Headout logo. Link to home.
Help
Day Trips

From Florence: Siena and Chianti Day Trip with Dinner & Wine Tasting

Group of tourists enjoying a wine tasting session on a Chianti Half Day Afternoon Tour in a Tuscan vineyard, Italy
Scenic view of Chianti vineyards during a half day afternoon tour
Guests enjoying wine tasting in Chianti
Guests enjoying dinner during Chianti Half Day Wine Tasting Tour

Discover the picturesque countryside of Tuscany as you visit Siena and Chianti. Dig into local delicacies and sip the finest wine.

Highlights

  • 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 or the interesting Santa Maria della Scala museum.

  • Make your way to a rustic vinery in the heart of Chianti, where traditional pasta and other seasonal dishes are accompanied by the perfect wines!

  • Did you know? The republics of Florence and Siena fought over Chianti in the Middle Ages – and divided the territory using roosters and knights!

Inclusions

  • 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

Itinerary

Cancellation policy

You can cancel these tickets up to 24 hours before the experience begins and get a full refund.

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.

A carefully curated itinerary

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.

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.

What's not allowed

  • Safety is a priority so the wine tasting experience is restricted for guests under the age of 18 years.

  • Guests under the age of 18 years can join the tour if they are each accompanied by at least one adult.

Accessibility

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

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

Meeting Point

  • Refer to the meeting point details in your final voucher.

Similar experiences you'd love

Arcade of the Uffizi Gallery
Museums
Uffizi Gallery Tickets
4.1
Rated 4.1 out of 5.0 from 15459 ratings.
from
€23
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 12783 ratings.
from
€28.90
Florence Cathedral exterior with tourists, featuring optional dome climb and audio guide.
Landmarks
Florence Cathedral Tickets with Optional Dome & Bell Tower Climb
Instant confirmation
4.0
Rated 4 out of 5.0 from 6311 ratings.
from
€20
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
€38
Visitors viewing art in Uffizi Gallery with skip-the-line tickets and host in Florence, Italy.
Combo
Uffizi and Accademia Skip-the-Line Tickets with Host
Instant confirmation
3.6
Rated 3.6 out of 5.0 from 7995 ratings.
from €52
€49.40
Save up to 5%

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