Montepulciano & Beyond / a guidebook
Where Hills Get Dramatic and Wine Gets Serious
Montepulciano and its surroundings offer a perfect blend of history, nature, and the kind of charm that makes you want to just slow down and take it all in. Start with Montepulciano itself—its Renaissance streets, wine cellars, and, of course, the view from the top that seems to have been designed for postcards.
Head out into the Val d’Orcia, and you’ll find rolling hills that are so picturesque they could be the backdrop of any movie about Tuscany. The countryside here feels timeless, dotted with cypress trees, ancient farmhouses, and the kind of serenity you can only find in this part of the world. Pienza, not far away, is a UNESCO gem—a town built on Renaissance ideals, known for its stunning architecture and famous pecorino cheese. Then there’s Cortona, perched high on a hill, offering sweeping views and a peek into the region’s Etruscan past, with narrow streets and plenty of history to explore.
And let’s not forget the hidden gems—the quiet thermal springs, the vineyards where you can lose yourself in a glass of Vino Nobile, and the charming villages that make you feel like you’ve stumbled into a well-kept secret. Whether you’re a foodie, a history buff, or simply someone who loves beautiful landscapes, this area offers a bit of everything.
As for those lesser-known treasures, you’ll want to check out Castelmuzio and Lucignano d’Asso, two villages that offer a quiet escape from the crowds, where the pace of life is slower and the charm is undeniable. The Crete Senesi, with their unique lunar landscapes, are another hidden beauty to explore, offering vistas unlike anywhere else in Tuscany. Trequanda and Montisi, nestled in the rolling hills, are perfect for a leisurely stroll, while Rocca d’Orca provides a fascinating glimpse into the region’s medieval past. And on the other side, there’s Sant’Angelo in Colle, offering views over the rolling vineyards, and Castelnuovo dell’Abate, a gateway to the famous Abbey of Sant’Antimo. And of course, the Brunello vineyards—because let’s be real, no trip to this area is complete without a nod to the world-class wine of Montalcino!
The basics: Food&Wine Tours
...It’s Also About the Wine (and Olive Oil)!
In addition to hearty, satisfying meals, no food experience in Tuscany would be complete without its exceptional wines. From the world-renowned Brunello di Montalcino to the refined Nobile di Montepulciano, Tuscany’s red wines pair perfectly with bold, savory dishes. The region also shines with its white wines, especially the crisp and refreshing Vermentino. Tuscany is equally proud of its olive oil, often considered among the finest in the world. Its rich, robust flavor enhances everything from simple bread drizzles to complex sauces. For beer lovers, Tuscany’s craft beers add an interesting twist, reflecting the region’s creativity and passion for quality. Whether you’re cooking, tasting, or simply savoring, a Tuscan food experience is a true journey through the heart of Italy’s culinary heritage…
It’s Not All About the Food...
Tuscany is a land of culinary treasures, where food is a celebration of flavors, tradition, and local ingredients. Whether you’re joining a cooking class or embarking on a food tour, you’ll explore dishes that have made Tuscan cuisine famous worldwide. A standout is pici, a thick, hand-rolled pasta often paired with savory sauces like garlic, tomato, or wild boar. But Tuscany offers much more—ravioli, tagliatelle, tender filetto, and the legendary bistecca alla fiorentina (Florentine steak) are all must-tries. You can’t miss Antico Peposo, a slow-cooked beef stew that’s perfect for cozy, cool evenings. For those seeking rustic flavors, crostoni (toasted bread with delicious toppings) and pappa al pomodoro (tomato bread soup) offer comforting tastes, while ribollita, a traditional vegetable and bread soup, brings a taste of Tuscan history. Vegetarians will also find plenty to savor, with fresh, local vegetables featured in many traditional dishes.
Legs in motion: Active tours
Getting Lost (in Style) on Trails and Backroads
Walking, hiking, biking, and beyond…
Tuscany is made for exploration—on foot, by bike, or even on horseback if you want to add a bit of drama to your journey. Whether you’re in search of unique things to do in Tuscany or a day tour in Tuscany, there’s no better way to uncover hidden gems. Pedal through vineyards, hike up rolling hills, or wander charming villages. Some itineraries allow you to return to your base every evening (a shuttle service can conveniently bring you back, if needed).
And if you’re feeling adventurous, you can add a touch of elegance by exploring on horseback—just for that extra “Tuscany dream” experience.
The classics: Cooking & Truffle hunting
Cooking, Truffle Hunting, and the secrets of local cuisine
The most requested classic Tuscan experiences—cooking classes, pizza and pasta making, and truffle hunting—bring you closer to the region’s authentic flavors and traditions. These activities are led by locals who share their expertise, offering a true taste of Tuscany.
Learn to craft handmade pasta, stretch pizza dough, or hunt for prized truffles in the rolling hills, all while enjoying ingredients sourced right from the land. With hands-on experiences and a focus on zero-kilometer products, these activities provide an unforgettable, authentic journey into the heart of Tuscany.
Hot Air Balloon Rides Over Tuscany
Float through Tuscany’s skies: a unique adventure over cities, villages, and rolling hills
A Different Perspective
As the first light of dawn stretches over the Tuscan landscape, your adventure begins. Around 7:30 AM, while the world below is still waking up, you’ll witness the mesmerizing process of balloon inflation—giant fabric canopies slowly filling with air, transforming into majestic flying vessels. It’s the perfect time to snap some incredible photos or capture the magic on video.
Before takeoff, the pilot will guide you through a short but essential briefing, sharing key details to help you enjoy the flight safely and fully. Then, it’s time to rise into the sky.
For about an hour, you’ll float over rolling hills, ancient villages, and historic cities, experiencing Tuscany from a breathtaking new perspective. But the journey doesn’t end when you touch back down. To celebrate, a delightful post-flight breakfast awaits—both sweet and savory local specialties, accompanied by prosecco and other refreshments.
From start to finish, the entire experience lasts around three hours—three hours of wonder, beauty, and a bit of bubbly to top it all off…
Step Back in Time: Drive La Dolce Vita
Live the charm of Tuscany in true vintage style
Take a step back in time and cruise through Tuscany in the ultimate vintage style. Picture yourself behind the wheel of a classic car like a Fiat 500 or a Fiat Topolino, or zipping along on a Vespa or even an APE Piaggio, feeling the wind in your hair as you explore rolling hills, charming villages, and endless vineyards. These timeless vehicles aren’t just about the ride; they’re about living the Dolce Vita dream, with every twist of the wheel or throttle. But let’s be clear—while these vintage beauties ooze charm, they don’t come with modern luxuries like automatic transmissions.
That’s right, those classic cars require you to master the art of the double clutch, and the Vespa… well, balancing those two wheels on winding Tuscan roads could challenge even the most experienced rider!
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Podere Belvedere – San Quirico d’Orcia
