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Day Tour from Florence: Siena, Montepulciano, Cortona & Val d’Orcia with Lunch & Wine Tastings

★5.0·8 reviews

280,00 €

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  • Description

Description

Discover the essence of Tuscany on a full-day small group tour from Florence, visiting some of the region’s most iconic hill towns and landscapes while traveling comfortably through the countryside by minivan.

Your day begins with a morning departure from central Florence near Porta Romana at 8:00 am. As you leave the city behind, your local tour leader will introduce you to Tuscan history, culture, and daily life while you enjoy a scenic drive through rolling hills, vineyards, and landscapes made famous by cinema for generations.

Cortona

The first stop of the day is Cortona, the charming hilltop town made famous by Under the Tuscan Sun. Enjoy free time to explore its narrow streets, artisan shops, and panoramic views at your own pace, soaking in the relaxed atmosphere that has inspired travelers and writers for generations.

Local Farm Experience & Lunch

The journey continues to a picturesque local Tuscan farm, surrounded by vineyards and olive groves. Here, Cinta Senese pigs are raised naturally and traditional farming methods are still part of everyday life. You’ll enjoy a tasting board featuring cured meats and bruschetta made with fresh garden ingredients, paired with the farm’s own wine — a simple and authentic Tuscan lunch in a beautiful countryside setting.

Montepulciano

Next, arrive in Montepulciano, renowned for its elegant Renaissance architecture and the prestigious Vino Nobile di Montepulciano DOCG. After an introduction from your tour leader, enjoy free time to explore the town before visiting a historic 14th-century underground cellar, where a complimentary tasting of local wines and products is offered.

Val d’Orcia Scenic Drive

Relax on board as the tour continues through the breathtaking Val d’Orcia, one of Tuscany’s most photographed landscapes. Rolling hills, vineyards, and iconic cypress-lined roads create unforgettable views and perfect photo opportunities along the way.

Siena

The final stop is Siena, one of Tuscany’s most beautiful medieval cities. Your tour leader will accompany you from the parking area to the historic center, passing through the main streets before leaving you free time to explore Piazza del Campo, local shops, and the city’s timeless atmosphere.

Return to Florence

After Siena, enjoy a comfortable drive back to Florence, arriving at approximately 8:00 pm.

EXPERIENCE ORGANIZED BY:

Authentic Italy Adventure

  • 10 Hours

  • Up to 8 people

  • Offer in Italian and English

WHAT’S INCLUDED 

  • Round-trip transportation from Florence by private minivan

  • Small group tour (maximum 8 participants)

  • Local tour leader throughout the day

  • Visits to Cortona, Montepulciano, Siena & Val d’Orcia

  • Light Tuscan lunch at a local farm

  • Wine tastings in countryside and historic cellar

  • Free time in each destination

MEETING POINT

Florence: Parking Oltrarno, Piazza della Calza 1, right in front Porta Romana at the blue P (parking) sign, 50125 Firenze, IT

 

BOOKING METHOD AND CANCELLATION TERMS

  • Online Booking
  • We will charge a cancellation fee of 100% if booking is cancelled 1 day or less before the event
  • We will charge a cancellation fee of 0% if booking is cancelled 1000 days or less before the event

 

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What guests say about this experience

Verified guests only
★5.0·8 reviews
Mags
November 2025
★★★★★

Giovanni is THE BEST tour guide ever! Very knowledgeable, very considerate, and most importantly FUN! The experience was unforgettable and I recommend getting him as your tour guide.

Tej
November 2025
★★★★★

Giovanni was an EXCELLENT tour guide! He made our experience extra special! He was very passionate, knowledgeable, personable, and really made an extra effort to make our tour relevant and tailored to our interests! Highly recommended!!!

Luis
November 2025
★★★★★

Our day started off with a drive out to Cortona followed by a drive through Tuscany. Antonello, our tour guide was very informative and helpful during our stops and drive. We really enjoyed his company. Our tour ended at Sienna a beautiful town with lots of sites to see. I recommend this tour to anyone who wants to see the authentic Tuscan side of Italy while staying in Florence.

Mackenzie
October 2025
★★★★★

This tour was a perfect way to experience Tuscany’s charm, scenery, and culture in one day. Cortona, Montepulciano, and Siena were all breathtaking, and the local farm visit with wine and food tasting was a highlight. Our guide Francesca was outstanding—friendly, knowledgeable, and passionate about the region. She shared great stories, movie trivia, and insider tips that made the day unforgettable. Comfortable van, well-paced itinerary, gorgeous views. Highly recommend this tour!

Evan
October 2025
★★★★★

Giovanni is the best Tuscany Tour Guide! He was the best tour guide we’ve had during our trip. He went out of his way to make sure we saw the sights. Outside of the tours we were able to learn so much about Italy from talking with him. He literally has a degree in history so he taught us about the history of Florence, Siena and Tuscany! I learned so much on this trip to Tuscany. Definitely ask for Giovanni specifically if you have the option.

Lori
October 2025
★★★★★

We had a delightful day traveling the countryside visiting the 3 cities with Luigi. He was engaging, knowledgeable and fun. Went to visit a farm to table ranch for tasting wine, olive oil and pork products and met a few new friends along the way. The Tuscan views were magical and made for fantastic pictures.

Neil
September 2025
★★★★★

Amazing views of Tuscany and great farm tour. Elisa is a good guide and driver. Was great to get to Siena before most of the tour groups came in. The other towns were even more charming.

Kerri
February 2025
★★★★★

We had an amazing day in Tuscany, Cortona, Multepulciano, and Siena! The sights were incredible and we learned so much about each city. Lorenzo was a great guide and shared so much history along the way. Everything was on time and ran smoothly. This tour is worth the price and I highly recommend it if you’re looking for a way to explore Tuscany in one day!

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