Florence · MONTALCINO AND VAL D ORCIA DAY TRIPS

The 15 Best Montalcino & Val d’Orcia Day Trips

44 tours  ·  from $37

Brunello country is the far side of Siena, so this is a full day in a small vehicle rather than a coach. The 15 below cover the cellar visits, the cypress-road stops and Pienza’s cheese, priced with lunch made clear.

Full Day Tour to Val d'Orcia and Gladiator's Fields with Wines - Montalcino and the first Brunello tasting
Florence Day Trips, Florence Wine Tastings, Full-Day, Montalcino and Val d Orcia Day Trips, Tour Reviews, Tours, Wine Tours

Full Day Tour to Val d’Orcia and Gladiator’s Fields with Wines

1.Full Day Tour to Val d’Orcia and Gladiator’s Fields with Wines

★★★★★★★★★★4.5 · 1,106 reviews · 11 hours 30 minutes (approx.) · from $94Our pick

Travel by air-conditioned coach from Florence to Montalcino, Pienza, and Montepulciano with an English-speaking guide. Expect two winery visits, Brunello and Vino Nobile tastings, pecorino cheese, free time in each town, and a quick look at the Gladiator filming area.

“We had a really good experience - it was a great way to see lots of the Val D’Orcia in a day. Tabatha was a really knowledgeable helpful guide and gave the best places to get food so we had a lovely picnic in Pienza. The ancient cave for the second winery was really cool to see.”

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From Florence: Val D'Orcia Tour with Wine Tasting - Leaving Florence for Montalcino
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From Florence: Val D’Orcia Tour with Wine Tasting

2.Val D’Orcia Tour with Wine Tasting

★★★★★★★★★★4.6 · 1,106 reviews · 11.5 hours · from $108

Spend 11.5 hours in Val d’Orcia with stops in Montalcino, Pienza, and Montepulciano. You’ll taste Brunello and Vino Nobile, sample Pecorino cheese, and hear local stories from guides such as Alex, Julia, and Constantino. Comfortable coach transport keeps the day simple.

“I had a wonderful one-day trip to Val d'Orcia. The views were amazing – beautiful hills, vineyards, and small towns like Pienza and Montalcino. Our guide, Jan, was great! He was very friendly and knew a lot about the area. He made the trip fun and relaxing, and he shared interesting stories and local tips. It was a perfect day in the Tuscan countryside. I highly recommend this tour”

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Val d'Orcia Brunello Wine Tour with Montalcino and Montepulciano - Montalcino’s fortress in a 15-minute stop
Florence Wine Tastings, Montalcino and Val d Orcia Day Trips, Tour Reviews, Tours, Wine Tours

Val d’Orcia Brunello Wine Tour with Montalcino and Montepulciano

3.Val d’Orcia Brunello Wine Tour with Montalcino and Montepulciano

★★★★★★★★★★4.5 · 359 reviews · 10 hours 30 minutes (approx.) · from $277

Spend 10.5 hours exploring Montalcino, Pienza, and Montepulciano from Florence in a luxury air-conditioned van. Taste Brunello and Vino Nobile, tour a vineyard and ancient cellar, enjoy a three-course lunch, and travel with no more than eight people. Drivers such as Simona, Luca, Mike, and Salvo share local history along the way.

“We had a wonderful trip with Luca as our driver. There was so much to see and learn and it was just what I’d hoped for.”

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Florence: Valdorcia Wine, Brunello Montalcino, Montepulciano - The road into Val d’Orcia
Florence Wine Tastings, Montalcino and Val d Orcia Day Trips, Tour Reviews, Wine Tours

Florence: Valdorcia Wine, Brunello Montalcino, Montepulciano

4.Valdorcia Wine, Brunello Montalcino, Montepulciano

★★★★★★★★★★4.8 · 238 reviews · 10.5 hours · from $265

Spend 10.5 hours in Val d’Orcia with an English-speaking driver and a group capped at eight. Visit a family winery near Montalcino, taste Brunello, enjoy a three-course lunch in Pienza, and explore Montepulciano’s underground cellars with wine, olive oil, and local foods.

