DAY 1: Check-in at Grand Hotel Continental Siena & Welcome Dinner

DAY 2: State Archives, Palazzo Pubblico, Meeting with a Palio Jockey & General Trial Race

DAY 3: Siena Cathedral Terraces, Cathedral Museum, Blessing of the Horses & PALIO RACE

DAY 4: Monte Olivetto Maggiore, Montisi, Pienza & Winetasting at Casanova dei Neri

DAY 5: Check-out of Grand Hotel Continental

The Palio…

Twice a year, on July 2 and August 16, the city of Siena transforms its main medieval square into an arena of unbridled fury. Ten bareback horses and their respective jockeys race three laps at breakneck speed around a dirt-covered piazza that is filled with fifty-thousand people! That is the Palio, and for the past seven centuries winning it has been the most important objective of every Sienese citizen.

”Many race for the palio, but just one takes it.”

Dante Alighieri, Il Convivio

Although the race lasts only ninety seconds, it is the climatic catharsis of an entire year of preparations, negotiations, contracting, festivities and prayers for the ten contrade or “neighborhoods” who know that they will be running in the next Palio. The Sienese veritably live and die for the Palio. The members of a winning contrada (or contradaioli) will celebrate with pacifiers in their mouths as a symbol of being reborn in victory. The contrada that has not won in the longest time is called la nonna – “the grandmother”. The flag bearer of a contrada will always be present at the funeral (not to mention baptism, first communion, wedding, and 25th and 50th wedding anniversaries) of one its contradaioli with the characteristic colors and animal symbol of the contrada held high. As one historian put it, “…the Sienese never really stop thinking about the Palio.”

But seeing the Palio is not enough! In order to truly understand this seven-century-old tradition, you must live it.

Accompanied service

Main Attractions Sightseeing Tickets Guide Hotel Meals

Special offer


Join us for an authentic insider experience of the Palio where participants will:

  1. View the actual Palio race on August 16, 2021 from an exclusive front-row balcony on the Piazza del Campo!
  2. Visit and learn about the main art historical and architectural sites of Siena with Rocky
  3. View the General Trial Race (Prova Generale) on the eve of the Palio from an exclusive venue
  4. Participate in the blessing of the horse
  5. Visit the State Archive of Siena and actually touch the original 13thdocuments describing the origins of the race
  6. Visit the sublime Tuscan countryside around Siena for luncheon and wine tasting
  7. Luncheon with one of the contrada veterinarians to learn about the extraordinary horses that participate in the race
  8. Listen to a celebrity Palio jockey recount tales of his past races
  9. Sit side by side and eat, drink and sing with contradaioli at their outdoor neighborhood dinners.
  10. Sojourn at the historical and leading-luxury hotel in Siena



Walking tours may entail uneven terrain (e.g. cobblestones, city hills, stairs without handrails, the absence of elevators); archaeological sites; and some longer walks to get to city centers where coaches are prohibited.

PLEASE NOTE: This program is SOLD OUT. If you would like to be added to the waitlist for The Palio Program 2022, please send us an email at [email protected]


A Unique and Exclusive Program…


Arrival in Siena and check-in at Grand Hotel Continental Siena.

6:00pmWelcome Aperitivo at the Hotel

7:00pmSurprise Visit

9:00pmWelcome Cena in Contrada

Dinner in a contrada (one of the 17 Sienese neighborhoods). These outdoor dinners characterize the festive days leading up to the Palio as members of the contrada open up their streets to their own residents and outsiders alike in order to eat, drink, sing and make merry.


9:30am Visit to the Archivio di Stato di Siena (State Archives)

One of the most important medieval archives in the world, the Archivio contains some of the oldest-known documents regarding the Palio. We will examine and actually touch these 13th-century documents with gloved hands to begin our investigation into the history of the Palio.

10:30am Visit to the Palazzo Pubblico
This on-site visit will discuss the civic architecture of Siena as embodied in the city’s most important political structure – the Palazzo Pubblico. This late 13th-century building still serves as Siena’s town hall and preserves some of the most important 14th-century murals in the world. Through an in-depth analysis of these murals, beginning with Simone Martini’s Maestàin the former room of the “Great Council” and then the Allegory of Good and Bad Governmentby Ambrogio Lorenzetti in the “Room of the Nine”- Siena’s medieval Oval Office – we will come to understand that the governing principles of an effective democracy transcend time.


12:30pmGroup Lunch with a contrada veterinarian
One of the most celebrated veterinarians in Siena, who is specialized in treating and examining the horses used in the Palio, will be our guest at lunch and recount hard-to-believe tales of both famous and infamous horses who have raced in past and present Palios.

