Best of Tuscany 3 Day Tour from Florence

Visits Florence, San Gimignano, Chianti, Siena, Montereggioni, Pienza, MontepulcianoStarts in FlorenceAvailable Every Thursday, SaturdayClick on 'check availability' to view the calendar
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Accommodation Included
Expert Tour Guide
3 day package
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€399per person
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Our Best of Tuscany 3 Day Tour will take you on an exciting adventure through the Tuscan countryside as you indulge in local wines, traditional foods, breathtaking scenes, and rich history. Step back into the 15th century to learn all about the royal Medici family. Tour the magnificent exteriors of the Medici Palace and Uffizi Gallery to better appreciate the legacy of these wealthy nobles. Participate in a food-tasting tour of Storico Mercato Centrale and close out the day with an aperitivo on a rooftop with sunset city views. Continue your journey to San Gimignano – a UNESCO World Heritage Site. After enjoying a self-guided stroll through the ancient streets, head to the medieval ruins of Monteriggioni. In the Chianti region, sip on some of the finest Italian wines and enjoy a traditional Tuscan lunch before discovering Siena’s beauty. Take in the rolling hills and lush vistas of Val D’Orcia Valley, home to fine Italian wines your palate will be lucky to try. Explore the charming surrounding towns of Pienza and Montepulciano before concluding your 3-day adventure.

For food and wine lovers seeking a short and sweet Tuscan getaway, our Best of Tuscany 3 Day Tour is just the right choice for you. As your local guide takes you around Florence, gain insider info about the royal Medici family and some of the best landmarks of the city. Discover quaint towns, taste great food and wine, and indulge in self-guided tours at your own pace. This experience includes wine tastings, a Tuscan lunch, hotel accommodations, and expert guides. Book your Tuscan adventure today!

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Best of Tuscany 3 Day Tour from Florence Highlights

  1. Learn all about one of the richest families in all of Tuscany – the Medici – and discover their claim to fame
  2. Explore the stalls of the Storico Mercato Centrale, learning about and sampling various traditional foods and drinks
  3. Taste some of the finest Chianti wines Italy has to offer and tour wine cellars in Montepulciano
  4. Journey through San Gimignano and enjoy a self-guided tour at your own pace where you can take in the surroundings
  5. Feast on a traditional three-course lunch whilst you look out at the picturesque, rolling Tuscan hills
  6. Enjoy luxurious stays in the City of the Renaissance, at a hotel of your choice from our personalized list
  7. Visit Pienza and Montepulciano and marvel at their landscape panoramas of Va d’Orcia Valley - a UNESCO World Heritage Site
  8. Be led by experienced guides across famous attractions and enjoy magnificent views of the cities along the way
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Best of Tuscany 3 Day Tour from Florence Itinerary

Day 1 - Florence
  • 10:45 - Meet your guide at Palazzo Vecchio
  • Head towards Florence City Hall, exploring the streets and discovering Florence's Renaissance legacy at Piazza della Signoria
  • Admire Loggia dei Lanzi's open-air sculpture gallery, pass by the Uffizi Gallery, and marvel at the exterior of the Cattedrale di Santa Maria del Fiore
  • Walk by the Basilica di San Lorenzo and the Riccardi Medici Palace, while delving into the Medici family's impact on Florence's history
  • Visit two local artisan stores in Florence
  • 14:00 - Start tasting tour at Storico Mercato Centrale, kicking off with a Limoncello group shot
  • Explore the market, indulging in food and wine tastings like truffle, gelato, pizza, local chocolates, and Vino Santo
  • 16:30 - Head to the city center and follow the guide to a hotel’s exclusive rooftop
  • Relax with an Italian aperitivo and cold-cut platter, enjoying sunset views while the expert guide shares insights about the Italian Aperitif
  • 17:30 - The tour concludes at the venue
  • Overnight in Florence
Day 2 - San Gimignano, Chianti, Siena & Montereggioni
  • Meet your guide at a centralized location in Florence
  • Start your Tuscan explorations in the village of San Gimignano, a well-preserved and charming medieval town that's a designated UNESCO World Heritage Site
  • Your guide will drop you off at the historical center, where you will have 2 hours to wander through the labyrinthine streets on a self-guided tour. Take some free time to visit the sweeping squares, grand palaces, towering churches, and the towers that stand above it all. Contemporary art lovers can check out one of the many galleries like Galleria Continua. Or, visit Il Criollo or Gelateria dell’Olmo for world-class ice cream
  • Continue to Monteriggioni, a charming medieval village enclosed by walls, and spend around 30 minutes exploring its beauty
  • Head to the Chianti region, making your first stop at a traditional Tuscan winery to learn more about the varietals grown here and taste what makes this table wine so globally popular
  • Sample 3 of their finest wines and balsamic vinegar before tucking into a 3-course lunch, comprised of local products like cold cuts, olive and truffle oils, Pecorino cheeses, penne with meat ragout, and homemade tarts. Finish off with "cantucci e vin santo"
  • Proceed to Siena, starting at the magnificent Basilica of San Domenico
  • Explore the narrow medieval streets of Siena, passing through iconic landmarks such as Piazza del Campo, Palazzo Pubblico, and Siena Cathedral
  • Avoid the crowds with your included skip-the-line entry tickets and discover the Cathedral of Siena's artistic treasures. These include mosaics, Donatello's St. John the Baptist, Duccio di Buoninsegna's rose window, and Nicola Pisano's marble pulpit
  • Explore the Piccolomini Library, home to a rich collection of manuscripts
  • Conclude the tour with some free time to soak in the unique atmosphere of Siena before returning to Florence
  • Overnight in Florence
Day 3 - Val D'Orcia, Pienza & Montepulciano
  • Meet your guide at a centralized location in Florence. Please be there 15 min before departure
  • In Montepulciano, visit a winery and tour the wine cellars with a local guide. Taste fine wines with a delicious snack of local products before strolling through the town
  • In the charming towns of Pienza and Montepulciano, take in the landscape views of Val d’Orcia Valley, a UNESCO World Heritage Site. Admire the Renaissance buildings and ancient streets on your own in Pienza and learn from your guide about wine’s significant mark in Montepulciano
  • The tour ends in Florence
NB - all timings on Best of Tuscany 3 Day Tour from Florence are approximate
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All touring and accommodation
Tuscany Tour: Skip-the-line tickets to Siena Cathedral & Piccolomini Library , Wine tasting & 3 course lunch
Val D'Orcia Valley: Wine tasting & appetizer, self-guided visit of Montepulciano & Pienza
Florence: Food tastings, aperitivo & platter of cold cuts
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.
Please note that the Siena Cathedral is closed on Sundays and Bank Holidays. During special event the opening times can change