“What a wonderful day! Mike, our driver, was so nice and provided some great history along the drive. We never felt rushed by him. The wineries and towns were spectacular. I would absolutely recommend this tour to others!”

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Florence: Monteriggioni & Val d'Orcia Optional Wine Tasting - Meeting at Santa Maria Novella station
Florence Wine Tastings, Food & Drink, Montalcino and Val d Orcia Day Trips, Siena and San Gimignano Day Trips, Tour Reviews, Wine Tours

Florence: Monteriggioni & Val d’Orcia Optional Wine Tasting

5.Monteriggioni & Val d’Orcia Optional Wine Tasting

★★★★★★★★★★4.6 · 180 reviews · 11 hours · from $51

Spend 11 hours touring Tuscany by air-conditioned bus, from Monteriggioni’s medieval walls and Templar Museum to Montalcino’s wine country and Pienza’s pecorino shops. Choose the wine tasting for Brunello, Rosso, cured meats, and cheese, or keep the extra free time for exploring.

“The scenery was absolutely incredible, and our guide (Ana) was absolutely wonderful! The bus was very comfortable and it was great getting to see 3 uniquely different cities in one day. Can't thank y'all enough for such an awesome experience! We'll be recommending you to all our friends and family who are going to Florence.”

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Siena, Cortona, Montepulciano & Val D'Orcia in a Small Group Tour - The 7:45am meeting at Porta Romana
Montalcino and Val d Orcia Day Trips, Siena and San Gimignano Day Trips, Tour Reviews, Tours

Siena, Cortona, Montepulciano & Val D’Orcia in a Small Group Tour

6.Siena, Cortona, Montepulciano & Val D’Orcia in a Small Group Tour

★★★★★★★★★★5.0 · 107 reviews · 12 hours (approx.) · from $241Top rated

Ride from Florence in an eight-seat minivan with a local tour leader to Cortona, Montepulciano, Siena, and the Val d'Orcia. You get free time in each town, a farm tasting of cured meats and bruschetta, and wine in a 14th-century cellar. Guides such as Alessandro, Dom, and Julia have earned praise for friendly help.

“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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Brunello and Nobile, Wine Lover Tour Montalcino and Montepulciano - Montepulciano and Piazza Grande
Florence Wine Tastings, Montalcino and Val d Orcia Day Trips, Tour Reviews, Tours, Wine Tours

Brunello and Nobile, Wine Lover Tour Montalcino and Montepulciano

7.Brunello and Nobile, Wine Lover Tour Montalcino and Montepulciano

★★★★★★★★★★5.0 · 88 reviews · 9 hours (approx.)

Spend about nine hours with a private driver-guide such as Luca, Matteo, Tommaso, or Dario, visiting Montalcino, Montepulciano, and two wine estates. Expect Brunello and Nobile tastings, Tuscan food, medieval towns, Val d’Orcia scenery, and flexible photo stops.

“Luca picked our group up right outside our accomodations in Florence and led us out of town by way of a quick stop at Piazzle Michaelangelo and gave us an overview of the city and its history. We made our way from there down towards Montalcino. Along the way Luca explained about the differences between the wines (e.g. Brunello di Montalcino, Brunello di Montalcino Riserva, Rosso di Montalcino vs. Chianti). We were in awe as the sunshine broke through the clouds as a we approached the town of Montalcino. Luca drove us up to the town center and dropped us off to walk and explore for half an hour before…”

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Olive Oil Tours and Tasting at Frantoio di Montalcino - Why the 12-person limit matters
Food & Drink, Montalcino and Val d Orcia Day Trips, Tour Reviews, Tours, Tuscan Olive Oil Tastings

Olive Oil Tours and Tasting at Frantoio di Montalcino

8.Olive Oil Tours and Tasting at Frantoio di Montalcino

★★★★★★★★★★5.0 · 85 reviews · 1 hour 30 minutes (approx.) · from $60

At Frantoio di Montalcino, guides such as Daniel and Alisha explain how olives become extra virgin oil, from grove to bottle. In a small group of up to 12, you will tour the mill, taste several oils and EVOO condiments with warm bread, then shop for bottles to take home.

