untold italy small group tours

Tuscany in Fall Tour Overview

Come with us for a once in a lifetime trip to Tuscany. Much has been written about this beautiful part of the world, famous for rolling green hills lined with cypress trees, Medieval hilltop towns, fascinating festivals, and incredible food. Discover what makes Tuscany such a well-loved destination as we bring you on an immersive trip into its very heart and soul.

Our exclusive week-long experience offers you a VIP pass to discover Tuscany like a local. We visit some of the popular bucket list destinations (in our signature “untold” way) but also discover authentic, off-the-beaten towns you’ve never heard of. You’ll meet the makers of Tuscany’s most famous products, Chianti wine and Tuscan olive oil, the artisans honouring time old traditions, and the local people as they go about their day.

Fall is a wonderful time to visit Tuscany. Leaves change color, the wine harvest draws to a close, and the fields are awash with olive pickers – it is when the delicious new season olive oil is produced. It’s the time of year when truffles are in season and sagre (food festivals) are in full swing, and evenings get a little chillier – the perfect conditions for enjoying the region’s delectable cuisine.

Upcoming Tuscany in Fall Tours


Fall in Tuscany Tour Highlights

Wine tastings • Meet the locals • Luxury farmhouse accommodation • New season olive oil • Truffle hunting • Life-changing Cheese • Under the Tuscan Sun meals • Artisan crafts • Lucca • Thermal Baths

vin santo grapes tuscany
chianti spring tour
pistoia spring in tuscany
tuscany truffle hunt

If you want to relax and not worry about how, where and what you should do in Tuscany this is the way to travel – read full review

Marilyn / USA

The Tuscany tour far exceeded our expectations. We would recommend this to anyone who is looking for a once in a lifetime experience! – read full review

Rita & Ed / USA

Although we originally chose this trip as a wine and foodie trip, the real surprise and gift, was the warmth and generosity of the people – read full review

Crystal / USA

Fall in Tuscany Tour Itinerary

chianti tuscany in fall

Day One


Meet your group and host in Florence this morning before we head deep into the beautiful Tuscan countryside. We are off to picturesque Chianti – home to some of the most important red wines and stunning landscapes in Italy. Relax over a traditional ‘cucina Chiantigiana’ lunch at a family owned winery and get to know your new amici.

After lunch, we visit a nearby fortified village with Etruscan roots. Explore the charming winding streets, behold the mighty fortress or pop into one of its many local shops. Together, we visit the workshop of a local ceramic artisan and learn about her crafts. 

Then it’s onwards to our luxury farmhouse, which will be our home base in Chianti for the next few days. Unpack and relax  – you have a week of untold magical Tuscany waiting for you!

A fun Tuscan festa to officially welcome you on tour awaits you this evening. Enjoy a light dinner in the hamlet and prepare to be wowed with a musical surprise.

  • ACTIVITIES: Chianti winery,  Artisan ceramics visit
  • MEALS: Lunch with wine, Dinner with wine
  • ACCOMMODATION: Beautiful Tuscan farmhouse in Chianti
san gimignano tuscany

Day Two

 Medieval Manhattan

Perhaps the most quintessential Tuscan town you can imagine awaits you this morning when we head to gorgeous San Gimignano. Think of it as a ‘Medieval Manhattan’. Encircled by 13th century walls, with towers that jut out upwards to the sky, you’re sure to be entranced by this magical town. We’ll have some free time to get lost along the winding alleys, grab coffee at a charming bar in the piazza, people watch, and explore.

All that walking has got us thirsty, so it’s time to head to a gorgeous family owned farm for a tour and tasting. Admire the view of the Medieval towers of San Gimignano in the distance as we taste the estate’s Vernaccia wine and delicious extra virgin olive oil and tuck into a traditional Tuscan lunch.

In the afternoon we make our way back to the farmhouse where we have time to relax or stretch our legs for a walk around the hamlet. We set out to one of the village’s wonderful restaurants – of course paired with Chianti Classico wine.

  • ACTIVITIES: Farm and winery visit, San Gimignano free time
  • MEALS: Breakfast, Lunch with wine, Dinner with wine
  • ACCOMMODATION: Beautiful Tuscan farmhouse in Chianti
cooking class tuscany

Day Three


If you’ve ever wanted to learn how to make handmade pasta, today is your day. We visit a local chef at her family house in the Sienese countryside. Here, you will roll up your sleeves and wear an apron, as we learn to make traditional recipes passed down from generations and sit for a family-style meal. 

