San Gimignano, Siena, Monteriggioni: Fully Escorted Tour, Lunch & Wine Tasting

Siena , Italy

San Gimignano, Siena, Monteriggioni: Fully Escorted Tour, Lunch & Wine Tasting

Active

(171 reviews)

11h

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

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Mobile or paper ticket accepted

About this experience

Experience Tuscany in a day from Florence: San Gimignano, Monteriggioni, Chianti, and Siena. 11-hour coach tour through medieval towers, walled hamlets, and rolling vineyards. Explore the UNESCO historic center of San Gimignano at your own pace; step inside Monteriggioni’s perfectly preserved fortress. Follow the scenic Chiantigiana road to a cozy winery for a guided tasting of 3 Chianti wines and a zero-mile, 3-course lunch, finishing with cantucci & vin santo. Enjoy free time in Siena to wander Gothic lanes, browse artisan shops, and relax in lively enotecas. Quick stops at the striped Duomo and shell-shaped Piazza del Campo, home of the Palio. Ideal for travelers seeking art, wine, and views in one effortless day—round-trip transport and tour leader included.

(*) From November to March, the itinerary does not include the stop at Monteriggioni and the return to Florence is approx 30 minutes earlier

Available options

Siena, San Gimignano, Chianti

Round Trip by bus to Siena and San Gimignano with hostess aboard, commentary on the bus about the history, art and landscape.

What's included

Caf Tour staff assistance at the meeting point for smooth check-in

Licensed English-speaking tour escort throughout the day

Chianti winery experience: guided visit of cellars and vineyards & 3-course traditional Tuscan lunch

Wine tasting: three different Chianti wines plus classic vin santo

Tasting of three different Chianti Wines, extra virgin olive oil, balsamic vinegar & vin santo

Round-trip transport by air-conditioned coach

Detailed itinerary

Stop 1

Explore a perfectly preserved walled hilltown famed for its soaring medieval towers and fresco-filled churches. Stroll the UNESCO-listed historic center at your own pace, browsing artisan shops and quiet lanes. Enjoy panoramic viewpoints over the Val d’Elsa and time for gelato or souvenirs.

Step inside a storybook fortress village encircled by intact 13th-century walls. Wander the tiny piazza and gates, soaking up its authentic medieval atmosphere. Quick, easy visit with great photo spots from the ramparts.

(*) From November to March, the itinerary does not include the stop at Monteriggioni and the return to Florence is approx 30 minutes earlier

Cruise one of Tuscany’s most scenic roads, rolling past vineyards, olive groves, and stone farmhouses. Settle into a cozy winery for a guided tasting of three Chianti wines paired with a zero-mile, three-course lunch. Finish sweetly with traditional cantucci and vin santo.

Enjoy generous free time to feel Siena’s Gothic soul—narrow lanes, noble palaces, and lively enotecas. Browse artisan boutiques, sample local specialties, and capture the city’s warm, terracotta hues. Ideal for independent discovery and relaxed photos.

Stop 5

Pause for an exterior and brief interior look at Siena’s striking striped-marble cathedral. Admire its ornate façade, sculptures, and masterworks that hint at the city’s artistic power. A swift but unforgettable highlight.

Stop 6

Descend into one of Italy’s most beautiful squares, famed for the Palio horse race. Take a moment to sit at a café, admire the shell-shaped slope, and view the Torre del Mangia and Palazzo Pubblico. A perfect finale for people-watching and photos.

What's not included

Guided Service in Siena

Cathedral admission in Siena

Available languages

Guide guide

Reviews breakdown

Viator 4.4

86 reviews

5★

4★

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Tripadvisor 4.6

85 reviews

5★

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1★

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

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

Please note that the order of the visits may change

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 excursion, 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.

Meeting point

An Assistant waits for you wearing blue clothing with Caf Tour and Gray Line Logos, at the end of the ramp connecting with the railway station.

Important notes

Meeting Point and Check in Time:

at 07:45am 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 escort service could be replaced with an English speaking driver-guide service, while maintaining unchanged the entire program of the excursion.

Caf Tour & Travel 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 Siena

Siena is a medieval city in Tuscany, Italy, renowned for its rich history, stunning architecture, and the famous Palio horse race. The city's well-preserved historic center is a UNESCO World Heritage site, offering a glimpse into Italy's medieval past with its cobblestone streets, towering churches, and grand piazzas.

