Spend six days visiting historical sites, eating delicious food, and relaxing in Italy. Start in Tuscany for a wine tour of the Chianti region and admire the beautiful villages of the Italian countryside. Catch a high-speed train to Rome and explore the Eternal City with visits to the Vatican City and Colosseum, then round out your trip with a food tour of the city's famous markets and gelaterias.
Follow the scenic Chiantigiana wine road in the direction of Castellina in Chianti. Along the way, we suggest taking a quick detour to Fattoria Pomona, a family-run winery. Since 1890, the land has been farmed by the same family, and they warmly welcome visitors interested in tasting and buying their organic Chianti Classico wines.
Next, continue to Castellina in Chianti, admiring the castle in the main square and the great fortress walls. Stroll along Via delle Volte, a charming street with local shops and enoteca wine bars. The town is also home to the Archeological Museum. Besides viewing interesting exhibits, you can also climb one of the towers and enjoy spectacular views over the countryside.
Then tackle the last stretch of the day to Greve in Chianti, a portion of the drive enveloped in olive groves and vineyards. The explorer Giovanni da Verrazzano, who discovered the bay of New York, was born here in 1485 CE. As a celebrated resident of Greve in Chianti, you'll find his statue in the main square, Piazza Matteotti. Stroll the porticos around this three-sided piazza and soak up the relaxed pace of life as locals and visitors mingle in the heart of town.
On your way back, make a stop at Castello di Verrazzano winery and Viticcio winery. Both offer tours, wine tastings, and food pairings, which you can pre-book on their website. We highly recommend a visit if you're in the area. Other places of interest in the Chianti area (for those not looking to visit wineries) are the Chianti Sculpture Park, a permanent exhibition of contemporary sculptures in beautiful countryside, and the Chianti Astronomical Observatory & Botanical Gardens.
Read more about unique and interesting activities in the Tuscany region.
Itineraries with Day Trip to the Villages of Chianti
Northern Italy Family Road Trip: Florence, Chianti, Italian Riviera, Lake Como & Lake Garda - 10 Days
Wheel your way through northern Italy on this road trip with stops that school-aged children and parents can enjoy, with timing adjustable to your own preferences. You'll start amid the Renaissance influences of Florence, then set out into the Tuscan countryside and Chianti Valley on winding olive- and vineyard-lined roads. From there, head to the coast to wander the beaches of the Italian Riviera and then up to Lake Como to explore its luxurious shores. Wrap up your Italian sojourn on the playful shores of Lake Garda before you return to Florence.
From Florence, the symbol of the Renaissance, to the vistas of the Val d'Orcia, classified as a UNESCO World Heritage Site, this route will allow you to discover all the facets of Tuscany. You'll trek through some of Tuscany's most famous landscapes, including Chianti, Pienza, and Montepulciano, and explore Tuscany's two most famous cities, Florence and Siena.
From the canals of Venice to Rome's buzzing nightlife, this incredible trip through the highlights of Italy is perfect for travelers who want to see it all, making your way across the country with a mix of trains and rental car. Start in Venice to see the famed Grand Canal, then head to Florence for its famed cathedrals and da Vinci's art. From here, start the self-drive portion of your trip exploring the stunning region of Tuscany to its fullest before ending in Rome, where ancient history, eclectic neighborhoods, and a vibrant food scene await.