The menu is completely seasonal based on the best produce from our chef’s local market. Learn to make a full Tuscan meal from scratch, from appetizers to dessert, as our local chef recounts family stories or a local tradition behind each dish. Your wine glass will never be empty during the day either. Afterwards, we sit down to enjoy our feast in a beautiful olive garden.

In the afternoon, we head to a truly off-the-beaten-path Tuscan town renowned for its crystal production. Walk through the old town gates and take in stunning views of Tuscany, and its Medieval atmosphere. Together we visit some local artisans before you have some free time to wander. 

We return to our farmhouse in the late afternoon where you have time to relax and unwind before we meet for a fun apericena (light dinner).

  • ACTIVITIES: Cooking class, Artisan visits
  • MEALS: Breakfast, Lunch with wine, Apericena (light dinner) with wine
  • ACCOMMODATION: Beautiful Tuscan farmhouse in Chianti
tuscan cheese - spring in tuscany

Day Four

Cheese and Bistecca Fiorentina

We hope you like cheese because this morning we head to a wonderful family owned cheese farm in the Tuscan countryside. After visiting the stables to watch the baby animals play hide and seek we’re ready to roll up our sleeves and become ‘cheese masters’.

During our cheese making class, you’ll learn how to make the freshest incredible goat cheese. Afterwards, we’ll sit down together for a delicious cheese-themed lunch with homemade pasta and other specialties paired of course with locally made wine.

In the afternoon we adventure to  a special spot in Tuscany. We’re visiting the gastronomic paradise and lively market village, Greve in Chianti, with time to enjoy the beautiful shops, wander, and take in the beauty of the area. Whilst here, we’ll delight your tastebuds with the best combination of mixology and Tuscany’s liquid gold that we’ve ever seen.

This evening we are bidding farewell to Chianti in style as we head to dinner at Tuscany’s most famous butcher shop. Florence’s prized bistecca fiorentina (Tuscan steak) is on the menu with plenty of Chianti Classico to wash it down.

  • ACTIVITIES: Tuscan town visit, Goat cheese farm, Olive oil cocktail experience
  • MEALS: Breakfast, Lunch with wine, Aperitivo, Dinner with wine
  • ACCOMMODATION: Beautiful Tuscan farmhouse in Chianti

Day Five

Thermal Baths and PRETTY PISTOIA

Arrivederci Chianti, this morning we pack our bags and set off to explore the northern part of Tuscany. Our adventures begin in one of Italy’s culture capitals – Pistoia. Considered a mini Florence without the crowds, this charming town is nestled at the foot of the Apennine mountains. 

We meet our local guide for a walking tour where we learn about Pistoia’s underground Medieval passages and incredible chocolate shops (with a tasting of course). Enjoy some free time before we meet again for lunch.

In the afternoon, we head to a nearby town famed for its hot mineral waters. Enjoy a soak in the thermal baths (or an optional massage treatment) and appreciate the healing waters. Alternatively, enjoy some free time to wander around this delightful town.

Later, we check-in to another beautiful farmhouse nestled between Lucca and San Miniato. Enjoy some time to relax before we meet for a delicious dinner featuring delicious local produce. 

  • ACTIVITIES: Guided tour of Pistoia with chocolate tasting, Thermal baths visit
  • MEALS: Breakfast, Lunch with wine, Dinner with wine
  • ACCOMMODATION: Beautiful Tuscan farmhouse near San Miniato
San Miniato Tuscany

Day Six

A Medici Villa and San Miniato

Today we enjoy everything we love most about Tuscany – superb hamlets, romantic villas, delicious food, new Tuscan friends and of course great wine and views. 

We pay visit to the truffle obsessed town of San Miniato. It sits on the ancient pilgrimage route, Via Francigena, that went to Rome and on to Puglia. Here you have free time to wander the winding Medieval streets and enjoy a bite to eat in town. We have lots of recommendations to share. 

In the afternoon, enjoy some time back at our countryside hotel to relax, go on a walk or curl up with a good book.

Later, we head off to explore a gorgeous Medici villa nestled among the Tuscan hills and vineyards. We enjoy a guided tour marveling that the likes of Galileo Galilei and Leonardo da Vinci once walked these floors. 

Tonight we gather round a long table at a favorite restaurant with incredible views of the northern Tuscan countryside. Pour yourself a glass of local wine, dive into your by now favourite Tuscan dishes, and reflect on our week so far with newfound friends.

