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Tuscany’s Most Beautiful Hilltop Towns: Volterra, Monteriggioni & San Gimignano – Private Tour

Explore the breathtaking hilltop towns of Volterra, Monteriggioni, and San Gimignano on a private day tour.

Step Back in Time with Tuscany’s Most Beautiful Hilltop Towns

Experience Tuscany like never before with a private day trip to three of its most charming hilltop towns: Volterra, Monteriggioni, and San Gimignano. This tour takes you on a journey through medieval streets, ancient stone walls, and picturesque landscapes that have made Tuscany one of Italy’s most iconic destinations.

Volterra: Land of Etruscans and Medieval Marvels

Begin your day in Volterra, a town known for its ancient Etruscan roots and well-preserved medieval architecture. Stroll along cobblestone streets and marvel at the imposing town walls, which have guarded Volterra for centuries. Volterra’s alabaster craftsmanship is famous worldwide, and its fortress and Roman theater are stunning historical highlights. Learn from your guide about the Etruscan and Roman legacies that continue to shape Volterra’s unique charm.

Monteriggioni: The Perfect Medieval Fortress

Next, we visit Monteriggioni, an enchanting medieval fortress town known for its distinctive ring of walls and 14 towers that have stood proudly since the 13th century. Built by the Sienese to protect against Florentine forces, Monteriggioni’s fortifications make it one of the most memorable sights in Tuscany. Walk through the Porta Franca gate and imagine life within these walls as you explore this small, perfectly preserved medieval gem.

San Gimignano: The Town of Towers

Our final stop is San Gimignano, often called the “Medieval Manhattan” for its stunning skyline of ancient towers. This UNESCO World Heritage site features 14 towers that soar above the town, remnants of the wealth and power held by noble families during the Middle Ages. As you wander San Gimignano’s lively piazzas and charming alleys, your guide will share stories of rivalries, art, and commerce that shaped this extraordinary town. Don’t miss the chance to taste Vernaccia di San Gimignano, a famed white wine produced in this region.

Lunch at a Traditional Trattoria

Midday, pause to enjoy an authentic Tuscan lunch at a traditional trattoria in one of these charming towns. Savor a selection of regional dishes prepared with fresh local ingredients, experiencing the true flavors of Tuscany. Your guide and the restaurant staff will be happy to suggest wine pairings to enhance your meal, giving you a complete Tuscan culinary experience.

FAQs about Tuscany hilltop towns tour:

What towns are included in this Tuscany hilltop towns tour?
This tour includes visits to the hilltop towns of Volterra, Monteriggioni, and San Gimignano, each known for its unique history, beauty, and charm.

Is lunch included in the tour price?
Yes, lunch is included at a local trattoria in one of the towns. Please note that the cost of additional wine during lunch is not included, allowing you the freedom to choose from a curated selection.

Are transfers from Florence included?
Yes, transfers from Florence are included in this tour. If you’d like to be picked up from another location, please contact us for additional transfer options.

How long does this tour last?
This is a full-day tour, typically lasting around 8-9 hours, including travel time, guided visits, wine tasting, and lunch.

Is the Tuscany hilltop towns tour suitable for children?
While this tour is designed for adults who appreciate history and wine, children are welcome to join and will enjoy exploring the castles and medieval streets.

Can we customize this tour?
Yes, we are happy to customize the tour to suit your interests. Please contact us in advance to discuss any specific preferences.

What You Will Love About Tuscany’s Most Beautiful Hilltop Towns Tour

Step Into Tuscany’s Timeless Beauty
Travel through Tuscany’s rolling hills to explore three of its most picturesque hilltop towns: Volterra, Monteriggioni, and San Gimignano. Each town offers a unique glimpse into the region’s history, from ancient Etruscan roots to medieval rivalries and Renaissance charm.

Volterra: A Blend of Etruscan, Roman, and Medieval Wonders
Wander the streets of Volterra, a town rich in history and known for its stunning Etruscan gates, Roman theater, and medieval fortress. Discover its world-famous alabaster craftsmanship and admire panoramic views of the Tuscan countryside.

Monteriggioni: The Perfect Medieval Fortress
Experience Monteriggioni, one of the best-preserved medieval walled towns in Italy. Walk along its ancient walls, pass through the Porta Franca gate, and imagine the knights and soldiers who once defended this Sienese stronghold.

San Gimignano: The Iconic Town of Towers
Marvel at San Gimignano’s soaring medieval towers, which define its skyline and earned it the nickname “Medieval Manhattan.” Stroll through its charming piazzas, admire its well-preserved frescoes, and sip on the famous Vernaccia di San Gimignano white wine.

Savor Authentic Tuscan Flavors
Enjoy a traditional Tuscan lunch at a charming trattoria, featuring regional specialties made with fresh local ingredients. Wine pairings are available to enhance your meal, offering a true taste of Tuscany’s culinary heritage.

A Relaxing and Immersive Experience
With expert guidance, comfortable transfers, and a carefully curated itinerary, this tour offers a seamless and enriching way to explore Tuscany’s historic hilltop towns. Perfect for history lovers, food enthusiasts, and anyone seeking the magic of Tuscany beyond the usual tourist trails.

Suggestions for Other Tours and Experiences You May Like:

 

Meeting Point

We’ll confirm the meeting point with you after booking.
If you would like a private transfer to the meeting point please choose the optional add-on.

FAQ's

We accept most major credit cards and payment forms. Please see the bottom of our website for the payment types accepted.

Most of our customers enjoy having the benefits of a private tour. You have your own guide. You can have rest stops when you like. We can tailor the tour to suit your needs and preferences. We always choose the best guide for your needs, whether you are a family, an art school, or a company doing an incentive event.

All our tours except our Sex, Drugs and Renaissance tour are kid friendly. When doing a private tour with us, you have your own guide, so tell us in the notes of the booking the ages of your kids and we will tailor the tour and choose a guide that’s great for kids for you. We also have 4 special kids’ tours in Florence.

No large bags or backpacks in museums, in churches shoulders and knees must be covered so bring a scarf to cover your shoulders. IF it’s a walking, bicycle or a countryside tour make sure to bring comfortable shoes.

It’s important for everyone to bring their ID

student or children for the museum

All tours are conducted in English only unless otherwise noted or requested. Other languages available for all private tours on request.

We recommend arriving 15 minutes before departure time for all tours and services

We are offering mainly Private and some Semi-private tours at the moment. We do not offer many semi private small group tours anymore due to the consequences of the Covid-19 pandemic. The difference between Private and Semi-private is that the private tours are fully private tours with your own guide and the Semi-private are small shared group tours where individuals can join others.

Knees and shoulders must be covered to enter the churches! Travelling in hot weather? Don’t worry, you can drape a shawl over your shoulders.

If you enjoyed your tour and would like to give your guide a token of appreciation, tips are happily accepted. When asked, the office staff recommends whatever amount you feel comfortable with giving.

Yes, visit our Get In Touch page for all our contact details.

Save time by browsing our website for ideas on romantic getaways, historic residences, palace and castle stays, beautiful views, good value vacations, classic Tuscan country holidays and top attractions. Stop by to chat with us about the best shopping and restaurants in Florence and Tuscany!

Yes. ArtViva, The Original and Best Walking Tours is an ASTA registered company based in Florence, Italy, respecting national and international laws and regulations regarding tourism. (Chamber of Commerce Number 516411)

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