Golden harvest season, Tuscan style
Tuscany in Fall Tour
Embrace the rhythm of Tuscany in fall - from Chianti’s golden hills to San Gimignano’s towers and Lucca’s quiet charm. Taste, toast, and celebrate autumn’s bounty.
Tour Details
A week immersed in harvest season - truffle hunts, vineyard tastings, and countryside meals that celebrate Tuscany’s most flavorful time of year.
Price
From US$8,390 per personGroup Size
Maximum 12 guestsDuration
8 days / 7 nightsDepartures
September/October 2026Starts/Ends
Florence
Inclusions
Boutique stays, guided experiences, and meals with wineAccommodation
Luxury agriturismo in the countryside and boutique hotel in LuccaActivity Level
Light walking — some uneven terrain
Highlights
Why You'll Love This Tour
Taste autumn’s bounty among Chianti’s golden vineyards and ancient hills.
Feel the thrill of discovery on a truffle hunt through misty oak forests.
Savor the season’s warmth with new olive oil, rich wine, and slow, laughter-filled meals.
Connect through tradition as you roll handmade pasta in a rustic Tuscan kitchen.
Wander sunlit villages where time slows and every view feels like a painting.
What our guests say
your untold italy tour Includes
7 nights in charming luxury 4 star accommodation – 4 nights at luxury agriturismo (countryhouse) in Chianti countryside and 3 nights in a boutique hotel in Lucca
Winery visits, Tuscan cooking class, cheese farm visit, boat ride, visits to several Tuscan towns and villages, and artisan workshop visits.
7 breakfasts, 7 lunches, 1 aperitivo and 7 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 Florence.
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 one free lunch to explore the local food scene at your own pace.
Tour Overview
Tuscany in Fall Tour Description
Experience authentic Tuscany at its most captivating. Fall transforms the landscape into a canvas of gold and green – rolling hills, cypress-lined roads, and medieval towns glowing under soft light. It’s harvest time: olive groves hum with pickers, vineyards celebrate the grape’s final bounty, and the scent of truffles drifts through the forests.
Harvest Flavors and Local Connection
This week-long journey invites you to slow down and savor Tuscany like a local. Meet the winemakers, olive growers, and artisans who keep centuries-old traditions alive. Taste Chianti straight from the source, sample the season’s first olive oil, and share laughter over long, rustic meals that celebrate the region’s abundance.
Hidden Hilltowns and Off-the-Beaten-Path Discoveries
Beyond the postcard icons, discover Tuscany’s quieter corners – hilltop villages, family-run farms, and historic kitchens where hospitality still feels deeply personal. Join truffle hunters and their dogs on the trail of Tuscany’s most prized delicacy, wander through sagre (food festivals) alive with music and local pride, and soak up the warmth of everyday Tuscan life.
Tuscany in Fall 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
A Taste of Chianti Life
Your journey begins in the heart of Tuscany, where vine-covered hills roll toward the horizon and the air carries the scent of wine and fresh earth. Visit a beautiful Chianti winery and sip the region’s signature reds while learning about the families who’ve tended these vines for generations.
At a family-run cheese farm, milk the goats and taste their creamy goat cheese straight from the source. Wander through a lively market village, chat with the locals, and end the day in a rustic kitchen where you’ll make wood-fired pizza – a delicious introduction to the flavors and warmth of rural Tuscany.
See Details
- Places: Greve in Chianti, Chianti countryside
- Activities: Winery visit and tasting, cheese making, pizza making class
- Accommodation: Querceto di Castellina (or similar)
Day 3-4
Olive Groves, Pasta, and Timeless Towns
Travel deeper into Tuscany’s countryside, where silvery olive trees shimmer in the autumn light. Visit a local olive farm and discover how the season’s first press becomes Tuscany’s beloved “liquid gold.”
Join a local chef in her family home for a joyful pasta-making class, learning how to roll, shape, and savor Italy’s most iconic dish. Later, stroll through San Gimignano, the “medieval Manhattan,” and admire its famous towers glowing gold in the late afternoon sun.
See Details
- Places: Colle di Val d’Elsa, San Gimignano
- Activities: Olive oil tasting, hands-on pasta class, winery dinner
- Accommodation: Querceto di Castellina (or similar)
Day 5-7
Hilltowns, Truffles, and the Tuscan Coast
In San Miniato, follow the earthy aroma of truffles through narrow lanes and market stalls – a true autumn treasure of Tuscany. Continue to Lucca, a city of music and grace, where elegant walls hold centuries of stories. Visit the villa once owned by Napoleon’s sister Elisa and enjoy a local opera performance, a moving tribute to the region’s rich culture.
At the coast, board a small boat in Livorno and glide along its tranquil canals, passing grand palazzos and historic fortresses before tasting the best produce at the city’s vibrant 19th-century market. Evenings are for slow dinners, good wine, and the easy rhythm of Tuscan life.
See Details
- Places: Lucca, San Miniato, Livorno
- Activities: Opera performance, Livorno guided food tour and canal boat ride, villa visit and guided walking tour of Lucca
- Accommodation: Hotel Ilaria (or similar)
Day 8
Truffles and Tuscan Farewell
Venture into the forest for a truffle hunt, guided by an expert and his loyal dogs. As you listen to stories of local legends and traditions, you’ll understand why these hidden treasures are the pride of Tuscany.
Celebrate your journey with a truffle-inspired lunch at a local winery paired with organic wines, including the region’s sacred dessert wine, vin santo. It’s a final toast to Tuscany – its beauty, its generosity, and the unforgettable memories made along the way.
See Details
- Places: Tuscany countryside and Florence
- Activities: Truffle hunt, truffle lunch, wine tasting
Over 1000+ satisfied guests
Departures
Upcoming Dates and Prices
Book now →Tuscany in Fall Tour
Mon 28 Sep - Mon 5 Oct 2026- Book now →
Tuscany in Fall Tour
Sat 10 Oct - Sat 17 Oct 2026
Private Tour
Private Tour
Go with just your friends?
Request Itinerary
Want more information about this trip?
Enter your details and we’ll send you a complete PDF version of the Tuscany in Spring tour itinerary so you can start planning your escape to this beautiful region in central Italy.
Frequently Asked Questions
Our Tuscany in Fall tour departs in the morning from the Renaissance city of Florence from the Florence Santa Maria Novella train station at 10am.
Our Tuscany in Fall tour ends back at the Florence Santa Maria Novella train station in the late afternoon.
Florence can be reached by high speed train in an hour and 30 minutes from Rome, and under two hours from Milan. If you prefer to travel by plane, the city has a small international airport that services Italian and European destinations.
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 Tuscany in Fall tour offers unbeatable value for money and includes 4 star accommodation, luxury transportation, most 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 September departures can be combined with our Cinque Terre and Beyond tour and Puglia tours. Our October departures can be combined with our Dolomites & South Tyrol 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
Dishes from Tuscany in Fall
Learn about what we eat on this tour
