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Siena, Cortona, Montepulciano & Val D'Orcia from Florence - Semi private tour

Florence, IT
90% of travellers recommend this
Excellent (33 reviews)
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Free Cancellation up to before the experience starts (local time)

    • Duration 11 hours
    • Small group tour (max 8)
    • Includes wine tasting
    • Transport in a minivan
    • Free time in 3 towns

    Discover the breathtaking beauty of Tuscany on a semi-private tour, exploring iconic towns and savoring exquisite local wines.

    Featured Reviews

    Excellent (33 reviews)
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    Viator
    pstatler
    Jul 24
    This was a semi-private tour, within 16 hours before the tour I received a message that there were originally four for the tour and two had just cancelled and wanted to know if we wanted to change to a different tour if not they would still provide the tour for the two of us. So we ended up with a private tour with Alessandro. We had a great do seeing Cortona with its hills and wonderful fields of sunflowers. The family farm we went to was very unique and interesting. The food and wine was good. Then on to Montepulciano and Siena for a great day. Alessandro was very knowledgeable and fun. We had a great day and would recommend the tour.
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    Viator
    Kerri_B
    Jul 24
    We had. Really fantastic day in Tuscany with this tour! Seeing where Under The Tuscan Sun was filmed was a highlight of the trip for me. The wineries, towns and scenic route were incredible. This tour is well worth the money in my opinion!
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    coqui2530
    Jul 24
    Such an awesome tour ! Sienna is beautiful. Medieval towns are so enchanting. Montepulciano, Cortona and Val D’Orcia are gorgeous as well. Light lunch at the Agroturismo is just a charcuterie board and wine. So don’t too excited about that. Our tour guide Alessandro was great. Full of knowledge, enthusiasm and cheerfulness. Myself and another guest are “Under the Tuscan Sun” fans, so Alessandro drove us by the Bramasole house. It was gated and closed to the public. At least we tried ! For sure, this tour must be on your to-do list !
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    Blanca_R
    Jul 24
    What a wonderful day tour ! So much beauty & enchantment on the mountain-top towns. Alessandro was a super tour guide. Very informative, full of happiness and excitement. As per our request, he even took us to the front of Bramasole, the house where “Under the Tuscan Sun” was filmed, even though it was closed.
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    Patti_D
    Jun 24
    This was a 10 hour tour, and not cheap for the 6 of us. The driver (Ned) was very nice, but he wasn’t a tour guide. He wasn’t fully knowledgeable about what we were seeing. There were long stretches of time when nothing was said. We never stopped for lunch, nor were we offered a bottle of water. Our first stop was Sienna, a lot of walking up sidewalks and streets. One hour nonstop. Then a 3 hour ride through the Tuscan countryside. One stop for a photo, no water or lunch break. 4 people fell a sleep. Then we went to a farm at 2pm and looked at pigs, before being offered wine, water, a platter of cold cuts, cheese and stale bread. Then off to Montepulciano for a wine tasting. Finally onto Cortona. However most everything was closed for siesta. Then a 90 minute drive back to Florence. If you need to use a bathroom, be sure the coffee shop is open and you will have to buy a coffee to use the bathroom. This tour could have been so much better, but the tour operator doesn’t want to offer even the basics, such as water and bathrooms. The operator could make arrangements that when he brings tourists to their shops, they can use the bathroom. And how about lunch? We don’t need a 3 hour ride through the Tuscan countryside. A 90 minute drive is sufficient. We get it… Feed the tourists!!!
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    Included

    • inclusion
      Alcoholic beverages
    • inclusion
      Snacks
    • inclusion
      Visit of cortona with 1h approx free time to explore
    • inclusion
      Transport on a 8 seat minivan
    • inclusion
      Your local tour leader providing directions, stories and info about all places.
    • inclusion
      Visit of siena with free time to explore
    • inclusion
      Visit of montepulciano with free time to explore

    Excluded

    • exclusion
      Gratuities
    • exclusion
      Pick up / drop off
    • exclusion
      Guided walking tours of the 3 villages
    0 / 0
    Siena, Cortona, Montepulciano & Val D'Orcia from Florence - Semi private tour

    Discover the breathtaking beauty of Tuscany on a semi-private tour, exploring iconic towns and savoring exquisite local wines.

    Highlights

    • Explore the most beautiful Tuscan towns
    • Lunch overlooking the rolling hills of Montepulciano
    • Walk the winding streets of Cortona
    • Visit the locations made famous by movies
    • Enjoy a taste of the local lifestyle with wine tasting

    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.

    Meeting point

    Strada di Sant' Appiano, 9/i, 50028 Barberino Tavarnelle FI , Italy

    End point

    End 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.

    Meeting point

    Strada di Sant' Appiano, 9/i, 50028 Barberino Tavarnelle FI , Italy

    End point

    What to expect

    1

    Parcheggio Oltrarno

    Meet us in Piazza della Calza right in front Porta Romana at the blue P ( parking ) sign at 08:00am.

    2

    Porta Romana

    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.

    Duration 90 minutes
    3

    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!

    Duration 60 minutes
    4

    Montepulciano

    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.

    Duration 90 minutes
    5

    Piazza Grande a 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.

    Duration 120 minutes
    6

    Val D'Orcia

    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.

    Duration 90 minutes
    7

    Piazza del Campo

    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.

    Duration 110 minutes
    8

    Porta Romana

    We will have then 1 hour approx ride and we will finally head back to Florence for approximately 8:00pm

    9

    Parcheggio Oltrarno

    Meet us in Piazza della Calza right in front Porta Romana at the blue P ( parking ) sign at 08:00am.

    Additional Information

    • Additional information
      Not recommended for pregnant participants
    • Additional information
      Not recommended for participants with poor cardiovascular health
    • Additional information
      Suitable for all physical fitness levels
    • Additional information
      Please note that this tour involves a fair amount of driving due to the distance of these villages.
    • Additional information
      The order of the stops may change to ensure the best experience possible
    • Additional information
      Please note, the tour requires a minimum of 3 participants. If not reached, a private option with a supplement will be offered.
    Provided by Italy on a Budget tours

    What our experts say

    • icon
      Sample local cheese at Montepulciano
    • icon
      Visit artisan shops in Cortona
    • icon
      Take photos at Val d'Orcia's hills
    • icon
      Enjoy sunset views in Siena
    • icon
      Reserve a table at a local trattoria

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