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Hill Towns of Tuscany

5 Days 4 Nights

Experience the essence of Tuscany with our bespoke vacation package, designed to immerse you in the region's timeless beauty and rich cultural tapestry. Your journey includes a collection of handpicked experiences, each uniquely showcasing the charm of Tuscany.

Delight in a private tour through the scenic Chianti area, culminating in the enchanting town of San Gimignano. Here, relish a lunch sourced directly from a local farm and explore the nuances of Tuscan wines with a visit to a renowned winery, complete with a cellar tour and tasting. Enjoy the tranquility of overnight stays in the heart of Tuscany, surrounded by picturesque landscapes.

Engage in a captivating cooking class in Certaldo, where you'll master the art of Tuscan cuisine, complemented by exquisite local wines. Venture to the historic city of Volterra to witness the intricate craft of alabaster in a local artisan's workshop, adding a touch of unique culture to your trip.

Discover the architectural marvels and rich history of Siena, including a guided tour of the magnificent Duomo. Opt for a personalized experience with a private tour or join a small group to explore this vibrant city. Enhance your stay with an optional wine tasting class, diving deeper into the world of Tuscan wines.

Conclude your adventure with a journey through the idyllic Val d'Orcia, visiting iconic towns like Montalcino and Pienza. Experience the rustic charm of a dairy farm lunch and a Brunello winery tour with tastings, ensuring a memorable finale to your Tuscan escape.


Day 1

Discovering the  Chianti & San Gimignano

11 AM: Morning: Departure from Florence

Your Tuscan adventure begins with a pick-up from your chosen location in Florence. As you leave the city behind, prepare to be mesmerized by the panoramic vistas of the Chianti Classico route. The journey takes you through the picturesque landscapes of Tuscany, where rolling hills and vineyards paint a scene straight out of a Renaissance masterpiece.

12:30 PM: Authentic Tuscan Experience at a Family-Run Winery

Around midday, you'll arrive at a charming, family-run winery nestled in the heart of Chianti. Here, you'll be welcomed by the wine-making family, offering you a unique glimpse into the local way of life. Enjoy a fresh, seasonal lunch that perfectly complements the array of Chianti wines. This meal is not just about savoring delicious food and wine; it's an opportunity to engage with the traditions and stories behind Tuscany's celebrated culinary culture.

2:30 PM: Exploring Montefioralle and Greve in Chianti

Continue your journey to the medieval hamlet of Montefioralle. This enchanting village, with its cobblestone streets and stone houses, is a hidden gem in the Chianti region. Wander through the narrow lanes and soak in the atmosphere of a bygone era. Next, visit the Chianti town of Greve in Chianti. Known as the gateway to the Chianti region, Greve boasts a charming piazza, artisan shops, and quaint cafés, making it a delightful place to explore and absorb the local vibe.


5 PM: Arrival and Leisure Time in San Gimignano

Your first day culminates with a 5 pm arrival in San Gimignano, the iconic UNESCO-listed hill town famed for its medieval towers. Check into your centrally located accommodation and take the evening to relax and explore at your own pace. As the day-trip crowds dissipate, San Gimignano's true enchantment comes alive. Stroll through its historic streets, admire the stunning views of the Tuscan countryside, and choose from one of the many renowned restaurants to enjoy a tasty Tuscan meal. The tranquility of the evening in this beautiful town offers the perfect setting to unwind and reflect on the day's experiences.


This first day of your vacation package promises a beautiful blend of scenic beauty, cultural immersion, and gastronomic delights, setting the tone for a truly memorable Tuscan escape.

Day 2

Culinary Delights and Historical Exploration in Certaldo and Volterra

9:30 AM: Authentic Tuscan Cooking Class

Your day begins with a 10 AM departure from your San Gimignano accommodation, whisking you away to the picturesque town of Certaldo. Here, you'll dive into the heart of Tuscan cuisine with an authentic cooking class. This hands-on experience is a culinary journey, where you will learn to prepare a full Tuscan meal, including the art of making fresh pasta. Under the guidance of local chefs, you'll discover the secrets behind traditional recipes and the importance of fresh, local ingredients. The cooking class isn't just about food; it's a gateway to understanding Tuscan culture and history through its flavors.

3 PM: Discovering Volterra's Rich Heritage

Your journey continues to the historic hill town of Volterra. This town is a treasure trove of history, boasting Etruscan, medieval, and Roman influences. As you stroll through its ancient streets, you'll be captivated by the sweeping views and the town's rich architectural tapestry. Enjoy some leisure time exploring the town, perhaps visiting its well-preserved ruins or browsing local shops.

A highlight of your visit to Volterra will be stopping at an authentic artisanal workshop. Here, you'll witness a local craftsman at work, sculpting alabaster – a translucent stone that has been carved into intricate artworks for centuries in this region. This visit offers a rare glimpse into an ancient craft, allowing you to appreciate the skill and tradition that goes into every piece.

5 PM: Return to San Gimignano

As the afternoon fades, a return to San Gimignano awaits you. Spend another night in this medieval gem, where the towers and historic ambiance create a perfect backdrop for an evening at leisure. Explore the town further, perhaps visiting sites you missed the day before, or simply relax and enjoy the unique atmosphere. For dinner, choose from a variety of local restaurants offering delightful Tuscan cuisine, the perfect way to conclude your day of culinary and historical discoveries.


Day 2 of your Tuscan getaway is designed to blend the joys of cooking and the pleasure of discovery, offering an intimate connection with the region's culinary heritage and its storied past.

