Tuscany, Italy

Here’s a detailed 3 to 4-day itinerary for visiting Tuscany, Italy, a region known for its rolling hills, picturesque vineyards, and charming medieval towns. This itinerary covers some of the most iconic Tuscan destinations, including wine tasting, exploring historic towns, and indulging in the local cuisine.

Day 1: Florence – The Heart of Tuscany

• Morning:

  • Start your trip in Florence, the capital of Tuscany and the birthplace of the Renaissance. Begin by visiting the Cathedral of Santa Maria del Fiore (Duomo), one of Italy’s most iconic landmarks. Climb to the top of Brunelleschi’s Dome for panoramic views of the city and the surrounding hills.

  • Visit the Baptistery of St. John and admire the Gates of Paradise, the bronze doors created by Lorenzo Ghiberti.

  • Walk to Piazza della Signoria, Florence’s political heart, and see the impressive statues, including a replica of Michelangelo’s David and Perseus with the Head of Medusa.

• Afternoon:

  • Have lunch at Trattoria Mario, a local favorite known for traditional Tuscan dishes like ribollita and bistecca alla fiorentina.

  • After lunch, visit the Uffizi Gallery, home to masterpieces by Botticelli, Michelangelo, and Leonardo da Vinci. Don’t miss Botticelli’s The Birth of Venus.

  • Cross the Ponte Vecchio, Florence’s historic bridge lined with jewelry shops, and explore the Oltrarno district. Visit the Boboli Gardens for a peaceful walk and great views of Florence.

• Evening:

  • Dine at Osteria Santo Spirito in the Oltrarno district, offering traditional Tuscan dishes with a modern twist.

  • End your evening with a walk to Piazzale Michelangelo for a sunset view over Florence.

    
    

Day 2: Siena and San Gimignano – Medieval Gems

• Morning:

  • Drive or take a bus to Siena, a beautiful medieval city. Start at Piazza del Campo, known for its unique shell shape, and visit the Siena Cathedral (Duomo), with its intricate facade and the Piccolomini Library.

  • Climb the Torre del Mangia in Piazza del Campo for panoramic views of Siena and the countryside.

• Afternoon:

  • Have lunch at Osteria Le Logge, a traditional Tuscan restaurant using local ingredients.

  • After lunch, drive to San Gimignano, famous for its medieval towers and UNESCO World Heritage status. Walk through the narrow streets, visit Piazza della Cisterna and Piazza del Duomo, and explore the Collegiate Church of San Gimignano with its stunning frescoes.

• Evening:

  • Dine at Ristorante La Mandragola in San Gimignano, located in a quiet courtyard offering Tuscan cuisine and stunning views.

  • Enjoy a peaceful evening walk through the town as it quiets down after sunset.

    
    

Day 3: Chianti Wine Region – Vineyards and Wine Tasting

• Morning:

  • Explore the Chianti wine region, famous for its vineyards and rolling hills. Start in Greve in Chianti, visiting Piazza Matteotti and Antica Macelleria Falorni, a butcher shop selling local cheeses, meats, and wines.

  • Visit a winery like Castello di Verrazzano or Fattoria Viticcio for a wine-tasting tour of Chianti Classico, made with Sangiovese grapes.

• Afternoon:

  • Have lunch at Ristoro di Lamole, offering local dishes like pappardelle with wild boar ragu.

  • Continue to Castellina in Chianti, a picturesque hilltop town. Walk along the Via delle Volte, an underground walkway offering views of the vineyards.

• Evening:

  • Return to your accommodation or have dinner at La Cantinetta di Rignana, a restaurant with an outdoor terrace overlooking the Chianti vineyards.

    
    

Day 4 (Optional): Val d’Orcia – Rolling Hills and Pienza

• Morning:

  • Take a day trip to the Val d’Orcia, known for its rolling hills and cypress-lined roads. Visit Pienza, a UNESCO World Heritage town, and explore Piazza Pio II, the Pienza Cathedral, and Palazzo Piccolomini.

  • Sample local pecorino cheese, a specialty of the region.

• Afternoon:

  • Have lunch at Osteria La Porta in Monticchiello, a small hilltop village near Pienza.

  • Visit Montepulciano, another beautiful hilltop town famous for Vino Nobile di Montepulciano wine. Visit Piazza Grande and stop by a local wine cellar for a tasting.

• Evening:

  • Dine at La Terrazza del Chiostro in Pienza, offering stunning views of the Val d’Orcia and delicious Tuscan dishes made with local ingredients.

    
    

Tips for Visiting Tuscany:

• Getting Around: Renting a car is recommended for exploring the countryside and visiting smaller towns and vineyards. Tuscany’s roads are scenic and easy to navigate.

• Best Time to Visit: The best time to visit is in spring (April to June) or autumn (September to October), with mild weather and fewer crowds.

• What to Pack: Bring comfortable walking shoes for the cobbled streets, a light jacket for cool evenings, and sunscreen for sunny days.