This day was a perfect mix of medieval towns, iconic architecture, and bold Brunello – a true Tuscan trifecta. We started in the walled village of Monteriggioni, where we explored the hands-on Il Mistero dei Templari Museum, complete with medieval weapons and armor you can actually try on. After a quick gelato stop, we headed to Siena to admire the stunning Siena Cathedral and fuel up on pici pasta, a thick Sienese spaghetti that’s basically Tuscany’s gift to noodle lovers everywhere. In the afternoon, we made our way to Montalcino, the heart of Brunello country, where we visited wineries like the majestic Castello Banfi and the elegant Poggio Antico. We wrapped up the day with a check-in at our agriturismo, Castello di Spedaletto, a 12th-century castle turned countryside retreat, where we explored the grounds and wrapped it all up with a cozy dinner inside the castle walls.

Itinerary

This itinerary highlights our visits to the Tuscan hill towns of Monteriggioni, Siena, and Montalcino as part of our 2016 Italy trip (September 4).

• 🍷 Optional stop: Barone Ricasoli (Italy’s oldest winery and birthplace of Chianti, 20-min out of the way)
• 🚗 Drive (48-min) to Monteriggioni and explore
  • ⚔️ Visit il Mistero Dei Templari Museum (free, try out medieval weapons and armor)
  • 🍨 Gelato
• 🚗 Drive (27-min) to Siena and explore
  • ⛪ Admire city and Siena Cathedral
• 🍝 Lunch in Siena (Try pici pasta – a thick, Sienese spaghetti)
• 🚗 Drive (45-min) to Montalcino
• 🍷 Visit wineries in Montalcino (home to Italy’s best wine – Brunello di Montalcino)
  • Castello Banfi (10 AM – 7:30 PM, gorgeous castle and views, 🎟️ Reservation appreciated, not required for tasting and tours)
  • Poggio Antico (10 AM – 7 PM, €40-€150 per tasting/tour depending on selection, 🎟️ Reservations appreciated, not required)
  • Enoteca la Fortezza (9 AM – 8 PM, shop & tasting inside the fortress, €25-€80 per tasting depending on selection)
  • Bar Circolo Arci wine at Palazzo dei Priori
  • Biondi Santi Franco (Birthplace of Brunello, 🎟️ Reservations required, 5-min outside town)
  • Podere II Cocco (Small organic family-run winery, 🎟️ Reservation required, 8-min outside town)
• 🏰 3:30 PM – 4:30 PM: Check-in to Agriturismo Castello di Spedaletto (starting at €100/night) and explore castle grounds. See more including pictures on our Pienza blog.
• 🍽️ Dinner at Castello di Spedaletto Ristoranti

Monteriggioni

Monteriggioni is a tiny, walled medieval village in Tuscany that looks like it was lifted straight out of a fairytale. Gamers may recognize it from the Assassin’s Creed series. Built in the 13th century by the Sienese for defense against Florence, the town is encircled by remarkably intact stone walls and 14 towers, offering panoramic views of the surrounding countryside. Its quiet charm, preserved architecture, and quirky attractions – like the Templar museum where you can try on medieval armor – make it a perfect stop for history lovers and curious wanderers alike.

Hill Town

Il Mistero Dei Templari Museum

Siena City

Siena is a beautifully preserved medieval city in the heart of Tuscany, known for its Gothic architecture, rich history, and uniquely fan-shaped Piazza del Campo. Once a powerful city-state, it now captivates visitors with its stunning Duomo and intricate marble floors. Beyond the art and architecture, Siena is also beloved for its local cuisine – especially pici, a thick, hand-rolled spaghetti that’s a must-try for pasta lovers. With winding cobblestone streets and sweeping views of the Tuscan hills, Siena offers an authentic and atmospheric glimpse into Italy’s past.

Montalcino

Montalcino is a picturesque hill town in southern Tuscany, world-renowned as the home of Brunello di Montalcino, one of Italy’s most prestigious red wines. Perched on a ridge overlooking the Val d’Orcia, Montalcino offers a mix of medieval charm, scenic vineyard views, and historic landmarks like the Fortezza, a 14th-century fortress now housing Enoteca la Fortezza shop and wine tasting. The town is a paradise for wine lovers, with countless wineries and cellars to explore, from grand estates like Castello Banfi to boutique producers tucked into the hills. One standout is Poggio Antico, where the winding, cypress-lined driveway sets the stage for a refined tasting experience with sweeping views of the countryside. With its relaxed pace, world-class wine, and breathtaking landscapes, Montalcino is a quintessential Tuscan experience.

Hilltown

Castello Banfi

Poggio Antico