Our three-day adventure through Tuscany was the ultimate mix of wine, hill towns, and jaw-dropping views – with a few surprises (and cats) along the way. We kicked things off in Greve in Chianti, sipping wine in the tiny medieval village of Montefioralle, visiting the rumored birthplace of Mona Lisa at Villa di Vignamaggio, and touring the legendary Castello di Verrazzano before settling into Castellinuzza B&B, a dreamy vineyard stay with 22 cats and some of the warmest hospitality we’ve ever experienced. From there, we explored the fortified village of Monteriggioni, where we stepped back in time at the Templar Museum, trying medieval armor and weapons. We wandered the streets of Siena and savored pici pasta. We then made our way to Montalcino, tasting our way through Brunello at stunning estates like Castello Banfi and Poggio Antico. That night, we checked into Castello di Spedaletto, a 12th-century castle-turned-agriturismo complete with a working mill and peaceful countryside views. On our final day, we visited Pienza for pecorino and Renaissance charm, had a wine-with-a-view moment in Monticchiello, and explored Montepulciano’s underground wine cellars, where we met Adamo, the charismatic and passionate vintner at Contucci. Tuscany stole our hearts with every sip, view, and cobblestone step.

Tuscany Highlights

Here’s a quick look at the highlights from our unforgettable Tuscany adventure during our 2016 Italy trip (September 2–4). From wine-soaked hill towns to castles, cats, and pecorino, this summary captures the best of our three-day journey. Be sure to check out the full blog posts for detailed itineraries, travel tips, and tons of photos from each region we explored!

Day 1 – Greve in Chianti

• 🍷 Montefioralle – Intimate wine tasting in a storybook medieval village surrounded by vineyards
• 🍷 Villa di Vignamaggio – Sip wine at the rumored birthplace of Mona Lisa
• 🍷 Castello di Verrazzano – Classic winery tour with Renaissance gardens, hillside cellars, and tastings of wine, olive oil & balsamic over pecorino
• 🏡 Stay at Castellinuzza B&B – A dreamy 19th-century villa winery with sweeping vineyard views and 22 friendly cats 🐈
  ✨ This was hands-down my favorite place I’ve ever stayed!

Day 2 – Monteriggioni, Siena & Montalcino

• ⚔️ Monteriggioni – Step back in time with a walk through this walled medieval village and try on armor at the Templar Museum
• 🍝 Siena – Explore the stunning cathedral and try pici pasta for the first time
• 🏰 Montalcino – Stroll along fortified city walls with panoramic countryside views
• 🍷 Castello Banfi – Taste Brunello di Montalcino at a gorgeous castle estate with sweeping vistas
• 🍷 Poggio Antico – Enjoy a refined wine tasting and wander the estate’s cypress-lined drive
• 🏰 Stay at Castello di Spedaletto – A magical 12th-century agriturismo with a working mill

Day 3 – Pienza, Monticchiello & Montepulciano

• 🧀 Pienza – Discover Renaissance urban design, stroll Piazza Pio II, and sample pecorino cheese in the town where it’s legendary
• 🌄 Monticchiello – Soak up epic views with wine at Osteria La Porta, one of Tuscany’s most scenic lunch spots
• 🐈 Montepulciano – Explore ancient alleys, meet local cats, and fall in love with the town’s charm
• 🍝 Caffè Poliziano – Savor lunch with breathtaking vineyard views in a historic café
• 🍷 Contucci Cantina – Tour medieval wine cellars and meet Adamo, the warm and legendary vintner
• 🍷 La Città Sotterranea – Wander the fascinating “Underground City” of cellars and end with a free wine tasting

Tuscany Travel Tips

🚗 Getting Around

• Rent a car – Public transport is limited between small hill towns. A rental car gives you freedom to explore scenic roads, vineyards, and remote agriturismos. We found driving in Tuscany to be easy and relaxing.
• Park outside town walls – Most hill towns (like Montepulciano and Pienza) are ZTL (“Zona Traffico Limitato,” meaning limited traffic). Use designated lots and walk in.

🍷 Wine Tastings

• Make reservations – Especially for popular wineries like Castello di Verrazzano and Poggio Antico. Some allow walk-ins, but bookings guarantee a spot and a better experience.
• Pace yourself – Many tastings include several generous pours. Space them out with scenic drives, shared tastings, light bites, and water.
• Look beyond the big names – Small producers like Montefioralle Winery offer intimate, authentic experiences (sometimes with fewer crowds and more character!).

🧀 Food & Local Specialties

• Don’t miss pici pasta – A Sienese specialty. Thick, chewy, and delicious.
• Pecorino cheese heaven = Pienza – Try it aged, fresh, or drizzled with honey.
• Lunch with a view – Restaurants like Caffè Poliziano (Montepulciano) and Osteria La Porta (Monticchiello) offer amazing food with even better panoramas.

🏰 Where to Stay

• Agriturismos are everything – An agriturismo, or “farm stay,” is typically a small, family-run property that rents out very affordable rooms to supplement their income. Often, these end up being wineries in centuries-old castles. Places like Castello di Spedaletto and Castellinuzza B&B offer authentic countryside charm, local wine, warm hosts, and unforgettable views.
• Ask about tastings at your accommodation – Some hosts, like at Castellinuzza, will surprise you with free and generous cellar tastings.

🏛️ Sightseeing & Activities

• Get hands-on in Monteriggioni – The Templar museum is fun and free, and you can try on medieval armor!
• Don’t skip the smaller towns – Monticchiello and Montefioralle may be tiny, but they pack a punch with peaceful charm, dramatic views, less crowds, and hidden gems.
• Early mornings = fewer crowds – Especially in popular places like Siena’s Duomo or Montepulciano’s wine shops.

🐈 Random Bonus Tips

• There are cats. Everywhere. Prepare to make furry friends (looking at you, Monte).
• Buy wine + olive oil early – Some wineries can ship home, but local shops often sell limited bottles you won’t find elsewhere. Be sure to allot room in your luggage to bring home wine.