Tuscany Road Trip



Hit the Road for an Unforgettable Trip Through Chianti, Tuscany: Vineyards, Medieval Towns, and Culinary Delights!

Day 1: Arrival in Lucca

  • Morning: Arrive in Lucca and start your day walking atop the Renaissance-era walls that encircle the city. Enjoy the panoramic views of both the city and the surrounding countryside.
  • Afternoon: Explore Lucca’s cobblestone streets, visiting landmarks like the Cathedral of San Martino, Torre Guinigi, and Piazza dell’Anfiteatro. Enjoy lunch at a local trattoria.
  • Evening: Dine at one of Lucca’s renowned restaurants, enjoying traditional dishes.
  • History: Lucca traces its roots back to Etruscan and Roman times, later becoming an important medieval city-state. Its intact city walls, dating from the 16th-17th centuries, are a testament to its rich history as a fortified city
Lucca Italy

Day 2: Lucca to San Gimignano

  • Morning: Depart Lucca for San Gimignano, known as the “Town of Fine Towers.” The drive through the Tuscan countryside is picturesque.
  • Afternoon: Arrive in San Gimignano and explore its medieval architecture and towers. Don’t miss visiting the Piazza della Cisterna and the San Gimignano 1300 Museum.
  • Evening: Stay overnight in San Gimignano. Enjoy dinner with views of the Tuscan hills.
  • History: San Gimignano flourished during the medieval period as a center of trade and commerce along the Via Francigena pilgrimage route. Its iconic tower houses were built by wealthy families as symbols of power and prosperity.

Day 3: San Gimignano to Siena

  • Morning: After breakfast, head to Siena. Once there, start with the Piazza del Campo, one of Europe’s greatest medieval squares.
  • Afternoon: Visit the Siena Cathedral and the Palazzo Pubblico. Spend the rest of the afternoon wandering through Siena’s enchanting streets.
  • Evening: Experience Siena’s culinary scene with dinner at a local osteria.
  • History: Siena boasts a rich history dating back to Etruscan times. During the medieval period, it rivalled Florence in power and prestige. The Palio horse race, held in the Piazza del Campo, is a tradition dating back to the 16th century.

Day 4: Exploring Siena

  • Day: Dedicate another day to Siena to fully appreciate its beauty and history. Consider a guided tour to learn about the city’s art, history, and architecture. Explore more of the countryside or visit local vineyards.
  • Evening: Try another of Siena’s excellent restaurants, exploring different Tuscan specialties.
  • History: Siena’s historic center is a UNESCO World Heritage site, renowned for its well-preserved medieval architecture and art. The Siena Cathedral, or Duomo, is a masterpiece of Italian Gothic architecture.
Siena Italy

Day 5: Siena to Montepulciano

  • Morning: Depart Siena for the short drive to Montepulciano, famous for its Vino Nobile wines. Enjoy the scenic route, perhaps stopping at the Abbey of Sant’Antimo.
  • Afternoon: In Montepulciano, visit wine cellars for tastings and explore the town’s Renaissance buildings and squares.
  • Evening: Stay in Montepulciano or a nearby agriturismo. Dinner in town offers a chance to sample more Tuscan cuisine.
  • History: Montepulciano is perched on a limestone ridge overlooking the Val d’Orcia and Val di Chiana. It has a rich history dating back to the Etruscan and Roman periods, with Renaissance palaces and churches.

Day 6: Montepulciano and Surroundings

  • Day: Spend a day exploring the area around Montepulciano. Consider a visit to Pienza, a UNESCO World Heritage site, known for its Renaissance town planning and pecorino cheese. Alternatively, explore the natural beauty of the Val d’Orcia.
  • Evening: Enjoy a leisurely dinner in Montepulciano, soaking in the town’s atmosphere.
  • History: Nearby Pienza was redesigned as an ideal Renaissance town in the 15th century by Pope Pius II. Its harmonious layout and architectural beauty make it a UNESCO World Heritage site.

Day 7: Montepulciano to Florence

  • Morning: On your final day, take your time driving back towards Florence, the capital of Tuscany. Stop at any small towns or vineyards you missed earlier in the trip.
  • Afternoon: Arrive in Florence. If time permits, visit some of the city’s iconic sights such as the Duomo, Uffizi Gallery, or Ponte Vecchio.
  • History: Florence, the birthplace of the Renaissance, was a center of trade, finance, and culture in medieval Europe. Its iconic landmarks, such as the Duomo and Ponte Vecchio, reflect its rich artistic and architectural heritage.
Florence Italy

This itinerary offers a blend of Tuscany’s most picturesque towns and landscapes, along with its rich history and culinary delights. Remember to book accommodations and any special tours or tastings in advance, especially during peak travel seasons. Enjoy your Tuscan adventure!