“The tour was informative about their production facilities, how they make olive oil, and the differences between olive oils.”

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Medieval Tour in Monteriggioni and Val d'Orcia from Florence - Monteriggioni and its old stone walls
Florence Renaissance History Tours, Montalcino and Val d Orcia Day Trips, Siena and San Gimignano Day Trips, Tour Reviews, Tours

Medieval Tour in Monteriggioni and Val d’Orcia from Florence

9.Medieval Tour in Monteriggioni and Val d’Orcia from Florence

★★★★★★★★★★5.0 · 54 reviews · 11 hours (approx.) · from $51

Spend a full day exploring Monteriggioni, Montalcino, and Pienza from Florence by air-conditioned bus. Walk medieval walls, visit the Templar Museum, enjoy Val d’Orcia views, and add a tasting of Brunello, Rosso, cheeses, and cold cuts. Guides such as Caterina and Vanessa have led the multilingual tour.

“El tour a Monteriggioni y Pienza fue increíble. ¡Una experiencia que recomendaría a cualquiera que visite la Toscana!”

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Exclusive Brunello di Montalcino tour from Florence - Tenuta Fanti and a three-course lunch
Montalcino and Val d Orcia Day Trips, Tour Reviews, Tours

Exclusive Brunello di Montalcino tour from Florence

10.Exclusive Brunello di Montalcino tour from Florence

★★★★★★★★★★5.0 · 45 reviews · 11 hours 30 minutes (approx.) · from $611

Leave Florence at 8:30 a.m. for a private, 11.5-hour Brunello tour with a sommelier-guide such as Angel, Paola, or Francesco. Visit three wineries, taste Sangiovese and other Tuscan wines, tour cellars, enjoy a three-course lunch, and return by private car.

“Our wine tour in Montalcino was an absolutely fantastic experience, thanks to our incredible guide Angel. From start to finish, Angel was simply wonderful – not only very informative but also genuinely kind and engaging. We learned so much about the region and the winemaking process. The tour included three different tastings, each offering a unique insight into the local production, and a delicious lunch. Every aspect was perfectly arranged and thoroughly enjoyed. We would highly, highly recommend this Montalcino wine tour, especially if you have the chance to book with Angel. His guidance truly elevated the experience. We would gladly book another tour with him in a heartbeat! Thank…”

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From Florence: Siena, Cortona, Montepulciano & Val D'Orcia - Cortona, where the day begins with a film connection
Montalcino and Val d Orcia Day Trips, Siena and San Gimignano Day Trips, Tour Reviews

From Florence: Siena, Cortona, Montepulciano & Val D’Orcia

11.Siena, Cortona, Montepulciano & Val D’Orcia

★★★★★★★★★★4.9 · 43 reviews · 10 - 12 hours · from $265

Travel from Florence in an eight-seat minivan with an English-speaking guide such as Dom, Francesca, Elisa, or Giovanni. Visit Cortona, Montepulciano, Siena, and Val d'Orcia, with farm-made meats, bruschetta, wine, and a cellar tasting included.

“This tour was fantastic and I would say the best that we have done in Italy. The route was very well designed traveling through the incredibly beautiful Tuscan countryside enroute to the various towns. We were very lucky to have Francesca as our guide! She was very knowledgeable, professional, friendly and welcoming. We can't say enough about how wonderful Francesca was and made our Tuscany tour one that we will never forget. If you're considering visiting Tuscany for a day, this tour is a must.”