Top Attractions

Piazza del Campo

Piazza del Campo is the heart of Siena and the site of the famous Palio horse race. This stunning, shell-shaped square is surrounded by historic buildings and is a must-visit for its architectural beauty and vibrant atmosphere.

Historical 1-2 hours Free

Siena Cathedral (Duomo di Siena)

The Siena Cathedral is a masterpiece of Italian Gothic architecture, featuring stunning marble facades, intricate mosaics, and beautiful frescoes. The cathedral's interior is equally impressive, with a richly decorated nave and a magnificent marble floor.

Religious 1-2 hours €8-12

Basilica of San Domenico

The Basilica of San Domenico is one of the largest churches in Siena and houses the relics of St. Catherine of Siena. The church's interior is adorned with beautiful frescoes, sculptures, and a magnificent choir.

Religious 1 hour Free (donations appreciated)

Palazzo Pubblico

The Palazzo Pubblico is a historic palace that houses the Museo Civico, which showcases a collection of medieval and Renaissance art. The palace's courtyard and tower offer panoramic views of the city and surrounding countryside.

Historical 1-2 hours €9-12

Santa Maria della Scala

Santa Maria della Scala is a historic hospital and museum complex that showcases the city's rich history and art. The complex features beautiful frescoes, sculptures, and a labyrinthine network of underground passages.

Historical 1-2 hours €7-10

Must-Try Local Dishes

Pici all'Aglione

A traditional Tuscan pasta dish made with hand-rolled pici pasta and a garlic and tomato sauce.

Main course Vegetarian

Ribollita

A hearty bread and vegetable soup, often made with cannellini beans, kale, and carrots.

Soup Vegetarian

Panforte

A traditional Siena dessert made with dried fruits, nuts, and spices, often enjoyed during the Christmas season.

Dessert Vegetarian, contains nuts

Peposo

A traditional Tuscan beef stew, slow-cooked with wine, garlic, and spices.

Main course Contains meat

Popular Activities

Hiking in the Tuscan countryside Cycling tours Wine tasting tours Visiting hot springs Enjoying local cuisine Exploring historic sites Visiting museums Attending the Palio horse race

Best Time to Visit

June to August, July 2 (Palio di Provenzano), August 16 (Palio di Assunta)

The peak season in Siena is during the summer months, especially around the Palio horse races. The weather is warm and sunny, perfect for exploring the city's outdoor attractions and enjoying the vibrant atmosphere.

22°C to 34°C 72°F to 93°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

Siena is generally safe for tourists, with low crime rates. However, pickpocketing and petty theft can occur in crowded areas, so it's important to stay vigilant.

Important Precautions:

• Keep valuables secure
• Be cautious of pickpockets in crowded areas
• Use licensed taxis or ride-sharing apps

Getting there

By air

Florence Airport • 80 km (50 miles)
Pisa International Airport • 120 km (75 miles)

By train

Siena Station

By bus

Siena Piazza Gramsci, Siena Piazza del Duomo

Getting around

Public transport

The bus system in Siena is efficient and covers most parts of the city and nearby towns. Buses are a convenient way to get around, especially for those staying outside the city center.

Taxis

Available • Apps: MyTaxi, FreeNow

Rentals

Car, Bike, Scooter

Neighborhoods

San Martino San Domenico Santa Maria della Scala

Day trips

Chianti Wine Region

20-40 km (12-25 miles) • Half day to full day

The Chianti region is famous for its vineyards, rolling hills, and picturesque villages. It's a perfect day trip for wine enthusiasts and those looking to explore the Tuscan countryside.

San Gimignano

35 km (22 miles) • Half day to full day

San Gimignano is a medieval hilltop town known for its towering houses and stunning views of the Tuscan countryside. It's a UNESCO World Heritage site and a must-visit for history buffs.

Val d'Orcia

60-80 km (37-50 miles) • Full day

Val d'Orcia is a UNESCO World Heritage site known for its stunning landscapes, hot springs, and picturesque villages. It's a perfect day trip for nature lovers and those looking to relax in a beautiful setting.

Festivals

Palio di Siena • July 2 and August 16 Siena Jazz Master Classes • July Siena International Film Festival • November

Pro tips

Visit the historic sites early in the morning or late in the afternoon to avoid crowds
Try local specialties like pici pasta, ribollita, and panforte
Explore the city's hidden gems, such as underground passages and historic streets
Attend the Palio horse race for a unique cultural experience
Take a day trip to the Chianti wine region for wine tasting and scenic landscapes