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.
Travel Style
Local Living
Service Level
Standard
Physical Grading
2 - Light
What's Included
Your Welcome Moment: Welcome Moment - Meet Your CEO and Group
Your Local Living Moment: Home Cooked Dinner with Ugo, San Gimignano
Your Foodie Moment: Half-day Cooking Class, San Gimignano
Your Local Living Moment: Local Wine Tasting, San Gimignano. Orientation walk Florence. Welcome briefing with local host. Dinner at Ugo's. Cooking class in San Gimignano. Orientation walk San Gimignano. Orientation walk Volterra. Alabaster workshop tour and demonstration. Hike through the Tuscan Countryside. Free time to explore Siena. All transport between destinations and to/from included activities.
What are the main highlights of this trip?
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.
How large will the group be?
Max 8, Avg 6
What meals are included in this trip?
6 breakfasts, 1 dinner
What are the modes of transportation on my trip?
Local bus, train, walking
Is there an extra cost for travelling solo?
We believe single travellers should not have to pay more to travel so our group trips are designed for shared accommodation and do not involve a single supplement. Single travellers joining group trips are paired in twin or multi-share accommodation with someone of the same sex for the duration of the trip. Some of our Independent trips are designed differently and single travellers on these itineraries must pay the single trip price.
Where will we stay during the trip?
Hotel (1 nt), apartments in a locally owned home (5 nts).
Itinerary
Florence
Arrive at any time.
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.
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.
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.
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.
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.
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.
Is travel insurance required for my trip?
Travel Insurance: Travel insurance is compulsory in order to participate on any of our trips. When travelling on a group trip, you will not be permitted to join the group until evidence of travel insurance has been sighted by your CEO, who will take note of your insurance details. When selecting a travel insurance policy please bear in mind that all clients must have medical coverage and that we require a minimum coverage of USD 200,000 for repatriation and emergency rescue. We strongly recommend that the policy also covers personal liability, cancellation, curtailment and loss of luggage and personal effects. If you have credit card insurance we require proof of purchase of the trip (a receipt of credit card statement) with a credit card in your name. Contact your bank for details of their participating insurer, the level of coverage and emergency contact telephone number.
Terms, conditions and restrictions apply; pricing, availability, and other details subject to change and/ or apply to US or Canadian residents. Please confirm details and booking information with your travel advisor.
