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Il Palio

Il Palio di Siena, Italy

4-day tailor-made city break from £2,895 pp incl. flights


Short description

A four-day break, taking in the spectacular Il Palio di Siena festival


  • Take in the colour and pageantry of Italy's most famous horse race
  • Enjoy included dinners and seats with first-class views
  • Spend a day at leisure taking in Siena's historical landmarks
  • Stay in style at Castel Monastero - a luxury spa hotel surrounded by the Chianti countryside


Recommended for:
Activity adventure | August holidays | City | History & culture | Short break

More than a simple horse race, Il Palio di Siena, held twice a year in July August, is the culmination of an ongoing rivalry and competition between the contrade, with part of the game being to prevent a rival from winning. When the winning silk is presented to the victorious ward the spectacular celebrations start immediately and are something to behold. Resplendent in the colours of the city wards (contrade) ten horses and their rider's race bareback three times around the circular Piazza del Campo in the city centre. The winner is the first horse to cross the line, with or without its jockey. The race is preceded by a spectacular pageant, the Corteo Storico, which includes flag wavers in medieval costumes and a squad of carabinieri on horseback, wielding swords, demonstrating a mounted charge around the track. 

Day by day itinerary

Day 1

After complimentary airport lounge access, board a flight to Florence. Upon arrival we've arranged a private car transfer to the Castel Monastero, your accommodation for the next three nights.

Stay: Castel Monastero, Tuscany

Day 2

Today has been left free for you to explore the historic medieval city of Siena, which has been declared a UNESCO World Heritage site hosting such architectural treasures as the Piazza del Campo and the Siena Cathedral. Siena also has a rich tradition of arts and artists and many well known Renaissance pieces still remain in galleries or churches in Siena. Back at the hotel, enjoy your complimentary spa treatment, and access to the acqua benessere area of the spa. In the evening enjoy a typical dinner for two including Castel Monastero wine selection. 

Stay: Castel Monastero, Tuscany

Meals: B D

Day 3
Il Palio

This is the day of the Il Palio and a chance for you to savour the pomp and pageantry of this event. Throughout today you'll be able to experience the traditional build up to the Palio including the 'Jockey Mass', celebrated by the Archbishop of Siena and followed by the final trial, known as the provaccia. Later in the morning, in the presence of the Mayor, the jockeys are enlisted before a blessing that takes place at around 3:00pm in the contrade church. The horses and their jockeys will then gather at the Piazza del Duomo from where they'll move, in order, to the Piazza del Campo for the start of the race a three lap dash covering around 1,000 metres. After the race the festivities begin with the people of the winning contrada receiving the Palio banner and heading to the Duomo for thanksgiving. To make the day run smoothly, we've included return transfers to Siena from Castel Monastero on the day of the Palio, a window space overlooking the Piazza del Campo, cocktails and refreshments during the afternoon, and a light buffet dinner with a selection of local specialties at the end of the event. 

Stay: Castel Monastero, Tuscany

Meals: B D

Day 4

Breakfast at leisure and we have arranged a private car transfer back to Florence in good time for your return flight home.

Meals: B


Any element of this itinerary can be adjusted to suit your needs. Just contact us to find out more.

Accommodation rating: Superior

4-day tailor-made city break from £2,895 pp incl. flights

Superior room

Valid for travel: Il Palio is held twice each year on July and August

Il Palio happens on 2 separate days every year. The first race Palio di Provenzano will take on 02 July on the holiday of the Madonna of Provenzano. The second race Palio dell’Assunta will be held on 16 August, on the holiday of the Virgin Mary.


  • Complimentary UK airport lounge access
  • Return flights to Florence
  • 3 nights at Castel Monastero on a B&B basis
  • one dinner for two including Castel Monastero wines
  • return transfer to Siena from Castel Monastero on the day of the Palio
  • a window space overlooking the Piazza del Campo 
  • Cocktails and refreshments during the afternoon of Il Palio 
  • a light buffet dinner with a selection of local specialities at the end of Il Palio 
  • One SPA treatment per person (50 min. face or body), access to the “acqua benessere” indoor water area of the SPA.

Terms & Conditions

Prices are per person based on two people sharing a twin/double room; prices are subject to availability and possible change; normal booking conditions apply.

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At Wexas, we specialise in bespoke travel experiences. Our itineraries are just samples of what we can arrange, and can be changed depending on your precise needs, finances and ideas by our experienced destination specialists.

Contact one of our consultants on 020 7590 0796 to discuss how we can tailor your holiday.

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