3:00pm-4:00pmIn-hotel discussion with celebrity jockey

6:30pm Depart hotel for viewing of the General Trial Race (Prova Generale)
The General trial race is the most important of the “dress rehearsal” trials as it is the last time that horses and riders can try to get a feeling for each other and for the race track. It is also when the contradaioli and general public can get a general impression about the probability of a particular combination winning the race. In fact, the trial race held on the actual morning of the Palio is called the provaccia, or “bad trial” because jockeys and horses listlessly go through the motions of the race for fear of injuring themselves on the day of the race.

7:00pm Private viewing of horse trials from privileged balcony position

8:30pm General Trial Dinner in Contrada
This special dinner held on the eve of the Palio is one of joy and anticipation. The table of honor hosts the high-ranking members of the contrada and their jockey, who make speeches and toasts in hopes of a successful race. Hundreds of people fill the table-filled streets eating traditional Sienese foods, drinking wine, and singing centuries-old songs about the greatness of their contrada. The energy is palpable and contagious, as all those present anxiously dream of winning the next day’s race.



9:30am – Exclusive visit of the Porta al Cielo (Siena cathedral terraces)

In the first half of the 14th century, the city of Siena was Florence’s main political, economic and artistic rival. Artists such as Duccio, Simone Martini and Ambrogio Lorenzetti made up of one of Europe’s most important school of painting. This lecture will examine the religious art and architecture in Siena in order to understand the city’s unique beauty and rivalry with Florence. We shall also discuss the striking Gothic cathedral of Siena from a unique and exclusive vantage point dozens of feet above the ground on the interior and exterior terraces of the cathedral.


11:00am – Visit to the Museo dell’Opera del Duomo

We shall also examine the various artistic works which adorned the cathedral, including the largest altarpiece ever painted in Italy – Duccio’s Maesta’, which is housed in the Museo dell’Opera.


12:00pm – Early Lunch at a local Enoteca

2:00pm –Depart hotel to participate in the blessing of the horse

We shall witness firsthand this incredibly solemn and tense moment when the horse is brought into the contrada chapel in order to be blessed by a contrada priest just before the race.

4:45pm – Depart hotel for the Piazza del Campo and the Palio

We will have exclusive access to and use of a terrace directly in the square that will provide us with an extraordinary and close-up view of the parade, ceremony and fanfare that precede the race, and then the race itself. Our exclusive front-row seats will literally allow us to feel the ground tremble as the horses races past!! Refreshments and appetizers will also be provided.

6:30pm – PALIO!!!!!!!



9:00pm – Dinner at the exceptional Osteria Le Logge

One of Rocky’s favorite restaurants in the whole world, there is no better place to enjoy exquisite food and wine while recounting the excitement of Palio that we just witnessed.


9:30am – Depart hotel by private transportation for Monte Olivetto Maggiore

This Benedictine monastery dates back to the 14th century and truly reflects medieval monastic life. Its main cloister is decorated with 15th and 16th- century frescoes by two great Renaissance masters – Luca Signorelli and Il Sodoma – that depict scenes from the life of St. Benedict.


 11:00amDepart Monte Olivetto for Montisi

Montisi is a tiny and charming village (less than 400 inhabitants) in the countryside around Siena that offers stunning views of the olive-grove and vineyard-filled countryside around it.


12:00pm – Lunch at Farmhouse La Romita for traditional Tuscan lunch

2:00pm – Depart for Pienza

Pienza was originally named Corsignano, until its most famous inhabitant, Pope Pius II, renamed it after himself. This charming little town was the only ideal city ever built in the Renaissance and is home to some of the world’s most important Renaissance-style buildings designed by the great Florentine architect Leon Battista Alberti.


3:00pm – Winetasting at the famous vineyard Casanova dei Neri

The Casanova dei Neri vineyard produces some of the world’s top wines, such as the Brunellos Tenuta Nuova and a more structured reserve called Cerretalto. Both of these wines have been awarded 100 points by Wine Spectator on various occasions and also declared by the same periodical as the world’s best wine.


5:00pm – Return to Siena & (Sadly) End of Program



All participants will be staying at the Grand Hotel Continental Siena. A 5-Star hotel part of the Leading Hotels of the World.



Commissioned by Pope Alexander VII Chigi in 1609 for his niece Olimpia on the occasion of her marriage, the Palazzo Gori (which took its name from Giulio de Gori, husband of Olympia) became, the preferred destination of young aristocrats and intellectuals of Europe in the 19thcentury. After a careful restoration that has revived the ancient frescoes and precious decorations, today the palace houses the Grand Hotel Continental.


Located in the medieval heart of Siena, in the Salimbeni Square, the Grand Hotel Continental is the only 5-star luxury hotel in Siena. A few steps from Piazza del Campo, the hotel is about 70 Km from Florence.


