siena cathedral
southern tuscany sunset
siena
tuscan fiat 500
tuscan flower farm
tuscan castle

Tuscan legends and iconic wine

Southern Tuscany Tour

Relax into the rhythm of southern Tuscany, where every day is savored over Brunello wine and farm-fresh flavors. Connect with local families, timeless traditions, and the beauty of slow travel.

Tour Details

Explore the beauty of Val d’Orcia through Brunello wines, hilltop villages, and thermal springs that define Tuscany’s peaceful heart.

  • Price

    From US$7,990 per person
  • Group Size

    Maximum 12 guests
  • Duration

    7 days / 6 nights
  • Departures

    May/October 2026
  • Starts/Ends

    Rome
  • Inclusions

    Boutique stays, guided experiences, and meals with wine
  • Accommodation

    Luxury agriturismo in the Val d’Orcia countryside
  • Activity Level

    Light walking — some uneven terrain

Highlights

Why You'll Love This Tour

  • Meet warm-hearted locals who open their homes, vineyards, and hearts - sharing stories that linger long after you return home.

    Lorenza house
  • Wander medieval hilltop towns that feel untouched by time, each view more breathtaking than the last.

    siena cathedral
  • Unwind completely - whether soaking in natural thermal baths or coasting through the countryside on an e-bike.

    bagno vignoni
  • Ride through cypress-lined roads in a vintage Fiat 500, the wind in your hair and Tuscany all around you.

    fiat500
  • Share a private lunch in a centuries-old castle, hosted by the gracious sisters who still call it home - an experience few ever have.

    tuscan castle lunch
  • What our guests say

    your untold italy tour Includes

    6 nights in a luxury agriturismo (countryhouse) in Val d’Orcia (Southern Tuscany)

    Fiat 500 vintage car tour, 2 winery visits, thermal spa / e-bike tour, farm visits, cooking class, pizza making class, abbey and castle visit

    6 breakfasts, 5 lunches, and 5 dinners as specified in the itinerary, wine and bottled water is included with meals other than breakfast

    Air-conditioned minibus/minivan will get you around on tour.

    Tips and gratuities are included for local guides and your driver. Tips are not included for your tour host.

    We pick up and drop off in central Rome.

    Not included

    Fly into Rome or Milan. Florence can be reached in about 1.5 hours by fast-speed train

    No one books a trip expecting the unexpected – travel insurance ensures you’re covered if plans change. See our trip FAQ below for more information and suggested providers.

    Nearly all meals are included – you’ll have two free lunches to explore the local food scene at your own pace.

    Tour Overview

    Southern Tuscany Tour Description

    Slow down and sink into the rhythm of southern Tuscany, where time seems to stretch as wide as the rolling hills. This is a region built for restoration – golden light over vineyards, the scent of wild herbs in the air, and the unhurried joy of sharing a meal with new friends.

    montalcino winery

    The Heart of Val d’Orcia

    Discover the authentic soul of Tuscany in the UNESCO-listed Val d’Orcia, a landscape of cypress-lined lanes, medieval villages, and olive groves that have stood for centuries. Taste world-famous Brunello di Montalcino wines, learn the secrets behind Tuscan olive oil, and meet the artisans who still work by hand, guided by tradition and care.

    Moments Made to Remember

    Float effortlessly between indulgence and discovery – soaking in natural thermal baths, savoring long countryside lunches, and exploring ancient hilltowns that whisper with history. Then, for a touch of magic, ride through the valley in a vintage Fiat 500 and enjoy a private lunch in a centuries-old castle with the sisters who still call it home.

    Southern Tuscany Tour Itinerary

    We often don’t publish specific destinations in order to preserve the local flavor of your trip and allow you to enjoy special surprises along the way.

    • Day 1-2

      Castles, History, and Homemade Pizza

      Begin your Tuscan journey with a visit to a magnificent Renaissance castle, its gardens bursting with color and stories of noble life. In nearby Siena, wander through medieval streets and learn about the city’s beloved Palio horse race, guided by locals who keep its traditions alive.

      As the sun sets over the countryside, roll up your sleeves for a joyful pizza-making class at a family-run farm. Between laughter, flour-dusted hands, and panoramic views of bella Toscana, you’ll feel instantly at home.

      • Places: Ruspoli Castle, Siena, Val d’Orcia countryside
      • Activities: Castle visit, hands-on pizza class
      • Accommodation: Il Miraggio (or similar)
    • Day 3-4

      Southern Tuscan Tastes and Timeless Traditions

      Meet the warm-hearted locals who bring Tuscany’s traditions to life. Visit a 17th-century villa and an ancient abbey, where fragrant herbs and history fill the air of the old monastic pharmacy. Enjoy free time in Montalcino to wander, shop, or sip Brunello in a quiet piazza.

      Join a Tuscan cooking class in a welcoming country kitchen, where local ingredients tell their own stories. Crush sweet aglione garlic for a silky tomato sauce, munch on grape-studded schiacciata straight from the oven, and finish with zuppa inglese, a layered dessert kissed with alchermes liqueur. As you cook and taste alongside your host, you’ll feel part of a tradition that has flavored Tuscan tables for generations.

      • Places: San Quirico, Montalcino, Abbey of Monte Oliveto
      • Activities: Historic villa and abbey visits, Tuscan cooking class
      • Accommodation: Il Miraggio (or similar)
    • Day 5

      Wellness in the Heart of Tuscany

      Today is all about rejuvenation. In Bagno Vignoni, soak in natural thermal waters that have soothed travelers for centuries, or opt for a guided e-bike ride through the golden countryside. The pace is yours to choose – restful or gently adventurous.

