Romantic Tuscany Escape: Wine, History, and Scenic Walks Itinerary

Begin your day with a visit to the Basilica of St. Francis of Assisi (Basilica di San Francesco d’Assisi) in Assisi, a UNESCO World Heritage site known for its stunning frescoes. Afterward, explore the charming town of Assisi and its medieval streets.

For lunch, savor the flavors of Tuscany at La Taverna di San Giuseppe, a family-run restaurant in Siena. After lunch, take a guided tour of the San Gimignano Torre Grossa and Duomo Tickets and learn about the history of this medieval hilltop town. Then, indulge in a wine tasting experience at San Gimignano Winery Tour with Wine Tasting and Lunch.

Enjoy a romantic dinner at La Bottega del Nobile, a cozy restaurant specializing in traditional Tuscan cuisine. After dinner, take a leisurely walk through Siena's historic center and admire the illuminated landmarks.

Start your day with a delicious breakfast at Il Canto del Maggio, a charming restaurant located in the heart of the Chianti countryside. After breakfast, embark on a scenic drive through the picturesque Chianti region, stopping at local vineyards for wine tastings and enjoying the stunning countryside views.

For lunch, enjoy a farm-to-table experience at Antica Trattoria Botteganova, where you can savor traditional Tuscan dishes made with fresh, local ingredients. After lunch, visit the Chianti Terre Di Perseto Winery Guided Tasting & Tour and learn about the winemaking process while sampling a variety of Chianti wines.

Indulge in a romantic dinner at La Grotta di Montepulciano, a restaurant located in a historic wine cellar. After dinner, take a moonlit walk through the vineyards and enjoy the peaceful ambiance of the Chianti countryside.

Enjoy a leisurely breakfast at Osteria dell'Orsa, a cozy cafe known for its delicious pastries and coffee. After breakfast, take a guided tour of the Private Guided Tour in San Gimignano and learn about the history and architecture of this medieval town. Then, visit the San Gimignano Olive Oil Tasting and Tuscan Snacks and sample a variety of local olive oils and snacks.

For lunch, head to Ristorante La Torre, a restaurant located in a historic tower with panoramic views of the Tuscan countryside. After lunch, explore the Basilica of Santa Maria Assunta (Duomo di San Gimignano) and climb the Riomaggiore for breathtaking views of the town and surrounding countryside.

Enjoy a romantic dinner at Enoteca I Terzi, a stylish wine bar and restaurant offering a diverse selection of Italian wines. After dinner, take a moonlit walk through the town's narrow streets and admire the illuminated medieval towers.

Start your final day with a delightful breakfast at Osteria Acquacheta, a popular restaurant known for its hearty Tuscan dishes. After breakfast, visit the Leonardo da Vinci Museum (Museo Leonardiano di Vinci) and explore the life and works of the renowned artist and inventor. Then, take a guided tour of the Vinci Entrance ticket to the Leonardiano Museum and visit the Vinci Leonardiano Museum & Da Vinci Birthplace Ticket.

For lunch, enjoy a gourmet meal at Ristorante Il Falconiere, a Michelin-starred restaurant located in the heart of the Tuscan countryside. After lunch, take a scenic drive to the Carrara Marble Quarry and learn about the history and extraction of Carrara marble.

Conclude your trip with a romantic dinner at Antica Trattoria Botteganova, where you can savor traditional Tuscan dishes in a charming countryside setting. After dinner, take a moonlit walk through the vineyards and enjoy the peaceful ambiance of the Chianti countryside.