Montalcino Fortress (Fortezza di Montalcino) Tours and Tickets

18 results

San Gimignano, Chianti and Montalcino Tour through Tuscan wine

Take a day excursion to San Gimignano, Chianti, and Montalcino to experience the charm of the Tuscan countryside. Savor the best local blends during a wine tasting at a renowned Chianti winery. Optional lunch for an authentic gastronomic experience. Begin your full-day journey by seeing San Gimignano, well known as the City of Fine Towers. With your tour guide's insights, take advantage of your free time to explore the historical center and its artisan stores. Explore the birthplace of Vernaccia, the renowned white wine that is regarded as Italy's first DOCG wine, after that. Enjoy a sample of Chianti and you can choose to buy the optional lunch at a nearby winery. Discover the UNESCO World Heritage Site of Val d'Orcia before continuing on to Montalcino, which is famous for its panoramic vistas of Brunello grapes. Finish your tour by visiting a local wine cellar to experience the renowned Brunello di Montalcino.

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San Gimignano, Chianti and Montalcino Tour through Tuscan wine

11 hoursFree Cancellation

4.8

(8)

from $166

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

Spend a day sipping one of Italy’s top wines, Brunello di Montalcino, on this trip from Siena to Montalcino. Travel first to a small winery to explore the vineyards and cellars and taste the famous Rosso and Brunello di Montalcino wine. Then, visit a family-run winery in Montalcino, where you tour the grounds and sit down for a classic Tuscan meal with more wine. Visit the Abbey of Sant'Antimo before tasting even more wine at your third and final winery of the day.

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

9 hoursFree Cancellation

4.9

(983)

from $225

Val D’Orcia Tour From Siena Montalcino Pienza and Montepulciano

DEPARTURE GUARANTEED! Enjoy a perfect day trip visiting 3 of the most impressive places in Tuscany. Montalcino, house of "Brunello" wine; Pienza, well known for the "Pecorino" cheese and Montepulciano where the undisputed symbol is the "Nobile di Montepulciano" wine! Please note that from November to April I cannot guarantee the restaurant with view, as stated in the inclusions. The Valdorcia has been recognized as UNESCO world heritage site since 2004, as it was an inspiration for many Renaissance painters. There you will be surrounded by impressive views, art, culture, amazing wine and delicious food! Your semi private tour will be on board of a premium minivan with an English speaking driver, air conditioning and free water. WHY CHOOSE ME? Secure bookings, Guaranted Departures! 48 hours Cancellation policy, best rates guaranteed! Group of maximum 8 people.

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Val D’Orcia Tour From Siena Montalcino Pienza and Montepulciano

10 to 11 hoursFree Cancellation

4.7

(3)

from $271

Likely to Sell Out

San Gimignano, Chianti, and Montalcino Day Trip from Siena

Explore Tuscany outside Siena on this small-group day trip, visiting San Gimignano and Montalcino. Don't worry about hiring a car, as all transportation is arranged. Take a break from the city as you discover medieval architecture and scenic views of Tuscany, with ample free time in each of the hill towns. The tour also includes a visit to a Montalcino winery, with the opportunity to sample Chianti and Brunello di Montalcino.

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San Gimignano, Chianti, and Montalcino Day Trip from Siena

11 hoursFree Cancellation

4.3

(151)

from $166

Val d'Orcia Brunello Wine Tour with Montalcino and Montepulciano

Embark on a delightful day trip through Tuscany's iconic Val d'Orcia, a UNESCO World Heritage Site. Visit Montalcino, home of Brunello wine, Pienza, famed for Pecorino cheese, and Montepulciano, celebrated for Nobile wine. Enjoy breathtaking views, rich culture, and mouthwatering food. Travel in comfort aboard a premium minivan with an English-speaking driver. Indulge in wine tastings, a superior lunch with a view (seasonal), and guided vineyard and cellar tours.

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Val d'Orcia Brunello Wine Tour with Montalcino and Montepulciano

10 hours 30 minutesFree Cancellation

4.7

(384)

from $271

Price varies by group size

Medieval Tour in Monteriggioni and Val d'Orcia from Florence

Experience medieval Tuscany on a group day trip. Visit the fortified town of Monteriggioni with tickets to its Templar Museum and panoramic views from its walls (if selected). Continue on to the UNESCO heritage area of Val d'Orcia and stop at the medieval village of Montalcino for an optional taste of local wine and nibbles. Finish your tour with a wander through Pienza before the scenic drive back to Florence.

