San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch & Wine Tasting
Active
11h
For a full refund, cancel at least 24 hours before the scheduled departure time.
Instant confirmation
Mobile or paper ticket accepted
About this experience
Discover Tuscany in one day from Florence. Begin in the hilltop UNESCO town of San Gimignano with about 2 hours of free time to explore towers, lanes, and artisan shops. Continue to Monteriggioni (seasonal; see note), a perfectly preserved walled village, with time to wander inside the walls. Cross the rolling Chianti hills to a cozy winery for a tasting of three wines and a three-course farm-to-table lunch, ending with cantucci & vin santo. In the afternoon, enjoy a guided walking tour of Siena: stroll Piazza del Campo and see the Palazzo Pubblico, then admire the Cathedral (interior visit if option selected). Finish with free time before returning to Florence.
Please note that the order of the visits may change
(*) November to March, the Tour does not include the stop at Monteriggioni and the return to Florence is approx 30 minutes earlier
Available options
Spanish Tour with Cathedral
Lunch<br/>Siena Cathedral Visit included: It includes: Transport, Tour Leader on board, Typical Lunch, Siena Guided Visit and Cathedral admission
Tour in Spanish
Lunch<br/>Shared Day Trip from Florence: It includes: Siena Guided Visit, Lunch and wine tasting, Transport, Tour Leader on board.
Not included: Cathedral admission
Spanish-Shared Round Transport
Lunch<br/>Shared round Trasport & Lunch: It includes: Transport, Tour Leader on board, Typical Lunch.
Not included: Siena Guided Visit and Cathedral admission
Tour in English
Lunch<br/>Shared Day Trip from Florence: It includes: Siena Guided Visit, Lunch and wine tasting, Transport, Tour Leader on board.
Not included: Cathedral admission
English-Shared Round Transport
Lunch <br/>Shared Round Transport & Lunch: It includes: Transport, Tour Leader on board, Typical Lunch.
Not included: Siena Guided Visit and Cathedral admission
English Tour with Cathedral
Lunch<br/>Siena Cathedral Visit included: It includes: Transport, Tour Leader on board, Typical Lunch, Siena Guided Visit and Cathedral admission
What's included
Licensed Tour Escort for on-board insights and coordination
If option selected: Skip-the-line access to visit inside Siena Cathedral & Piccolomini Library
If option selected: from April to October monolingual guided visit in Siena
Wine tasting: three Chianti wines plus traditional vin santo
If option selected: Guided walking tour of Siena with a professional local guide
Chianti winery experience: guided cellar & vineyard visit plus 3-course Tuscan lunch
Assistance by Caf Tour Team at the meeting point
Round-trip transport by comfortable, air-conditioned coach from Florence
Detailed itinerary
1
Discover the UNESCO-listed “town of towers,” a perfectly preserved medieval hilltop gem with panoramic views, artisan boutiques, and photogenic alleys. Enjoy ample free time for your own exploring, from award-winning gelato to snapshots of the skyline—ideal on a day trip from Florence.
2
The atmospheric heart of San Gimignano, framed by tower-houses and a medieval stone well that anchors the square. A short, curated stop for photos and storytelling that brings the town’s merchant past to life.
3
Glide past the 14th-century fortifications and the most iconic gate, imagining pilgrims and traders entering centuries ago. Your tour leader shares context and highlights so you can appreciate the engineering and defense of a Tuscan walled city.
4
Step inside a storybook fortress village encircled by intact walls and ramparts, beloved by filmmakers and history fans alike. Enjoy free time to browse tiny craft shops, stroll the piazza, and soak up authentic medieval Tuscany.
(*) From November to March, the itinerary does not include the stop at Monteriggioni and the return to Florence is approx 30 minutes earlier
5
Travel the legendary wine route through rolling vineyards, stone farmhouses, and cypress-lined ridges—classic Tuscany in every direction. Stop at a welcoming Chianti winery for a tasting of three wines and a farm-to-table 3-course lunch, ending sweetly with cantucci e vin santo.
6
Join a guided walking tour (if option selected) through contrade banners, artisan storefronts, and grand palazzi that reveal Siena’s golden age. Afterward, enjoy free time to sip an espresso, browse boutiques, or continue exploring this Gothic masterpiece at your own pace.
7
Admire refined Renaissance architecture and hear how the world’s oldest operating bank shaped Siena’s wealth and culture. It’s a concise stop with rich history and elegant façades perfect for quick photos.
