Local Living Italy—Tuscany San Gimignano

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 (Chief Experience Officer) there to point you in the right direction. Prepare to fall in love with Italy.

Day 1 Rome
Arrive at any time.

Day 2 Rome/San Gimignano
Enjoy a morning orientation walk in Rome, then travel in the afternoon via train and bus to your home for the week. Take an orientation stroll with the CEO for a first glance at San Gimignano.

Day 3 San Gimignano
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.

Day 4 Florence Day Trip
Enjoy a day trip to Florence with plenty of free time to check out local museums and plazas. Opt to go out for a group dinner back in San Gimignano or cook together at the apartments.

Day 5 San Gimignano
Enjoy free time to visit the San Gimignano market in the morning before a leisurely walk through the Tuscan countryside along the historical Via Francigena path to Montauto, where great views of San Gimignano from afar await. In the evening, enjoy a tasting of some local wines.

Day 6 Siena Day Trip
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.

Day 7 San Gimignano/Rome
Transfer by bus and train to Rome. Depart in the early afternoon from the Rome train station (Termini). Book flights for no earlier than 6 pm.