I propose a journey that is not just an itinerary, but an immersion in the most authentic soul of Tuscany — a compact territory of winding hills, medieval villages, unmistakable flavors and fine wines, where the Val d'Orcia, a UNESCO World Heritage Site, will turn you into a true Italian. Get ready to pick up your new passport — the real turtleneck passport.
Your adventure begins in Arezzo, a city rich in history, art and a unique atmosphere, and ends in an oasis of peace and taste.
Once you arrive in Arezzo, park conveniently at the Pietri parking lot. From here, you can easily reach the historic center via escalators. Start your walk from Piazza Duomo, then continue to Piazza Libertà and the striking Casa del Petrarca, a "must see" in these parts. The beating heart of the city is Piazza Grande, with its unique medieval architecture. Treat yourself to an unforgettable aperitif at the Chiantineria, enjoying the tables in the small alley, a true corner of authenticity. Don't miss the impressive Roman Amphitheater. As you make your way down to Saint Augustine Square and Saint Francis Square, devote yourself to shopping along the main street, full of stores and boutiques.
Tips for Day 1
Hotel Le Capanne
Head to Hotel Le Capanne and its adjoining restaurant — in my opinion, one of the best in the area, renowned for fresh homemade pasta and top-notch meats, frequented by locals. A true gastronomic paradise to end the day.
Check availability on Booking.com →Compare on Trip.com →Day two will take you through the iconic landscapes of the Val d'Orcia, including charming villages and one of Montalcino's most prestigious wineries.
The first stop is Pienza, the "ideal city" of the Renaissance. After parking in Piazza Martiri, admire the magnificent Palazzo Piccolomini. Treat yourself to a coffee overlooking the square at the Caffè della Posta. Visit the Duomo di Santa Maria and enjoy the breathtaking view from Via del Casello and Porta al Giglio. Don't forget to visit the Municipio and indulge in shopping, buying excellent Pienza pecorino cheese from the Fratelli Dezi.
On the way to San Quirico, stop for a rest at the Cappella Madonna di Vitaleta for a photo that captures the pure essence of "Tuscany." Beware of dirt roads if you have a low car.
Reach San Quirico d'Orcia. Enter through Porta Cappuccini, admire the Municipio and the church in front. Continue your visit with the Church of San Francesco, the Horti Leonini and the Hospital della Scala.
Around mid-afternoon, head (book in advance!) to Cantina Fuligni. Here you will be welcomed by the winemaker himself, the only one authorized to lead tours and tastings: very friendly, he speaks excellent English and will surprise you with anecdotes in what is undoubtedly one of the best Brunello di Montalcino wineries.
Tips for Day 2
Drogheria e Locanda Franci
Head into Montalcino, park and check in at the delightful and renovated Drogheria e Locanda Franci. Before dinner, enjoy a frugal aperitif at Il Gallo or, if you prefer something more structured, at La Grotta del Brunello.
Check availability on Booking.com →Compare on Trip.com →The third day will take you to discover Montalcino, a hidden gem of the Val d'Orcia and a charming spa town.
Franci's à la carte breakfast is a sight to behold; get a table by the well. Explore the imposing Fortress, then People's Square, the Concathedral, the Bishop's Palace and the Church of Sant'Egidio. Have fun exploring its streets and don't forget to reach a nice vantage point to admire the surrounding hills.
A true little-known gem of this area. Park here for free and head to Piazza IV Novembre and Via Aldobrandeschi. Here you absolutely must visit the site of the Rocca Aldobrandesca, which alone is worth the trip — the incredible view will stay with you for a long time! Then reach Piazza Cesare Battisti and, for a glass of wine, the Enoteca dell'Orcia. Here, sitting on a shady bench, you will feel like you are really Italian; it will be a good feeling, enjoy it. Visit the Pieve dei Santi Stefano and then retrieve your car to visit the equally amazing and scenic Rocca Tentennano.
Bagno Vignoni is worth a stop. Visit the square and its unique spa bath, then continue on to the St. Catherine Chapel, the Mill Park and the Ancient Roman Baths.
Tips for Day 3
Relais Ortaglia
Head for your dinner and night at the Relais Ortaglia, a short distance from Bagno Vignoni.
Check availability on Booking.com →Compare on Trip.com →The last day will take you to discover Montepulciano, a charming village famous for its Vino Nobile and Renaissance architecture.
Make a stop at the majestic Temple of San Biagio, a Renaissance masterpiece. Its Vino Nobile may not be among the best known, but the town will certainly thrill you — and arriving here you will surely have been able to look up at much of downtown Montepulciano.
After lunch, explore Piazza Grande, the Cathedral of Santa Maria Assunta, the Municipality of Montepulciano, the Museo Civico and the Cantina Storica Talosa (beautiful!). End your walk by visiting Via della Stamperia and the Church of Santa Lucia — and so your 4 days in Val d'Orcia are over.
Tips for Day 4
Experiences nearby
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