New Chat
Download App
Ask me about your trip!
There are no messages for this conversation.Travel AI
![Montalcino and Tuscany Delights 5 days](https://storage.googleapis.com/bd-app-dev-375714.appspot.com/itineraries/019071c0-3119-73c9-9047-cf7b12817401/location447.jpg)
Montalcino and Tuscany Delights 5 days Itinerary
Last updated: 2024 Jul 02Exploring Montalcino's Rich Heritage
Morning
Start your day with a visit to Montalcino. This charming town is renowned for its medieval architecture and picturesque landscapes. Wander through the narrow streets, taking in the local shops and cafes that give Montalcino its unique character. Don't forget to stop by Caffè Fiaschetteria Italiana for a delightful morning coffee.
Afternoon
In the afternoon, head to Montalcino Fortress (Fortezza di Montalcino). This imposing fortress offers stunning views of the surrounding countryside. Explore the historic walls and learn about the fortress's role in Montalcino's history. For lunch, enjoy a meal at Osteria di Porta al Cassero, known for its traditional Tuscan dishes.
Evening
End your day with a tour from your wishlist: Val d'Orcia: Private Photography Safari Tour with Aperitif. Capture the breathtaking beauty of Val d'Orcia during this private photography tour, followed by an aperitif as you watch the sunset over the rolling hills. For dinner, dine at Ristorante Boccon DiVino, which offers spectacular views and delicious local cuisine.
Bedtime
Find amazing hotels in Montalcino.
![Visit Montalcino in Montalcino](https://media.tacdn.com/media/attractions-content--1x-1/0b/2c/f6/a7.jpg)
4.86Montalcino
Book Now
![Visit Montalcino in Montalcino](https://media.tacdn.com/media/attractions-content--1x-1/0b/2c/f6/a7.jpg)
Montalcino
Book Now
![Visit Montalcino Fortress (Fortezza di Montalcino) in Montalcino](https://media.tacdn.com/media/attractions-content--1x-1/0b/39/9f/dd.jpg)
4.78Montalcino Fortress (Fortezza di Montalcino)
Book Now
![Visit Montalcino Fortress (Fortezza di Montalcino) in Montalcino](https://media.tacdn.com/media/attractions-content--1x-1/0b/39/9f/dd.jpg)
Montalcino Fortress (Fortezza di Montalcino)
Book Now
![Visit Val d'Orcia Private Photography Safari Tour with Aperitif in Montalcino](https://cdn.getyourguide.com/img/tour/7f383856f832f40e.jpeg/21.jpg)
5.00Val d'Orcia: Private Photography Safari Tour with Aperitif
Book Now
![Visit Val d'Orcia Private Photography Safari Tour with Aperitif in Montalcino](https://cdn.getyourguide.com/img/tour/7f383856f832f40e.jpeg/21.jpg)
Val d'Orcia: Private Photography Safari Tour with Aperitif
Book Now
Wine Tasting and Historical Wonders
Morning
Begin your second day with a visit to Abbey of Sant'Antimo (Abbazia di Sant'Antimo). This stunning Romanesque abbey is set in a serene valley and is known for its Gregorian chants. Take some time to explore the beautiful architecture and peaceful surroundings. Enjoy breakfast at Bar Alle Logge di Piazza before heading out.
Afternoon
After visiting the abbey, embark on another wishlist tour: Montalcino: Walk of Wine Tour with Vertical Brunello Tasting. This guided tour will take you through some of Montalcino's best vineyards, culminating in a vertical tasting of Brunello wines. For lunch, savor local flavors at Enoteca la Fortezza di Montalcino, located within the fortress walls.
Evening
In the evening, take part in yet another unique experience from your wishlist: Val D'Orcia: Private Olive Oil Tasting and Tuscan Dinner. Learn about olive oil production and enjoy a sumptuous Tuscan dinner paired with exquisite olive oils. Conclude your day with a relaxing drink at Caffè Sant'Angelo, where you can unwind and reflect on your day's adventures.
Bedtime
Find amazing hotels in Montalcino.
