Local Living Italy - Tuscany San Gimignano

The adventure

If Tuscany has ever called your name, this is your chance to answer. For seven days, you’ll settle into a charming farmhouse in San Gimignano — your home for the week and your base for exploring the heart of central Italy. Wake up to vineyard views, stroll medieval streets, and soak up sunsets over rolling hills, all at a pace that feels truly local. With free days to embrace the countryside or head out on day trips to Florence, Siena, and Volterra, this isn’t just a visit — it’s living Tuscany, one unforgettable day at a time.

At a glance

Where you'll go

Day by day

Your journey through

Italy

Day 1Arrival dayArrivalArrive at any time.

Arrive at any time.

Day 2Enjoy a morning orientation walk in FlorenceTransfer 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.

Florence

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.

Day 3Enjoy an included half-day cooking class this morning…

Enjoy an included half-day cooking class this morning before setting out on an afternoon walk on top of the medieval city walls of San Gimignano for a new perspective on the town and sweeping views of the area.

Day 4Set off for Volterra today

Set off for Volterra today, a medieval city known for its ancient Etruscan walls, and visit an Alabaster workshop. Tour the facility and take in a demonstration before exploring on your own with a free afternoon.

Day 5This morning

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

Day 6Enjoy a day trip to Siena including…

Enjoy a day trip to Siena including an orientation walk with the CEO. Spend one final evening at the the agriturismo as you see fit with free time.

Day 7Transfer by bus and train to Florence

Florence

Transfer by bus and train to Florence. Depart in the early afternoon from the Florence train station. Book flights for no earlier than 3 pm.

Discover Italy

A glimpse of the destination you'll explore.

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