Tour Description

If you have never heard of The Palio, it is a passionate horse race and probably one of the most popular horsing events in Italy. Happening every year in Siena, you can finally be part of this passionate horse race in the heart of the city, explore the hidden gems of Tuscany and see what drags Italians to this horsing event year after year.

Aside from Siena and The Palio, our tour will introduce you to Florence and its rich history, splendid architecture and variety of arts dating back to the Italian Renaissance. From the Duomo to the lovely square Piazza della Signoria and one of the oldest bridges in Italy - Ponte Vecchio, you will see why Florence has been one of the leading medieval towns when it comes to history and tradition.

The end of this tour is symbolic with a trip to Montepulciano and Pienza, both wine towns known for their oldest wines. While Montepulciano is built on a volcanic rock, the charm of Pienza has been protected by UNESCO for years.

Detailed Itinerary

 Day 01: Florence Arrival | Welcome to Italy!  Upon arrival at Florence airport please proceed through the Passport Control and collect your luggage inside the customs area.  Just outside this area meet your driver who will transfer you to your Hotel in central Florence. The rest of the day is at leisure. Overnight in Florence.

Day 02: Florence| Breakfast at the Hotel. Your private guide will meet you at the hotel lobby for your private walking tour of the city. Florence's rich past as the cultural centre of the Italian Renaissance can still be seen today in the wealth of art gathered here and in the preservation of its splendid architecture. The tour includes visits of the Duomo and the Baptistry, the Piazza della Signoria, Ponte Vecchio, and the famous Accademia Gallery (entrance fee included). Duration 3 hours. Lunch and afternoon at leisure. Overnight in Florence.

Day 03: Florence - San Gimignano - Siena | After Breakfast a the Hotel meet your driver at the Hotel Lobby.  Today on route to your Siena Hotel visit San Gimignano, a splendid example of medieval town declared a World Heritage Site by Unesco. San Gimignano, a charming Tuscan hill-top town, famous all over the world for the skyline of its medieval tower, rich in history, ancient traditions, delightful wine and food. Continue on to your Siena Hotel.

Day 04: Siena | Breakfast at the Hotel. This morning, enjoy a private guided tour of Siena, probably Italy's loveliest medieval city. Siena's heart is Il Campo or Campo's square, where the famous horse race Il Palio, that takes place two times each summer. The town offer magnificent masterpieces and incredible views.  Siena is the embodiment of a medieval city. This afternoon our English-speaking driver will take you through the scenic hills of Chianti. Only a few regions in Italy can offer such a beautiful and rich panorama as the Chianti wine region. This is the classic Tuscan countryside - Green hills with miles after miles of vineyards producing some of Italy’s best marketed wines, olive groves, gentle rolling hills, ancient walled villages and panoramic roads like you have never seen before. Chianti Classico spreads from Florence to Siena and includes the small municipalities of Castellina, Greve, Panzano, Radda and Gaiole In Chianti. The splendid Romanesque churches, farmhouses, villas and castles dotting the landscape complement the region’s enchanting natural beauty. Overnight in Siena

Day 05: Siena Palio  | Breakfast at the Hotel. A full day of Palio related activities, before the final race in the evening. The morning brings the final trial race, then around 2:30pm the individual horse blessings begins to take place. The contradaioli (Contrada members) begin their parade in medieval costume through the city, stopping at various key points to display their colors and flag waving skills. All paths will eventually lead to Piazza del Campo, where in the late afternoon (5:00pm), the formal historical parade begins. This colorful pageantry is followed by the most famous horse race in all of Italy. Overnight in Siena.

Day 06: Montepulciano - Pienza  | After breakfast, our English-speaking driver will transport you to Montepulciano, a wine town built on volcanic rock. Meet your expert historian for a tour of this Renaissance town, known for its beautiful churches and Vino Nobile, one of Italy’s oldest wines. After lunch, the tour will continue with a panoramic drive to Monticchiello and Pienza, a UNESCO World Heritage Site. Late afternoon return to Siena. Overnight in Siena.

Day 07: Siena - Florence Airport | After breakfast at the hotel enjoy a Private Transfer from Siena to Florence Airport.

Tour Inclusions
  • 3 nights Florence
  • 3 nights Siena
  • Private excursions by
    car and English speaking driver as per program
  • Professional Local
  • Details up on request
Prices in Euro


4* Boutique Hotels

€4185 per person


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Clients Testimonial
  • Thank you for coordinating such a wonderful trip in Italy. Terence and I learned many things about Italy. The weather was great and we had so much fun. All hotels, staff and guides were superb! We especially appreciated our driver who served us from Venice through our time in Florence, I believe his name was Lorenzo. Again, thank “you” for doing such a great job in planning our vacation.
    Melissa R. xxxxx.Wassenaar, NL
  • Hope, you are doing well. My wife and I had a great trip to Italy. The place, the people, and the food and wine were out of this world. Warm and kind people including hotel staff, tour guides and drivers went beyond their ways to help us and make this visit very special for us. It was very hard to leave Italy. You, your staff and company did an extraordinary job. You over delivered. Bravo!
    Barry and Paula J. xxxxxx. Omaha, Nebraska
  • We have just returned from our trip to Italy since we took a cruise after the program you and I put together. I just wanted to let you know that everything you planned worked out perfectly. Both hotels were excellent and the rooms were fine. All the drivers were on time and got us to our destinations promptly. We were especially glad to have someone meet us at the train station with the tickets in hand and directions to our car in Milan. The best part of the trip was the all day private boat trip in Bellagio with the great restaurant on the private island. So thanks for your help and hopefully we can do it again.
    John B. xxxxx. Collegeville, Pennsylvania