  • Participants will enjoy a SUPERIOR DOUBLE ROOM (possibility to upgrade room)
  • Breakfast is included

Race Information


During the actual Palio race on August 16, 2021, our group will be enjoying the race from a private balcony on Piazza del Campo:

  • Private balcony facing the Palazzo Pubblico in Piazza Del Campo
  • Elevated 2nd-floor location that provides extraordinary panorama of the whole race
  • Exclusive access to underlying bar



Dates & Prices


AUGUST 14 – 18, 2021

Double Occupancy – $6,950.00/person

Single Occupancy – $7,750.00/person



–        4 nights of accommodations in Superior Double rooms in the luxurious Grand Hotel Continental in Siena (breakfast included)

–        Exclusive use of an exceptionally-well-positioned front-row balcony from which to view the Palio

–        Extraordinary view of the General Trial Race from the windows of the State Archive directly above the treacherous “San Martino Curve”

–        All lectures with Rocky and other celebrity guests

–        All lunches, dinners, winetastings and appetizers

–        All admissions to museums and churches

–        All private transportation

Not included:

Air fare and transportation to Siena

Terms & Conditions

A deposit of 30% of the course fee is required to reserve a space on a program. All payments may be made by credit card or check. Deposits are applied to final payment of the program price.
The balance is due 60 days prior to departure, unless otherwise noted. If full payment is not received by the final payment due date, your place cannot be guaranteed on the program.

Wait List:
If the program of your choice is fully subscribed, you may choose to be placed on a waitlist by contacting us at [email protected] or by phone. Individuals on the wait list will be contacted if space becomes available and can inquire about program status by contacting us. If you choose to withdraw from a wait list, please notify us.

Cancellation and Refund Policy:
Following enrollment, a participant’s withdrawal from the program for any reason, including, but not limited to, illness, injury, family engagements, work-related issues, or geopolitical concerns, etc., will be deemed a cancellation. Please understand that there will be no exceptions to our cancellation policy.
Per person cancellation fees are based on date of written notice to Rocky Ruggiero. We will refund on the following basis:
– Cancellations within 10 days of booking: Full Refund
– Cancellations after 10 days of booking: Full Deposit Retained
– Cancellations made within final payment date, 60 days before departure: No Refund
– Cancellation by Rocky Ruggiero: Full Refund or Credit

COVID-19 Cancellation Policy:
In light of the current worldwide pandemic, should a program be postponed or cancelled due to covid-19:

– we can transfer your reservation to a rescheduled date, or
– if you prefer a refund, we will provide you with one.

We will communicate any changes as they happen, but please feel free to contact us if you have any questions.

Special Travel Arrangements:
Participants may wish to extend their stay in the group hotel either before or after the tour. We will work with you on these arrangements, dependent upon space availability.
Should you decide not to participate in certain parts of the program, no refunds will be made for those unused parts of the program.

Neither Rocky Ruggiero nor faculty shall be held liable for personal injury, death, property damage or accident, delay or irregularity arising out of any act or omission of these suppliers. Rocky Ruggiero and other faculty reserve the right, without penalty, to make changes in the published itinerary whenever, in their judgment, conditions warrant, or if they deem it necessary for the comfort, convenience, or safety of tour participants.

Rocky Ruggiero and designated faculty also reserve the right, without penalty, to withdraw the program announced, to decline to accept any person as a participant in a program, or to require any participant to withdraw from the program at any time (including, but not limited for inappropriate, or offensive behavior) when such action is determined by program staff to be in the best interests of the health, safety or general welfare of the program group or the individual participant.
Dates, schedules, tour details, and costs, although provided in good faith based on information available at the time of publication on the website, are subject to change and revision.

The undersigned has read carefully the Responsibility Statement and Liability Disclaimer set forth above, the schedule of activities for this program, as well as the terms and conditions of application and participation as set forth in the program materials and recognizes and accepts any risk associated with the program and the conditions, including the refund policy, set forth in the program materials. The undersigned further acknowledges that there are many risks and uncertainties inherent in any travel program, including but not limited to the hazards of various modes of transportation, forces of nature, acts or omissions of foreign governments, terrorism, war or insurrection, theft, illness, and damage to person or property due to the negligent acts or omissions of program staff or others. In consideration of, and as part payment for, the right to participate in the program, the undersigned, on behalf of himself, his dependents, heirs, executors, administrators and assigns, agrees to release Rocky Ruggiero, its Regents, officers, employees, representatives or agents, the United States, from liability for personal injury, death, property damage or loss suffered by any person in connection with this tour, even if caused by the negligence (but not the reckless, willful, or fraudulent conduct) of program staff or other related persons or entities. In addition, by registering for this program, the applicant certifies that he or she is mentally and physically capable of full participation in this tour. By registering for a “Rocky Ruggiero Program in Italy”, the participant agrees to the Responsibility Statement and Liability Disclaimer and the Terms and Conditions herein.