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Medieval Tour in Monteriggioni and Val d'Orcia from Florence

11 hoursFree Cancellation

4.8

(64)

from $51

Special Offer

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

11 hours 30 minutesFree Cancellation

Likely to Sell Out

Signature Brunello di Montalcino Wine Tour from Siena

Take a break from the crowds in Siena, and spend an afternoon in the wine town of Montalcino on this group tour. Don't worry about hiring a car to get there, with transportation all sorted. Learn about Brunello di Montalcino wine and its production, along with wine tastings paired with local snacks. Admire views of the Tuscan countryside from this hill town as you discover the region’s generations-old winemaking traditions.

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Signature Brunello di Montalcino Wine Tour from Siena

5 hours 30 minutesFree Cancellation

4.0

(66)

from $141

Aperitif on the Terrace of Podere Montale at Sunset

1 hourFree Cancellation

4.8

(21)

from $47

Visit to the Cellar with Wine & Food Tasting over the Val d'Orcia

Try some of Italy’s best wines over some delicious Tuscan cuisine on this group tour, where all the details are taken care of for you. Learn all about the regional wines from your wine connoisseur, who knows all there is to know about local Sangiovese grapes. Enjoy a leisurely lunch overlooking Val d’Orcia with choices like artisanal Tuscan cured meat, cheese, and of course, Seggiano’s finest wine.

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Visit to the Cellar with Wine & Food Tasting over the Val d'Orcia

2 hoursFree Cancellation

4.9

(41)

from $71

Grand Tour of Pienza, Montalcino, Montepulciano + wine and cheese tasting

Discover three of Tuscany’s most beautiful towns as you explore Pienza, Montalcino, and Montepulciano in one day on this walking tour. With a private guide, see the splendid 16th-century Renaissance palaces of Montepulciano and walk through the town of Pienza, built by Pope Pius II. In Montalcino, take a guided tour of a winery and taste the renowned Brunello de Montalcino wine. Note: transportation is not included.

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Grand Tour of Pienza, Montalcino, Montepulciano + wine and cheese tasting

8 hoursFree Cancellation

5.0

(1)

from $414

Per group

Brunello di Montalcino, small biodynamic wineries

Sip wine and go back to medieval times during this small-group guided tour that includes an authentic Tuscan lunch. Wander the streets of the ancient, hilltop town of Montalcino known for its wine before touring the Brunello di Montalcino winery. Learn how biodynamic wines are made and sample varieties straight from the barrel. After lunch, visit a second winery to sip samples and eat Tuscan fare.

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Brunello di Montalcino, small biodynamic wineries

8 hoursFree Cancellation

5.0

(13)

from $472

Price varies by group size

Likely to Sell Out

Brunello Wine Tasting from San Gimignano

6 hours 30 minutesFree Cancellation

3.9

(12)

from $141

Private: Tuscany Day Tour from Rome with Optional Wine Tasting

Escape the hustle and bustle of Rome and explore the serene, UNESCO-listed Val d’Orcia with a private, customizable tour. Enjoy hotel pick-up and drop-off with an English-speaking driver in a comfortable Mercedes sedan or minivan, stopping in the charming towns of Montepulciano, Pienza, and Montalcino. Opt for a winery visit and wine tasting along the way at additional cost, or adjust the itinerary to suit your preferences.

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Private: Tuscany Day Tour from Rome with Optional Wine Tasting

10 to 11 hoursFree Cancellation

5.0

(13)

from $710

Price varies by group size

Likely to Sell Out

Tuscany Brunello wine tour (12hrs) Montalcino, Montepulciano

Escape the bustle of the city and journey to Italy’s most celebrated wine districts during this scenic day trip to Tuscany. Visit family-run wineries and learn about centuries of wine-making traditions while strolling through the picturesque towns of Montalcino, Pienza, and Montepulciano. Tours are fully customizable, allowing you to choose between wine tastings and sightseeing visits, with add-ons like savory Tuscan lunches.