8
Stop 8
Stand in Siena’s shell-shaped stage, home to the legendary Palio horse race, and take in Palazzo Pubblico and Torre del Mangia. Your guide unpacks centuries of tradition so the square’s drama and design truly resonate.
9
Stop 9
Gaze at the striped marble exterior, a Gothic marvel that crowns the city; (if option selected) interior visit to admire polychrome floors and masterpieces. A powerful highlight that pairs art history with unforgettable visuals.
10
Stop 10
Step into a jewel box of vivid Pinturicchio frescoes and illuminated manuscripts that glow with Renaissance color. A quick but dazzling stop that rewards art lovers and casual visitors alike. (if cathedral option selected)
11
Return along vineyard-draped hills and ancient hamlets, the perfect finale for golden-hour photos across the Tuscan countryside. A smooth, scenic drive back to Florence rounding off a day of towers, wine, and medieval splendor.
What's not included
Our Shared Round Transport option does NOT include: Siena Guided Visit, Cathedral admission
From November to March, the itinerary does not include the stop at Monteriggioni
Available languages
Guide guide
EN
ES
Reviews breakdown
Viator
4.1
2,299 reviews
5★
1058
4★
759
3★
267
2★
142
1★
73
Tripadvisor
4.8
2,104 reviews
5★
1822
4★
211
3★
33
2★
22
1★
16
Important information
Infants and small children can ride in a pram or stroller
Public transportation options are available nearby
Specialized infant seats are available
Travelers should have at least a moderate level of physical fitness
A dress code is required to enter places of worships and selected museums. No shorts or sleeveless tops are allowed. Knees and shoulders MUST be covered for both men and women. This dress code is strictly enforced and you will risk refused entry if you fail to comply with requirements.
For small groups, up to 8 pax, the Tour escort service could be replaced with an English speaking driver-guide service, while maintaining unchanged the entire program of the excursion.
Comfortable walking shoes are recommended.
From November to March, the itinerary does not include the stop at Monteriggioni and the return to Florence is approx 30 minutes earlier
It is mandatory to arrive at the meeting point at the mentioned check in time. In case of delay or no show it will not be possible to join the tour, nor to have a refund or reschedule the tour.
Please be advised that it is required to bring your original ID with you during the tour.
Once the audio guides are handed over before the guided tour, they become the full responsibility of the customer. In case of loss, a fee of €80 will be charged.
Clients with motor disabilities or wheelchair users are encouraged to notify the tour organizer in advance and seek medical advice to ensure suitability of services. Our tours and transportation are not suitable for people with motor disabilities or wheelchair users, so to prioritize the safety and well-being of all involved, the driver and tour manager retain the right to decline participation if they believe it may compromise safety. This decision rests solely with them, and no compensation will be provided in such cases. By accepting these terms, clients agree to respect decisions made by staff regarding participation.
Meeting point
Check in time: 07:45am - Montelungo Square, at the end of the ramp connecting with the train station. An assistant will be waiting for you wearing blue clothing with CAF Tour - Gray Line logos.
Important notes
• Check-in time and Meeting Point:
at 7:45 am at Piazzale Montelungo, at the end of the ramp connecting with the train station. An assistant will be waiting for you wearing blue clothing with CAF Tour - Gray Line logos.
How to reach the meeting point from Santa Maria Novella Station Square:
Take "Via Valfonda" (Valfonda street) and go straight on at the end of the street, until you see the Fortress (Fortezza da Basso). Cross the street in front of you and keep your left side, until you see on the right side Piazzale Montelungo (big square with car and Bus parking)
It is mandatory to arrive at the meeting point at the mentioned check in time. In case of delay it will not be possible to join the tour, nor to have a refund or reschedule the tour.
Once the audio guides are handed over before the guided tour, they become the full responsibility of the customer. In case of loss, a fee of €80 will be charged.
Please be advised that it is required to bring your original ID with you during the tour.
- For small groups, up to 8 pax, the Tour will be by Minivan and the Tour escort service will not be provided. The remaining services will be as scheduled.
- It is recommended that participants wear comfortable shoes and appropriate clothes to visit museums or places of worship.
• Our Contacts:
Agency address: via dei Tavolini 15red - 50122 Firenze - Phone +39 055 29.55.72 or +39 055 28.32.00 - Whatsapp: +39 3458025842
email address: tours@caftours.com
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
From $25
per person
Price varies by option
Secure booking
Free cancellation available
Instant confirmation