  • ACTIVITIES: Free time in San Miniato, Medici villa tour
  • MEALS: Breakfast, Dinner with wine
  • ACCOMMODATION: Beautiful Tuscan farmhouse near San Miniato

Day Seven


We start our morning with a visit to a local apiary to learn about how organic honey is made before enjoying a light lunch and sample of their delectable honey.

Then it’s onwards to charming Tuscan gem Lucca. There are thousands of stories to be told from behind her sturdy walls, and we’ll learn all about them via a guided tour of this beautiful city. 

In the late afternoon, you have free time to pop into Lucca’s many gorgeous shops, bike around the city walls or explore its incredible churches. In the evening, we meet for an aperitivo and tasty dinner in town and enjoy some music the city is famous for thanks to Giacomo Puccini.

  • ACTIVITIES: Honey farm visit, Guided tour of Lucca
  • MEALS: Breakfast, Lunch with wine, Dinner with wine
  • ACCOMMODATION: Beautiful Tuscan farmhouse near San Miniato

Day Eight

Truffles and Holy Vin Santo

Have you ever wondered just how delicious a truffle might be? Well today is the day you’re going to find out! Our journey begins with a unique truffle hunt in the forest with trained dogs and an experienced local truffle hunter, who will captivate us with the fascinating legends and curiosities that surround this precious gift of nature.

After hopefully finding a truffle (or two), we head inside to learn more about our host’s lovely biodynamic winery.  Most special is the holy dessert wine known as ‘vin santo’- you will be amazed by the drying room and effort required to produce this wine

Sit back and relax as our winery hosts pour us some of their finest drops to enjoy during a guided tasting with lunch – of course truffles are on the menu too.

In the afternoon we return to Florence. You leave with hearts full of love for this extraordinary part of the world, and a newfound appreciation for the everlasting traditions that make Tuscany so special.

  • ACTIVITIES: Winery visit and truffle hunt
  • MEALS: Breakfast, Lunch with wine
  • GROUP TRANSFERS: Back to Florence
vin santo grapes tuscany
tuscany fall pasta

Tuscany Fall Tour Inclusions

We have strived to make our Tuscany in Fall tour as all inclusive as possible with no hidden surprises. Included in your tour are:

  • 7 nights in two charming Tuscan farmhouses
  • Transfers: to and from Tuscany from central Florence
  • Unique experiences: 3 winery visits, truffle hunt, cheese farm visit, olive oil farm, guided walks in Lucca and Pistoia, thermal baths, visits to several Tuscan towns and villages, and artisan workshop visits
  • Meals: 7 breakfasts, 7 lunches, 1 aperitivo and 7 dinners as specified in the itinerary, Wine and bottled water are included with most meals other than breakfast
  • Luxury air-conditioned transportation
  • Tips and gratuities for drivers and guides

Tuscany in Fall Tour FAQ

Accommodation on Tour

farmhouse in tuscany

Our Tuscan Farmhouses

We have two beautiful bases on our Tuscany Fall trip. In the Chianti region we stay in a restored property with a wonderful outdoor swimming pool that is part of a charming hamlet. Just 52 people live in the village and you are within walking distance to explore the local church and the village bakery and restaurants.

Nestled between Lucca and San Miniato, our restored country house is family-run and our hosts are proud of the produce grown there. Each room has been thoughtfully decorated with locally sourced furniture. Surrounded by 10 hectares of countryside and hills, there are many trails to explore if you like hiking as well as a beautiful outdoor swimming pool. 

Meet Your Host

Olivia is an Australian woman living in Rome, with a passion for the land of la dolce vita, cooking and wine. Her super powers include finding the most charming villages and delectable cheeses.

Olivia is your local host that ensures your trip is memorable for all the right reasons.

Arrivals and Departures

The tour begins in central Florence at 10am when you are whisked away to the Tuscan countryside. Our activities conclude back in central Florence at Santa Maria Novella train station at approximately 4pm on our final day.

Upcoming Tour Dates

  • 2025 – September 15 – 22 – book now • October 6 – 13 – book now
  • Exclusive tours available on request for groups of 6-10 – inquire

Booking information

  • Price from $US 6,790 per person based on twin share accommodation
  • A supplement applies for solo travelers wanting a private room
  • 30% deposit required to reserve your spot
  • Cancel for a full refund up to 120 days before departure
  • Read complete terms and conditions

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.

Beautiful Towns in Tuscany

Discover the highlights and hidden treasures

read the guide

Tuscany Travel Guide

Learn what to do and see in Tuscany