There are few places on Earth as idyllic and romantic as Tuscany, where rolling vineyards, rustic farmhouses, and medieval towns make every turn feel like a postcard. The region’s deep-rooted wine culture, combined with its natural beauty and culinary delights, makes Tuscany a dream destination for wine lovers. Whether you’re sipping Chianti Classico or indulging in Brunello di Montalcino, a weekend in Tuscany will transport you to the heart of Italian culture.
Here’s a two-day itinerary to help you explore the best of Tuscany’s wine country.
Day 1: Chianti Classico Region and Medieval Towns
Morning
- Start in Florence and Head to Greve in Chianti
Your journey begins in Florence—just an hour’s drive from the heart of the Chianti Classico wine region. Rent a car in the morning and head to Greve in Chianti, a charming village known as the gateway to Tuscany’s wine country. Stop for breakfast at Caffè le Logge, where you can enjoy pastries and an espresso in the picturesque town square. - Visit a Local Winery: Castello di Verrazzano
Your first stop is Castello di Verrazzano, a historic vineyard located just outside Greve. Take a guided tour of the estate, which includes exploring the ancient wine cellars and sampling the winery’s Chianti Classico. The tour concludes with a tasting of several wines accompanied by olive oil and cheese—an introduction to the region’s flavors.
Afternoon
- Lunch in Panzano in Chianti
Continue to Panzano, a small hilltop town known for its rustic charm. Dine at Officina della Bistecca, where you can savor local specialties, such as the famous bistecca alla Fiorentina (Florentine steak) and fresh pasta paired with local wine. - Explore Radda in Chianti
After lunch, take a leisurely drive through the rolling hills to Radda in Chianti. This medieval town is perfect for an afternoon stroll, with narrow streets, artisan shops, and breathtaking views over the vineyards. Stop by Enoteca Radda to pick up a bottle of wine or two to take home.
Evening
- Dinner and Overnight Stay in a Vineyard Villa
End your day at Villa Le Barone, a boutique hotel nestled among olive groves and vineyards. Enjoy a Tuscan dinner in their garden restaurant, with dishes made from seasonal ingredients and paired with local wines. After dinner, sit under the stars with a glass of wine, soaking in the serenity of the Tuscan countryside.
Day 2: Montalcino and the Brunello Trail
Morning
- Drive to Montalcino
Wake up early and enjoy a light breakfast at your villa before setting off for Montalcino, about 1.5 hours south of Chianti. Montalcino is home to one of Italy’s most prestigious wines—Brunello di Montalcino. - Tour and Tasting at Biondi Santi Winery
Start your exploration at Biondi Santi, one of the most iconic Brunello producers, credited with creating this famous wine. The tour takes you through the vineyards, cellar, and fermentation rooms, ending with a guided tasting of aged Brunello.
Afternoon
- Lunch with a View at Il Leccio
For lunch, head to Il Leccio, a charming restaurant located in the tiny town of Sant’Angelo in Colle. Here, you can enjoy traditional Tuscan dishes like pappardelle al cinghiale (wild boar pasta) and ribollita (a hearty bread and vegetable soup), along with a glass of Brunello. - Visit the Fortress of Montalcino
After lunch, explore the Fortezza di Montalcino, a medieval fortress offering panoramic views of the surrounding countryside. Inside the fortress, you’ll find a small wine shop where you can sample more Brunello and other Tuscan wines.
Evening
- Sunset in Pienza and Dinner at La Bandita Townhouse
On your way back, make a quick stop in Pienza, a UNESCO World Heritage site known for its beautiful Renaissance architecture and delicious pecorino cheese. Wander through its charming streets and enjoy the sunset over the Val d’Orcia.
For your final dinner, head to La Bandita Townhouse, a chic restaurant in the heart of Pienza, where modern Italian cuisine meets rustic charm. Celebrate your last night with a bottle of local wine and toast to the perfect weekend in Tuscany.
Where to Stay
- Villa Le Barone, Chianti: A romantic vineyard villa offering scenic views, traditional decor, and top-notch Tuscan hospitality.
- Castello Banfi, Montalcino: A luxurious wine resort with elegant rooms, vineyards, and a Michelin-starred restaurant.
- La Bandita Townhouse, Pienza: A boutique hotel in a Renaissance-era building, perfect for those looking for a mix of history and style.
Travel Tips
- Best Time to Visit: Late spring (April-June) and fall (September-October) offer pleasant weather and fewer tourists.
- Getting Around: Renting a car is the best way to explore Tuscany’s wine regions at your own pace.
- Book Wine Tours in Advance: Many wineries, especially those producing Brunello, require advance reservations for tours and tastings.
A weekend in Tuscany is an unforgettable journey into the heart of Italy’s wine country. From the rolling vineyards of Chianti to the historic estates of Montalcino, every moment offers a taste of Tuscany’s rich cultural heritage. Whether you’re sipping a glass of Chianti under a starlit sky or exploring medieval towns, Tuscany is the perfect destination for wine lovers and romantics alike.
Pack your bags, raise a glass, and prepare for a Tuscany weekend filled with incredible wines, breathtaking landscapes, and cherished memories.
