Tuscany Tours in October 2026
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10 best Tuscany tour packages in October
Compiled by

NadineTuscany travel expert at TourRadar
- A Taste of Tuscany - Hilltop Towns and Vineyards
- Florence: Amazing Tuscany & Cinque Terre 2026: Independent Tour with shared daily tours - Small Group
- Gems of Tuscany & Cinque Terre 2026: Semi-Escorted Small Group Tour from Montecatini Terme
- Two Hearts in Tuscany: A Romantic Getaway for 2
- Private Gourmet Wine Tour in Tuscany, Italy
- Tuscany, Timeless Emotions 2026 - Semi-Escorted Tour
- 7 Day Rome, Florence, Tuscany & Venice Tour Package
- Flavours of Tuscany 2026 - Semi-Escorted Tour
- Tuscany Highlights, Semi-Private Tour
- Taste of Tuscany: A 3-Day Escape of Wine, Relax, and Fun
A Taste of Tuscany - Hilltop Towns and Vineyards
12 Reviews by TourRadar travelers“Excellent food and wine visits couldn't have asked for more. Highly recommend this trip.”
Elizabeth, traveled in May
Duration 8 days Destinations Pisa, Livorno, Tuscany, Montalcino, Buonconvento, Pienza, Montepulciano, Siena, Florence, Greve in ChiantiSee all destinations Age Range Ages 16+ Operator Explore! October departure dates
See All Departure Dates4 Oct, 2026 10+ spaces left 11 Oct, 2026 10+ spaces left From
- NZ$5,260
Duration 8 days Destinations Florence, Montecatini, Montecarlo, Cinque Terre, Vinci, Siena, San Gimignano, Monteriggioni Age Range All Ages Welcome Operated in English, Italian, French Operator RANIERI TOUR OPERATOR October departure dates
See All Departure Dates1 Oct, 2026 4 spaces left 4 Oct, 2026 4 spaces left From
- NZ$2,557
Two Hearts in Tuscany: A Romantic Getaway for 2
2 Reviews by TourRadar travelers“The itinerary and people behind 'Italy on a budget' and 'Italy on Wheels' exceeded our expectations. It was magical!”
Belen, traveled in October
Duration 4 days Destinations Florence, Castellina in Chianti, San Gimignano Age Range Ages 18+ Operated in English, Italian Operator Italy on a Budget Tours October departure dates
See All Departure Dates7 Oct, 2026 2 spaces left 14 Oct, 2026 2 spaces left From
- NZ$1,981
Private Gourmet Wine Tour in Tuscany, Italy
4 Reviews by TourRadar travelers“Everything simply wonderful and comfortable with our van and private driver. We loved the wine tasting and walk in the Brunello vineyards!”
MichaelKev, traveled in October
Duration 4 days Destinations Florence, Colle di Val d'Elsa, Castellina in Chianti, Val d'Orcia, Montalcino, Siena, Volterra, San Gimignano, Castagneto Carducci, Pisa Age Range Ages 24+ Operator Soleto Travel October departure dates
See All Departure Dates3 Oct, 2026 8 spaces left 7 Oct, 2026 8 spaces left From $5,983
20% Off- NZ$4,787You save $1,197
Duration 7 days Destinations Florence, Montecatini, Montecarlo Age Range All Ages Welcome Operated in English, Spanish Operator RANIERI TOUR OPERATOR October departure dates
See All Departure Dates1 Oct, 2026 2 spaces left 6 Oct, 2026 2 spaces left From
20% Off- NZ$2,304
Duration 7 days Destinations Rome, Vatican City, Florence, Siena, San Gimignano, Pisa, Venice Age Range All Ages Welcome Operator Tourist Journey October departure dates
See All Departure Dates1 Oct, 2026 10+ spaces left 2 Oct, 2026 10+ spaces left From
20% Off- NZ$3,556
Flavours of Tuscany 2026 - Semi-Escorted Tour
2 Reviews by TourRadar travelers“The views, the atmosphere, the place it self and that night we had the pleasure to meet the Company Owner seen she pop out for a quick welcome to our group tour.”
Dilcen, traveled in October
Duration 6 days Destinations Florence, Montecatini, Montecarlo, Siena, San Gimignano, Monteriggioni Age Range All Ages Welcome Operated in English, French Operator RANIERI TOUR OPERATOR October departure dates
See All Departure Dates1 Oct, 2026 4 spaces left 8 Oct, 2026 4 spaces left From
20% Off- NZ$2,137
Tuscany Highlights, Semi-Private Tour
2 Reviews by TourRadar travelers“All services were provided as promised and in a timely manner. The itinerary offered us the enjoyment of experiencing Italy in a variety of settings and different experiences.”
Judith, traveled in September
Duration 8 days Destinations Florence, Lucca, Pisa, Siena Age Range All Ages Welcome Operated in English, German, Italian, French, Spanish Operator TUI Italia October departure dates
See All Departure Dates1 Oct, 2026 10+ spaces left 2 Oct, 2026 10+ spaces left From $6,927
10% Off- NZ$6,234You save $693
Taste of Tuscany: A 3-Day Escape of Wine, Relax, and Fun
1 Review by TourRadar travelers“The accommodations were full of charm, right in the heart of a historic hilltop town with views that didn't feel real.”
Jane, traveled in June
Duration 3 days Destinations San Gimignano, Ulignano, Tuscany Age Range Ages 18+ Operator Italy on a Budget Tours October departure dates
See All Departure Dates1 Oct, 2026 10 spaces left 2 Oct, 2026 8 spaces left From
10% Off- NZ$910
What people love about Tuscany Tours in October
- Private Gourmet Wine Tour in Tuscany, Italy
The tour operator was very easy to work with. Some changes that we requested were easily handled. Drivers were on time, courteous, and the cars/vans were very nice. The initial tour was 4 days basing out of Mormoraia. We added Cinque Terre and Lucca with no problems. Wine tastings were all very fine and we shipped wine home from two of them. Generally speaking this was a very good way to see a great deal of Tuscany which was our purpose. I can feel good about recommending this tour and operator to anyone wanting to see all of Tuscany.
