Road Trip Itinerary: Exploring the Charms of Tuscany & Beyond

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Advisor - Allison Vieira
Curated By

Allison Vieira

  • City Travel

  • Arts & Culture

  • Tuscany

  • Italy

  • Road Trip Travel

  • Sightseeing

A low-angled shot of the famous Pisa Tower, taken during daytime.
Curator’s statement

Tuscany, with its iconic landscapes, historic cities and delectable cuisine, offers an enchanting journey through Italy's rich cultural heritage. From the leaning tower of Pisa to the medieval streets of Siena, the picturesque vineyards of the countryside to the artistic wonders of Florence, each stop on this road trip promises unforgettable experiences and memories to cherish.

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Day 1: Pisa

Two pizzas on a blue tablecloth shot from above.

Explore Pisa by snapping selfies with the iconic leaning tower, indulging in mouthwatering pizza, wandering through the Campo dei Miracoli and visiting the Piazza dei Cavalieri and the Church of Santa Maria della Spina. Enjoy an overnight stay at Palazzo Feroci in Pisa.

Day 2: Cinque Terre

Multi-colored buildings of Cinque Terre on a hillside overlooking the ocean.

Leave Pisa and drive to Cinque Terre. Explore Cinque Terre by hiking along the breathtaking coastal trails, indulging in fresh seafood by the Ligurian sea and visiting the colorful villages of Monterosso, Vernazza, Corniglia, Manarola and Riomaggiore. Stay overnight in Cinque Terre or a nearby area.

Day 3: Tuscan Countryside

A natural-colored brick villa covered with ivy in a courtyard during the daytime.

Depart from Cinque Terre and drive to the Tuscan countryside (Borgo San Felice). Explore the Tuscan countryside by relaxing and enjoying the serene beauty of Tuscany's rolling hills, vineyards and picturesque villages. Take a local pasta-making class or wine tasting tour, and visit nearby attractions such as San Gimignano, Volterra or Montepulciano. Stay overnight at Borgo San Felice.

Day 4: Siena

A colorful stained glass window inside a cathedral with statues on either side.

Explore Siena as a day trip from the Tuscan countryside. Lose yourself in the medieval streets, visit the stunning Siena Cathedral, experience the Palio di Siena horse race, climb the Torre del Mangia for panoramic views and enjoy a traditional Tuscan lunch at a local trattoria. Return to Borgo San Felice for an overnight stay.

Day 5: Florence Museums & Duomo

Michelangelo's The David statue from the waist up.

Depart from the Tuscan countryside and drive to Florence. Explore Florence by immersing yourself in Renaissance art at the Uffizi Gallery, marveling at the Duomo, strolling across the Ponte Vecchio and visiting the Accademia Gallery to see Michelangelo's David. Stay overnight at St. Regis Florence.

Day 6: More Florence Sightseeing

Trees overarching a path at the Boboli Gardens.

Continue exploring Florence by visiting the Boboli Gardens and Pitti Palace, taking a walking tour of the Oltrarno district, and enjoying a traditional Tuscan dinner at a local trattoria.

Advisor - Allison Vieira

Travel Advisor

Allison Vieira

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For more travel tips, check out my guide, Summer in Dubrovnik. This guide is part of our ongoing series on travel to Italy.