
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 personGroup Size
Maximum 12 guestsDuration
7 days / 6 nightsDepartures
May/October 2026Starts/Ends
Rome
Inclusions
Boutique stays, guided experiences, and meals with wineAccommodation
Luxury agriturismo in the Val d’Orcia countrysideActivity 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.

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

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

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

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

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.

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.
See Details
- 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.
See Details
- 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.
See Details
- 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.
See Details
- Places: Montepulciano, Pienza, Val d’Orcia countryside
- Activities: Wine tastings, Pienza and Montepulciano visit, vintage Fiat 500 ride
- Accommodation: Il Miraggio (or similar)
Departures
Upcoming Dates and Prices
Book now →Southern Tuscany Tour
Sat 16 May - Fri 22 May 2026
Book now →Southern Tuscany Tour
Sun 11 Oct - Sat 17 Oct 2026

Private Tour
Private Tour
Go with just your friends?
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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.
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.

Read
Tuscany Travel Guide
Uncover the highlights of the region



Listen
Perfect Pienza – Hilltop Town of Dreams
An iconic spot in the Val D’Orcia

































