From Florence: Private Siena, Cortona, Montepulciano & Val D'Orcia Small Group Tour
- Free cancellation up to 6 days before
- Instant confirmation
- Guided tour in English
About this experience
Experience the best of Tuscany on a private small-group tour from Florence to Siena, Cortona, Montepulciano, and the breathtaking Val d’Orcia. Travel in comfort with a maximum of 8 guests as you explore medieval hill towns, scenic Tuscan countryside, and UNESCO-listed landscapes. Discover the charm of Siena’s historic center, wander the cinematic streets of Cortona, enjoy wine tasting in Montepulciano, and admire the iconic rolling hills of Val d’Orcia. This exclusive Tuscany day tour from Florence is perfect for travelers seeking authentic villages, world-famous wines, stunning photo opportunities, and a personalized local experience.
Next available dates
What’s included
- Food and drinks
- Round-trip transportation on an 8-seat minivan
- Your local Tour leader providing directions, stories, and info about all places
- Tastings at a local Farm based on cured meats and bruschetta made from garden-fresh ingredients, paired with their own wine
- Visit of Cortona with free time to explore
- Orientation walk in Montepulciano with free time to explore
- Orientation walk of Siena with free time to explore
- Stop at a 14th-century cellar with the possibility of having a complimentary wine and cheese tasting
Not included
- Tips and gratuities
- Guided walking tours in Siena, Cortona and Montepulciano
- Car seat for kids under 150cm
- Hotel pick up and drop off
Itinerary
- 1
Ready to Depart
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
Cortona
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
Local Farm
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
Montepulciano
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
Val d'Orcia Photo Stop
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
Siena
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
Back to Florence
We will have then 1 hour approx ride and we will finally head back to Florence for approximately 8:00pm Departure Points available for this tour: Florence: 08:00am - 8:00pm | 12h Address: Parcheggio Oltrarno , in front of the blue “ P” sign by Porta Romana , Piazza della Calza 1, Florence. Take me here Tuscany on Wheels: 08:45am - 7:00pm | 11.30h Address: Tuscany on Wheels office, Strada di Sant’ Appiano 9/i, Barberino Tavarnelle ( FI ). Take me here
Good to know
- Duration
- 12 hours
- How you meet
- Meet on location
- Confirmation
- Instant confirmation
- Cancellation policy
- Free cancellation up to 6 days before
- Difficulty
- Moderate
- Minimum age
- 3+ years
- Guide
- Guided tour in English
- Start times
- 08:00
Know before you go
- Not wheelchair accessible
- Not stroller accessible
- Not suitable for pets
- 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
- Not recommended for travelers with walking disabilities
- Car Seat Regulations:
- Kids under 150cm ( approx 4 ft 11 in ) according to Italian Laws are required to use an appropriate car seat. Carry your own car seat or inform the Tour Operator in advance in order to hire one for EUR 35 per car seat
- An inflatable car seat can be used only if:
- it has a European approval label
- it is suitable for the child’s weight/height
- it is installed correctly
Cancellation policy
Free cancellation up to 6 days before the experience starts.
- 6 days or more before: full refund
- 2–5 days before: 50% refund
- Less than 2 days before: no refund
Meeting point
View on map
From Florence
- Address
- Parking Oltrarno, Piazza della Calza 1, right in front Porta Romana at the blue P (parking) sign, Firenze, 50125, IT
- How you meet
- Meet on location
- Coordinates
- 43.76095, 11.24181
Illustrative map. Open it in Maps for the exact spot and live directions.
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Frequently asked questions
How long does this experience last?
It lasts 12 hours.
Can I cancel this booking?
Free cancellation up to 6 days before the experience starts. 6 days or more before: full refund · 2–5 days before: 50% refund · Less than 2 days before: no refund
Is this experience guided, and in what language?
Guided tour in English
Is hotel pickup included?
No — you make your own way to the meeting point.
Where does this experience start?
It starts at From Florence, Parking Oltrarno, Piazza della Calza 1, right in front Porta Romana at the blue P (parking) sign, Firenze, 50125, IT.
Is there a minimum age?
Travellers must be 3 or older.
Still have a question?
Message our team on WhatsApp — we can help with dates, group bookings and anything else before you book.
From AED 948 per personFree cancellation
