Siena, Chianti and the Palio tour Package

4 Days/3 Nights
Starting from
$
per person*

Siena, Chianti and the Palio tour Package

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A Travel Experience Like No Other

Curated by our Italy travel experts, this sample itinerary is a starting point for your dream Italy vacation. Tell us your interests and budget, and we’ll tailor it to your pace so you can enjoy Italy like a local.

Day 1
  • Arrive and check in to your hotel in Siena

  • Free time to explore Siena’s highlights

  • Overnight stay in Siena

Day 2
  • 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
  • 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
  • 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.

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Day 1

SIENA
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.

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Day 2

CHIANTI WINE REGION, PALIO’ S EVE DINNER IN CONTRADA
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.

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Day 3

PALIO’S RACE
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.

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Day 4

SIENA

After breakfast, check out from your hotel and bid farewell to Siena. Your tour and our services conclude.

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