5 Day Siena Food & Wine Tour Package

Visits Siena, Val D'Orcia, Montepulciano, Pienza, Chianti, San Gimignano, MontalcinoStarts in SienaAvailable Every dayClick on 'check availability' to view the calendar
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5 day package
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Our 5 Day Siena Food & Wine Tour Package offers a flavorful adventure of Siena’s finest cuisine and rich wines. In the historic city of Siena, learn all about the traditional dishes from your guide and sink your teeth into some of the best foods this region serves: charcuterie delights, Tuscan pork with herbs, tasty soups, and more. Tour the UNESCO World Heritage town of San Gimignano and explore the magical Monteriggioni. Kick back and relax at a Chianti winery before heading to Val d’Orcia and Montalcino for a Brunello wine tasting. Get lost in the charm of Montepulciano and Pienza at your own pace, promising authentic flavors and local delights.

For foodies and wine lovers, this 5 Day Siena Food & Wine Tour Package will excite and delight your palate like no other! Tour Tuscan gems – from Siena to Pienza – and eat the best authentic foods. Appreciate the culinary history of the Tuscan region with immersive experiences led by expert guides. Enjoy 4 nights of hotel accommodation, food & wine tastings, comfortable transport, and more. Book your delicious adventure today!

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5 Day Siena Food & Wine Tour Package Highlights

  1. Experience Sienese cuisine with tastings ranging from Tuscan pork to savory soups
  2. Learn about traditional dishes in the cities you’ll visit and gain valuable insight from local guides
  3. Tour the UNESCO World Heritage town of San Gimignano admiring hilltop views
  4. Tour a winery and sample high-quality wines paired with tasty appetizers
  5. Get lost in the beauty of Montepulciano, Monteriggioni, and Pienza
  6. Choose your own hotel accommodations from our hand-picked selection
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5 Day Siena Food & Wine Tour Package Itinerary

Day 1 - Arrival in Siena
  • Arrive in Siena and make your way to your hotel
  • Overnight Siena
Day 2 - Siena Food Tour
  • Meet your guide and begin touring Siena’s incredible food scene
  • Learn about the history of the traditional foods in this gorgeous city
  • Taste delicious charcuterie and sample from cheese boards paired with local wines of the region
  • Try traditional pasta that was made using the same methods from ancient times
  • Enjoy tasty soups and Tuscan pork with herbs
  • End the tour with a delectable dessert of marzipan biscuits
  • 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
  • Indulge in a wine-tasting experience paired with snacks
  • Head to Montepulciano to explore its Renaissance beauty and winemaking methods
  • In Pienza, enjoy free time to explore at your own pace
  • Overnight in Siena
Day 5 - Departure
  • Independent departure
NB - all timings on 5 Day Siena Food & Wine Tour Package are approximate
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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.

All touring and accommodation
Meals & tastings: Food & drink tastings on the Siena Tour, Wine tasting in Val D'Orcia, Wine Tasting in Chianti
Anything not mentioned above
Personal travel insurance
Essential Information
Each day of this tour package will be led by a local guide who opitimizes Tourist Italy's values: to provide you with an authentic, passion-filled tour
Choose your own hotel from our hand-picked selection during the booking process
The order of the days is subject to change so that we can optimize your 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
For a small fee, you can upgrade to a private airport transfer with hotel pickup/drop off on arrival & departure day. Please contact us for more information
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