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​Palio di Siena 2027 hospitality inclusive packages from £3,895 per person.

Experience a timeless tradition of passion, pageantry, and pure adrenaline. The Palio di Siena is an electrifying fusion of medieval tradition, fierce local rivalry, and breathtaking spectacle — where the thunder of hooves racing through Siena’s historic Piazza del Campo is matched only by the vibrant colours, centuries-old pageantry, and the palpable pride of each Contrada. This is not just a horse race; it’s a cultural phenomenon that captures the heart of a city and leaves a lasting impression on all who witness it.

Why book with Racing Breaks

Official Tickets & Hospitality

We work in partnership with the Palio di Siena and offer official tickets or hospitality in exclusive apartments overlooking the square

Bespoke Experiences

Let our team of racing & travel experts build you your perfect itinerary with your choice of hotel, hospitality and more.

Exclusive Excursions

Enjoy access to exclusive an “Contrada dinner” the night before the Palio, along with wine tasting, and other optional extras

Ultimate Luxury

Witness this incredible event whilst staying in luxury at a 5* resort just outside of Siena

Rated Excellent

Our customers rate us excellent 5* on Trust Pilot with over 1,700 reviews! Read reviews.

The Palio di Siena with Racing Breaks

We craft bespoke journeys that envelop you in every exquisite moment of the Palio di Siena — from privileged vantage points and official hospitality to tailored itineraries and rare, behind-the-scenes encounters.

Whether you prefer the pulse of the race from an exclusive grandstand, the refined calm of a private balcony overlooking Piazza del Campo, or complete immersion in centuries-old Contrada traditions through invitation-only celebrations and pre-race dinners, our meticulously curated packages deliver an experience of rare elegance and authenticity for the discerning traveller.

Overview
Day 1

Weds 30th Jun 2027 | Sat 14th Aug 2027

  • Upon arrival at Florence or Pisa airport, you will be met by a private chauffeur and transferred in comfort directly to Castel Monastero, the exquisitely restored medieval monastery and 5-star resort amid Chianti’s vineyards and forests.
  • After a warm welcome and settling into your elegant room or suite, the remainder of the afternoon is yours to unwind at leisure — explore the historic hamlet or simply savour the serene Tuscan landscape.
  • As evening falls, dine at your leisure in one of the resort’s refined restaurants: the Michelin-starred Contrada on the medieval piazza, or the atmospheric Cantina in a historic wine cellar.
Day 1
Day 2

Thurs 1st Jul 2027 | Sun 15th Aug 2027

  • Begin with a leisurely breakfast, then devote the morning to restoration — enjoy complimentary access to the Acqua Benessere spa for treatments, yoga, or simply relax by the pool.
  • In the afternoon, enjoy a private wine tasting guided by the hotel’s expert sommelier, sampling exceptional Tuscan wines while learning the stories of the region’s celebrated terroir.
  • As dusk approaches, a private transfer takes you into Siena for an exclusive Contrada Dinner: an invitation-only outdoor banquet, previously hosted by the Eagle Contrada at the feet of the Cathedral of Siena.
Day 2
Day 3

Fri 2nd Jul 2027 | Mon 16th Aug 2027

  • Savour a leisurely breakfast at Castel Monastero, followed by a morning entirely at your disposal to enjoy the spa, grounds, or tranquil countryside.
  • In the afternoon, a private transfer brings you to Siena and your privileged place in a historic palace apartment overlooking Piazza del Campo. From a shared window with superb views, enjoy a light Tuscan buffet and open bar as the atmosphere builds toward the race.
  • Once the Palio has concluded, you will be transferred in comfort back to the serene luxury of Castel Monastero.
Day 3
Day 4

Sat 3rd Jul 2027 | Tues 17th Aug 2027

  • Enjoy a final, unhurried breakfast at the hotel, lingering over the flavours of Tuscany one last time.
  • The remainder of the day is yours at leisure to relax by the pool, revisit the spa, or simply take in the peaceful surroundings of this medieval sanctuary before your private chauffeur collects you for a seamless transfer to the airport and your onward journey home.
Day 4
Future

Extend your trip?

Travel to another destination?

  • Your time in Italy need not end with the Palio. Remain a few extra nights at Castel Monastero or in Siena itself, basking in the late-summer sunshine and the quieter rhythms of the countryside.
  • Alternatively, continue your travels to Pisa, Florence or Rome — all within easy reach by private transfer — or connect onwards from the airport to your next destination. The choice is entirely yours.
Future

Palio di Siena Packages

Experience the Palio di Siena with one of our carefully curated packages starting from £3,895 per person.

