meal. The rule at their kitchen is you eat as much as you want, and then a little more!
But before we eat, we must cook! So while we’re here we’ll roll up our sleeves and learn how to create and cook a traditional Tuscan menu. After our fun culinary experience, we’ll sit down to some of the best Tuscan farmhouse cuisine imaginable, complemented by the farm’s wines.

After lunch we'll have the afternoon free for exploring the wonderfully bizarre town of San Gimignano. The high walls and narrow streets of this imposing fortress are typical of Tuscan hill towns, but the 14 medieval towers that dominate San Gimignano's skyline set it apart from all the rest. Here you can "get lost" in the maze of streets, shops, and cafes. San Gimignano is rumored to have one of the best gelato shops in all of Italy...may be worth a visit? For the not-so-faint-of-heart, a tour of the fascinating (and gruesome) Museum of Medieval Justice will provide an interesting yet terrifying glimpse of the past.

You'll have the rest of the day free in Siena to explore and get lost. We’ll meet later in the evening to enjoy yet another facet of the Palio experience as we watch the beautiful Procession of the Candles, followed by the evening training session in the campo for the horses. Then you can wander the town to hear all of the contrada drummers warming up as their big day draws near.

Day 4 - Charming Chianti

After breakfast this morning, we board our private motorcoach to venture into the countryside and explore. We’re still working on our activities for the day, but suffice to say it will involve beautiful Tuscan scenery, wine, and excellent food!

Tonight another Palio spectacle is on display as we watch the amazing Mounted Carabinieri as they ride through town, just as they have for hundreds of years. Afterwards we’ll enjoy a unique experience as we sit down with our host contrada for a festive neighborhood meal! There will be lots of food, wine, and probably a bit of singing as we all prepare for the big day tomorrow!

Day 5 - The Day of the Palio

This is IT…the Day of the Palio! An early trial run by the horses will be followed by a mass for the jockeys, celebrated by the Archbishop to start this amazing day of festivities and spectacle. In the early afternoon the “Blessing of the Horses” takes place in the chapel of each contrada…attendance at this event can be difficult, it depends on the size of the chapel, the amount of the contrada residents, and if we can find room to squeeze in…but hopefully we’ll be able to attend ours. In the afternoon we’ll meet our specialized “Palio Guide” to walk through town for a view of the famed Cathedral Parade, and then make our way to our private apartment overlooking the Piazza del Campo, where we’ll feast on a buffet of catered local specialties from one of Siena’s renown restaurants while enjoying Federico’s selection of amazing wine! Our apartment has a huge corner balcony (in the shade) with a magnificent view of the track. At 4 pm the historic parade that precedes the Palio begins. All manner of medieval costumes are on display, and competition between the flag bearers and drummers is fierce. The parade winds throughout the town and culminates in the Campo. At 7:30 pm the horse race begins! After much parading and jostling, prepare yourself for the most thrilling 90 seconds possible! It’s a timeless event that has been celebrated by generation after generation of Senese, and it’s exhilarating to witness it!

The post-race pandemonium will provide it’s own unique entertainment for the next hour or so, especially when viewed from the comfort of our apartment.

After the race the town will be in an uproar, with parties, celebrations, lamentations, and an energy level that is hard to fathom! Wandering the town tonight will truly be a most fascinating and interesting experience.

Day 6 - Go Get Lost Day

Today is our Go Get Lost day…you’re free to do whatever you want! Of course in the unlikely event the Palio is rained out, today will be the day it is held. So there is a good reason to plan to be here in Siena if necessary today. But if it isn’t rained out, then you have the whole day ahead of you! The entire day is all about freedom, exploration, and getting lost on your own! You can choose to do as little or as much as you want.

Maybe you celebrated with the locals until the wee hours last night and now it’s pure luxury to sleep in. Or maybe you want to get some last minute shopping done before you depart tomorrow. Or perhaps you plan to venture out into the surrounding area to explore a region you’ve not yet visited.

Day 7 - Arrivederci

Your Go Get Lost tour ends today after breakfast. You a few options... you could make your way to nearby Florence airport for a flight onwards, or you could head to the local train station to continue your travels in Italy.


Due to availability at the time of booking, hotel listed may change to similar hotels

Siena - 4 Star Hotel Athena: This hotel has a superb location in the city center of Siena. With furnishings by local artisans, colors that echo the tones of the Tuscan landscape and the many comforts available, you will feel completely at home.

What´s Included

  • 6 Nights, Double Occupancy at listed hotels (or similar)
  • 6 Breakfasts
  • 2 Lunches
  • 3 Dinners
  • 4 Wine tastings
  • Cooking class in San Gimignano
  • Tour and tasting at wine estate in Chianti
  • Dinner with Siena Contrada
  • Private Apartment for viewing the Palio
  • Attendance at various Palio events and pageants
  • All transportation once the tour starts
  • All listed activities, tours, visits, as per itinerary
  • All tips except for your primary local tour leader
  • Fully escorted by a local Go Get Lost tour leader

What´s not Included

  • Meals not specified in itinerary
  • Beverages at meals unless specified in itinerary (all group meals include water and local wine)
  • Trip Cancellation/Interruption and Medical Insurance (strongly recommended), call for details
  • Single supplement charge
  • Items of a personal nature; phone calls, laundry, etc.
  • Arrival and departure transfers
  • International airfare, tour begins in the afternoon in Siena, Italy on Day 1, and ends after breakfast at the hotel in Siena, Italy on the morning of Day 7
  • Tip for your primary local guide
  • Any costs associated with options on Go Get Lost Day or free time

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