Best of Tuscany 3 Day Tour from Siena

Visits Siena, San Gimignano, Chianti, Montalcino, Pienza, MontepulcianoStarts in SienaAvailable Every dayClick on 'check availability' to view the calendar
Tour Package
Accommodation Included
Expert Tour Guide
3 day package
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€468per person
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On our Best of Tuscany 3 Day Tour, you will get to escape the hustle and bustle of the city and explore the lush Tuscan countryside. Arrive in Siena and see the incredible sites of this medieval city, like the Palazzo Pubblico and the stunning Piazza del Campo. Witness the Basilica of San Domenico before strolling the walkways on your own. In the UNESCO World Heritage Site of San Gimignano, marvel at the wondrous views and take in more Tuscan delights with a visit to Monteriggioni. Indulge in a delicious lunch of salamis, cheeses, and other accompanying delicacies paired with the amazing wines of this region. See Val d’Orcia, and be amazed as you sample Brunello wines, one of the first DOCG wines. Before your whirlwind adventure concludes, pay a visit to charming Pienza and explore the churches and architecture of Montepulciano.

For wine aficionados seeking a Tuscan getaway, our Best of Tuscany 3 Day Tour is a marvelous choice. See an ancient fortress, and great architecture, taste delicious wines, and indulge in the finest Tuscan flavors. Our tour includes expert guides with locals, food & wine tastings, hotel accommodation, and Siena’s Cathedral entry. Book your Tuscan adventure today!

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Best of Tuscany 3 Day Tour from Siena Highlights

  1. Taste delectable flavors of Tuscany, from Brunello DOCG wines to local salamis, cheeses, and accompanying delicacies
  2. Visit Siena’s captivating city and see sites like Piazza del Campo and Palazzo Pubblico
  3. Take in all the breathtaking views of Tuscany and marvel at the lush greenery and rolling hills
  4. Tour Montalcino’s enchanting fortress and discover ancient secrets of this 14th-century structure
  5. Relax with 2 nights of hotel accommodation picked by you from our personalized list
  6. Be guided by experienced and knowledgeable experts and be provided with valuable insight along the way
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Best of Tuscany 3 Day Tour from Siena Itinerary

Day 1 - Siena Walking Tour
  • You will be picked up from a centralized location in Siena
  • Start by meeting your tour group, and your tour guide before you head out into this city with virtually no traffic, making it the perfect setting for a walking tour
  • Begin your day in Siena with stops at some of its most magnificent highlights, like the expansive Piazza del Campo in the heart of the city that's home to an intricate fountain, and the Palazzo Pubblico
  • Continue to the exquisite Basilica of San Domenico and the Sanctuary of St Catherine of Siena before you slowly wander down the Banchi di Sopra, one of the city's main streets and part of the famous Francigena Route, an ancient pilgrimage road
  • As you pass the beautiful cityscapes, listen as your guide tells you stories of Siena's oldest noble families, like the Piccolomini, Tolomei, and Salimbeni families, and the world-famous Palio horse races that take place in the streets of the city
  • Visit the Palazzo Salimbeni and Palazzo Tolomei to witness the opulence these ancient families enjoyed
  • Once you've learned all about this captivating city, return to the starting point to end the guided tour and continue your explorations independently
  • Overnight in Siena
Day 2 - San Gimignano, Chianti & Montalcino
  • Meet your guide at a centralized location in Siena and head out to San Gimignano
  • Begin in the hilltop town and UNESCO World Heritage Site of San Gimignano. See its medieval towers and taste Vernaccia white wine
  • Explore on your own with a self-guided tour to discover artisanal shops and quaint charm
  • Reach Monteriggioni, a fortress adorned with centuries-old ancient walls
  • Enjoy a lunch of salamis, cheeses, and other local delicacies paired with fine wines
  • See Val d’Orcia, another UNESCO World Heritage Site, and tour Montalcino’s vineyards
  • Sample some Brunello wine, one of the first DOCG wines from the region
  • Overnight in Siena
Day 3 - Pienza & Montepulciano
  • Meet your group leader at a centralized location in Siena and head out for the day
  • Arrive at a local winery and tour and taste the amazing flavors paired with a variety of snacks
  • Discover Pienza, a charming town that’s home to brilliant architecture. Take in the views of Val d’Orcia and explore the culinary heritage of this UNESCO World Heritage Site
  • Visit Montepulciano and study its Renaissance beauty as you marvel at the great churches and architecture. Taste some excellent cheeses
  • Overnight in Siena
  • (Please note: this tour doesn't include a guide, but offers multilingual assistance on the bus)
NB - all timings on Best of Tuscany 3 Day Tour from Siena are approximate
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All touring and accommodation
Siena: Cathedral entrance ticket (On Sundays, the Siena Cathedral is closed for public)
San Gimignano, Chianti & Montalcino: Wine tasting & light lunch consisting of typical Tuscan dishes, snack with sliced cold meats & typical salami
Pienza & Montepulciano: Brunello di Montalcino wine tasting
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
On Sundays, the Siena Cathedral is closed for public. From June 27th to July 31st, and August 18th the cathedral tour costs 5 euros that must be paid on the spot