All experiences can be booked from just a 10% deposit and include accommodation, official hospitality, all transfers, and some truly unique excursions to make your trip a memorable one.

from £3,895 per person

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Castel Monastero offers a unique opportunity to experience the Palio di Siena while enjoying the serenity and sophistication of one of Tuscany’s finest countryside retreats. Set within a beautifully restored medieval village, it is the perfect choice for those seeking a blend of five-star luxury and effortless access to the excitement of race day.
What's included?

Trip Dates: 30th June – 3rd July 2027 or 14th – 17th August 2027

  • Private return airport transfers
  • Three (or more) nights accommodation
  • Breakfast each morning
  • Welcome amenities in room upon arrival
  • Wine tasting at Castel Monastero with the hotel’s sommelier
  • Dinner in one of the “Contrada” the night before the Palio
  • Access to the “acqua benessere” indoor Spa
  • Access to a shared window in a historic palace overlooking Piazza del Campo
  • A light Tuscan buffet and open bar during the race
Why stay here?
  • Luxurious 5* Resort
  • Historic Charm
  • Wellness Retreat
  • Gourmet Dining
  • Scenic Surroundings

Tell us what you're looking for

View Enquire
Looking for something a little more bespoke? Get in touch with our racing experts and we'll help you design your perfect Palio di Siena experience. Whether you're looking for hospitality, luxury accommodation or some exclusive added extras, let us help make your trip unique.
What's included?

Your trip could include…

  • Return flights (including optional upgrades)
  • Return airport transfers
  • Accommodation at your choice of hotel
  • Hospitality overlooking the historic race (including private apartments)
  • Optional excursions
  • Optional trip extensions to other destinations

Palio di Siena Tickets & Hospitality

Our experiences include hospitality in a private apartment looking over the historic square, however there are also alternative options such as grandstand seats for those looking to be in the heart of the atmosphere.

Apartment Hospitality

included in experience

Witness the historic race from the comfort of a private apartment overlooking the square. You'll have access to watch proceedings from a window offering stunning views of the action. Inside the apartment you'll buffet and complimentary drinks throughout the day.
What's included?
  • Access to a private apartment
  • Access to a shared window looking over the historic square
  • A light Tuscan buffet lunch
  • Complimentary drinks

Exclusive Inclusions

Contrada Dinner

included in experience

You'll have access to an exclusive Contrada Dinner - an outdoor, invitation‑only feast held in Siena on the evening before the big Palio race. It’s not just a meal — it’s a living tradition that plunges you deep into the heart of one of Italy’s most passionate cultural events.

Each of the Contrade (the city’s historic neighbourhood association) that has a horse running in that year’s race sets up long tables under torches and lanterns in their own streets or piazzas. You’ll be joining one of these contrade — locals and guests alike — to dine together as neighbours and supporters of the race.

Wine Tasting

included in experience

You'll step into the world of Tuscan winemaking with a private tasting led by Castel Monastero’s knowledgeable sommelier. You’ll sample a selection of exceptional local wines, from robust reds to elegant whites, each paired with insights into the region’s centuries‑old traditions and unique terroir.

Learn first hand why this corner of Tuscany is celebrated worldwide for its vineyards, discover the stories behind each estate, and experience the rich aromas and flavours that make these wines truly unforgettable.

About the Palio di Siena

This is a bi-annual race which takes place in the charming Piazza Del Campo; the centre square of Siena. The Palio is steeped with history and dates back to medieval times. A thrilling spectacle as jockeys race round the square bareback, using force to push past any opponent who stands in the way.

​Packages include an insight into the culture and traditions of this Tuscan town and the race which brings each of the small contrades (city subdivisions) to battle for the ultimate title. Experience a banquet of Tuscan delicacies and listen to stories and tales of times gone by.

Enjoy the luxuries of the Castel Monastero hotel hidden amongst the rolling hills and vineyards of the Tuscan countryside. Relax and enjoy the spa, pool, restaurants, and elegant rooms at this stunning location and prepare for the energetic jamboree that is the Palio di Siena.

2nd July 2027

July Palio

The July race is dedicated to Our Lady of Provenzano. It takes place in the iconic Piazza del Campo, where ten contrade selected by lottery race bareback around the track. The city celebrates for days with neighborhood dinners, parades, and the colorful Corteo Storico historical procession.

16th August 2027

August Palio

The August edition honors the Assumption of the Virgin Mary. While the structure and traditions are similar, this Palio is often seen as the more solemn and spiritually symbolic of the two, coinciding with major summer festivities and attracting large crowds.

Palio di Siena Flights

If required, our experiences can include flights to either Florence, Pisa or Rome.

