5 Day Siena City Break Tour Package

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Visits Siena, Chianti, Pienza, Montepulciano, San Gimignano, Montalcino, MontereggioniStarts in SienaAvailable Every day - varies seasonallyClick on 'check availability' to view the calendar
Tour Package
Air Conditioned Transport
Accommodation Included
Expert Tour Guide
5 day package
English
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Discover Siena’s authentic beauty on our 5 Day Siena City Break Tour Package. Your journey begins with a walking tour of the medieval town’s best sites, like Piazza del Campo and Basilica of San Domenico. In the evening, take a food tour of Siena’s unique flavors. Taste foods like Ribollita, a traditional soup, Ricciarelli, marzipan biscuits, indulge in charcuterie boards, and more. The next day, take the scenic route to the UNESCO town of San Gimignano and the fortress of Monteriggioni. Enjoy a visit to a Chianti winery, overlooking Brunello vineyards. Sample the world-renowned Brunello of Montalcino, one of Italy’s first DOCG wines, in Val d’Orcia. Next, explore the stunning towns of Pienza and Montepulciano, with visits to local wineries and free time to wander at your own pace.

Seeking an alternative Tuscan adventure? Look no further than our 5 Day Siena City Break Tour Package. This immersive experience offers a deep dive into the heart of Tuscany, uncovering architecture and medieval history, and tasting delectable foods along the way. Discover landmarks with your expert guides and enjoy 4 nights of hotel accommodations. Book today!

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5 Day Siena City Break Tour Package Highlights

  1. Experience the essence of Siena with expert guides
  2. Learn about Tuscan wine production and sample amazing wines
  3. Uncover the rustic landscapes of Chianti, Pienza, and Montepulciano
  4. Savor traditional and local foods on a walking tour
  5. Visit iconic landmarks like Piazza del Campo and Palazzo Tolomei
  6. Select your hotel from our great selection for 4 nights of comfort and relaxation
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5 Day Siena City Break Tour Package Itinerary

Day 1 - Arrival in Siena
  • Independent arrival to your hotel in Siena
  • Overnight in Siena
Day 2 - Siena Morning tour & Food Experience
  • See all of Siena's iconic landmarks: Piazza del Campo, Basilica of San Domenico, and the Sanctuary of St. Catherine of Siena
  • Walk down Banchi di Sopra - one of the main streets and part of the famous Francigena Route, an ancient pilgrimage road
  • Stop at the Palazzo Salimbeni and Palazzo Tolomei to learn more about Siena's rich past
  • Free time to explore on your own
  • In the evening, take a food tour of Siena's unique flavors
  • Taste Ribollita, Ricciarelli, biscuits, cheese & charcuterie boards, etc.
  • Overnight in Siena
Day 3 - San Gimignano, Chianti & Montalcino
  • Visit San Gimignano, a UNESCO World Heritage Site
  • Enjoy free time in the historical center, exploring local artisan shops and millenarian palazzos
  • Head to Monteriggioni, the ancient crown-shaped fortress
  • Relax at a Chianti winery with an optional lunch featuring salami, cheeses, and local wine
  • Continue to Val d’Orcia and Montalcino, overlooking the Brunello vineyards
  • Visit a local wine cellar to taste the renowned Brunello of Montalcino, one of Italy's first DOCG wines
  • Overnight in Siena
Day 4 - Pienza & Montepulciano
  • Visit a local winery in the Val d'Orcia area and indulge in a wine-tasting experience paired with snacks
  • Head to Montepulciano to explore its Renaissance beauty and winemaking methods
  • Continue to Pienza and enjoy some free time to explore at your own pace
  • Overnight in Siena
Day 5 - Departure
  • Independent departure
NB - all timings on 5 Day Siena City Break Tour Package are approximate
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Availability

Available dates are shown in green along with the starting price for that date based on recent searches. Click on a date to move to the next step and customize your trip such as adding airport transfers, choosing your hotel, and adding extra nights.

Includes
All touring and accomodation
Entrance fees: Siena Cathedral
Meals & tastings: Food tastings on the Siena tour, Wine tasting in San Gimignano, & on the Pienza and Montepulciano Tour
Excludes
Anything not mentioned above
Personal travel insurance
Gratuities
Essential Information
Each day will be led by an expert guide to provide an enhanced experience along Tourist Italy's values
You can choose your hotel from our hand-picked selection during the booking process
The order of the days might change because we optimize the itinerary to provide the best experience
During the booking process, it's possible to add extra nights of accommodation before or after the tour package
Airport transfers: Please contact us if you would like to add an airport transfer
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