Exploring Tuscany: A 4-Day Itinerary Through Hill Towns, Wine and Delicious Food
Curated By
Katie Harris
Curator’s statement
Tuscany was a dream — rolling hills, incredible food and some of the best wine I’ve ever had. We based ourselves just outside Florence, which gave us the flexibility to explore without feeling rushed. Staying at COMO Castello Del Nero made it feel like a true escape, the kind of place where you slow down and soak up every moment. The tiny towns we visited felt like scenes from a postcard, and the meals were consistently unforgettable (I still think about that pasta from Osteria La Gramola). It’s a region I could return to over and over again and still find new favorites each time.
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Day 1: Arrival & settling into Chianti
After flying into Florence (with a quick layover in Paris), we picked up a rental car at the airport and drove about 40 minutes to COMO Castello Del Nero, a restored 12th-century castle and our home base for the next few days. The property is stunning, perched in the hills of Chianti, with panoramic views, a beautiful pool and an overall sense of peace. We spent the afternoon unwinding at the hotel before heading into the nearby village for dinner at Osteria La Gramola. This tiny, no-frills spot turned out to be one of our favorite meals in Italy — homemade pasta, local wine and prices that made us double-check the bill (in a good way).
Day 2: Farm lunch & a Tuscan hill town
After a relaxed breakfast at the hotel, we drove to Fattoria Poggio Alloro, an organic farm with incredible views and even better food. Everything was fresh, local and served family-style, a true Tuscan experience. From there, we continued on to San Gimignano, one of Tuscany’s most charming towns, known for its medieval towers and cobblestone streets. We strolled through the town, popped into a few shops and grabbed gelato from the tiny but world-famous Gelateria Dondoli in the main square — absolutely worth the hype. Parking just outside the city walls was easy to find.
Day 3: A full day of wine tasting
We booked a private wine tour, which made the logistics effortless. Our guide planned the full day and handled all the driving, so we could fully enjoy the wine. Our first stop was Avignonesi, a beautiful estate with biodynamic vineyards and seriously good wines. From there, we headed to Pienza for lunch and a short walk through the hilltop town, picturesque and full of charm. Afterward, we visited Montepulciano, another stunning town known for its Vino Nobile, before wrapping up the day at Podere Le Ripi, a biodynamic vineyard known for its Brunello. It was a full day, but so worth it!
Day 4: A final stroll through Siena
On our last day, we made the short drive to Siena for a casual lunch and one last wander through a postcard-perfect town. The Piazza del Campo is a must-see, and we loved just taking our time with no set agenda. In the afternoon, we headed back to the hotel to relax and enjoy all the hotel had to offer. We spent one additional day in Florence before our trip home. Tuscany is filled with so many vineyards and villages — you truly can’t go wrong.
Need to know
The food Is amazing: Tuscany’s food scene is a highlight of any trip. Be sure to try the local specialties like pappa al pomodoro (tomato bread soup), ribollita (vegetable soup), bistecca alla fiorentina (Florentine steak) and lots of truffle! But some of the best meals can be found in small, unassuming trattorias and osterias — don’t be afraid to explore off the beaten path!
Rent a car: To really experience Tuscany, renting a car is essential. It allows you the freedom to explore its charming hill towns, vineyards and hidden gems at your own pace.
Timing your visit: The best times to visit Tuscany are in spring (April to June) and fall (September to October), when the weather is mild and the crowds are smaller. Harvest season (September and October) is also a fantastic time for wine lovers and when we went!
Hire a local guide/driver for a day: If you're a wine enthusiast or want a deeper dive into Tuscany’s history, consider hiring a local guide for a private tour. They can provide insightful recommendations and take you to hidden vineyards and charming towns that you might miss on your own.
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Katie Harris
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For more inspiration and insider recommendations, visit our Tuscany page.