Rural Tuscany

Type of accommodation:

Agriturismi (farm-stays) and refined rural hotels

 

Duration:

8–15 days

 

Recommended for:

Ideal for families and nature lovers seeking an authentic, locally rooted experience, where true luxury is found in simplicity and in reconnecting with the region’s purest essence. Perfect for travellers who value open landscapes, traditional cuisine, and the unhurried rhythm of rural life.

 

Best time to travel:

Spring and autumn offer the most rewarding conditions. If summer is your only option, please get in touch with us—we will craft a thoughtfully balanced, comfortable tailor-made journey aligned with your expectations.

Rural Tuscany: experience the region’s most authentic essence

This bespoke tour is designed for travellers who appreciate unhurried exploration and a deeper connection with rural life. You will stay in carefully selected country houses and agriturismi (farm-stays), many nestled among Chianti vineyards or amid gently contoured hills dotted with centuries-old olive groves.

Each stay will let you dive in the purest essence of Tuscany, where nature and local traditions take centre stage. This experience will transform your idea of authenticity, revealing that true luxury lies in simplicity, heartfelt hospitality, and the timeless beauty of the Tuscan landscape.

Ideal for families or small groups, this tailor-made tour unfolds at a leisurely pace, inviting you to experience Tuscany from a more intimate and meaningful perspective. Savour regional cuisine, enjoy tastings at family-run wineries, and explore historic villages such as Montepulciano and San Gimignano, where centuries of history quietly shape daily life.

By choosing Rural Tuscany, you will embark on an unforgettable journey, where nature, culture, and heartfelt hospitality converge in perfect harmony.

Small, intimate boutique hotels along the route

Sleeping in the heart of the Tuscan countryside is an essential part of this experience, with stays in agriturismos and rural houses surrounded by vineyards, rolling hills, and centuries-old olive groves. Tranquil accommodations where nature, local hospitality, and the unhurried pace of life complement a journey designed to discover the most authentic Tuscany.

These spaces, imbued with rural character and selected for their connection to the land and their welcoming atmosphere, are ideal for those seeking an intimate and genuine experience. Places where country life, local cuisine, and iconic landscapes allow you to immerse yourself in the purest essence of Tuscany.

  • 1

    Relais Poggio Borgoni


    Relais Poggio Borgoni captures the essence of a classic Tuscan agriturismo (farm-stay).

    From the moment you arrive, the sweeping countryside views—particularly from the pool—encourage you to slow down and savour the breathtaking landscape. Nestled in the heart of Chianti, it offers an authentic rural atmosphere, complemented by comfort and attentive hospitality.

    Type of accommodation: Agriturismo (farm-stay)

    Feature: Nestled in the countryside

    Number of rooms: 9

    Highlights: Open rural landscapes, on-site dining, ideal for couples and families.

    Services

    • Hotel parking
    • Swimming pool
    • Pets allowed
    • Relax area
    • Television
    • Air Conditioning
    • Heating
    • Safe
    • Towels
    • Shower gel
    • Mini-Bar or Fridge
    • Internet / Wi-Fi zone
  • 2

    Podere Spedalone


    Podere Spedalone is a welcoming organic farm stay in the Val d’Orcia countryside, just a few kilometres from Pienza.

    This historic Tuscan farmhouse is a peaceful place to pause for a few days, surrounded by open countryside and the familiar landscapes of Tuscany.

    Run with care for the environment, the property has spacious gardens, an outdoor pool and a restaurant serving traditional Tuscan dishes made with locally sourced ingredients. The atmosphere is warm and relaxed, with shared tables where guests can get to know one another over a meal.

    Accommodation includes Comfort and Superior rooms, suites and family rooms, offering options for different needs. The location makes a convenient base for exploring the Val d’Orcia, with Pienza, San Quirico d’Orcia and Montalcino all within easy reach.

    Type of accommodation: Organic Agriturismo (farm-stay)

    Feature: surrounded by nature

    Number of rooms: 14

    Highlights: peaceful surroundings, location, a working farm stay and a warm family atmosphere. There is no air conditioning.

    Services

    • Hotel parking
    • Garden
    • Swimming pool
    • Pets allowed
    • Restaurant
    • Relax area
    • Fan
    • Safe
    • Towels
    • Shower gel
    • Internet / Wi-Fi zone
    • Washing machine
    • Disabled access
  • 3

    Agriturismo tra gli ulivi


    Agriturismo Tra Gli Ulivi – Chiappini Winery is a welcoming Tuscan farmhouse surrounded by vineyards and olive groves on a 27-hectare estate managed using organic farming methods.

    A cypress-lined drive leads to this welcoming farm stay, a peaceful stop in the Tuscan countryside.