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Tuscany Brunello wine tour (12hrs) Montalcino, Montepulciano

12 hoursFree Cancellation

5.0

(1)

from $650

Price varies by group size

Ancient Wine Cities: Montalcino, San Gimignano and Chianti

10 hoursFree Cancellation

4.5

from $501

Price varies by group size

Unique Tuscany Experience in 1 week with the locals

Explore the best of Tuscany and its timeless secrets with a small, intimate group on this 8-day excursion that begins in Florence. Take in all of the captivating sights from Arezzo to Anghiari. Get up close and personal with San Gimignano, Volterra, and Val d'Orcia – uncovering their stories and marveling at the ancient wonders. Then, dive further into the culture by visiting Siena and discovering some world-famous vineyards where one can sample Italy's finest drops.

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Unique Tuscany Experience in 1 week with the locals

8 daysFree Cancellation

4.3

(4)

from $4,003

Price varies by group size

Private Tuscany Wine and Hill Towns Day Trip with Hotel Pick up

Escape the bustling streets of Rome and explore the picturesque Val d’Orcia on this private day trip. With a friendly English-speaking driver, visit the charming towns of Montepulciano, Pienza, and Montalcino, known for their stunning landscapes and rich wines. Enjoy the flexibility to customize your itinerary to include a winery visit and tasting, or simply savor the breathtaking views and local cuisine at your own pace. This tour offers a unique glimpse into Tuscan culture, perfect for wine enthusiasts and travellers seeking a personalized experience. - Private transportation in a comfortable Mercedes sedan or minivan - Explore UNESCO-listed Val d’Orcia, stopping in Montepulciano and Montalcino - Customize your itinerary with optional winery visits and lunch - Full-day tour lasting approximately 10 to 11 hours from Rome, with hotel pick-up and drop-off

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Private Tuscany Wine and Hill Towns Day Trip with Hotel Pick up

9 to 10 hoursFree Cancellation

from $1,128

Price varies by group size

What are people saying about Montalcino Fortress (Fortezza di Montalcino)

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

Donna_N, May 2026

Must do tour!

Absolutely amazing experience in the Tuscan countryside. Our tour guide Paulo was so much fun and so knowledgeable of the area and the history of Siena and the region. All three wineries offered fantastic tasting experiences and were so welcoming. Lunch with the wine maker at his home was a highlight. This tour is an absolute must!

San Gimignano, Chianti, and Montalcino Day Trip from Siena

Mei_X, May 2026

Nicely organized tour,...

Nicely organized tour, great food and wine. San Gimignano is beautiful but packed with tourists (including myself too) during mid day. Would love to visit it during some quieter time if any.

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

Merissa_W, May 2026

It was wonderful! William...

It was wonderful! William was funny, knowledgeable and took us to great wineries. I enjoyed it a lot. I recommend doing this tour with William!

Val d'Orcia Brunello Wine Tour with Montalcino and Montepulciano

Cynthia_P, May 2026

Great scenery and wine

Beautiful scenery and lovely wine. Second time taking this tour. The quality of the lunch has decreased since last year but the scenery is still wonderful from restaurant terrace. Wine pours seemed to be smaller and wine prices are up. Driver was diligent but parking was a challenge and we needed to walk further than last year to reach the restaurant in Pienza and the winery in Montepulciano. This was a bit of a challenge for me in 90+ F degree heat.

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

Joshua_T, May 2026

Outstanding Tuscany Experience!

This was a fantastic day that we really enjoyed!! We learned a ton about the history of the region and how it’s been tied to wine making. Our guide Paulo was so nice, knowledgeable, and a joy to have as a host and driver throughout the day! Cannot thank him enough for a very memorable experience on our trip!! For sure book this trip if you can, as you will not regret it!

Montalcino Fortress (Fortezza di Montalcino)

5.0

(3,043)

Siena

Know before you go

Montalcino Fortress (Fortezza di Montalcino)

The view over the rolling hills of Val d’Orcia from the Fortezza di Montalcino is unforgettable, so be sure to bring your camera.
The courtyard and wine shop are accessible to wheelchair users, but the ramparts and watchtowers are not.
Tours of Montalcino and Tuscany’s wine country require a fair bit of walking. Choose comfortable shoes and dress for the weather.
This authentic medieval fortress is a fun stop for kids.

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