Local Living Italy—Tuscany San Gimignano

Was $1399  — Savings of 15% on select departures.
7 days,Rome to Rome

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.

Special Offers and Promotions

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Select Departures Aug 09 - Sep 26
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Room Prices

  • From$1359USDEn suite bathroom Twin
  • From$1189USDShared bathroom Twin

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 with a CEO there to point you in the right direction, prepare to fall in love with Italy.

What's Included

  • Orientation walks in Rome, San Gimiganano, and Siena
  • Walk along San Gimignano's medieval wall
  • Home-cooked dinner with host Ugo, a San Gimignano native
  • Half-day cooking class
  • Wine tasting at a local cooperative
  • Quarter-day walk through the Tuscan countryside to Montauto
  • Day trips to Siena and Florence
  • Transport between destinations and included activities
  • 6 breakfasts, 2 dinners. (Allow EUR240-320 for meals not included.)
  • Local bus, train, walking
  • Chief Experience Officer (CEO) throughout.
  • Small group experience; Max 8, Avg 6
  • Hotel (1 nt), apartments in a locally owned home (5 nts).


Day 1Rome

Arrive at any time.

Day 2Rome/San Gimignano(1B)

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 3San 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.

Day 4San Gimignano(1B)

Enjoy a day trip to Siena including an orientation walk with the CEO.

Day 5San Gimignano(1B, 1D)

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 wine tasting of some local wines before sitting down to a home cooked dinner with Ugo.

Day 6San Gimignano(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.

Day 7San Gimignano/Rome

Transfer by bus and train to Rome. Depart any time after 2pm from the Rome train station (Termini).

Find dates, prices, and more trip options.

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