Local Living Italy—Tuscany San Gimignano

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.

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Room Prices

  • From$1599USDEn suite bathroom Twin
  • From$1399USDShared 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 and Siena. Orientation 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. Half-day walk through the Tuscan countryside to the Colle Val d'Elsa Alta. Day trips to Siena and Florence. Transport between destinations and included activities.
  • 6 breakfasts, 2 dinners. (Allow EUR240-320 for meals not included.)
  • Hotel (1 nt), apartments in a locally owned home (5 nts).
  • Local bus, train, walking
  • Chief Experience Officer (CEO) throughout.
  • Small group experience; Max 8, Avg 6
Day 1 Rome

Arrive at any time.

Day 2-6 San Gimignano (5B,2D)

Morning orientation walk in Rome, then travel in the afternoon via train and bus to your home for the week. Located in the Tuscan countryside just outside the city wall of the beautiful medieval hill town of San Gimignano, you will be sharing a remodeled medieval house split into apartments. The outdoor sitting areas and garden filled with herbs and produce are available for your use, and the property owner and neighbour Ugo – a San Gimignano native – lives on site and loves helping make your stay the best it can be. Throughout your stay in San Gimignano, breakfast essentials and local delicacies are included and will be topped up throughout your stay so you can make breakfast at your convenience.

Day 7 Rome (1B)

Transfer back to Rome and depart any time after 2pm.

Included activities and day trips

• Orientation walks in Rome and Siena
• Home-cooked dinner with host Ugo, a San Gimignano native
• Orientation walk along San Gimignano's medieval wall
• Half-day cooking class
• Day trips to Siena and Florence
• Wine tasting at a local cooperative
• Half-day walk through the Tuscan countryside to the Colle Val d'Elsa Alta
• Day trips to the world-famous cities of Siena and Florence

Optional activities

While most days are full with inclusions, any day trips can be skipped in favour of relaxation and independent exploration. Day trips also include free time that can be filled with cycling, walking, shopping, market scouring and museum-going.

Making your stay seamless

One of our Chief Experience Officers (CEOs) will be on hand in San Gimignano to make your trip the best it can be, occasionally tagging along to show you the best spots and keeping you company on optional daytime pursuits. Well-versed in the inner workings of the region and on-hand to help you with any questions you might encounter, your CEO wears many hats, covering everything from getting something translated to organizing day trips to finding a good spot to grab a meal or go out at night.

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