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 their 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 an “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 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

umbria italy

Fall in Tuscany Tour Highlights

Wine tastings • Meet the locals • Luxury farmhouse accommodation • New season olive oil • Bread making class • White truffle hunting • Medieval castles • Life-changing Cheese • Under the Tuscan Sun meals • Artisan crafts

fall tuscany tour
tuscany italy
pecorino cheese tuscany
tuscan bruschetta
tuscany grape harvest
truffle hunting in tuscany
winery tuscany

Magical! Beautiful! I’m a bit of a dreamer and I just got lost there last night. Lost in this beauty.. Magnificent! I just loved it – view video

Vicki / Australia

We have been to Italy several times, but never like this. It has been a wonderful experience – view video

Pati / USA

Aside from every little surprise around every corner, I’ll remember Cosimo and the genuine excitement and pride that come out of him and his storytellingview video

Steve / USA

Fall in Tuscany Tour Itinerary

chianti tuscany in fall

Day One


Meet your group and host in Florence this morning before boarding our luxury minivan to cruise 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 head to our luxury farmhouse, which will be our homebase for the week. Unpack and relax  – you have a week of untold magical Tuscany waiting for you!

This afternoon, we have our first opportunity to get our hands dirty! Thanks to our “Il Panaio” (trusted baker and bread expert), you will learn about different kinds of ancient grains before learning how to create delicious bread, pizza and focaccia.

Sit back and relax tonight over a welcome feast at the farmhouse with some special entertainment. Buon appetito!

  • Meals: Lunch with wine, Dinner with wine
  • Activities: Chianti winery visit and bread making class
  • Accommodation: Beautiful Tuscan farmhouse
  • Transfer: From central Florence to accommodation at 10.30am
tuscany chestnut festival stall

Day Two

A magical chestnut festival

Some of our favorite things in the world are Italy’s sagre, and today, you’re going to discover what’s so great about an Italian food festival!

This morning we head to an off-the-beaten-track mountain town to attend a popular local Chestnut festival – the most historical chestnut festival in Italy and renowned for its marrons glacés (candied chestnuts).

This local chestnut festival is full of food stands offering all the best local products and traditional food based on their prized chestnuts.

We have plenty of time to explore together and enjoy free time to wander the village and shop for souvenirs. Lunch, of course, is devoted to chestnuts and held right at the sagra as we taste our way through plenty of local specialities.

After our day of exploring, we have time to relax at our farmhouse this afternoon before a delicious dinner at home base.

  • Meals: Breakfast, Lunch with wine, Dinner with wine
  • Activities: Chestnut festival
  • Accommodation: Beautiful Tuscan farmhouse
tuscan saffron

Day Three

The red jewel of Tuscany

Did you know that saffron grows all over Tuscany? This prized ingredient is a Fall speciality that comes out to play with its splendid lilac flowers for only a handful of weeks in October. Today, we head off to a gorgeous saffron farm where we’ll don an apron and learn how to cook a lovely meal all based on this prestigious ingredient. We’re bringing farm to table to life today – all of the ingredients in our class are freshly grown directly on the farm.

Take in the stunning view of the vineyards and olive trees during our class. The farm stands on top of a hill in an oasis of peace and tranquility away from noise, cars and pollution. A perfect Tuscan dream! After our lesson, we’ll feast on our incredible saffron inspired lunch together.

Fortified after our delicious lunch, we head off to explore a true Tuscan treasure on the Via Francigena. Let us enchant you with the town’s fascinating stories as we wander through its beautiful Medieval castle. You’ll feel like time stands still here, especially when we reveal a special surprise in town organised just for us…

Late this afternoon we head back to the farmhouse for some time to relax, before meeting again for a tasty dinner at home.

  • Meals: Breakfast, Lunch with wine, Dinner with wine
  • Activities: Cooking class and castle visit
  • Accommodation: Beautiful Tuscan farmhouse
san gimignano tuscany

Day Four

Holy wine & 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 sort of ‘Medieval Manhattan’! Encircled by 13th century walls, with towers that jut out upwards to the sun, 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 winery that specializes in the prestigious Vin Santo (Holy Wine) dessert wine. Also known as the nectar of the gods, we’ll enjoy a delicious homemade lunch and have the opportunity to taste this heavenly wine all the while gazing out over the vineyards.

After lunch, we head to one of Tuscany’s iconic cities – Medieval masterpiece Siena. Tuscans love their traditions, but there’s perhaps no town that holds on to them quite as strongly as Siena does thanks to their twice yearly Palio dating back to the Middle Ages. We’ll learn what this special horse race is all about and why rivalries and alliances run so deep even up to this very day in the contrade of Siena.

Tonight we’ll head out from our farmhouse for a spectacular dinner, sampling some of the tastiest local recipes.

  • Meals: Breakfast, Lunch with wine, Dinner with wine
  • Activities: Wander in San Gimignano, Winery visit and guided tour of Siena
  • Accommodation: Beautiful Tuscan farmhouse
tuscany olive harvest

Day Five

Discovering liquid gold: Tuscan olive oil

Our day starts with an adventure to the very heart of our 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.

