Category Val d’Orcia, Montepulciano & Montalcino

Italy · VAL D’ORCIA, MONTEPULCIANO & MONTALCINO

The 15 Best Val d’Orcia, Montepulciano & Montalcino Tours from Florence

18 tours

Rome: Tuscany & Montepulciano Day Trip with Lunch & Wine Tasting

Rome: Tuscany & Montepulciano Day Trip with Lunch & Wine Tasting - Piazza del Popolo Start, Coach Comfort, and Why Headsets Help

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

Full Day Tour to Val d'Orcia and Gladiator's Fields with Wines - Fortezza di Montalcino: Use Your Hour for Views and a Slow Wander

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

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

Full day coach tour from Florence through Val d'Orcia, Montalcino, Pienza, and Montepulciano with Brunello and Vino Nobile tastings.

“It was an awesome and memorable experience. The lady tour guide who was speaking in English and Spanish was very friendly and helpful and was excellent in doing her job. The driver was very good as well. This travel company is highly recommended”

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From Florence: Val D’Orcia Tour with Wine Tasting

From Florence: Val D'Orcia Tour with Wine Tasting - Montalcino: Brunello tasting plus medieval town time

3.From Florence: Val D’Orcia Tour with Wine Tasting

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

Val d’Orcia day trip from Florence with Brunello and Vino Nobile tastings, plus Pecorino in Pienza and medieval hill towns.

“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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Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena

Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena - How to Make the Most of Montalcino Time and Fortezza Views

4.Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena

★★★★★★★★★★5.0 · 952 reviews · 9 hours (approx.) · from $217Near perfect

Small-group Brunello di Montalcino day trip from Siena with three tastings, family lunch, and Sant’Antimo Abbey.

“Spent a wonderful day with our exceptionable guide Georgia! Georgia was incredibly knowledgeable and entertaining throughout our day trip to experience Brunello wine and the producing region. Great winery picks! Very easy pickup/dropoff in Siena. Highly recommend!”

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Montepulciano: Wine Tasting and Cellar Tour

Montepulciano: Wine Tasting and Cellar Tour - Inside the cellar: barrels, wood choices, and tufa soil

5.Montepulciano: Wine Tasting and Cellar Tour

★★★★★★★★★★4.8 · 545 reviews · 1 hour · from $38Cheapest on the page

Taste 5 DOC/DOCG Montepulciano wines in a medieval cellar, paired with pecorino and bruschetta, plus a guided look at tufa and barrels.

“I recently took part in a wonderful tour that exceeded my expectations. The guide was exceptional - her friendly and engaging personality made the experience even more enjoyable. She was incredibly knowledgeable and provided us with fascinating information that truly enriched the entire tour. In addition to the excellent guiding, the wine tastings were a real highlight. We had the opportunity to sample some amazing wines, each paired with delicious cheeses that complemented the flavors perfectly. The combination of the informative tour and the delightful tastings made for a memorable experience. I highly recommend this tour for anyone interested in learning more about the area while enjoying...”

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Val d’Orcia Brunello Wine Tour with Montalcino and Montepulciano

Val d'Orcia Brunello Wine Tour with Montalcino and Montepulciano - Fortezza di Montalcino: short castle views and a quick walk

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

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

Small-group Brunello wine tour from Florence with Montalcino, Pienza, and Montepulciano, plus two tastings and a scenic lunch.

“Great day trip from Florence. We traveled with our two adult children and both generations enjoyed the day. We toured two wineries, with tastings, visited a quaint city after lunch that offered fun shopping and tremendous views of the rolling hills, enjoyed a very tasty local lunch, and learned about the history of Montepulciano. Our driver Mike, was a great (and safe) driver, who shared feedback about local culture and history along the way. The van had an eight guest capacity, but was much more comfortable with our six guest booking. As it was, our 6’2” son was a bit cramped in the back seat. Nothing that took away from…”

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From Siena: Brunello di Montalcino Guided Wine Tour W/ Lunch

From Siena: Brunello di Montalcino Guided Wine Tour W/ Lunch - Vineyard Walks and Cellars Where Brunello Really Happens

7.From Siena: Brunello di Montalcino Guided Wine Tour W/ Lunch

★★★★★★★★★★4.9 · 357 reviews · from $203

Small-group Brunello di Montalcino tour from Siena with 3 winery tastings, family lunch, and Sant'Antimo Abbey in 9 hours.

“Our guide Giovanni was really nice and knowledgeable about the area and answered all of our questions. He picked us up in a van and we went to three wineries plus a quick stop at Abbey Of Sant’Antimo. The three wineries we went to were Casanuova Delle Cerbaie, Cava D’Onice (where we had the best homemade pasta ragu lunch prepared by the grandmother) and Poggio Dell’Aquila. I did end buying some bottles and had them ship it home. Overall I would recommend this tour (and tour guide Giovanni). It sounds expensive but don’t think too much about the price, it will be worth the time and money.Read more”

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Montalcino: Brunello Wine Tasting & Lunch in a Tuscan Castle

Montalcino: Brunello Wine Tasting & Lunch in a Tuscan Castle - Vineyard walk with a professional sommelier, not a lecture hall

8.Montalcino: Brunello Wine Tasting & Lunch in a Tuscan Castle

★★★★★★★★★★4.6 · 324 reviews · 1.5 hours · from $69

A 1.5-hour Brunello tasting at Castello Tricerchi, paired with a traditional Tuscan 3-course lunch, plus a vineyard walk.