Day 3

Historic Exploration in Siena and Leisure Time

Morning: Journey to Siena and Private City Tour

9:30 AM checkout from your accommodation in San Gimignano, marking the beginning of your journey to the captivating city of Siena. Upon arrival, embark on a private 2.5-hour tour of this renowned Tuscan city, known for its rich medieval history and stunning architecture. Your expert guide will lead you through the winding streets of the city center, unveiling the stories and secrets that each corner holds. The highlight of this tour is a visit to the magnificent Duomo cathedral, a masterpiece of Italian Romanesque-Gothic architecture. This tour is not just a visual feast; it's an insightful journey into the heart of Sienese culture and history.

Afternoon: Check-In to Hotel and Leisure Time in Siena

After the tour, proceed to check into your centrally located Siena hotel, which will be your base for the next two nights. From 1 PM onwards, the day is yours to enjoy at your leisure. Siena, a UNESCO World Heritage Site, offers a wealth of experiences. You might choose to delve deeper into its historical treasures, relax in one of the city's charming cafés, or explore its bustling piazzas.

For those seeking more structured activities, optional services can be arranged. Whether you're interested in further exploring Sienese art and culture, enjoying a wine tasting experience, or simply wandering through the local markets, Siena has plenty to offer. This time is an opportunity for you to soak in the ambiance of this historic hill town at your own pace, creating memories that resonate with your personal travel aspirations.


Day 3 of your Tuscan escape is designed to balance structured exploration with personal leisure, offering you the freedom to discover the many facets of Siena in your own unique way.

Day 4

Scenic Drives,  Brunello Wines and the Enchanting Pienza

9:30 AM: Panoramic Drive Through Crete Senesi

Pick-up from your accommodation in Siena, setting out on a panoramic drive through the Crete Senesi. This region is renowned for its idyllic landscapes, characterized by rolling hills, ancient oak trees, and quaint farmhouses. The drive itself is a serene experience, offering a chance to admire the picturesque beauty of the Tuscan countryside.

11 AM: Visit to Monte Oliveto Maggiore Monastery

Arrive at the serene Benedictine monastery of Monte Oliveto Maggiore. Here, you can stroll through the frescoed cloister, marveling at the stunning artwork that adorns its walls. Explore the monastery's rich collection of ancient books and art, providing a glimpse into the religious and cultural history of the region. A visit to the centuries-old pharmacy is a unique experience, showcasing natural remedies and liquors that have been produced by the monks for generations.

1 PM: Brunello Wine Experience near Montalcino

Your journey continues with a visit to a renowned Brunello-producing winery near Montalcino. Enjoy a tour of the estate, learning about the meticulous process of creating Brunello, one of Italy's most prestigious wines. Following the tour, indulge in a delightful lunch paired with Brunello wines, an experience that perfectly combines gastronomic excellence with vinicultural expertise.

4 PM: Exploring Pienza

Arrive in Pienza, the iconic Renaissance town known for its architectural beauty and breathtaking views of the Val d'Orcia valley. Take your time to stroll through the picturesque streets, admiring the harmonious layout designed by Pope Pius II. The town offers a perfect blend of historical significance and natural beauty, making it a must-visit destination in Tuscany.

6:30 PM: Return to Siena

Conclude your day with a return to your accommodation in Siena. The evening is yours to relax and enjoy at your leisure. Whether you prefer a quiet night in or exploring the vibrant streets of Siena, this day offers the perfect balance of guided exploration and personal downtime, wrapping up another memorable day of your Tuscan adventure.

Day 5

Farewell to Siena and Departure

10 AM: Checkout and Farewells

As your Tuscan journey comes to a close, day five begins with a leisurely morning in Siena. After breakfast, prepare for checkout from your accommodation, taking a moment to reflect on the unforgettable experiences and memories you've gathered over the past days.

Departure: Optional Transfer to Next Destination

As you bid farewell to the enchanting city of Siena, we understand that your journey may take you further. To facilitate a seamless transition to your next destination, we offer an optional transfer service upon request. Whether you're headed to another Italian city, returning to the airport, or continuing your adventure elsewhere, we are here to ensure a smooth and hassle-free departure.

End of Tour

This marks the end of your exquisite Tuscan escapade with us. As you move forward to your next destination, we hope that the beauty, culture, and flavors of Tuscany linger in your heart, inspiring future travels and stories to share. Arrivederci, and may your travels always be filled with such enriching and delightful experiences!



  • 1 Day Trip of the Chianti with winery visit

  • 1 Hand On Cooking Class with lunch and wine

  • 1 Day Trip to Certaldo and Volterra

  • 1 Visit to Alabaster Sculptor's workshop

  • 1 Private 2.5 Hours Siena Walking tour and Duomo entrance tickets

  • 1 Full Day Val d'Orcia Day Trip

  • 1 Visit to Brunello Winery with Tasting

  • 1 Visit to Benedictine Monastery with entrance tickets


  • 2 Nights in Hotel in Center of San Gimignano

  • 2 Nights in Hotel in Siena Center
    Accommodation in Double or Twin Room, Single Room Supplement available


  • 4 Breakfasts in Hotels

  • Lunch With Wine at Chianti Producer

  • Lunch with Wine at Cooking Class

  • Lunch With Wine Brunello Winery


  • Transportation in Comfortable 8 Seater Vehicle with AC

  • All Transfers and day trip transportation

  • All Motorway and Transportation Fees


  • Comapany of Experienced English Speaking guide for the day trips

  • Authorized City Guide for Siena Walking Tour

Shared Tour Dates

  • 16 - 21 June 2024

  •  10 - 25 October 2024



€ 1,350 per person *

* tour will depart with minimum of 4 persons

Book Private Vacation

Flexible Dates and Itinerary

Price According to number of Persons and Chosen Accommodation

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