Tuscan Hill Towns Vacation

4 days, 3 nights


Enjoy a 4 day stay in Siena at selected accommodations and discover its surrounding countryside and hill top towns with English-speaking local guides. Learn about the local history and culture on Day trips and Experiences that include the region’s best historical sites and culinary delights!


Arrive in Siena, check in to your accommodation and enjoy an Italian Style Aperitivo Dinner sampling local wines and savory and sweet bites at the Tuscan Wine School in Siena’s city center * 2 hours, includes 4 wines and food See more >
Come to the Tuscan Wine School just paces from Siena’s Cathedral for an Italian-style Apritivo with vino and lots of bites of local cheeses, cold cuts and seasonal dishes. Enjoy different local white and red wines and local culinary delights in a pleasant atmosphere.


Explore Siena’s Province to the north on a full day sight-seeing tour with an expert local guide. Visit the Chianti, learn about Tuscany’s history all the way back to the Etruscans, see its architecture and medieval towers and be immersed in the local culinary and crafts culture
*8 hours, includes visits to Monteriggioni, San Gimignano and Volterra, saffron farm lunch with wine, visit to local craft workshop, accommodation pick-up and drop-off. See more >
Travel north of Siena and into the first Chianti hills and take a walk around Monteriggioni, a
medieval and perfectly preserved fortress mentioned by Dante in his Divine Comedy: this was once Siena’s main bastion of defense against the armies of Florence. Visit one of the most characteristic hill towns of Tuscany, San Gimignano, with its many austere medieval towers that defiantly survived the centuries. Recognized as a UNESCO site of world heritage, a great testimony of medieval architecture and Via Francigena, the main route that took all travelersand pilgrims of Europe to Rome and the Holy See. Explore the bustling town’s artisanalboutiques of the local trades and stores. Enjoy a wholesome meal at a small family-run farmprepared using the farm's own grown saffron and seasonal products accompanied with the localVernaccia white wine. Marvel at the panoramic landscapes and reach Volterra, the ancient Velathri, a city that harmoniously combines Etruscan and Roman ruins with medieval and Renaissance architecture. Visit a small, artisanal workshop and meet the craftsmen that havebeen working the local alabaster for decades. Enjoy leisure time walking the streets, marvelingat the millennia old Etruscan arch and the Roman amphitheatre or the town’s more modernshops and cafés.


Enjoy a full day exploring the Unesco-protected val d’Orcia to the south of Siena with stunning views, historic towns and the local culinary delights with an expert local guide in a small group *8 hours, includes visits to Pienza and Montepulciano, dairy farm lunch with wine, optional cellar tour and tasting, accommodation pick-up and drop-off. See more >
Travel south of Siena and see the characteristic moonscapes of the Crete Senesi and the
UNESCO heritage site of the Val d’Orcia, enjoying brief stops in Tuscany’s most panoramic
landscapes. Visit the beautiful town of Pienza, built by Pope Pius II, the Humanist pope who engaged the best Renaissance architects to renovate his native town. Spend your leisure time exploring the Cathedral and scenic routes overlooking the valleys and hills or browsing its many shops of local crafts and products. A wholesome and refreshing farm to table lunch at a dairy farm will include a tasting of the local pecorino sheep cheese and wine. The proud town of Montepulciano was under the dominance of medieval Siena and then became an ally to Renaissance Florence, allowing you to marvel at the influences of both Republics in its architecture and art. Visit the main square and explore one of the many old wineries carved out of the ground below the city to taste the Vino Nobile that was produced by the many important and noble families that once lived here.


Visit Siena’s medieval centre on a Walking Tour with a local guide and discover the city’s fascinating history and traditions. Learn about the traditional Palio horse race and marvel at one of the oldest banks, the shell shaped Piazza del Campo and the Gothic masterpiece that is Siena’s Cathedral before ending your Vacation.
*2 hours, includes local expert guide and entrance tickets to the Duomo.
See more >
Visit the Basilica of San Domenico to admire its architecture and art and to learn more about Italy and Europe’s patron, Saint Catherine, who was born in Siena. Marvel at Siena’s medieval streets and squares and listen as your guide points out the most important historical buildings linked to the city’s main houses of power. Rocca Salimbeni houses the most ancient bank in the world, Monte dei Paschi, and the imposing Torre del Mangia is a symbol of the Town Hall’s pride. Admire the Piazza del Campo built in the shape of a shell, home to one of the most famous medieval tournaments, the Palio horse race, held twice a year by the city's Contrada neighborhoods. End the tour with a guided visit to one of the most spectacular cathedrals inItaly, the Siena Duomo with its rich interiors that span the centuries. Your guide will escort youinto this breathtaking monument to see impressive masterpieces by Donatello, Bernini andMichelangelo, exquisite Gothic architecture, an ancient pulpit and many side chapels.


Where You Will Stay

Hotel of a 4 star standard in a
central location in Siena


What’s Included

  • 3 nights accommodation

  • 2 full-day Sight-seeing Tours

  • 2 farm lunches in San Gimignano and the val d’Orcia Visits to Monteriggioni, San Gimignano, Volterra, Pienza and Montepulciano

  • 2h Walking Tour of Siena with entrance to the Duomo

  • 1 Cellar tour and Wine Tasting

  • 1 Alabaster workshop visit with demonstration Sight-seeing stops for photo opportunities

Places You Will See

  • Siena

  • Monteriggioni

  • San Gimignano

  • ​Volterra 

  • Pienza

  • val d’Orcia

  • Montepulciano

from €650 per person in double room

Book your Tuscan Hill Towns Vacation
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