- Flavours of Tuscany 2026 - Semi-Escorted Tour
I had the pleasure to explore Tuscany gem places/towns and some wineries with this tour operator Ranieri... and what a TRIP!!! Where. Let me beginning with saying the communication is on point and prompt, their Team clearly had the experience and had beeing doing this for a while as they said. Then since the moment we arrived, my husband and I they took care of every single detail of our trip, it was My Birthday week so it was a big relief for my husband not having to worry about anything but just enjoying AMAZING TUSCANY and enjoying the TASTE of it, we are two foodie people and toor was very focused on the Culinary and wine aspects of the region, Just being at FLORENCE was a dream and 5 starts treatment we were receiving from the guides and tour lead. Luke walking inside a art paint while trying all the good food along the way Then going to a country side farm and trying there the local produce, jellies, food, and of course the great Tuscany wine was just the start of it. The views, the atmosphere, the place it self and that night we had the pleasure to meet the Company Owner seen she pop out for a quick welcome to our group tour. What a lovely lady she is, that was a treat for sure. CHIANTI wineries were an enchanted place to be, we also had a tasting there and some olives and little bites food tasting... I Love the medieval architecture so just coming on the private buss we were being transported and seeing San Gimignano up on top of the hills with those impressive walls and Italian cypress trees got my heart raising...even better the great walking experience inside of it. However I have to say for me SIENA stole my heart ❤️ the whole trip was so worthy but Siena is out of this world, they have everything ready to explore the city, that is where I have my bday dinner, it was surreal to be seated at the piazza surrounded but the beautiful buildings and walls, my head was going 360 trying to catch up with all that beauty. Oh btw in every place we stopped they gave us recomendaciones of were to sho go shopping, or takes breaks. I Love that part that they were conscious about giving us FREE time for us to enjoy in our onw but always guided, we felt so safe and cared at every moment. Thank you Letizia for all your great work and for taking care of our amazing experience. I DEFINITELY recommend and would use this tour operator again in the future. I had been wanting to make a review since then, better now than never. Until next time Italy ?? ? ❤️ ??
- The Best of Tuscany - 4Days/3Nights
It was good tour. Even got the free wine from the wine owner :). Over all it was good experience.
What our customers ask about Tuscany Tours in October 2026
What special events and festivals can I experience in Tuscany during October?
Tuscany comes alive in October with food and wine celebrations across the region. The White Truffle Festival draws crowds to San Miniato while the Chestnut Festival fills the streets of Mugello with local vendors and traditional foods. Wine enthusiasts can join grape harvest celebrations throughout the Chianti region including hands-on grape stomping in Montalcino. The EVO Festival in Montepulciano showcases the region's olive oils. At Villa Lecchi estate visitors can watch both olive harvesting and wine production in action. A TourRadar traveler noted "The timing was perfect to experience the local harvest festivals and the authentic Tuscan culture."
What are the advantages of visiting Tuscany in October versus peak summer months?
October delivers a more relaxed Tuscan experience with shorter lines at major sites like Florence's Uffizi Gallery and Pisa's Leaning Tower. The mild weather makes walking tours comfortable while harvest activities add seasonal charm. Visitors find better availability at sought-after restaurants and hotels including Florence's Hotel Roma. Room rates drop significantly and interactions with locals feel more genuine. A TourRadar traveler noted "Visiting in October meant we could really enjoy the museums and churches without the summer crowds plus the autumn colors in the vineyards were spectacular."
Which wine experiences are unique to Tuscany in October?
The October harvest transforms Tuscan wineries into hubs of activity especially in Chianti and Montalcino. Visitors can join grape picking sessions watch pressing demonstrations and tour cellars during production. A family vineyard in San Gimignano lets guests taste fresh-pressed juice and learn winemaking basics. Special harvest festivals pop up across the region while historic Montepulciano cellars offer tastings of their famous Vino Nobile. As one TourRadar traveler shared "We visited a family vineyard in San Gimignano where we could taste the fresh-pressed juice and learn about the entire wine-making process."
What is the weather like in Tuscany during October?
October temperatures in Tuscany hover between 12-20°C (54-68°F). The Chianti region and San Gimignano start the day with cool crisp air that's ideal for wine tasting while Florence stays slightly warmer. A TourRadar traveler noted: "The October weather was perfect for exploring the vineyards and medieval towns without the summer crowds." Villa San Donato near San Gimignano provides clear views of the changing fall colors during this season.
What are the best food experiences in Tuscany Country Region during October?
October brings white truffles to San Miniato and the hills around Siena. Traditional dishes like ribollita soup and porcini mushroom preparations appear on menus across the region. NH Siena Hotel creates special seasonal menus that highlight local ingredients. A TourRadar review noted: "The truffle hunting experience near Volterra in October was amazing followed by a fantastic lunch at a local farm."
What is the price range for accommodations in Tuscany Country Region during October?
Accommodation costs in October range from 150-450 USD nightly. The Grand Hotel Adriatico in Florence starts at 300 USD while countryside properties like Hotel Le Pozze di Lecchi charge between 200-350 USD. Farm stays (agriturismos) present good value at 150-250 USD. A TourRadar traveler shared: "The Dimora dell'erbe in Montepulciano offered excellent value for the autumn season with amazing views of the fall foliage and reasonable rates compared to summer months."
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