5-Day Tuscany Road Trip: Architecture and Wine Itinerary

Begin your day in Florence with a visit to the famous Florence Duomo (Cattedrale di Santa Maria dei Fiori). Marvel at its stunning architecture and climb to the top for panoramic views of the city. Next, head to the nearby Giotto's Bell Tower (Campanile di Giotto) for another perspective of Florence.

In the afternoon, explore the art treasures at the Uffizi Galleries (Gallerie degli Uffizi). This world-renowned museum houses masterpieces by artists like Botticelli, Michelangelo, and Leonardo da Vinci. Don't forget to book your tickets in advance for a seamless experience. Afterward, enjoy lunch at Trattoria Mario, known for its delicious Tuscan dishes.

As evening approaches, take a leisurely walk across the iconic Ponte Vecchio. This historic bridge is lined with charming shops selling jewelry and souvenirs. For dinner, indulge in traditional Florentine cuisine at Osteria del Cinghiale Bianco.

Start your day in Siena with a visit to the magnificent Siena Cathedral (Duomo). This Gothic masterpiece is adorned with intricate details both inside and out. Make sure to also explore the adjacent Baptistery of San Giovanni (Battistero di San Giovanni) for more architectural wonders.

In the afternoon, wander through Siena's historic center and visit the famous Piazza del Campo, known for its unique shell shape. Here you can also see the impressive Mangia Tower (Torre del Mangia), which offers breathtaking views of Siena from its top. Enjoy lunch at Ristorante Guidoriccio, located near Piazza del Campo.

Conclude your day with a tour of Siena's medieval streets on foot or by joining an organized walking tour such as Siena: Walking Tour with Duomo or Contrade Museum Visit. For dinner, savor local specialties at Osteria Le Logge, renowned for its cozy ambiance and delectable menu.

Siena: Siena Cathedral & Piccolomini Library Entrance Ticket will be your first stop of the day. Explore this architectural marvel and its stunning library filled with ancient manuscripts and beautiful frescoes.

Siena: Small Group Cooking Class in Chianti Farmhouse is perfect for those looking to dive into Tuscan culinary traditions. Spend your afternoon learning how to prepare classic dishes from scratch in a picturesque farmhouse setting, followed by enjoying your creations for lunch.

From Siena/Chianti: Dinner & Drinks in the Chianti Vineyards offers an unforgettable experience to conclude your trip. Enjoy an evening under the stars with delicious food, fine wine, and live music amidst the beautiful vineyards of Chianti.

Begin your day with a scenic drive through the Tuscan countryside, heading towards the picturesque town of Montalcino. Your first stop will be at the Montalcino Fortress (Fortezza di Montalcino), where you can explore the historic fortress and enjoy panoramic views of the surrounding vineyards.

In the afternoon, immerse yourself in Tuscany's renowned wine culture with a visit to a local winery. Join the Montalcino: Brunello Wine Tasting Experience tour, where you'll learn about the winemaking process and sample some of the region's finest Brunello wines. Pair your tasting with a delicious lunch featuring local specialties.

As evening approaches, head to Pienza for a relaxing end to your day. Take a leisurely stroll through this charming town, known for its Renaissance architecture and stunning views of Val d'Orcia. For dinner, enjoy an authentic Tuscan meal at La Terrazza del Chiostro, offering both exquisite cuisine and breathtaking vistas.