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
Day Trips
Google Verified Seller

Duration: 7 hours (approx.)

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

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

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

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

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

Winding road through vineyards on Via Chiantigiana, Tuscany.

Winding road through vineyards on Via Chiantigiana, Tuscany.

Vineyards in Chianti landscape during wine tasting tour.

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.

Chianti winery tasting room with tables set for wine sampling.

Chianti winery tasting room with tables set for wine sampling.

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

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

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FAQs

The ideal time for dinner pairings in Florence, Siena, and Chianti is during spring (April-June) or autumn (September-November). These seasons offer pleasant weather with fewer tourists. Summer can be crowded but offers more dining options. Winter has smaller crowds but may be chilly.
Transportation options vary based on your starting point. Many tours offer pickup from central Florence hotels or train stations, with transfers by bus or minivan to multiple vineyards and towns like Siena and Greve in Chianti. Private car services are also available for more flexibility.
Photography is generally allowed throughout your dinner pairing experience in Florence, Siena, and Chianti regions, including during tastings and meals. However, some wineries may have restrictions on flash photography or specific areas off-limits to cameras due to privacy concerns.
A typical dinner pairing tour in Florence, Siena, and Chianti lasts around 6-8 hours including transportation between locations, wine tastings, and a gourmet meal. Plan for an early evening start to ensure you make the most of your experience.
Bring comfortable walking shoes as there will be some walking involved in vineyards and historic towns. Dress casually but comfortably, with layers if visiting during cooler months. Don't forget a camera for capturing the beautiful landscapes and memorable moments.
Your dinner pairing experience includes transportation between locations, guided tours of selected wineries, tastings of local wines, a multi-course gourmet meal at a traditional Tuscan restaurant, and sometimes olive oil tasting. Some packages may also include cheese tastings or cooking demonstrations.
While children are welcome on dinner pairing tours, some venues may have age restrictions or be more suitable for adults due to tasting experiences. It's recommended to check specific venue policies beforehand and plan activities that cater to the whole family.
It's highly recommended to book your dinner pairing experience well ahead of time, especially during peak travel seasons such as April through June and September through November. Booking early ensures availability at popular venues and helps secure the best deals.

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