Dive into Siena at its most electric. Gothic beauty, Chianti countryside, a once-in-a-lifetime contrada “vigilia” dinner, and the heart-pounding Palio race in Piazza del Campo.
Siena, Chianti and the Palio tour Package
4 Days/3 Nights
Starting from
$
per person*
Unforgettable Italian Journeys, Designed for You
Curated by passionate Italy experts, this sample itinerary is just the beginning of your Italian adventure. Every journey we design is unique, crafted around your interests, pace, and dreams so you can experience Italy’s beauty and culture like a true insider. Let us transform your vision into a one-of-a-kind travel experience, filled with authentic moments and lasting memories
Day 1
SIENA
Palio Fever, Chianti Sips and Contrada Pride
-
Arrive and check in to your hotel in Siena
-
Free time to explore Siena’s highlights
-
Overnight stay in Siena
Day 2
SIENA
Medieval Marvels with Palio Spirit
-
Breakfast at your hotel
-
Visit a local winery and enjoy a Chianti wine tasting
-
Free time at leisure in the afternoon
-
Return to Siena for the festive Palio’s Eve “contrada” dinner, joining locals in traditional celebrations
-
Overnight stay in Siena
Day 3
CHIANTI
The Famous Rolling Vines
-
Breakfast at your hotel
-
Experience the city’s transformation as Siena prepares for the Palio horse race
-
Enter Piazza del Campo early to secure your seat for the race
-
Immerse yourself in the excitement and pageantry of the Palio
-
Overnight stay in Siena
Day 4
SIENA
Arrivederci, Tuscany!
-
Breakfast at your hotel
-
Check out and end of services
MAKE THIS ITINERARY YOURS
Turn this sample itinerary into your dream Italy vacation – tailored to your pace, passions, and budget.
Day 1
SIENA
Palio Fever, Chianti Sips and Contrada Pride
Arrive in the medieval city of Siena and check in to your centrally located hotel. Enjoy free time to explore the city’s most iconic sights, including the magnificent Siena Cathedral, the historic Piazza del Campo with its soaring Mangia Tower, the impressive Basilica of San Domenico, and the House of Saint Catherine. Take in the vibrant atmosphere of the city of the Palio at your own pace. Dinner is at your leisure, followed by an overnight stay in your comfortable Siena hotel.
Day 2
SIENA
Medieval Marvels with Palio Spirit
After breakfast, embark on a scenic excursion to the renowned Chianti wine region, celebrated for its rolling hills, picturesque vineyards, and charming parish churches. Visit a local wine estate to sample world-famous Chianti wines and experience the beauty of Tuscany’s countryside. Return to Siena in the evening for a truly unforgettable event: the “vigilia” or Palio’s Eve dinner, held in one of the city’s historic contrade (districts). Join the local contradaioli in their festive chants and toasts, immersing yourself in the authentic traditions and excitement leading up to the legendary Palio horse race. Overnight stay in Siena.
Day 3
CHIANTI
The Famous Rolling Vines
Experience the thrill and passion of the Palio di Siena, one of Italy’s most celebrated and historic horse races. As the city comes alive with colorful flags and the rhythmic beat of drums, immerse yourself in the unique atmosphere that captivates locals and visitors alike. Secure your place in Piazza del Campo early in the afternoon and witness the pageantry, anticipation, and excitement of this world-famous event. The rest of the day is dedicated to enjoying the Palio festivities, followed by dinner at your leisure and overnight accommodation in Siena.
Day 4
SIENA
Arrivederci, Tuscany!
After breakfast, check out from your hotel and bid farewell to Siena. Your tour and our services conclude.
This Package Includes:
This Package Does Not Include:
Terms and Conditions:
Frequently Asked Questions
Which places are included in this vacation package?
Over 4 days this journey brings you to Chianti Wine Region, and Siena. Each stop is woven into the itinerary with time for the landmarks, the views, and the local flavor that make it special.
Is transportation arranged for us?
Transportation is arranged as part of the itinerary, with comfortable train segments between the cities and vehicle transfers where they serve you best. Every connection is planned for you, so you can focus on the scenery instead of the logistics.
Who is this trip designed for?
It suits independent travelers who love the freedom of the open road with the security of arranged hotels and routing.
Can the itinerary or hotels be adjusted?
Yes. Nothing here is fixed. Your travel consultant can add nights, change hotel categories, or swap experiences so the trip matches your wishes and your budget of time. A minimum of 2 travelers applies.
What time of year should we plan this vacation?
The package is available all year around on request. Spring and fall offer mild walking weather and lighter crowds at the major sights, summer brings long lively evenings, and winter rewards travelers with quieter museums and festive streets.