Local Living Italy - Tuscany San Gimignano - 7 Days

From £956£137 per daySave 31%

Trip Snapshot

Age range

12 - 100

Start / End

  • Florence
  • Florence

Physical rating

2/5

Group size

1 - 8

Meals included

7

Highlights

  • 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.
Recommended

Download Trip Brochure PDF

Uncover insider tips, see a packing list and view a detailed itinerary and accommodation information.

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 available

  • Local Guide

    Guided

    This 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

  • Jun 2026

    from £956
  • Aug 2026

    from £1,093
  • Sep 2026

    from £1,219
  • Oct 2026

    from £1,160
  • Nov 2026

    from £1,286
  • Mar 2027

    from £1,365
  • Apr 2027

    from £1,365
  • May 2027

    from £1,444
  • Jun 2027

    from £1,444
  • Jul 2027

    from £1,365
  • Aug 2027

    from £1,365
  • Sep 2027

    from £1,514
  • Oct 2027

    from £1,365
  • Nov 2027

    from £1,365
  • Save 31%
    Sunday 7 Jun 2026to Saturday 13 Jun 2026
    🔥3 spaces of 8 leftGuaranteed Departure
    £1,379£956
    Best offer
    Solo Room from +£1,387

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.

Frequently asked questions

  • What kind of accommodation can I expect on this tour?

    You will stay one night in a hotel and five nights in apartments within a locally owned home, specifically Agriturismo Casa Florelia, just outside San Gimignano. The property owner, Ugo, lives on-site.
  • Does the accommodation in San Gimignano have air conditioning?

    Please note that the rooms at Agriturismo Casa Florelia do not have air conditioning.
  • What are the bathroom arrangements at the San Gimignano accommodation?

    In Ugo's home, there are two bedrooms with private bathrooms, as well as two bedrooms with shared bathrooms.
  • What is the maximum group size for this tour?

    The maximum group size is 8 travelers, with an average of 6.
  • What is the minimum age to join this trip?

    You must be 18 to travel unaccompanied. For minors travelling with a guardian over 21 years old, the minimum age is 12.
  • What meals are included in this trip?

    The tour includes 6 breakfasts and 1 dinner.
  • What are the main highlights of this trip?

    The main highlights include sharing an apartment in our local friend Ugo's home, enjoying delicious Tuscan cuisine and regional wine tastings, strolling the medieval lanes of San Gimignano, walking through the beautiful Tuscan countryside, and making new friends.
  • Are there any cooking experiences included in the tour?

    Yes, a half-day cooking class in San Gimignano is included in the tour.
  • Will I have opportunities to explore other Tuscan cities?

    Yes, the itinerary includes a day trip to Siena with an orientation walk and a visit to Volterra to see ancient Etruscan walls and an Alabaster workshop.
  • What modes of transportation will be used during the tour?

    Intercity transport will primarily be by local bus and train, along with walking.
  • Do I need to carry my own luggage on the tour?

    Yes, you must be comfortable carrying your own luggage as you will need to transport it on and off trains and buses, and potentially up several flights of stairs, as elevators are rare in European train stations.
  • What currency is used in Italy and what should I know about money exchange?

    The local currency is the Euro. Credit and debit cards (especially Visa, with 4-digit PINs preferred) are useful for cash advances, but it's recommended to bring a combination of Euros, traveller's cheques (though less readily cashed), and cards. Always take more rather than less to avoid running short of funds.
  • How much emergency money should I bring?

    It is recommended to have access to at least an additional USD $200 (or equivalent) as an emergency fund for unforeseen circumstances.
  • Is tipping customary in Italy and for the tour staff?

    Yes, tipping is customary in Europe. A general rule is 10% for wait staff, and €1-€2 for other service providers. For local guides, €3-5 per day is recommended. For the Chief Experience Officer (CEO), €6-8 per person, per day (or €30-€40 per person, per week) is a guideline.
  • Are there any specific dress codes to observe in Italy?

    Yes, when visiting churches and cathedrals, shoulders should be covered. Your CEO can provide more specific advice.
  • What are the health considerations for this trip?

    You should consult your travel doctor for up-to-date medical information and required inoculations. It's recommended to carry a First Aid kit and personal medical requirements. For legal reasons, leaders cannot administer drugs. A Medical Form is required for travelers over 70.
  • What are the safety considerations for this trip?

    General safety advice includes using common sense, being aware of your surroundings, and safeguarding personal belongings with a neck wallet or money belt. Hotels often have safety deposit boxes. At night in major cities, it's recommended to stay in small groups and use taxis. The CEO can amend the itinerary due to safety concerns.
  • What optional activities are available on this tour?

    Optional activities include visits to the Uffizi Gallery, Accademia Galleries, Pitti Palace, and Medici Chapels in Florence. In San Gimignano, you can visit the Wine Museum, San Gimignano 1300 Museum, Collegiate Church, and Torre Grossa, or take a Francigena Walk. It's recommended to book popular museum tickets in advance during high season (May-October).
  • What kind of guidance can I expect from the tour leader (CEO)?

    Your Chief Experience Officer (CEO) will provide orientation walks to show the layout of towns and cities and local services. They are generally knowledgeable about the countries visited. However, local guides are licensed to provide historical facts in public places, not the CEO.
  • Is there an extra cost for solo travelers on this tour?

    No, our group trips are designed for shared accommodation, and single travelers are paired with someone of the same sex, so there is no single supplement.
  • Are laundry facilities available on this trip?

    Some hotels offer laundry facilities for a charge. It's advisable to bring non-polluting/biodegradable soap if you plan to do your own laundry.
  • Is travel insurance required for this trip?

    Yes, travel insurance is compulsory and must include medical coverage with a minimum of USD 200,000 for repatriation and emergency rescue. Proof of insurance will be required by your CEO.
  • What are the visa and entry requirements for Italy?

    All countries require a valid passport with a minimum of 6 months validity. For most nationalities, travel in Europe is simplified by the Schengen visa. However, it is your responsibility to check the most up-to-date visa requirements with your local embassy or consulate. ETIAS travel authorization may be required for visa-exempt nationals starting in 2025.
  • Who should I contact in case of an emergency during the trip?

    For urgent situations, first contact the local representative or local office. If no immediate answer, leave a detailed message. Emergency contact numbers for various regions are also provided in your pre-departure information.
  • Does the tour operator have an email newsletter?

    Yes, you can subscribe to their adventure travel e-newsletter for news, trip information, and special offers. You can also sign up for Planeterra's monthly news.
  • What is Planeterra?

    Planeterra International Foundation is a non-profit organization that helps local communities earn income from tourism by developing and supporting community-owned businesses, integrating them into the tour operator's itineraries globally. 100% of donations go directly to Planeterra projects.
  • Are there any rules regarding illegal drugs or exploitation during the trip?

    Illegal drugs are not tolerated and are against the law, putting the group at risk. The exploitation of people in the sex trade is also strictly against the tour operator's philosophy. CEOs have the right to expel any group member violating these rules.
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