Itinerary Highlights

  • Watch the famous medieval horserace from a window of a historical palace with an open bar
  • Take a limo tour to explore the historical buildings, savour local wines and visit quaint villages
  • Enjoy a walking tour that covers renaissance and medieval culture of Florence, visiting the Accademia and the Uffizi
  • Stay within the beautiful stretches of Tuscan countryside at Castel Monastero, offering a luxury spa, gourmet dining and more

What's Included

  • Accommodation Throughout
  • Breakfast
  • International Flights


Travel Specialist

I'm here to tailor-make your perfect Europe holiday. Give me a call and I'll use my expertise to create your personalised experience.

Step back in time and take a tour of the charming medieval cities, villages and countryside of Italy, and watch the iconic, historical Palio di Siena race. Stay in luxurious hotels throughout, and take fascinating tours of Siena, Chianti, Florence and more to bask in the timeless atmosphere and marvel at Renaissance architecture. You can join the tour on either 30 June or 14 August, as the traditional race takes place twice a year.

Day one begins with you settling into Castel Monastero, Tuscany. Come nightfall, enjoy an elegant dinner before a day exploring Siena. The UNESCO World Heritage Site is packed with timeless beauty and 14th century buildings, setting the scene for the medieval horse race the following day.

Upon the day of Palio di Sienna, you'll watch the exciting action from the window of a historical castle for a unique and scenic experience. You'll be kept fully refreshed with an open bar during the race and a Tuscan dinner to refuel. But of course, there is more to enjoy when the race is over. The next two days are filled with limo tours, the first being an exploration of Chianti. Wind through villages and regions of Chianti for gourmet dining, medieval charm and welcoming culture. The next day will be a limo tour of Monteriggioni and San Gimignano for more historical towns and a stay in Hotel Brunelleschi, where you can soak up the views of the Duomo from your window.

With a walking tour of Florence, you can see more of the historical art from the renaissance and medieval era, and explore the works of iconic names from Da Vinci, Botticelli and Michelangelo. You'll visit the Accedemia and Uffizi to see masterpieces including the Statue of David, Birth of Venus and Primavera. Finally, you’ll enjoy a day at leisure to explore independently before taking your flight home.


After arriving at Florence Airport, you’ll be transferred to the Castel Monastero. Spend the day at leisure before enjoying your dinner at the hotel.
Wake up to a fuelling breakfast at Castel Monastero before heading to Siena for the day. Spend your time marvelling at the medieval beauty of the city that is now listed as a UNESCO World Heritage Site. When the evening arrives, indulge in a dinner and drinks in one of Siena’s ‘Contrada’ restaurants.
On the day of Palio di Siena, you’ll be transferred to the race after breakfast. Watch the action from the window of a historical castle with other race enthusiasts and enjoy a drink of your choice from the open bar. Once the race has finished, enjoy a light dinner with a Tuscan buffet.
The trip doesn’t end when the race does. After a hearty breakfast in the Castel Monastero, enjoy a day of exploring Chianti’s most well-known villages and regions by limo. Visit Castellina, Gaiole, Radda and Greve, exploring the cultures, dining on their cuisine, and marvelling at the stunning views and medieval architecture.
Enjoy an exciting limo tour that starts at Castel Monastero, takes you through Monteriggioni and San Gimignano and ends in Florence. Soak in the medieval atmosphere of the towns under the glorious sunshine and immersing in the cultures of art, food, and wine. After your tour, you’ll be taken to Hotel Brunelleschi to stay in a Deluxe room with an excellent view of the Duomo just outside your window.
Spend the day on a walking tour of Florence that highlights the medieval and renaissance history of the region. Explore the Accedemia and Uffizi galleries and take a Monolingual guided tour through the city centre to discover the museums. See Michelangelo’s iconic masterpieces including the Statue of David, and the works of Botticelli and Leonardo Da Vinci.
After your breakfast, spend the day how you wish. Stroll through its narrow-cobbled streets and marvel at the timeless beauty of the architecture, indulge in the local cuisine or take to River Arno for picturesque views.
Have one last breakfast at your hotel before transferring to Florence Airport for your flight to the UK.


Travel Specialist

Not sure where to stay in Europe? I'm here to help. Give me a call and I'll share my first-hand insights to find your perfect spot.

Would you like to speak to an Europe expert?

Contact our Travel Specialists for a bespoke quote or some first-hand knowledge.

Call our Europe team on

Monday - Friday: 9am - 7:30pm

Saturday: 9am - 5pm

Sunday: 10am - 4pm 

Stay in Touch

Subscribe to our inspiring newsletter to hear about exciting offers, trending destinations and unparalleled experiences