Afternoon in Siena and Chianti Wine Tour with Dinner from Florence

4.0
(323 reviews)

7 hours (approximately)
Offered in: English and 1 more

Admire Siena in total freedom, tour a Chianti winery at a farmhouse, and finish the night with a 4-course dinner featuring divine Tuscan specialties and wine from an estate! This laid-back evening excursion from Florence is the perfect way to discover Siena’s charms once its daytime crowds have left. Explore Piazza del Campo at leisure, and then retreat to the Chianti hills to explore a winery and sample up to three glasses of its Tuscan wine with dinner.

Important notice: Starting from April 2026, the tour itinerary will be modified. The stop in Siena will be removed and replaced with a visit to a winery, where a wine tasting will be included. Dinner will also be provided at the second winery.

What's Included

Dinner at a wine estate with wine tasting
Professional tour leader
Air-conditioned vehicle
Free time in Siena
Gratuities
Hotel pickup and drop-off
Siena Duomo
Guided Tour in Siena with a Professional Guide

Meeting and pickup

Meeting point
Piazzale Montelungo

TOURS & NEWS KIOSK AT PIAZZALE MONTELUNGO BUS TERMINAL Located at 5-10 minutes walking distance from Santa Maria Novella Train Station. Look for our staff wearing a FUCHSIA CIAOFLORENCE JACKET and holding a CIAOFLORENCE CLIPBOARD!

End point
This activity ends back at the meeting point.

Itinerary

Duration: 7 hours (approximately)
  • 1
    Florence

    For those of you looking for a breathtaking tour of Tuscany during the golden hours of the afternoon, this tour is perfect for you! Meet your friendly tour guide at Piazzale Montelungo Bus Terminal. Piazzale Montelungo is located 5-10 minutes walking distance from Santa Maria Novella train station. Grab a seat on the comfortable coach bus, and prepare to depart! During your journey to Siena, your guide will dive into the fascinating history of the city, with some interesting facts and information. The drive will take about one hour.

    1 hour Admission ticket free
  • 2
    Siena

    Your guide will walk you through the perfectly-preserved medieval streets to the center of the city - Piazza del Campo. In a city that seems frozen in the Renaissance, it truly exemplifies medieval glory throughout the Tuscany region. With a rich history of architecture, art, and culture, the city of Siena itself is a UNESCO World Heritage Site! Enjoy plenty of free time for independent exploration throughout the medieval-style buildings, artisanal shops, local cafes, and picturesque alleyways.

    2 hours Admission ticket free
  • 3
    Piazza del Campo

    Piazza del Campo is a must-see in Siena. This (very) large, oval shaped “piazza” is a popular gathering place for locals to meet with family, friends, and classmates. You will probably notice Sienese locals resting on the wide slopes, which lead to Palazzo Comunale and Torre del Mangia. The vibrant square is also home to an annual palio horse race, an epic competition between the different neighborhoods of Siena!

    30 minutes Admission ticket free
  • 4
    Duomo di Siena

    exploring Siena as you please, it is recommended you take some time to visit the heart of the city - the Siena Cathedral. As you walk up to the church, you will immediately notice the breathtaking facade decorated colorfully in pink, green, white, and black marble. Constructed in the 1200’s, this is a perfect example of Romanesque-Gothic architecture. Inside the Cathedral, take some time to admire the unique floors filled with marbled mosaics, depicting biblical stories on 56 different scenes. As you look up, you will see masterpieces throughout the church from Renaissance masters including Donatello, Pisano, Pinturicchio, and Michelangelo. Stroll through the grandiose atmosphere inside, and before exiting, don't forget to stop in the hidden gem of the Cathedral - the deep-colored frescoes of the Piccolomini Library!

    30 minutes Admission ticket not included
  • 5
    Strada Statale 222 Chiantigiana

    A truly unforgettable evening awaits you… You will be brought to a rustic wine estate in the heart of the Chianti wine region. The estate overlooks the rolling hills and lush land. You will be seated at a prepared table among the vineyards of the estate. Does it get much better than this? One of the local wine producers will serve the appetizers of local, seasonal products such as bruschette, salami, and fresh cheese. Then, indulge in a home cooked pasta dish, all made with local products from the region. And the best part - your dinner will include a tasting of various high-quality wines, including Chianti Classico. Enjoy this fantastic meal under the glowing, colorful sky of Tuscany as the sun falls into the horizon.

    2 hours Admission ticket free
  • 6
    Florence

    After your delicious (and picture-perfect!) dinner under the Tuscan sunset, it will be time to head back to Florence. You will arrive back in the early evening.

    1 hour Admission ticket free

Additional info

  • Infants and small children can ride in a pram or stroller
  • Public transportation options are available nearby
  • Infants are required to sit on an adult’s lap
  • Specialized infant seats are available
  • Suitable for all physical fitness levels
  • Please advise any specific dietary requirements at time of booking
Supplied by Ciao Florence Tours Srl

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Tags

Day Trips
Wine Tastings
Full-day Tours
Bus Tours
Historical Tours
Walking Tours
Culinary Tours
Wine Tours
Food & Drink
Spring Break
Additional fees
Low Supplier Cancellation Rate
Low Last Minute Supplier Cancellation Rate
Short term availability

Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

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Rating

4.0 Based on 323 323 reviews
5 stars
177
4 stars
58
3 stars
39
2 stars
24
1 star
25
from per person
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