    The property has 6 rooms and 6 apartments set among vines and olive trees, with plenty of space to slow down and enjoy the rural surroundings. Guests can get to know the farm through guided visits to the vineyards, olive groves and winery, and tastings of the estate’s own wines and extra virgin olive oil.

    Care for the environment is part of everyday life here, from organic farming and solar-generated electricity to a stone-built saltwater pool. The buildings have been restored using local materials and natural paints. A welcoming base for a few quiet days exploring rural Tuscany.

    Type of accommodation: Agriturismo (farm-stay)

    Feature: a rural setting close to the village

    Number of rooms: 12

    Highlights: peaceful surroundings, close to the sea, a warm family welcome.

    Services

    • Hotel parking
    • Garden
    • Swimming pool
    • Barbecue
    • Pets allowed
    • Air Conditioning
    • Heating
    • Safe
    • Towels
    • Shower gel
    • Internet / Wi-Fi zone
    • Washing machine
    • Disabled access

July and August: minimum stay of 3 nights per agriturismo (farm-stay)*

*This tour has been designed around flights to and from Florence or Pisa. It can also be adapted for journeys using different arrival and departure airports, depending on your flight options.

Rural Tuscany: price, inclusions, and details

This tour is designed for travellers eager to discover Tuscany while staying in welcoming agriturismi (farm-stays) and charming family-run country houses, offering an authentic, locally rooted experience. To receive a personalised proposal, please request your tour using the form below. *The “from” price refers to a standard double room, based on 7 nights in low season (from January to Easter, and from 15 October to 20 December).

FROM: € 1.034,00 per person

Book with peace of mind.

Flexible conditions and expert advice before and during your trip.

All our fares include flexible change or refund conditions thanks to our Trinakria Flexible Fee policy.

If your plans change, you can modify or reschedule your trip according to applicable conditions.

Our team will be available to help you before and during your trip.

What's included in your trip

Accommodation, rental car, custom itinerary design, and pricing details.

This trip includes:

  • Daily breakfast
  • Category B rental car
  • Custom itinerary design
  • Trip management fees
  • VAT and taxes

Car rental includes: unlimited mileage, comprehensive damage and theft insurance, second driver, airport fees, and local taxes.

See our pricing policy here.

Personalize your experience

Add select activities and unique local experiences.

We can also add:

  • Travel insurance – Cancellation insurance and medical assistance (AXA).
  • Local experiences – Wine tastings, gastronomy, hiking and cultural visits.
  • Higher category vehicles – Possibility of reserving cars of higher categories.
  • Flights – We will advise you on the best options to reach your destination.

Regenerative tourism in the Mediterranean

Trips that contribute to caring for the land and local communities.

At Trinakria, we believe that travel can leave a place better than we found it.we found it.

Our itineraries support local economies, landscapes, and cultural traditionsin the Mediterranean.

We collaborate with small accommodations, local producers, and guides, creating authentic experiences connected to the land.

A portion of each trip contributes to funding local regeneration projects related to the conservation of the landscape, cultural heritage, and Mediterranean communities.

Because travel can also be a way to care for the places we visit.

Request your travel to Rural Tuscany

    ⓘ The phone is not mandatory, but it's useful for WhatsApp or for a first orientation chat.

     

    NUMBER OF TRAVELERS

     

     

    TRAVEL DATES

     

    ⓘ If the dates you provide are approximate, please specify below in the comments your date flexibility.

     

    ANY ADDITIONAL INFORMATION

     

     

     

    To inform you about the best flight you can buy, please let us know which city you would like to depart from:

     

     

     

    Discover what our travellers think…

    I wanted to thank you for your great availability and excellent service: our vacation was fantastic. We loved the accommodations, and although they were very different from each other, both seemed wonderful to us.
    We also want to highlight the kindness of the ladies at Muto di Gallura—so charming and warm. We bothered them quite a bit, making full use of their facilities, yet we were always greeted with a big smile and kind words.
    Additionally, we loved the agriturismo, the surroundings, and, above all, the amazing meals and dinners.
    We can’t wait to book another vacation with you! We just hope we can find a way to visit Sicily next year.

    5
    Isabel
    Barcelona

    Hello!!! Your interest in the outcome of our bespoke journey speaks volumes about your way of working. Sardinia truly lived up to our desires and expectations. Visiting this fantastic island away from the beaten path of tourists and getting away from the typical “canned and standard” vacation… has been a real pleasure.

    4.5
    Modesto B
    Valencia

    We have just returned from a wonderful vacation booked with you, where everything was perfect. Later on, if you’re interested, I can send you another email with more details about the places we visited. In short, EVERYTHING WAS PERFECT… the people, the landscapes, the food, the beaches, the nature… The only minor issue, which was no one’s fault, was the EXCESSIVE HEAT we endured, but we did our best to cope with it. Overall, a 9-10 vacation!

