Things to Do in Montalcino: Top Wine Tours, Truffle Hunting & Experiences

Planning a trip to the rolling hills of Tuscany’s Val d’Orcia means stepping into a postcard-perfect world of medieval history, dramatic landscapes, and world-class gastronomy. If you are wondering what to do in Montalcino, you’ve come to the right place. Beyond its iconic hilltop views, this charming Tuscan town offers exclusive activities designed for travelers seeking romance, luxury, and authentic local culture.

To help you build your itinerary stress-free, we’ve handpicked the very best Montalcino tours and experiences that you can book online in advance. Whether you want to drift over vineyards in a hot air balloon at sunrise or savor world-renowned Brunello di Montalcino inside a 14th-century castle, here is everything you need to know—including live prices, inclusions, and direct booking links.

All recommended activities feature free cancellation up to 24 hours in advance with a full refund and a “reserve now & pay later” option, giving you total flexibility for your Tuscan vacation.

Quick Comparison of the Best Montalcino Experiences

Truffle Hunting, Wine Tasting, and Lunch in Montalcino

If you’re looking for a hands-on outdoor adventure paired with an unforgettable feast, the Montalcino Truffle Hunting & Wine Tasting at Cordella Wine Resort is a top pick. Led by expert truffle hunters (tartufai) and their trained Lagotto Romagnolo dogs, you’ll trek through authentic Tuscan countryside to unearth one of nature’s rarest delicacies.

Following the 3-hour guided hunt, the experience moves to the table for a gourmet meal centered around fresh truffles: from appetizers and homemade tagliatelle to tender beef filet and truffle dessert. Each course is paired with 6 different Cordella estate wines (including Brunello di Montalcino, Riserva, Selezione Meleto, Rosso di Montalcino, and IGT reds), along with grappa tastings and extra virgin olive oil.

• Price: From €190 per person (Kids’ menu available upon request for €25, including child-friendly food and soft drinks).

• Flexible Booking: Free cancellation up to 24 hours before the activity and pay-later option.

• Best For: Couples, small groups, and foodies (not suitable for travelers with mobility impairments).

👉 Check availability and book the Truffle Hunting Experience on GetYourGuide

Brunello Tasting & Lunch in a Medieval Tuscan Castle

Soaking in the atmosphere of a 14th-century fortress while sipping one of Italy’s most prestigious red wines is a bucket-list item. At the stunning Castello Tricerchi, located on the northern slopes of Montalcino, you’ll join an expert sommelier for an exclusive tour of the historical estate and vineyards.

Learn about traditional winemaking techniques before enjoying a guided tasting of 3 benchmark Tuscan wines (including Sangiovese IGT and Brunello di Montalcino). Afterward, sit down for a traditional 3-course Tuscan lunch featuring local cured meats, artisan cheeses, handmade pasta with savory sauces, and dessert with coffee (vegetarian options available upon request).

• Price: €62 per person (all taxes and fees included).

• Duration: 1.5 hours.

• Flexible Booking: Free cancellation up to 24 hours prior and instant spot reservation without upfront payment.

• Note: This experience is high in demand and frequently sells out during peak season.

👉 Check available dates and book your Castle Lunch on GetYourGuide

Hot Air Balloon Ride Over Montalcino & Val d’Orcia

For a romantic milestone, an anniversary, or simply an unforgettable memory, a hot air balloon flight over Montalcino and Pienza offers breathtaking aerial views of Tuscany. Float peacefully on the morning breeze at altitudes ranging from 500 to 3,000 feet, admiring cypress-lined hills, historic villages, and sprawling vineyards bathed in golden sunrise light.

The entire activity lasts approximately 3 hours, including balloon inflation setup, a safety briefing by EASA-certified pilots, and a 1-hour flight. Upon landing, celebrate in classic aeronautical tradition with a sparkling champagne toast and a traditional local breakfast, followed by shuttle transport back to the meeting point.

• Price: €350 per person (includes flight, champagne, breakfast, return transfer, and ICAO insurance).

• Weather Guarantee: If your flight is canceled due to weather conditions on the day, you will receive a 100% full refund or the option to reschedule.

• Cancellation: Free up to 24 hours before departure.

👉 Check availability for the Hot Air Balloon Ride on GetYourGuide

Private Vineyard Picnic in Montalcino with a Bottle of Wine

For travelers who prefer a more intimate, laid-back vibe nestled in nature, the Corte Pavone winery (Loacker Wine Estates) offers a romantic private vineyard picnic in Montalcino.

If you opt for the full experience, your visit begins with a guided walk through the vines to explore the distinct cru terroirs of Brunello, followed by a tour of the vaulted cellar where vintage wines age in oak barrels. Afterward, head to your private spot among the grapevines, where a wicker picnic basket awaits—packed with homemade Tuscan specialties (vegetarian and vegan options available) and a full bottle of wine of your choice (red, white, or rosé).

• Price: From €40 per person.

• Duration: 1.5 to 2.5 hours.

• Flexible Booking: Free cancellation up to 24 hours prior and pay-later option.

• Best For: Couples and small groups looking for a scenic, relaxed afternoon.

👉 Reserve your Vineyard Picnic in Montalcino on GetYourGuide

How to Choose the Right Activity in Montalcino

To get the most out of your Tuscan vacation, keep these tips in mind when planning your itinerary:

1. For Ultimate Foodies: Book the Truffle Hunting Tour. While higher in price, it doubles as a full fine-dining experience featuring fresh truffle dishes and 6 premium wines.

2. For the Best Value: The Castello Tricerchi Lunch (€62) delivers incredible value, combining historical castle access, a professional sommelier, wine tasting, and a 3-course meal.

3. For Romance & Views: Choose the Corte Pavone Picnic (from €40) for an accessible, charming afternoon in the vines, or the Hot Air Balloon Flight (€350) for a once-in-a-lifetime adventure.

4. Book Ahead: Montalcino attracts visitors from around the world, and small-group tours (especially balloon flights and castle tastings) fill up quickly. Take advantage of GetYourGuide’s 24-hour free cancellation policy to lock in your dates risk-free.

Where to Stay in Montalcino and Tuscany

To match the beauty of Montalcino’s countryside and fine dining, your accommodation should be just as special. Whether you’re dreaming of a private villa with an infinity pool overlooking the hills or a restored historic estate, staying in a luxury villa elevates your entire trip.

For the finest selection of luxury hand-picked properties in the area, explore the private portfolio at TuscanMansions. Offering exclusive Tuscan villas, luxury country homes, and historic estates, it is the ideal place to find your home away from home while exploring Montalcino.