Depending on your choice of departure airport you will fly to one of these cities before having the option to include airport transfers to your hotel.

Onward flights are possible for those looking to spend a few nights in another European city either before or after your time in Siena.

Flight upgrades are available to Premium Economy, Business & First Class subject to being an option on the flight booked.

Customer Reviews

"If you're thinking of going to see the Palio, please book it with Racing Breaks. The trip was well organised and professional. All going to plan. The hotel RB use is 1st class and would recommend The Castel Monastero as the rooms, restaurants, spa and staff would be difficult to improve. If you book RB give you the flexibility to extend the trip before or after so you can link it with seeing other parts of Italy. They are flexible with airport transfers too. Great bucket List experience thank you."
Samantha, 2025
"An absolutely unforgettable experience! RacingBreaks.com organised every detail perfectly — from our stunning hotel to the exclusive race viewing and incredible Contrada dinner. The team made us feel looked after from start to finish. Seeing the Palio di Siena up close was a true bucket-list moment. Highly recommend!"
Michael, 2025
"The Palio di Siena was like stepping into history — the atmosphere, the colours, the passion were simply incredible. The whole trip was seamless and stress-free. We loved the mix of cultural experiences and relaxation at our beautiful countryside hotel. A truly unique way to explore Tuscany!"
Michelle, 2025
"If you're thinking of going to see the Palio, please book it with Racing Breaks. The trip was well organised and professional. All going to plan. The hotel RB use is 1st class and would recommend The Castel Monastero as the rooms, restaurants, spa and staff would be difficult to improve. If you book RB give you the flexibility to extend the trip before or after so you can link it with seeing other parts of Italy. They are flexible with airport transfers too. Great bucket List experience thank you."
Samantha, 2025
"An absolutely unforgettable experience! RacingBreaks.com organised every detail perfectly — from our stunning hotel to the exclusive race viewing and incredible Contrada dinner. The team made us feel looked after from start to finish. Seeing the Palio di Siena up close was a true bucket-list moment. Highly recommend!"
Michael, 2025
"The Palio di Siena was like stepping into history — the atmosphere, the colours, the passion were simply incredible. The whole trip was seamless and stress-free. We loved the mix of cultural experiences and relaxation at our beautiful countryside hotel. A truly unique way to explore Tuscany!"
Michelle, 2025
Trusted by over 1,700 people

Frequently Asked Questions

Approximately 20–25 minutes by private transfer. The resort sits in the Chianti countryside, offering serene luxury while remaining perfectly placed for the event.

An invitation-only outdoor banquet held the evening before the race in the streets of one of the participating Contrade (in past years often the Eagle Contrada near the Cathedral). Long tables, torchlight, local food and wine, and the passionate atmosphere of the neighbourhood create one of the most authentic experiences of Palio week.

Yes — private airport transfers on arrival and departure, plus transfers into Siena for the Contrada Dinner and race day, are all included.

Yes. Guests enjoy complimentary access to the Acqua Benessere spa, pools, and grounds throughout the stay. A private wine tasting with the hotel’s sommelier is also included.

Extensions at Castel Monastero or further travel to Florence, Pisa, or Rome are easily arranged. Simply let us know and we will tailor the onward arrangements.

As early as possible. Official hospitality positions and the best rooms at Castel Monastero are limited and in high demand, particularly for the August edition.

Access to a shared window in a historic palace overlooking Piazza del Campo, together with a light Tuscan buffet and open bar throughout the afternoon and evening. You enjoy the historic procession and race from a privileged, elevated position without the crowds and heat of the central square.

If heavy rain makes the track unsafe or the start is delayed past sunset, the race is postponed to the following day (or the day after if necessary). Tickets remain valid for the rescheduled date. If possible, we recommend adding an extra night to the end of your trip to ensure you can attend should there be a delay.

At Racing Breaks we only offer packages that include access to private apartments overlooking the Piazza, or grandstand seats.

Standing inside the centre of Piazza del Campo is free (space is limited and entrances close early) however we do not recommend this and it is typically only local residents that watch the race in this way.

The free central area of the square can be intense (heat, crowds, long wait, no facilities, and children under 10 are typically not permitted). Seated or window positions, such as those included in this itinerary, are far more comfortable for families.

Contact

Your ultimate racing break starts here

Tell us a little more about what you’re looking for, and our team will craft the perfect racing escape tailored just for you.

Call:

0800 193 6646

Email:

General Enquiries:info@racingbreaks.com

Customer Service:reservations@racingbreaks.com

Concierge/VIP:concierge@racingbreaks.com

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