Afternoon in Siena and Chianti Wine Tour with Dinner from Florence

Florence , Italy

Afternoon in Siena and Chianti Wine Tour with Dinner from Florence

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About this experience

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.

Available options

Tour in English

Tour in Spanish

What's included

Dinner at a wine estate with wine tasting

Professional tour leader

Air-conditioned vehicle

Free time in Siena

Detailed itinerary

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.

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.

Stop 3

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!

Stop 4

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!

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.

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.

What's not included

Gratuities

Hotel pickup and drop-off

Siena Duomo

Guided Tour in Siena with a Professional Guide

Available languages

Guide guide

EN ES

Reviews breakdown

Viator 3.8

189 reviews

5★

4★

3★

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1★

Tripadvisor 4.4

135 reviews

5★

4★

3★

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1★

Important information

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

English and Spanish are always guaranteed. In order to confirm the excursion in Italian, German, Portuguese or French a minimum of 4 pax is required

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

Meeting point

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!

Important notes

Please note that on the busiest days the entrance into the museums may experience some short delays

About Florence

Florence, the capital of Italy's Tuscany region, is a treasure trove of art, architecture, and history. Known as the birthplace of the Renaissance, it's home to iconic masterpieces, stunning cathedrals, and a rich cultural heritage that continues to captivate visitors from around the world.

Top Attractions

Duomo

The Florence Cathedral, known as the Duomo, is a masterpiece of Renaissance architecture. Its iconic dome, designed by Brunelleschi, offers panoramic views of the city.

Architecture/Religious 2-3 hours Free to enter the cathedral, €18 for the climb to the dome

Uffizi Gallery

One of the world's most famous art museums, the Uffizi Gallery houses works by Botticelli, Michelangelo, and Leonardo da Vinci.

Museum/Art 2-3 hours €20

Ponte Vecchio

A medieval stone bridge famous for its jewelry shops. It's one of the most iconic landmarks in Florence.

Architecture 30 minutes to 1 hour Free

Piazzale Michelangelo

A panoramic terrace offering breathtaking views of Florence. It's a perfect spot for sunset and photography.

Scenic Viewpoint 1-2 hours Free

Accademia Gallery

Home to Michelangelo's famous statue of David, the Accademia Gallery is a must-visit for art lovers.

Museum/Art 1-2 hours €16

Must-Try Local Dishes

Bistecca alla Fiorentina

A thick-cut, grilled T-bone steak, seasoned simply with salt and pepper. It's a must-try for meat lovers.

Dinner Contains beef, not suitable for vegetarians or vegans

Ribollita

A hearty vegetable and bread soup, traditionally made with leftover bread and vegetables. It's a classic Florentine dish.

Lunch/Dinner Vegetarian, can be made vegan

Lampredotto

A Florentine street food made from the fourth and final stomach of a cow. It's typically served in a sandwich.

Lunch Contains beef, not suitable for vegetarians or vegans

Cantucci

Almond biscotti traditionally served with Vin Santo, a sweet Tuscan wine. They are crunchy and perfect for dipping.

Dessert Contains almonds, can be made gluten-free

Popular Activities

Hiking in the Tuscan countryside Cycling tours Hot air balloon rides Wine tasting tours Spa day at a luxury hotel Strolling through the gardens of Villa medici Visiting museums and art galleries Attending opera or concerts

Best Time to Visit

April to June, September to October

These months offer pleasant weather and fewer crowds compared to the summer peak. Ideal for sightseeing and outdoor activities.

15-28°C 59-82°F

Practical Information

Language

Official: Italian
Widely spoken: English, French, Spanish
English: Moderately spoken

Currency

Euro (EUR)

Time Zone

GMT+1 (CET), GMT+2 (CEST during daylight saving time)

Electricity

230VV, 50HzHz

Safety Information

Overall Safety Rating: Generally safe

Florence is generally safe for tourists, but pickpocketing and petty theft can occur, especially in crowded areas. Be aware of your surroundings and take precautions to protect your belongings.

Important Precautions:

• Keep valuables secure and out of sight
• Be cautious of your surroundings, especially in crowded areas
• Use licensed taxis or ride-sharing apps

Getting there

By air

Florence Airport • 5 km from city center
Pisa International Airport • 85 km from city center

By train

Santa Maria Novella Station

By bus

Villa Costanza Bus Station, Florence Airport Bus Terminal

Getting around

Public transport

The bus network covers the entire city and is the primary mode of public transport. Buses are frequent and reliable.

Taxis

Available • Apps: MyTaxi, FreeNow

Rentals

Car, Bike, Scooter

Neighborhoods

Santa Maria Novella Oltrarno San Lorenzo Santa Croce

Day trips

Siena

70 km from Florence • Half day to full day

A medieval city known for its stunning Piazza del Campo and the Palio, a traditional horse race held twice a year.

Pisa

85 km from Florence • Half day

Home to the iconic Leaning Tower of Pisa, this city offers a mix of historic sites and scenic views.

Chianti Wine Region

30-50 km from Florence • Full day

A picturesque wine region known for its rolling hills, vineyards, and charming villages.

Festivals

Festa di San Giovanni • June 24 Calcio Storico Fiorentino • June (dates vary) Firenze dei Fiori • April to June

Pro tips

Visit major attractions early in the morning or late in the afternoon to avoid crowds
Book tickets for popular attractions in advance to save time and avoid long queues
Explore the city's hidden gems, such as the Oltrarno neighborhood and the secret passages of the Palazzo Vecchio
Try local specialties like Bistecca alla Fiorentina, Ribollita, and Lampredotto
Learn a few basic Italian phrases to enhance your experience and connect with locals