![Visit Abbey of Sant'Antimo (Abbazia di Sant'Antimo) in Montalcino](https://media.tacdn.com/media/attractions-content--1x-1/0b/39/9f/bd.jpg)
4.60Abbey of Sant'Antimo (Abbazia di Sant'Antimo)
Book Now
![Visit Abbey of Sant'Antimo (Abbazia di Sant'Antimo) in Montalcino](https://media.tacdn.com/media/attractions-content--1x-1/0b/39/9f/bd.jpg)
Abbey of Sant'Antimo (Abbazia di Sant'Antimo)
Book Now
![Visit Montalcino Walk of Wine Tour with Vertical Brunello Tasting in Montalcino](https://cdn.getyourguide.com/img/tour/64b80c514150d.jpeg/21.jpg)
4.82Montalcino: Walk of Wine Tour with Vertical Brunello Tasting
Book Now
![Visit Montalcino Walk of Wine Tour with Vertical Brunello Tasting in Montalcino](https://cdn.getyourguide.com/img/tour/64b80c514150d.jpeg/21.jpg)
Montalcino: Walk of Wine Tour with Vertical Brunello Tasting
Book Now
![Visit Val D'Orcia Private Olive Oil Tasting and Tuscan Dinner in Montalcino](https://cdn.getyourguide.com/img/tour/62fbb066ac2d4.png/21.jpg)
5.00Val D'Orcia: Private Olive Oil Tasting and Tuscan Dinner
Book Now
![Visit Val D'Orcia Private Olive Oil Tasting and Tuscan Dinner in Montalcino](https://cdn.getyourguide.com/img/tour/62fbb066ac2d4.png/21.jpg)
Val D'Orcia: Private Olive Oil Tasting and Tuscan Dinner
Book Now
Scenic Beauty and Culinary Delights
Morning
On your third day, venture out to explore more of Tuscany starting with Pienza. Begin with an early morning visit to Pienza: Scenic hiking on the Gladiator's movie location. Enjoy breathtaking views as you hike through this iconic landscape featured in movies like Gladiator. Have breakfast at Bar Il Casello before setting off.
Afternoon
Continue your exploration with another wishlist experience: Pienza: Guided E-bike Tour through the Val d'Orcia. This guided e-bike tour will take you through some of Tuscany's most beautiful scenery, including rolling hills and charming villages. Stop for lunch at La Buca di Enea, known for its delicious pasta dishes.
Evening
Wrap up your day with an immersive culinary experience from your wishlist: Cooking Class in a Brunello Winery - Private experience. Learn how to prepare traditional Tuscan dishes using fresh local ingredients while enjoying fine Brunello wines. End your evening with dinner prepared during your cooking class or head to Trattoria Latte di Luna for more Tuscan delights.
Bedtime
Find amazing hotels in Tuscany.
![Visit Pienza: Scenic hiking on the Gladiator's movie location in Tuscany](https://cdn.getyourguide.com/img/tour/ff681725003981828e341fec790c5390c354dd95d3d87ce079cfc0363f90432e.jpeg/21.jpg)
Pienza: Scenic hiking on the Gladiator's movie location
Book Now
![Visit Pienza: Scenic hiking on the Gladiator's movie location in Tuscany](https://cdn.getyourguide.com/img/tour/ff681725003981828e341fec790c5390c354dd95d3d87ce079cfc0363f90432e.jpeg/21.jpg)
Pienza: Scenic hiking on the Gladiator's movie location
Book Now
![Visit Pienza Guided E-bike Tour through the Val d'Orcia in Tuscany](https://cdn.getyourguide.com/img/tour/af037350329336e8d6bc1befbd2d534ad5b78c1468aa46c00838307bd531c78e.jpg/21.jpg)
5.00Pienza: Guided E-bike Tour through the Val d'Orcia
Book Now
![Visit Pienza Guided E-bike Tour through the Val d'Orcia in Tuscany](https://cdn.getyourguide.com/img/tour/af037350329336e8d6bc1befbd2d534ad5b78c1468aa46c00838307bd531c78e.jpg/21.jpg)
Pienza: Guided E-bike Tour through the Val d'Orcia
Book Now
![Visit Cooking Class in a Brunello Winery - Private experience in Tuscany](https://cdn.getyourguide.com/img/tour/769c0f8ce518f3cfbc00676b40e95c13b5506247ded748f646eeeef0153bd9fd.jpg/21.jpg)
Cooking Class in a Brunello Winery - Private experience
Book Now
![Visit Cooking Class in a Brunello Winery - Private experience in Tuscany](https://cdn.getyourguide.com/img/tour/769c0f8ce518f3cfbc00676b40e95c13b5506247ded748f646eeeef0153bd9fd.jpg/21.jpg)
Cooking Class in a Brunello Winery - Private experience
Book Now
Truffle Hunting and Wine Adventures
Morning
Start your fourth day with an exciting wishlist tour: Trequanda: Tuscan Truffle Hunting Experience with Lunch. Join expert truffle hunters and their dogs as you search for these culinary treasures in the beautiful Tuscan countryside. After the hunt, enjoy a delicious lunch featuring freshly found truffles. For breakfast, stop by Caffè Poliziano in Montepulciano for a delightful start to your day.
Afternoon
In the afternoon, continue your exploration with a visit to Montepulciano: Winery and Perfume Laboratory Sensory Tour. This unique tour combines wine tasting with a sensory experience at a perfume laboratory, allowing you to discover the intricate connections between scents and flavors. For lunch, savor local dishes at Osteria Acquacheta, renowned for its traditional Tuscan cuisine.
