Tuscany Tours in October 2025
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10 best Tuscany tour packages in October
Compiled by

NadineTuscany travel expert at TourRadar
- Two Hearts in Tuscany: an Escape for 2
- Tuscany Walking and Wine
- Private Gourmet Wine Tour in Tuscany, Italy
- Florence City Break - 3 Days/2 Nights
- A Taste of Tuscany - Hilltop Towns and Vineyards
- Discover Tuscany: Culture, Food & Wine
- Flavours of Tuscany - Semi-Escorted Tour
- Gems of Rome & Florence
- Tuscany Thrills: A 3-Day Escape of Wine, Relax, and Fun
- Discovering Florence
Two Hearts in Tuscany: an Escape for 2
2 Reviews by TourRadar travelers“We loved every moment. Amazing tuk-tuk ride, easy bag transfers. Exquisite wine tasting with two course meal.”
Marinda, traveled in May
Duration 4 days Destinations Florence, Castellina in Chianti, San Gimignano Age Range 18 to 99 year olds Operated in English, Italian Operator Italy on a Budget Tours October departure dates
See All Departure Dates1 Oct, 2025 2 spaces left 12 Oct, 2025 2 spaces left From
- NZ$1,856
Tuscany Walking and Wine
21 Reviews by TourRadar travelers“The hotel in Pienza was outstanding!!”
Madison, traveled in May
Duration 8 days Destinations Pisa, Castellina in Chianti, Castelvecchio National Park, San Gimignano, Monteriggioni, Siena, Pienza, Monticchiello, Montepulciano, San Quirico D'orciaSee all destinations Age Range 16 to 85 year olds Operator Explore! October departure dates
5 Oct, 2025 4 spaces left From
- NZ$4,280
Private Gourmet Wine Tour in Tuscany, Italy
4 Reviews by TourRadar travelers“Villa Lecchi was beyond our dreams. The views were spectacular of Tuscany.”
Colleen, traveled in September
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 24 to 86 year olds Operator Soleto Travel October departure dates
See All Departure Dates1 Oct, 2025 8 spaces left 4 Oct, 2025 8 spaces left From $4,644
15% Off- NZ$3,947You save $697
Florence City Break - 3 Days/2 Nights
5 Reviews by TourRadar travelers“Time seemed to fly by really quickly. The group was entertained.”
Billy, traveled in December
Duration 3 days Destinations Florence, Castellina in Chianti, San Gimignano Age Range 18 to 39 year olds Operator Italy on a Budget Tours October departure dates
See All Departure Dates2 Oct, 2025 8 spaces left 5 Oct, 2025 8 spaces left From
15% Off- NZ$630
A Taste of Tuscany - Hilltop Towns and Vineyards
11 Reviews by TourRadar travelers“The winetasting was a great time. Walk from Buonconvento was great as was farm visit.”
CJ, traveled in May
Duration 8 days Destinations Pisa, Livorno, Tuscany, Montalcino, Buonconvento, Pienza, Montepulciano, Siena, Florence, Greve in ChiantiSee all destinations Age Range 16 to 85 year olds Operator Explore! October departure dates
12 Oct, 2025 9 spaces left From $4,840
6% Off- NZ$4,570You save $270
Discover Tuscany: Culture, Food & Wine
2 Reviews by TourRadar travelers“Kept us informed of daily plans. Ensured our every question and need was met.”
Peter, traveled in October
Duration 8 days Destinations Pancole, San Gimignano, Florence, Colle di Val d'Elsa, Siena, Castellina in Chianti, Certaldo, Volterra, Tuscany Age Range up to 80 year olds Operator Exodus Adventure Travels October departure dates
4 Oct, 2025 8 spaces left From $4,617
5% Off- NZ$4,400You save $217
Flavours of Tuscany - 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, Vinci, Montecarlo, Siena, San Gimignano, Monteriggioni, Strada in Chianti Age Range 1 to 100 year olds Operated in English, French Operator RANIERI TOUR OPERATOR October departure dates
See All Departure Dates5 Oct, 2025 4 spaces left 7 Oct, 2025 4 spaces left From $2,011
10% Off- NZ$1,810You save $201
Gems of Rome & Florence
4 Reviews by TourRadar travelers“Lovely tour, particularly of Siena and San Gimignano. From cathedrals to cobblestones, turrets to towers, this all-day tour was a wonderful experience.”
Yvonne, traveled in June
Duration 6 days Destinations Rome, Florence, San Gimignano, Siena Age Range up to 80 year olds Operated in English, Spanish Operator TUI Italia October departure dates
See All Departure Dates1 Oct, 2025 10+ spaces left 2 Oct, 2025 10+ spaces left From $2,624
15% Off- NZ$2,230You save $394
Duration 3 days Destinations Tuscany, San Gimignano Age Range 18 to 99 year olds Operated in English, Italian Operator Italy on a Budget Tours October departure dates
See All Departure Dates3 Oct, 2025 4 spaces left 10 Oct, 2025 4 spaces left From
15% Off- NZ$764
Discovering Florence
2 Reviews by TourRadar travelers“The private tours of the Uffizi and Accademia Galleries were super - the guides were knowledgeable and open to any question.”
kelly, traveled in March
Duration 4 days Destinations Florence, Monteriggioni, Siena, San Gimignano Age Range up to 80 year olds Operator TUI Italia October departure dates
See All Departure Dates1 Oct, 2025 10+ spaces left 2 Oct, 2025 10+ spaces left From $1,356
15% Off- NZ$1,153You save $203
What people love about Tuscany Tours in October
- Two Hearts in Tuscany: an Escape for 2
Perfect getaway for anyone in need of a good rest and quality time with their partner. We loved every moment. Amazing tuk-tuk ride, easy bag transfers. Exquisite wine tasting with two course meal. The hotel in Tuscany with the room walking out onto one of the pools- amazing. Fantastic restaurant on site! Our SPA session was relaxing with a beautiful dinner (spectacular view) afterwards. Walking distance from medieval town.The tour guides were great, high energy, friendly and welcoming. I’m so glad I booked this as our Tuscany experience.
- Florence City Break - 3 Days/2 Nights
This was an amazing tour, Great to see Tuscany and taste amazing wine
- Icons of Italy: Venice, Florence, Tuscany and Rome Cruise by Rail
Passionate and kind tour guide. Elisabetta was fantastic!
What our customers ask about Tuscany Tours in October 2025
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."
Months