Discover Montalcino and More in Tuscany

Icon Share


Advisor - Alyson Ward
Curated By

Alyson Ward

  • Road Trip Travel

  • Off-the-Beaten-Path Travel

  • Food & Wine

  • Italy

  • Outdoor

  • Sighseeing

  • Wineries

the rolling hills of Tuscany beyond a flowering garden
Curator’s statement

The first time I visited Montalcino, many years ago, it stole my heart and I have since returned many times. Located about 50 minutes from Siena, It’s a dreamy medieval town, complete with a fortress. The area produces some of the most well known wines from Sangiovese grapes, Brunello di Montalcino (arguably the best..) and Rosso di Montalcino. It has all of the ingredients for an idyllic hilltop town: viniculture, vast rolling landscape, terracotta roofs, delicious tuscan cuisine and a touch of la dolce vita. When here, stroll the piazza, enjoy the local wine and watch the sunset each day from the panoramic view of the picturesque landscape, while enjoying an aperitivo from Caffe’ La Fortezza. This place is the reason I became a travel advisor, I believe Montalcino is place everyone should visit in their lifetime. This itinerary is built for those that are wanting to unwind, explore this beautiful area, without the hustle and bustle of large cities like Rome or Milan. Families, solo travelers, couples or groups can all enjoy their time here.

The Fora Difference

Book with Alyson to access exclusive perks and experiences on your trip.

[object Object]
Killer perks

Free upgrades, spa credits and more—we got you

[object Object]
Personalized recs

Customized travel planning for your style

[object Object]
Insider knowledge

Expert advice from people who’ve actually been there

Where to stay

Unlock perks by contacting Alyson to book your trip.

Day 1: Arrive in Montalcino

The rolling hills of Montalcino with a castle on top.

Arrive in Montalcino. This would be a great day to explore the property you’re staying at, stroll the town, grab gelato at Gelateria Artigianale Why Not? Get familiar with the area. Additionally, there are many locally owned, artisanal shops to visit. If you arrive in time, grab a seat outside and enjoy the sunset and aperitivo from Caffe’ La Fortezza.

For dinner, enjoy traditional tuscan fare at Taverna del Grappolo Blu. Included in the Michelin guide. I stop here each time I return to Montalcino, and to this day, think about my first meal here eight years ago.

Day 2: Bike tour of Val d’Orcia

an old stone building with a tall tree

Want to immerse yourself in the rolling tuscan hills? Biking through this region is a bucket list item for many. A bike tour can be arranged to explore a UNESCO World Heritage Site, Val d’Orcia, and more medieval villages. I recommend starting in Montalcino and head to Castiglione d’Orcia, make way through Bagno Vignoni (known for its thermal hot springs) and end in the charming town of Pienza.

Explore the town of Pienza and enjoy dinner at an osteria.

Day 3: Brunello di Montalcino & Rosso di Montalcino wine tastings

large glasses filled with a sip of red wine for a tasting

Explore a few of the 250 wineries producing Brunello di Montalcino in the region. From biodynamic wineries to more traditional methods, there is something for everyone. The wine tour will begin mid-morning with pick up at your hotel. From there, grab lunch at Il Pozzo in Sant'Angelo in Colle. After lunch, visit one or two more wineries during the afternoon. If you’re interested in olive oil tastings, several of the wineries also produce olive oil and can be included with you tour. If time permits, I recommend visiting the Abbey of Sant’Antimo and catch a vesper service performed each day by the monks.

After working with many local tour operators, I have several contacts that deliver an exceptional experience. I’ve also visited over 20 vineyards in the area, and am happy to share my favorites.

Enjoy innovative Tuscan cuisine at Locanda e Drogheria Franci, a restaurant inspired by flavors near and far. The menu changes frequently.

Day 4: Enjoy an organic farm-to-table cooking class

roasted eggplant slices and a red sauce on a marble counter

Enjoy an organic farm-to-table cooking class Interested in learning how to cooking traditional tuscan dishes? Visit Locanda Demetra where you will learn to make a multi-course lunch. This establishment was created by five entrepreneurs in the Montalcino area, where an abandoned farm house was given new life. They will start the cooking class with a tour of their garden and walk you through the ingredients you’ll be using. Each class will include starters, home made fresh pasta, a main course paired with a side dish and a dessert. Sound intimidating? Alessandro and his team make this experience fun, educational, and easy. After preparing the menu, all participants get to enjoy each dish, family style, in an al fresco setting.

No interest in cooking? You can still eat at Locanda Demetra as their farmhouse operates as an intimate restaurant, with about 10 tables. Reservations are necessary. 
Celebrate your last night spent in this beautiful part of the world at Boccon DiVino. Modern, tuscan cuisine served alongside views of Tuscan countryside. Another local establishment featured in the Michelin guide.

Advisor - Alyson Ward

Travel Advisor

Alyson Ward

Get in touch with Alyson

Did you like this guide? Reach out to customize and book your own experience. Or, just to chat about travel in general.

You can normally expect a response from Alyson within a business day or so. You’ll also be subscribed to our travel newsletter (you can unsubscribe at any time).

This guide is part of our ongoing series on travel to Italy.