Evening
Conclude your day with another memorable wishlist experience: Val d'Orcia: Magical 3-Course Dinner under the Oak Tree. Enjoy a magical evening dining under an ancient oak tree in the heart of Val d'Orcia, accompanied by exquisite Tuscan wines. End your evening with a nightcap at Bar La Dolce Vita, where you can relax and soak in the serene atmosphere.
Bedtime
Find amazing hotels in Tuscany.
![Visit Trequanda Tuscan Truffle Hunting Experience with Lunch in Tuscany](https://cdn.getyourguide.com/img/tour/63d3f7ca76877.jpeg/21.jpg)
4.50Trequanda: Tuscan Truffle Hunting Experience with Lunch
Book Now
![Visit Trequanda Tuscan Truffle Hunting Experience with Lunch in Tuscany](https://cdn.getyourguide.com/img/tour/63d3f7ca76877.jpeg/21.jpg)
Trequanda: Tuscan Truffle Hunting Experience with Lunch
Book Now
![Visit Montepulciano: Winery and Perfume Laboratory Sensory Tour in Tuscany](https://cdn.getyourguide.com/img/tour/63d92e3aa056d.jpeg/21.jpg)
Montepulciano: Winery and Perfume Laboratory Sensory Tour
Book Now
![Visit Montepulciano: Winery and Perfume Laboratory Sensory Tour in Tuscany](https://cdn.getyourguide.com/img/tour/63d92e3aa056d.jpeg/21.jpg)
Montepulciano: Winery and Perfume Laboratory Sensory Tour
Book Now
![Visit Val d'Orcia: Magical 3-Course Dinner under the Oak Tree in Tuscany](https://cdn.getyourguide.com/img/tour/62fbb7fd328b3.jpeg/21.jpg)
1.00Val d'Orcia: Magical 3-Course Dinner under the Oak Tree
Book Now
![Visit Val d'Orcia: Magical 3-Course Dinner under the Oak Tree in Tuscany](https://cdn.getyourguide.com/img/tour/62fbb7fd328b3.jpeg/21.jpg)
Val d'Orcia: Magical 3-Course Dinner under the Oak Tree
Book Now
Cultural Immersion and Farewell
Morning
Montalcino personal photo service for couples and families - Capture lasting memories of your trip with a professional photo session in Montalcino's most picturesque spots. Start your morning with breakfast at Pasticceria Mariuccia, known for its delicious pastries and coffee.
Afternoon
Montalcino: Castle and Vineyards Tour with Tasting - Spend your afternoon exploring Montalcino's historic castles and vineyards. This guided tour will take you through some of the region's most iconic sites, culminating in a wine tasting session. For lunch, dine at Ristorante Il Giglio, offering traditional Tuscan dishes made from fresh local ingredients.
Evening
Aperitif on the Terrace of Podere Montale at Sunset - End your trip on a high note with an aperitif on the terrace of Podere Montale as you watch the sun set over the stunning Tuscan landscape. Enjoy dinner at Ristorante Re di Macchia, where you can savor more of Tuscany's culinary delights before bidding farewell to this enchanting region.
Bedtime
Find amazing hotels in Montalcino.
![Visit Montalcino personal photo service for couples and families in Montalcino](https://cdn.getyourguide.com/img/tour/8bbb3dcc3fffe13ab07bcf547c29773a72fec9abf8376bcc2c35b7762c631547.jpg/21.jpg)
5.00Montalcino personal photo service for couples and families
Book Now
![Visit Montalcino personal photo service for couples and families in Montalcino](https://cdn.getyourguide.com/img/tour/8bbb3dcc3fffe13ab07bcf547c29773a72fec9abf8376bcc2c35b7762c631547.jpg/21.jpg)
Montalcino personal photo service for couples and families
Book Now
![Visit Montalcino Castle and Vineyards Tour with Tasting in Montalcino](https://cdn.getyourguide.com/img/tour/5de8128ed38cc.jpeg/21.jpg)
4.10Montalcino: Castle and Vineyards Tour with Tasting
Book Now
![Visit Montalcino Castle and Vineyards Tour with Tasting in Montalcino](https://cdn.getyourguide.com/img/tour/5de8128ed38cc.jpeg/21.jpg)
Montalcino: Castle and Vineyards Tour with Tasting
Book Now
![Visit Aperitif on the Terrace of Podere Montale at Sunset in Montalcino](https://cdn.getyourguide.com/img/tour/64819c9ef301c.jpeg/21.jpg)
3.67Aperitif on the Terrace of Podere Montale at Sunset
Book Now
![Visit Aperitif on the Terrace of Podere Montale at Sunset in Montalcino](https://cdn.getyourguide.com/img/tour/64819c9ef301c.jpeg/21.jpg)
Aperitif on the Terrace of Podere Montale at Sunset
Book Now
Top Tuscany Travel Videos