Headout logo. Link to home.
Help

1-Day Tour of Chianti Classico, Montalcino & Montepulciano

Tuscan vineyards with rolling hills in Chianti Classico, Montalcino, Montepulciano.
Chianti vineyards and rolling hills in Tuscany, featuring Montalcino and Montepulciano.
Tuscany vineyard landscape with Chianti Classico, Montalcino, Montepulciano tour highlights.
Vineyards in Tuscany's Chianti Classico region with rolling hills and cypress trees.

Experience Tuscany on a day tour across its medieval villages dotted with iconic olive groves and indulge in a guided wine and oil tasting in Chianti.

Highlights

  • Begin your Tuscan adventure and immerse yourself in the charm of Montalcino and Montepulciano on a day tour.

  • Relax in ultimate comfort as you travel in a deluxe minivan equipped with Wi-Fi, ensuring a seamless and enjoyable journey throughout your Tuscan escapade.

  • Savor the splendor of Tuscany's most stunning landscapes, including the picturesque regions of Chianti, Val d’Orcia, and Val di Chiana.

  • Experience the rich flavors of Tuscany through a wine-tasting extravaganza, featuring a selection that includes the renowned Brunello di Montalcino and the bold Supertuscan.

  • Fun Fact: Val d'Orcia’s picturesque landscapes served as a backdrop for iconic movies like Gladiator and The English Patient.

Inclusions

  • 1-day tour of Chianti Classico, Montalcino & Montepulciano

  • Transfers by a luxury minivan

  • English-speaking driver

  • Guided wine and oil tasting in Chianti

  • Tasting sample menu: 4 Tuscan wines including a Supertuscan, Bruschetta with extra-virgin olive oil and pecorino cheese with balsamic vinegar & chestnut honey

  • Guided wine tasting & typical lunch in Montalcino

  • Wine tasting in Montepulciano

Cancellation policy

These tickets can't be cancelled or rescheduled.

Reviews

4.5
1.9K ratings
5/5
1.4K
4/5
260
3/5
19
2/5
19
1/5
131

Travel in Style and Luxury

Immerse yourself in the heart of authentic Tuscany, where medieval villages exude an irresistible charm, and centuries-old farming traditions yield world-renowned treasures—wine, cheese, cold cuts, and exceptional meats that still captivate global palates today.

Start a journey through the Chianti region, where rolling hills adorned with ancient vineyards and olive groves paint a picturesque landscape. Indulge in a wine tasting, savoring the essence of the region with extra virgin olive oil on Tuscan bread, paired with vin santo and locally crafted 'cantuccini' biscuits, all complemented by the exquisite touch of lavender honey.

Delicious Delicacies & Renaissance Architecture

Venture along a panoramic route, unveiling the medieval gem of Monteriggioni, encircled by its time-honored walls. Traverse the distinctive terrain of the Crete Senesi—a mesmerizing hilly desert that evokes unforgettable emotions. The journey continues, contrasting with the lush greenery of UNESCO-listed Val d'Orcia. At a historic farm, relish a guided two-course lunch featuring the renowned Rosso di Montalcino, Brunello, and Supertuscan wines.

Pause in the medieval allure of Montalcino, where towering walls and a 14th-century fortress frame breathtaking Val d’Orcia views. Meander through narrow streets adorned with wineries and artisan shops showcasing local treasures. Finally, traverse a scenic route to Montepulciano. Enclosed by fortified walls, this town is famed for its Noble wine. Stroll its steep streets and elegant squares, marvel at Renaissance architecture, and partake in a wine-tasting adventure in one of the charming old-town cellars. Uncover the timeless allure of Tuscany in every sip and step.

Tasting Sample Menu

  • Tasting of 4 Tuscan wines

  • Bruschetta with extra-virgin olive oil and pecorino cheese with balsamic vinegar and chestnut honey

Additional information

  • This is a small group tour of 8 passengers ensuring a more intimate experience.

  • A minimum of 4 passengers are required for this tour.

  • The driver leads the tour while providing general introductory information. He is not allowed to lead a guided visit inside a city centre, nor to provide any historical and artistic context.

  • Your voucher will be emailed to you instantly. Please display the voucher on your mobile phone with a valid photo ID at the time of redemption.

  • If you have purchased reduced price tickets, please carry your valid photo ID proof for verification. Students must show their valid Student IDs.

  • Kindly ensure that you arrive 10-15 minutes before the start time of your tour to avoid any delays.

Meeting Point

  • Meet at Piazza Della Repubblica.

  • In front of Caffè Gilli, , 50123 Florence, Metropolitan City of Florence, Italy.

  • The cafe is located in the square where there is a carousel called Antica Giostra Toscana.

Getting There


Getting There

By Bus

  • The nearest bus stop is Roma Duomo Stop ID: 7@FM5350, it is a quick 1 minute walk.

  • Board bus #C1 or #C2 to get you there.

Validity

These tickets are valid for the date and time chosen during purchase.

Similar experiences you'd love

Tourists exploring art at Accademia Gallery in Florence with Reserved Entrance Tickets
Museums
Accademia Gallery Timed Entry Tickets
Instant confirmation
4.1
Rated 4.1 out of 5.0 from 12782 ratings.
from €26.90
€25.04
Save up to 7%
Arcade of the Uffizi Gallery
Museums
Uffizi Gallery Tickets
4.1
Rated 4.1 out of 5.0 from 15450 ratings.
from
€23
Free cancellation
Tour group with guide in Accademia Gallery, Florence, viewing Michelangelo's David.
Guided Tours
Accademia Gallery Skip-the-Line Guided Tour
Instant confirmation
4.3
Rated 4.3 out of 5.0 from 5042 ratings.
from
€31
Free cancellation
Florence Duomo guided tour with view of cathedral facade and optional cupola climb.
Guided Tours
Florence Cathedral Guided Tour with Optional Dome & Bell Tower Climb
Instant confirmation
4.1
Rated 4.1 out of 5.0 from 2514 ratings.
from
€29.99
Free cancellation
Rubens paintings in Niobe Room, Uffizi Gallery, Florence, Italy.
Guided Tours
Uffizi Gallery Skip-the-Line Guided Tour
Instant confirmation
4.3
Rated 4.3 out of 5.0 from 4687 ratings.
from
€48

World at your tap.

Get the Headout app to get tickets on your phone and access app-only deals. Talk about win-win.
Download iPhone appDownload Android app
iphone

We've served 33 million+ guests and we are here for you

33 million+

Happy customers across 10,000+ experiences

In the media

Featured and recommended by the best brands

24 x 7 help center

Have a question? Live chat with local experts anywhere, anytime