Local Living Italy - Tuscany San Gimignano - 7 Days



Trip Snapshot
Age range
12 - 100Start / End
- Florence
- Florence
Physical rating
Group size
1 - 8Meals included
7Highlights
- Settle into a charming Tuscan farmhouse in San Gimignano, your authentic home for the week, where you'll wake to vineyard vistas and embrace the serene rhythm of local life, complete with home-cooked dinners by your welcoming host, Ugo.
- Unleash your inner chef with an included half-day cooking class in San Gimignano, mastering traditional Italian flavours, and later indulge in a delightful evening of local wine tasting amidst the picturesque Tuscan hills.
- Explore the iconic medieval hill town of San Gimignano with an insightful orientation stroll, then ascend its ancient city walls to be rewarded with breathtaking panoramic views of its famed towers and the sprawling countryside.
- Embark on an enriching day trip to Volterra, a captivating medieval city steeped in Etruscan history. Witness the timeless artistry of alabaster carving with a guided workshop tour and demonstration, followed by leisure time to explore its unique charm.
- Immerse yourself in the stunning natural beauty of Tuscany with a leisurely hike along the historical Via Francigena path to Montauto, offering magnificent distant views of San Gimignano and tranquil moments in the rolling landscape.
- Discover the grandeur of Siena, a UNESCO World Heritage city, on a captivating day trip. Enjoy an orientation walk with your CEO through its historic streets and the legendary Piazza del Campo, soaking in centuries of art and architecture.
- Immersive Local Living in San Gimignano: Spend a magical week settled into a charming farmhouse in the heart of Tuscany, hosted by a local expert. Wake to stunning vineyard views and embrace the authentic pace of Italian life, making this more than just a visit – it's living like a local.
- Savour the Flavours of Tuscany: Indulge your culinary passions with an included half-day cooking class, mastering traditional regional dishes. Delight in a heartwarming home-cooked dinner with your gracious local host, experiencing true Italian hospitality and exquisite tastes.
- Wander Through Medieval Wonders: Explore the enchanting, UNESCO-listed hill town of San Gimignano, famous for its iconic medieval towers and panoramic views from its historic city walls. Journey further to Volterra, an ancient Etruscan city, where you'll witness traditional alabaster craftsmanship.
- Leisurely Walks Through Rolling Hills: Discover the breathtaking beauty of the Tuscan countryside with a serene walk along the historic Via Francigena path. This ancient pilgrim route offers unparalleled vistas and photo opportunities of the idyllic landscape, leading to spectacular views of San Gimignano from afar.
- An Evening of Local Wine Tasting: Unwind and connect with the essence of Tuscany during a delightful evening dedicated to local wine tasting. Sample the region's finest vintages, savouring the rich heritage and nuanced flavours of this world-renowned wine region.
- Captivating Day Trip to Siena: Embark on a memorable day trip to the magnificent city of Siena. Explore its stunning Piazza del Campo, historic cathedral, and charming medieval streets, soaking in the vibrant culture and rich history of this Tuscan gem.

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What's inside the PDF
Day-by-day itinerary
Every day mapped out, covering activities, travel times, meals and where you'll stay.Packing & kit list
Exactly what to bring, from clothing and essentials to luggage guidelines and what's available to hire locally.What's included
Accommodation, transport, guides and meals, so you can see exactly what your price covers.
Summary
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.
Itinerary
Day 1
Florence
Arrive at any time.
Day 2
Florence/San Gimignano
Enjoy a morning orientation walk in Florence, 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 then sit down to a home cooked dinner with your Local Living host, Ugo. 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 3
San Gimignano
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. 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 4
San Gimignano
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 5
San Gimignano
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. 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.
Day 6
San Gimignano
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 7
San Gimignano/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.
What's Included
Accommodation
Hotel (1 nt), apartments in a locally owned home (5 nts).
Meals
Breakfasts: 6, Lunches: 0, Dinners: 1
Vegetarian options are available on all meals throughout the adventure.
Vegetarian options availableLocal Guide
GuidedThis adventure is led by a local guide throughout. The main language of this adventure is English. Please contact us for other languages available.
Wifi
Wifi is available during the adventure. In some areas and / or accommodation / transport Wifi may be free.
Dates & Prices
Aug 2026
from £1,093Sep 2026
from £1,219Oct 2026
from £1,160Nov 2026
from £1,286Mar 2027
from £1,365Apr 2027
from £1,365May 2027
from £1,444Jun 2027
from £1,444Jul 2027
from £1,365Aug 2027
from £1,365Sep 2027
from £1,514Oct 2027
from £1,365Nov 2027
from £1,365
- Save 16%Sunday 9 Aug 2026to Saturday 15 Aug 2026🔥1 space of 8 leftGuaranteed Departure£1,399£1,177
- Save 16%Sunday 23 Aug 2026to Saturday 29 Aug 20264 spaces of 8 leftGuaranteed Departure£1,299£1,093Best offer
Essential trip information
Our Important Notes and Packing List cover all essentials, from necessary equipment to inclusions, ensuring you're fully equipped and informed for this extraordinary adventure and more.
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