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Winery tour & wine tasting in Montalcino - Six Wines Served in Three Flights
Florence Wine Tastings, Food & Drink, Montalcino and Val d Orcia Day Trips, Tour Reviews, Tours, Wine Tours

Winery tour & wine tasting in Montalcino

12.Winery tour & wine tasting in Montalcino

★★★★★★★★★★4.5 · 41 reviews · 1 hour 45 minutes (approx.) · from $47Best value

At Corte Pavone Winery near Montalcino, Emma or another trained guide leads you through the vineyards, grape-processing area, and cross-vaulted cellar. You’ll taste six wines in three flights, with four tasting options available. The tour lasts about 1 hour 45 minutes and is offered in English.

“Very informative walk through the vineyard followed by a great sampling of Brunello wines! Great for a small group or couple.”

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VIP Brunello Montalcino, Montepulciano & Val d'Orcia with Lunch - Montalcino and the Brunello lunch
Lunch Experiences, Montalcino and Val d Orcia Day Trips, Tour Reviews, VIP

VIP Brunello Montalcino, Montepulciano & Val d’Orcia with Lunch

13.VIP Brunello Montalcino, Montepulciano & Val d’Orcia with Lunch

★★★★★★★★★★5.0 · 40 reviews · 9 to 10 hours (approx.) · from $231

Spend a full day with a small group of up to six, traveling from Florence through Chianti to Montalcino, Val d’Orcia, and Montepulciano. Expect Brunello tasting, a homemade Tuscan lunch, cellar time, scenic photo stops, and guidance from Morad or another Moro Tuscany Tours guide.

“We had an amazing experience- breathtaking views, incredible wine and amazing food. We even had a little time to explore the 2 towns.”

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Best of Tuscany: Full Day Private Tour to Val D'Orcia - Pienza: a Renaissance town built around order
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Best of Tuscany: Full Day Private Tour to Val D’Orcia

14.Best of Tuscany: Full Day Private Tour to Val D’Orcia

★★★★★★★★★★5.0 · 24 reviews · 8 hours (approx.) · from $783

Travel privately from Florence through Val d’Orcia, stopping in Montepulciano, Pienza, and Montalcino. Guides such as Elena, Eva, and Paolo lead the town visits, with a winery stop for local wine and food. Lunch costs extra, and the full day is best for scenic, flexible sightseeing rather than a dedicated wine tour.

“Completely shocking I paid nearly $2,000 for a wine tour, which I thought would be a pre-arranged tour of notable wineries of Tuscany. I tried to confirm serval times this is what I had booked to which I received a vague answer. Instead I got : - an argumentative and generally unfriendly tour guide - a visit to a cheese factory, serving $5 per bottle wine which incurred a tasting fee of $40 (this wasn’t apparently included in the overall cost) - a walk around various small villages in Tuscany in the pouring rain, which included a visit to the hosts favourite cheese shop”

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Private Top Brunello Montalcino Wine Tour & Food Pairing Session - Florence and the road into the Tuscan hills
Florence Wine Tastings, Food, Food & Drink, Montalcino and Val d Orcia Day Trips, Private, Tour Reviews, Tours, Wine Tours

Private Top Brunello Montalcino Wine Tour & Food Pairing Session

15.Private Top Brunello Montalcino Wine Tour & Food Pairing Session

★★★★★★★★★★5.0 · 18 reviews · 10 hours (approx.) · from $600

Travel by air-conditioned Mercedes from Florence, Siena, or possibly Arezzo to three Montalcino estates. With a private guide such as Anna, Ana, Paola, or Max, taste Brunello and Rosso, tour cellars, and enjoy a farmhouse-style Tuscan lunch.

“Absolutely the highlight of our trip. We highly recommend Anna and of course the 3 vineyards we visited”

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New in Montalcino and Val d Orcia Day Trips

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★ 5.0Private Montepulciano & Pienza Day Trip from Florence8 reviews
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