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Siena, San Gimignano

/Wine/ Tasting & /Lunch/

Explore Tuscany's rich history in Siena, experience the tradition of il Palio, savor a wine tasting in Chianti Classico, and wander through the medieval town of San Gimignano, all with the comfort of luxury transport.

Discover What's Included

The Details

Tuscan Landscapes

Guided Walking Tour in Siena - with a local guide

Enjoy a drive-through of picture-perfect Tuscan Landscapes. Arrive in Siena to meet your local guide in the heart of the medieval city center. Take the road called ‘Banca di Sopra’ to learn about the thirteenth-century Sienese families involved in the most ancient bank in the world, ‘The Monte dei Paschi.’

The Heart of Siena

Piazza del Campo

Make your way to the stunning Piazza del Campo, where the most famous horse race in the world, ‘il Palio,’ has been held every year since the dark ages. Please continue to the Duomo to admire its stunning Facade.

A Gastronomic Journey

Wine Tasting and Culinary Delights in Tuscany

Enjoy lunch and a Wine Tasting Tour at a boutique Winery in Chianti Classico. Visit the wine cellars and learn about Regional winemaking. Your cellar tour will continue with lunch paired perfectly with estate wines.

Towers and Traditions

Free Time To shop and sight see in San Gimignano

Could you arrive in the medieval town of San Gimignano? You will have free time to visit the main squares of this architectural marvel, where you will see multiple towers once owned by Noble families. See a selection of artisans selling their local products, and stroll down the winding streets for spectacular views of the valley.  Our expert driver sommelier in V-Class Mercedes will drop you off at your Hotel.

"The view was absolutely /stunning/ & perfect on a nice /warm/ Tuscany day."

Today we toured Siena and San Gimignano with a stop at an amazing winery for lunch. Carlo was our driver and he was magnificent. Very courteous and knowledgeable about the area and wines. The winery he took us to for wine tasting and meal was extraordinary. Delicious wines (we sampled six) and wonderful food to go with it.

Doug Huls


Monday to Sunday
except public holidays

2024. 01. 01. - Capodanno - New Year's Day 2024. 01. 06. - Epifania - Epiphany 2024. 03. 31. - Pasqua - Easter Sunday 2024. 04. 01. - Lunedì dell'Angelo - Easter Monday 2024. 04. 25. - Festa della Liberazione - Liberation Day 2024. 05. 01. - Festa del Lavoro - International Workers Day 2024. 06. 02. - Festa della Repubblica - Republic Day 2024. 08. 15. - Ferragosto o Assunzione - Assumption Day 2024. 11. 01. - Tutti i santi - All Saints Day 2024. 12. 08. - Immacolata Concezione - Immaculate Conception 2024. 12. 25. - Natale - Christmas Day 2024. 12. 26. - Santo Stefano - St. Stephen's Day

Starting Time

09.00 am / 09.30 am


Includes English speaking Chauffeur Driver in V-Class Mercedes, Guided Walking Tour in Siena with private certified guide, full lunch at winery with wine and olive oil tasting - lunch includes starter, first course, dessert

Duration Of Tour

8 hours


1 Adult
2 Adults
3 Adults
4 Adults
5 Adults
6 Adults


Same as adult pricing

This exclusive activity is uniquely available as part of our tailor-made multi-day holidays crafted by Italy Customized. They can be seamlessly integrated into your personalized itinerary, providing an exceptional touch to your meticulously organized journey.

Can I book a standalone experience for my customized vacation?

Absolutely! You can book standalone tours with us, regardless of whether we're planning your entire vacation. If you're entrusting us to craft your whole vacation, simply mention your interest in specific tours or activities on the inquiry form, and we'll ensure they're included in your customized vacation plan.

Can I book a standalone experience if my vacation isn't planned by Italy Customized?

Absulutely! These exceptional tours are available for individual booking. They are NOT exclusively tied to our customized multi-day packages, allowing everyone to indulge in the beauty and culture of these meticulously crafted tours and activities

Does the cost cover everything?

The cost of the tour includes English speaking Chauffeur Driver in V-Class Mercedes, Guided Walking Tour in Siena with private certified guide, full lunch at winery with wine and olive oil tasting - lunch includes starter, first course, dessert.

What is the group size for this private tour?

Our tours offer an intimate experience with a maximum of 6 participants in a V-Class Mercedes and up to 8 in a Mercedes Sprinter. For larger groups of up to 20 persons, please contact us directly for a customized pricing arrangement.


Find answers to frequently asked questions about our itineraries. Gain insights into the details, inclusions, and personalized experiences offered within our tailor-made journeys.

Book Your Own Tour

Stress-free, quality-rich exploration of Italy's culture and beauty.

Customize Your Vacation With These Tours & Activities

01. Inquiry - Share Your Vision

Begin your journey by sharing your desires, preferences, and travel dreams with us through the contact form. Let us know your interests, destinations you wish to explore, and any unique experiences you seek. Your input fuels our customization process to create an Italian adventure crafted exclusively for you.

02. The Call - Dive Into Detail

Following your inquiry, we'll schedule a personalized call or video meeting. This is where we delve deeper into your requirements, refining every detail to mold your dream itinerary. Our expert team uses these conversations to craft a personalized journey that aligns perfectly with your aspirations.

03. Proposal - Tailored Just For You

After our discussion, a meticulously crafted proposal designed exclusively for you will be sent. This detailed plan captures your bespoke itinerary, accommodations, and experiences. Upon confirmation, you'll gain access to our intuitive app to review and confirm your tailored itinerary, securing your journey with a deposit.

04. Vacation - Relax & Enjoy

It's time to embark on your personally curated Italian escape. With everything meticulously arranged, you're set to savor every moment of your bespoke vacation, plus, we are also available during your holiday, serving as your dedicated 24-hour concierge throughout your Italian experience. From iconic sights to hidden gems, immerse yourself in a tailor-made journey created to surpass your expectations.

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