“We had a wonderful time exploring the castle and learning more about the region. The lunch was delicious and the wine was fantastic. This was definitely a highlight of our trip! Highly recommend!”

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Small-Group Montepulciano and Pienza Day Trip from Siena

Small-Group Montepulciano and Pienza Day Trip from Siena - Crete Senesi: The Gray Clay Hills That Look Like Another Planet

9.Small-Group Montepulciano and Pienza Day Trip from Siena

★★★★★★★★★★5.0 · 281 reviews · 8 hours (approx.) · from $217

Small-group day trip from Siena to Pienza and Montepulciano via Val d’Orcia, with pecorino tasting and farm lunch.

“What a fun day! Our guide, Paolo, was wonderful. His knowledge of the Tuscan hills was extensive. He could answer any questions we threw at him. His driving skills were also impressive. The time flew by. We had a great bunch of travelers in our tour group. So happy to be in a small group (8 travelers.) This was a great way to see Tuscany without renting a car. We drank plenty of wine, had a lovely farm lunch and had time alone to walk around Pienza and Montepulciano, too. It felt so casual, and yet we saw so much. When it was over, I was a little sad because…”

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Florence: Valdorcia Wine, Brunello Montalcino, Montepulciano

Florence: Valdorcia Wine, Brunello Montalcino, Montepulciano - Montalcino Winery Time: Brunello di Montalcino Tasting With Real Method

10.Florence: Valdorcia Wine, Brunello Montalcino, Montepulciano

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

Small-group Val d’Orcia day trip from Florence with Brunello tastings, Pienza pecorino lunch, and underground Montepulciano cellar.

“I like that our driver and tour guide Mike went above and beyond to consider my request to drop by a typical Tuscan house with pine trees to have pictures taken which is a dream come true. The medieval towns we visited are beautiful ❤️Truly had a wonderful trip and the wine tasting and the food is great . This complete my Tuscany Experience.So lovely !! I highly recommend this tour.”

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Florence: Orcia Valley, Montalcino, Pienza with Lunch & Wine

Florence: Orcia Valley, Montalcino, Pienza with Lunch & Wine - From Santa Maria Novella to Piazzale Montelungo, Then Off You Go

A Brunello Cooking Class with Vineyards View Winery

A Brunello Cooking Class with Vineyards View Winery - What you actually cook: filled pasta, handmade pasta, and Tuscan dessert

12.A Brunello Cooking Class with Vineyards View Winery

★★★★★★★★★★5.0 · 221 reviews · 4 hours (approx.) · from $313

A small-group half-day Brunello cooking class in Montalcino at Castello Tricerchi, with hands-on pasta, terrace lunch, and wine tasting.

“This was an absolutely amazing experience. We are traveling in a group of six married couples celebrating our 40th birthdays. The castle is a quiet dream originally constructed in the 1200s a top a hill overlooking the Tuscan hills and vineyard. You can see Montalcino a few miles away on its hilltop as well. The cooking class is in a small rustic building with gorgeous windows overlooking the winery. A mom and daughter team led our cooking class, starting with tiramasu, beef and pasta, while being served Persecco. We had lunch outside on a terrace where we were served their delicious wine. This has been the highlight of our two…”

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From Siena: Pienza and Montepulciano Small-Group Tour

From Siena: Pienza and Montepulciano Small-Group Tour - Pienza: the Pope’s planned town, and how to enjoy it

13.From Siena: Pienza and Montepulciano Small-Group Tour

★★★★★★★★★★4.9 · 220 reviews · from $203

Small-group day trip from Siena to Pienza and Montepulciano, with an organic-farm lunch, pecorino tasting, and a Vino Nobile cellar visit.

“Pienza and Montepulciano were breathtaking and every view was a postcard picture. But our guide., Keiko, was the best part of the trip. His knowledge, enthusiasm and. and warmth made this trip a perfect day.”

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Montalcino: Guided Winery Tour and Wine Tasting

Montalcino: Guided Winery Tour and Wine Tasting - The 105-Minute Flow, from Vineyards to a Cross-Vaulted Cellar

Siena: San Gimignano, Chianti & Montalcino Small-Group Tour

Siena: San Gimignano, Chianti & Montalcino Small-Group Tour - San Gimignano: City of Fine Towers, plus Vernaccia on the menu

15.Siena: San Gimignano, Chianti & Montalcino Small-Group Tour

★★★★★★★★★★4.6 · 195 reviews · from $158

Small-group Siena day trip to San Gimignano, Chianti wineries and Montalcino, with Val d'Orcia and Brunello tastings.

“Amazing experience !! I loved every moment. High recommend this wine tasting tour. It was more than I expected and very memorable. From beginning to end, everything was just wow. We explored wonderful cities, got to taste some exquisite wines from the Chianti and Montalcino lands - both Chianti and Brunello wines were such a tasteful delight . Above all, Fabio was amazing. Not only is he a man with class, charisma, and great character but he is funny and knowledgeable. He really taught us a lot and took us to wonderful picture sites and gave us tips and places to see for each little village we stopped at. Fabio…”

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