      As evening falls, unwind at an organic Montalcino winery for a private tasting and dinner. Surrounded by vines, share good food, local wine, and the contented quiet that defines Tuscany at its most peaceful.

      • Places: Bagno Vignoni, Montalcino
      • Activities: Spa day or e-bike experience, winery dinner
      • Accommodation: Il Miraggio (or similar)
    • Day 6-7

      Vineyards, Villages, and Val d’Orcia Magic

      Your final days capture the heart of Val d’Orcia – a landscape so beautiful it feels like a painting. Taste award-winning vintages at a Montepulciano winery, stroll through Pienza, the village of cheese and charm, and visit another historic estate outside Orvieto.

      For a perfect finale, ride through the cypress-lined hills in a vintage Fiat 500, the wind in your hair and Tuscany glowing around you. Every turn feels like a scene from a dream – the kind you’ll never want to wake from.

      • Places: Montepulciano, Pienza, Val d’Orcia countryside
      • Activities: Wine tastings, Pienza and Montepulciano visit, vintage Fiat 500 ride
      • Accommodation: Il Miraggio (or similar)
    From US$7,990 per person

    Deposit: $500

    Pay in your local currency at checkout (AUD, CAD, EUR, GBP)

    • Pay in Easy Instalments

    • Flexible Cancelation Policy

    • 30% of Guests Book Again

    Still have questions?
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    Departures

    Upcoming Dates and Prices

    Request Itinerary

    Want more information about this trip?

    Enter your details and we’ll send you a complete PDF version of the Southern Tuscany tour itinerary so you can start planning your escape to this beautiful region in central Italy.

    Frequently Asked Questions

    Our Southern Tuscany tour departs mid morning from the Eternal city of Rome.

    Our Southern Tuscany tour ends back at Rome’s Termini Railway Station in the late afternoon.

    Fly into Rome’s international airport Roma Fiumicino. If traveling from somewhere else in Italy, you can arrive by high speed train to the Roma Termini Station.

    Please let us know well in advance if you have any dietary needs, including allergies. It is quite a meat and dairy heavy cuisine so it can be a little difficult for vegetarians and not advisable for vegans. We’re happy to work with tour accommodation and restaurants to ensure that you have suitable meal options.

    You’ll feel completely at home – whether you enjoy a glass of wine or prefer to skip it. Our tours celebrate the stories, traditions, and people behind Italy’s incredible food and wine culture, so there’s always something meaningful to experience. Non-alcoholic local options are happily provided, and every tasting, vineyard visit, or shared meal is about connection, not just what’s in the glass.

    Absolutely! We always welcome solo travelers in our groups and generally have at least a couple of solo guests join.

    This tour includes light to moderate physical activity, with guided walks lasting around 1–2 hours at a time. If you have mobility concerns, please get in touch and we can help you determine if this itinerary is the right fit.

    Alongside USD, we offer payment in Australian, Canadian and New Zealand dollars, Euro and British pounds using the mid-market rate at time of payment on xe.com. Please reach out to us at info@untolditalytours for a quote.

    Pay a USD $500 deposit per person to secure your place. Then three easy instalments at 180 days, 120 days and 90 days prior to departure or as specified on our tour booking page. The balance is due 60 days before departure or on the date specified on the trip booking page. Email us if you’d like to break up the instalments even more.

    Our Southern Tuscany tour offers unbeatable value for money and includes 4 star accommodation, luxury transportation, nearly all meals, guided tours, entrance fees, artisan visits, local experiences, a dedicated tour host and more.

    Most guests find they spend money on souvenirs, a few snacks and additional services such as laundry and spa treatments.

    You have one free time lunch but our guests often find this a welcome relief from the sheer amount of food during the rest of the tour.

    When you book a tour with us, we take care of all the details so you can sit back, completely relax and enjoy your Italian experience.

    Yes our 2026 tour schedule has several opportunities to combine this tour with another Untold Italy experience. Our May departure can be combined with our Puglia tours. Our October departure can be combined with our Bologna, Modena and Parma tour. Please reach out for more information.

    The unexpected can occur and becoming ill or injured in a foreign country is a very daunting experience, therefore we require guests take insurance with international evacuation coverage for all trips.

    Please consider cancelation insurance also because refunds are made available only per our
    terms and conditions, and we are unable to make exceptions for any reason, including weather, injury/illness, or personal emergencies.

    You should book a policy as soon as the trip has been confirmed. Some companies to consider:

    • World Nomads – simple and flexible travel insurance for independent travelers. Includes 24×7 assistance when abroad
    • Safety Wing Nomad Insurance – designed to meet the unexpected medical and travel needs faced by people traveling outside of their home country
    • Travelex (USA residents only) – comprehensive travel insurance options covering medical assistance and delays

    Unfortunately these providers may not offer policies for those aged over 69. In this case you can try Travel Insurance Master – a service that allows you to compare quotes and insurance policies.

    Thoughts From Our Guests

    Untold Italy Tours Reviews

    Read More Reviews

    Discover Tuscany

    Tuscany needs no introduction, but, in the “untold” way, we like to go a little deeper. Discover Tuscany’s highlights and off the beaten path treasures when you read our articles and listen to our podcast about beautiful Tuscany.

    siena
    montalcino vineyard
    pienza view val d'orcia

    Listen

    Perfect Pienza – Hilltop Town of Dreams

    An iconic spot in the Val D’Orcia
    Listen to Podcast