Local Living Italy—Tuscany San Gimignano

Local Living, Rome to Rome

Image by G Adventures

Tour description provided by G Adventures

If you’ve ever wanted to forge a deeper bond with a destination, this is your chance. Centred in San Gimignano, this Local Living adventure places you in the heart of central Tuscany. You’re free to explore the town, visit vineyards, discover medieval highlights, or embrace your inner artist wandering the Tuscan countryside. If you’re looking for a deeper dive into Italian cities, there’ll be day trips to visit Siena and Florence. You’ll share the main accommodation with like-minded travellers and a CEO there to point you in the right direction. Prepare to fall in love with Italy.

What’s included

  • Your Foodie Moment: Half-day Cooking Class, San Gimignano Your Local Living Moment: Home Cooked Dinner with Ugo, San Gimignano Your Local Living Moment: Local Wine Tasting, San Gimignano
  • Orientation walks in Rome, San Gimignano, and Siena
  • Walk along San Gimignano's medieval wall
  • Quarter-day walk through the Tuscan countryside to Montauto
  • Day trips to Siena and Florence
  • Transport between destinations and included activities


  • Share an apartment in our local friend ugo's home
  • Eat delicious tuscan cuisine and sample regional wines
  • Stroll the lanes of medieval san gimignano
  • Walk along the beautiful tuscan countryside
  • Make new friends at your home away from home.


Day 1 Rome Arrive at any time. Additional Notes: We highly recommend booking pre-tour accommodations in Rome to fully experience all this amazing city has to offer. There's lots to explore! Please note that if Vatican City is on your must-see list, we highly recommend purchasing your tickets online several weeks prior to your trip. Same-day entrance to St. Peter's Basilica and the Vatican Museums (including the Sistine Chapel) cannot be guaranteed without advance tickets. Please speak to a G Adventures representative about booking accommodations in Rome before Day 1 of this itinerary. Included Activities: Arrival Day and Welcome Meeting
Day 2 Rome/San Gimignano (1B) Transfer by train and bus to San Gimignano and walk to your home for the week, which is located just outside the beautiful medieval hill town of San Gimignano. The property owner, Ugo, is a San Gimignano native and is a fountain of information about the area. He lives in one of the apartments in his remodeled medieval house. Included Activities: Orientation Walk Orientation Walk Transport: Train (2.50 hour(s)) Local bus (0.50 hour(s))
Day 3 San Gimignano (1B, 1D) Walk on top of the medieval city walls of San Gimignano for a new perspective on the town and sweeping views of the area. Enjoy an included half-day cooking class in the afternoon. Included Activities: Medieval City Wall Walk Half-day Cooking Class
Day 4 San Gimignano (1B, 1D) Enjoy a day trip to Siena including an orientation walk with the CEO. In the evening, sit down to a home cooked dinner with your Local Living host, Ugo. Included Activities: Siena Visit Orientation Walk Home Cooked Dinner with Ugo
Day 5 San Gimignano (1B) The Via Francigena, a historical path in use approximately 1,000 years ago by those making pilgrimage between Canterbury, England, and Rome, runs very close to the Local Living house. It is great path for those who wish to explore the Tuscan countryside by foot. Included Activities: Tuscan Countryside Walk Local Wine Tasting
Day 6 Florence (1B) Enjoy a day trip to Florence with plenty of free time to check out local museums and plazas. Opt to go out for a final group dinner back in San Gimignano or cook together at the apartments. Additional Notes: While the group will travel together to Florence, the return time is flexible and can vary by each person's touristing stamina. The return ticket is provided, but you decide when to leave. Transport: Local bus (0.50 hour(s)) Train (1.50-2.00 hours) Train (1.50-2.00 hours) Local bus (0.50 hour(s))
Day 7 San Gimignano/Rome (1B) Transfer by bus and train to Rome. Depart in the early afternoon from the Rome train station (Termini). Additional Notes: If you wish to extend your stay in Rome, consider booking post-tour accommodation with us. Please speak to a G Adventures representative about booking accommodations in Rome after your tour ends. Included Activities: Departure Day (Activities) Transport: Local bus (0.50 hour(s)) Train