    5
    Ricardo
    Ourense

    FREQUENTLY ASKED QUESTIONS

    WHAT KIND OF TAILOR-MADE JOURNEYS DO YOU OFFER? +

    Our private tours are tailor-made journeys created exclusively for you and the people travelling with you. They are not group departures and do not follow a fixed programme.

    Most of our travellers choose a self-drive journey: you travel independently in a hire car, following a route designed around your interests, your pace and the time you have available. Flights are booked separately, while we arrange the accommodation, car hire and other services included in your proposal.

    Where it adds value, we can include private local guides, transfers, wine tastings, cooking classes and other experiences. A private guide does not normally accompany you throughout the journey unless this has been specifically requested and included.

    The itineraries shown on our website are starting points. Every journey is adapted to the traveller, drawing on our first-hand knowledge of Sicily, Sardinia, Puglia, Tuscany and Greece.

    ARE YOUR TRIPS FULLY TAILOR-MADE OR BASED ON STANDARD ITINERARIES? +

    All our journeys are fully tailor-made.

    We don’t work with fixed programmes or pre-designed packages. Every itinerary is created from scratch, based on your travel style, your interests and the time you have available.

    Of course, our experience allows us to suggest routes and ideas that have proven to work well, but these are always adapted and refined for each traveller. No two journeys are exactly the same.

    This approach gives you the flexibility to shape the trip around what matters most to you — whether that means a slower pace, specific locations, particular types of accommodation or selected experiences along the way.

    In the end, the goal is not to fit you into an itinerary, but to design an itinerary that fits you.

    WHAT TYPE OF ACCOMMODATIONS DO YOU WORK WITH? +

    We primarily work with boutique hotels, small historic properties and charming independent stays.

    These are places with a strong sense of identity — where architecture, atmosphere and local hospitality reflect the character of the destination. Rather than large resorts or standardised hotels, we look for accommodations that feel authentic, personal and connected to their surroundings.

    Depending on the journey, this can include countryside estates, agriturismi, coastal hideaways or small town hotels, always selected for their quality, location and overall experience.

    Our goal is not simply to provide a place to stay, but to ensure that each accommodation becomes a natural and meaningful part of the journey.

    HOW DOES THE BOOKING PROCESS WORK? +

    The planning and booking process is straightforward, with our team supporting you at every stage.

    It usually starts with a first contact, where we learn about your travel plans, preferences and timing. Based on this, we prepare a tailor-made proposal, including a suggested route, selected accommodations and any experiences you may wish to include.

    Once the proposal is ready, you will receive it in a digital itinerary format, accessible through a private link. This allows you to explore your journey in a clear and structured way — including the route, accommodations, experiences and practical details — all in one place, at your own pace.

    You can review the proposal and we refine it together until everything feels right — in terms of itinerary, style and overall experience. When you are ready to proceed, you can confirm the trip by completing a short booking form directly within the itinerary.

    Once confirmed, we take care of all the arrangements. Before departure, you will receive all the necessary documents and practical information for your trip.

    Throughout the process, you are supported by one dedicated team, ensuring clarity, continuity and a smooth experience from start to finish.

    WHAT IS INCLUDED IN THE CAR RENTAL AND INSURANCE? +

    Our car rentals are designed to offer maximum peace of mind and simplicity.

    They typically include comprehensive insurance with no excess, so you can travel without worrying about unexpected costs in case of damage. We also include practical elements such as an additional driver and clear, straightforward conditions whenever possible.

    Our aim is to avoid the complexity often associated with car rentals, ensuring that everything is easy to understand, well covered and adapted to the journey.

    Full details are always provided in your travel documents, so you know exactly what is included before you travel.

    WHAT ARE YOUR PAYMENT AND CANCELLATION CONDITIONS? +

    Our booking conditions are designed to be clear, transparent and fair.

    Once your journey is confirmed, we typically require a deposit to secure the arrangements, with the balance due closer to the departure date. The exact details are always shared with you in advance, so you know exactly what to expect at each stage.

    In terms of cancellations, conditions may vary depending on the services included in your itinerary, as many of the accommodations and providers we work with have their own policies.

    For this reason, we always explain the applicable terms clearly before confirmation, so you can make your decision with full confidence

    We also recommend considering travel insurance, which can provide additional protection in case of unforeseen changes.

    DO YOU PROVIDE TRAVEL INSURANCE? +

    Yes — we can include travel insurance in your trip if you wish.

    We usually offer comprehensive policies covering both medical assistance and cancellation, tailored to the type of journey you are planning.

    We work with trusted providers such as AXA, and occasionally others, selecting options that offer a good balance of coverage, flexibility and price.

    As with any insurance, it is important to review the policy conditions carefully, as specific terms and exclusions may apply. We will always provide you with the full details in advance so you can choose the option that best suits your needs.

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