Local Living Italy - Tuscany San Gimignano - 7 Days

From £1,093£156 per daySave 16%

Trip Snapshot

Age range

12 - 100

Start / End

  • Florence
  • Florence

Physical rating

2/5

Group size

1 - 8

Meals included

7

Highlights

  • 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.
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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

  • 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 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 2026
    4 spaces of 8 leftGuaranteed Departure
    £1,299£1,093
    Best offer
    Solo Room from +£1,331

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.
  • What is the travel style of this tour?

    This tour is designed as a 'Local Living' experience.
  • What is the physical rating of this tour?

    The physical rating for this tour is 2.
  • What kind of accommodation can I expect during the tour in San Gimignano?

    For five nights, you will stay in apartments within a locally owned home, specifically Agriturismo Casa Florelia, just outside San Gimignano. The property owner, Ugo, lives in one of the remodeled medieval house apartments. There are two bedrooms with private bathrooms and two with shared bathrooms. Please note, the rooms at Agriturismo Casa Florelia do not have air conditioning. The first night is in a hotel in Florence.
  • Are there any age restrictions for this tour?

    You must be 18 years old to travel unaccompanied on this tour. For minors traveling with a guardian over 21, the minimum age is 12.
  • What is the maximum group size for this tour?

    The maximum group size is 8 travelers, with an average of 6.
  • What meals are included in the tour price?

    The tour includes 6 breakfasts and 1 dinner.
  • What modes of transportation will be used during the tour?

    Intercity transport will mainly be by train and occasionally by local bus. You must be comfortable carrying your own luggage, as there will be many stairs at stations, and elevators are rare in Europe.
  • Is there an extra cost for solo travelers?

    No, our group trips are designed for shared accommodation and do not involve a single supplement. Single travelers are paired in twin or multi-share accommodation with someone of the same sex.
  • Is travel insurance required for this trip?

    Yes, travel insurance is compulsory. All clients must have medical coverage with a minimum of USD 200,000 for repatriation and emergency rescue. Your CEO will need to see evidence of your insurance.
  • What are the local dress requirements, especially for visiting religious sites?

    In Italy, shoulders should be covered when visiting churches and cathedrals. Your CEO can provide more specific advice if needed.
  • What currency is used in Italy and what should I know about money exchange?

    The currency in Italy is the Euro. Credit cards and debit cards are useful for cash advances, but ensure you have your 4-digit PIN. It is advisable not to rely solely on cards; a combination of Euros, traveler's cheques, and cards is recommended. ATMs are commonly available, but verify with your bank that your cards will work in Italy.
  • What should I know about safety and security on this trip?

    In major cities, use common sense, be aware of your surroundings, and protect your personal belongings. It's recommended to use a neck wallet or money belt for valuables. Avoid wandering alone at night and consider taking taxis for evening excursions. Your CEO will provide guidance on safety.
  • Are there opportunities to do laundry during the trip?

    Laundry facilities may be offered by some hotels for a charge. If you plan to do your own laundry, we suggest bringing non-polluting/biodegradable soap.
  • What are some of the main experiences included in this tour?

    This tour includes sharing an apartment in a local's home, a home-cooked dinner with your local host Ugo, a half-day cooking class, a local wine tasting, an orientation walk in Florence, exploring the medieval streets of San Gimignano, a visit to Volterra including an Alabaster workshop, a hike through the Tuscan countryside along the Via Francigena path, and a day trip to Siena.
  • What is the role of the CEO (Chief Experience Officer) on this tour?

    The CEO (Chief Experience Officer) will accompany the group throughout the trip. Their role is to facilitate your travels, provide information on the areas visited, offer suggestions for activities and local dining, and introduce you to local contacts. While knowledgeable, they are not licensed guides for providing historical facts in public places.
  • What optional activities are available on this trip?

    Optional activities include visits to the Galleria dell'Accademia (20EUR), Uffizi Gallery (25EUR), Pitti Palace (17.75EUR), and Medici Chapels (9-32EUR) in Florence. In San Gimignano, you can visit the Wine Museum (Free-30EUR), San Gimignano 1300 Museum (Free), Collegiate Church of San Gimignano (5EUR), Torre Grossa (13EUR), and take a Francigena Walk. During high season (May-October), it's highly recommended to book reservations for popular activities in advance.
  • Is tipping customary in Europe and what are the guidelines?

    Tipping is customary in Europe. A general guideline is 10% of the bill for wait staff and €1-€2 for other service providers. Tipping local guides is recommended at €3-€5 per day, and for your CEO, a guideline of €6-€8 per person per day (or €30-€40 per person per week) is suggested if you feel they did an outstanding job.
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