Siena, Cortona, Montepulciano & Val D'Orcia in a Small Group Tour
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12h
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
Explore in the comfort of a 8 seat van the most beautiful Tuscan towns made famous through films together with a passionate local driving guide. Enjoy lunch overlooking the rolling hills of Montepulciano while tasting famous wine.
Wander the winding streets of Cortona walked by Diane Lane in "Under the Tuscan sun", watch out for the vampires of the Twilight saga " New Moon" in Montapulciano and taste the famous Noble of Montepulciano wine. Explore the locations made famous by Michelle Pfieffer in "A Midsummer night's dream" and Ralph Fienes in " The English patient". Spot the iconic rolling hills of Tuscany from " Letters to Juliet" and enjoy a taste of the local lifestyle by sampling fine local wine, cheese and other products from the region.
Available options
From Florence: Classic Tour
Departure Point: Central Florence, Piazza della Calza 1, by the "P" parking sign at 8:00am. Small group tour (max 8 people)<br/>Starting point:<br/>Parcheggio Oltrarno, Piazza della Calza, 1, 50125 Firenze FI, Italy
From Florence - Private Tour
8 Seat Minivan <br/>Starting point:<br/>Parcheggio Oltrarno, Piazza della Calza, 1, 50125 Firenze FI, Italy
From Chianti: Classic Tour
Departure Point: Tuscany on Wheels office, located on Strada di Sant'Appiano 9/I- Barberino Tavarnelle ( FI ). Small group tour (max 8 people)<br/>Starting point:<br/>Tuscany on Wheels tours from San Gimignano, Strada di Sant' Appiano, 9/i, 50028 Barberino Tavarnelle FI, Italy
What's included
Stop at a 14th century cellar with possibility to have a complimentary wine and cheese tasting
Transport on a 8 seat minivan
Your local Tour leader providing directions, stories and info about all places.
Visit of Siena with free time to explore
Tastings at a local Farm based on cured meats and bruschetta made from garden-fresh ingredients, paired with their own wine
Visit of Montepulciano with free time to explore
Visit of Cortona with free time to explore
Detailed itinerary
1
Meet your local tour leader by Porta Romana, central Florence at 07:45am ready to leave by 8:00am.
Travel for an hour and a half on board of a private 8 seat mini-van through the beautiful Tuscan countryside enjoyed by generations on the movie screen while listening to stories and info about the area from your tour leader.
2
Our first destination is the charming hilltop town of Cortona, famous for its olive groves and immortalized by Diane Lane in Under the Tuscan Sun. Explore independently the town with its narrow streets, artisan stores, and landmarks featured in Frances Mayes' beloved novel. Who knows, you might even start your own Italian love story!
3
Next, we travel just 40 minutes from Cortona to a picturesque local farm nestled in the heart of Tuscany. Here, Cinta Senese pigs roam semi-wild, thriving on natural feed. Stroll among olive trees and vineyards before savoring the farm's exceptional products in a tasting board we have organised for you —cured meats and bruschetta made from garden-fresh ingredients, paired with their own wine. This unforgettable experience will leave lasting memories.
4
We then head to the famous MONTEPULCIANO , where vampires converge in Twilight Saga: New Moon. This beautiful walled town is also home to the renowned Montepulciano DOCG wine. Your tour leader will provide during the journey local insights, information about specific film scenes, and other attractions of Montepulciano, allowing you free time to explore the town at your leisure. Located near the entrance of the village is a 14th-century underground cellar where you will be able to enjoy a complimentary tasting of local wines and products they offer to the guests.
5
Stop 5
After exploring Montepulciano, unwind in our comfortable van as we journey through the breathtaking Val d'Orcia. Marvel at the stunning landscapes, rolling hills, and iconic cypress trees. With ample time to relax, you can fully immerse yourself in the beauty of this enchanting region.
6
Stop 6
Our last stop is the Medieval town of Siena, the backdrop for movies like Letters to Juliet and Stealing Beauty. Prepare to be amazed by Siena's charm, with its narrow streets, local artisans, and medieval squares glowing in the setting sun. Your tour leader will escort you from the parking spot to the main piazza passing by the center. From there you will have 1hour approx free time to wander around.
7
We will have then 1 hour approx ride and we will finally head back to Florence for approximately 8:00pm
What's not included
Gratuities
Guided walking tours of the 3 villages
Available languages
Guide guide
EN
Reviews breakdown
Viator
4.4
18 reviews
5★
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Tripadvisor
4.9
89 reviews
5★
85
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3
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Important information
Not recommended for pregnant travelers
Not recommended for travelers with poor cardiovascular health
Travelers should have at least a moderate level of physical fitness
Please note that this tour involves a fair amount of driving due to the distance of these villages.
The order of the stops may change to ensure the best experience possible
Please note, the tour requires a minimum of 4 participants. If not reached, a private option with a supplement will be offered.
Not recommended for travelers with walking disabilities
Meeting point
Are you staying in Chianti or San Gimignano? Join the tour from our office Tuscany on Wheels located on Strada di Sant'Appiano 9/i. You can park your car for free!
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