Revived after our trip to Greve, we head off to learn all about one of the most important parts of Tuscan culture…olive trees! Today we are tasting the very essence of the land.

We visit a family owned extra virgin olive oil producer where we’ll discover just how this liquid gold is produced and why it’s so important to the local people. Afterwards, we’ll relax at the olive mill as we enjoy an incredible lunch, sampling delicious specialties all paired with olive oil.

After lunch we explore some of the most interesting Chianti villages, where you’ll have the opportunity to wander, and chat to the locals who are part of what makes this region so special. We’ll pop in to an artisanal oil mill for a tasting of the most vibrant olio nuovo or ‘new oil’ of your life!

This evening, there’s some time to relax before a convivial dinner together at the farmhouse.

  • Meals: Breakfast, Lunch with wine, Dinner with wine
  • Activities: Visits to Greve in Chianti and olive mills of the region
  • Accommodation: Beautiful Tuscan farmhouse
tuscany truffle hunt

Day Six

The elusive white truffle

Have you ever wondered just how delicious a white 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.

Our experience starts in the fields and ends up in their kitchen, as we learn all the secrets and some of the best recipes to make with fresh truffles – both white and brown – before sitting down for a long and relaxing lunch together.

With bellies full we take a relaxing walk in an impressive Medieval castle town and stop at a traditional pottery workshop. Here you can shop for unique gifts for family and friends if you choose.

This afternoon it’s onwards to one of the most Etruscan towns in all the region – Volterra. This gorgeous Medieval town is renowned for alabaster – one of the most important products of Italian craftsmanship. We’ll have time to wander, stop for photos and of course visit an historical alabaster workshop together.

We return to our farmhouse to unwind before we head out for dinner at our favourite trattoria, trying the best homemade pasta you’ve ever had!

  • Meals: Breakfast, Lunch with wine, Dinner with win
  • Activities: Truffle hunt, Medieval castle visit, pottery store and historic alabaster workshop visit
  • Accommodation: Beautiful Tuscan farmhouse
tuscan pecorino cheese

Day Seven

Pecorino cheese forever!

All good things must come to an end, but not before you get to try “life-changing” cheese! Our final day together is full of the things we love most about Tuscany – delicious food, new friends, Medieval towns and of course great wine!

We’ve planned a visit to a wonderful family owned cheese farm in the Tuscan countryside overlooking the gorgeous Val di Chiana. 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 ricotta, raviggiolo and pecorino cheese. The ricotta made here is so delicious that it is even mentioned in the Under the Tuscan Sun Cookbook by Frances Mayes!

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.

This afternoon is onwards to our final Tuscan town together – the stunning town of Arezzo. We’ll meet a wonderful local guide and enjoy a guided tour together as she brings the streets of La Bella Vita to life for us.

Tonight we gather round the long table at our farmhouse for our final dinner together. Pour yourself a glass of local wine, dive into your by now favourite Tuscan dishes, and reflect on the week that was with newfound friends.

  • Meals: Breakfast, Lunch with wine, Dinner with wine
  • Activities: Cheese making class and guided tour of Arezzo
  • Accommodation: Beautiful Tuscan farmhouse
farmhouse chianti tuscany

Day Eight


We enjoy a final breakfast together, before packing our bags and boarding our private bus onwards 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.

  • Meals: Breakfast
  • Transfer: From Tuscany back to central Florence by 11am
siena tuscany
tuscan musicians
pecorino cheese
artisan tuscany

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 a charming Tuscan farm house
  • Transfers: to and from Tuscany from central Florence
  • Unique experiences:  2 winery visits, truffle hunt, bread making class, cheese making class, saffron farm visit, guided walks in Siena and Arezzo, visits to several Tuscan towns and villages, artisan workshop visits, olive oil mill visits, festival visit
  • Meals: 7 breakfasts, 7 lunches, 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 Farmhouse

Nestled in the Chianti country, our Tuscan farmhouse is the perfect base and home away from home. With sweeping views over vineyards from many vantage points, a swimming pool and outdoor dining areas, it’s the perfect spot to experience life Tuscan style. When the weather is cool, the indoor dining area is a cosy haven to enjoy a glass of Chianti with your delicious home cooked meal.

Meet Your Tour 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 10.30am when you are whisked away to the Tuscan countryside. Our activities conclude back in central Florence at Santa Maria Novella train station at approximately 11am on our final day.

Upcoming Tour Dates

  • 2024 – September 30 – October 7 – sold out
  • 2024 – October 14 – 21 – sold out
  • Exclusive tours available on request for groups of 6-10 – inquire

Booking information

  • Price from $US 6,190 per person based on double or 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.

Tuscany’s Chianti region

All about our home base on tour

listen to podcast

Tuscany Travel Guide

Learn what to do and see in Tuscany