Siena Cathedral facade with visitors in Piazza del Duomo, Italy.
Santa Maria della Scala museum facade in Siena, Italy, with visitors in the courtyard.
Winding road through vineyards on Via Chiantigiana, Tuscany.
Vineyards in Chianti landscape during wine tasting tour.
Chianti winery tasting room with tables set for wine sampling.
Group toasting with wine at a winery table surrounded by barrels.
Siena cityscape with historic buildings and lush greenery during Chianti Half Day Wine Tasting Tour.

From Florence: Siena and Chianti Day Trip with Dinner & Regional Pairings, Florence

Florence
Day Trips
Google Verified Seller
Duration

Duration: 7 hours

Free cancellation

Free cancellation up to 24 hours before the start of your experience

Transfers included

Comfortable roundtrip transfers in a A/C Bus

Meals included

Dinner and Wine Tasting

Guided tour

Expert local tour guide

Get your booking confirmed instantly

Set off from Florence along the 'Via Chiantigiana' on a spacious AC bus, regaled by expert live commentary in English or Spanish.

Get ample free time at your first stop, Siena, and explore the central Plaza del Campo.

Head to a rustic vineyard in the heart of Chianti, where traditional pasta and seasonal fare are perfectly paired with locally crafted pours that elevate every bite.

Savor a delicious Tuscan dinner made with the finest regional ingredients.

Half-day trip around Siena and Chianti

Expert local guide in English or Spanish

Pick up from Florence

Round-trip AC bus transfer

Vineyard visit, wine tasting, and dinner in Chianti

Personal purchases

Hotel transfers

Your experience image 1

Siena Cathedral facade with visitors in Piazza del Duomo, Italy.

Tuscany one of the many cradles of the Italian Renaissance, has been the home to numerous influential figures in the fields of art and science. It is also well-known for its wines, such as Brunello di Montalcino, Morellino di Scansano, and Chianti, originating from the picturesque Chianti region. Tuscan foods are quite simple, with a wide variety of bread, cheese, meat and legumes used in their cuisine.

Getting started

Your ticket will be emailed to you. Once you reach the venue, head over to the TOURS & NEWS KIOSK at Piazzale Montelungo Bus Terminal, only a 5-10 minute walk from Santa Maria Novella Train Station. Just look for staff in bright fuchsia Ciaoflorence jackets with a clipboard!

What to expect

Depart Florence and spend an afternoon immersed in Siena’s medieval charm, exploring its Gothic cathedral and hidden gems like the Santa Maria della Scala museum. Cruise the scenic Via Chiantigiana aboard a cozy, air-conditioned bus, enjoying live commentary in English or Spanish.

Conclude your day at a picturesque Chianti winery, where you’ll savor a delectable dinner featuring traditional pasta and seasonal dishes, perfectly paired with exceptional local wines. This journey promises a rich tapestry of sights, flavors, and experiences that capture the essence of Tuscany.

Features

  • Explore Siena: Visit the medieval city and its Gothic cathedral
  • Discover hidden gems like the Santa Maria della Scala museum
  • Scenic drive on Via Chiantigiana: Enjoy the picturesque countryside
  • Visit a Chianti winery for an authentic Tuscan experience
Your experience image 2

Santa Maria della Scala museum facade in Siena, Italy, with visitors in the courtyard.

Your experience image 3

Winding road through vineyards on Via Chiantigiana, Tuscany.

Know before you go image 1

Vineyards in Chianti landscape during wine tasting tour.

What to bring

  • Wear walking shoes for vineries are usually located on the top of the hill and you start the visit with a short inclined walk.

Accessibility

  • This experience is not accessible by wheelchair and pram/strollers.

Additional information

  • Kindly inform in advance if you have any food intolerances or allergies.

  • English and Spanish tours are always available. To confirm the excursion in Italian, Portuguese, or French, we require a minimum of 4 participants.

  • Drinks will strictly not be served to patrons below the age of 18 years.

Know before you go image 2

Chianti winery tasting room with tables set for wine sampling.

Know before you go image 3

Group toasting with wine at a winery table surrounded by barrels.

Customer Reviews

Discover what our customers are saying about their experiences

4.3

Loading reviews...

5
-
4
-
3
-
2
-
1
-

By proceeding with any booking via Staybook, you acknowledge and agree to adhere to all the .

You might also like ...

Explore more experiences in Florence.

From
9,739per person
1

Were Online

How may

Why travellers trust Staybook

We've served 50 million+ guests and are here to serve you better

Premium support, curated experiences, and trusted reviews so every trip feels effortless.

Guests hosted
50 million+

Happy travellers across 12,000+ carefully curated experiences worldwide.

In the media
Featured brands

Recognised and recommended by leading travel and lifestyle publishers.

Support
24×7 help center

Live chat with local experts before, during, and after your experience.