Updated September 28, 2026
Four Tuscany Wineries We Loved Visiting
On our travels through Tuscany, we made time for wineries in Montepulciano, the Chianti hills, the Valdichiana and Cortona. The wine mattered, of course, but so did the people, food pairings and countryside settings. These four stops stayed with us for different reasons. Here is what we experienced and what to check before planning your own tasting.
Building a longer Italy trip around a wine day? Our Italy itineraries and day trips show how Tuscany wine country fits alongside Cortona, Bologna and other memorable stops.
Table of Contents
1. Avignonesi (Montepulciano)
Avignonesi was memorable for its Vino Nobile di Montepulciano and the chance to explore a historic estate. We appreciated how organized the visit and wine shipment process felt. Check Avignonesi’s current experiences for availability, language, prices and shipping terms before booking.
- In the glass: Avignonesi is known for Vino Nobile di Montepulciano, a Sangiovese-based wine. Its range also includes Rosso di Montepulciano and Vin Santo.
- At the estate: Our visit combined wine, the setting and a well-organized tasting experience. Ask about current tours and food pairings when reserving.
PLP Top Picks
- 50&50 Toscana IGT
- La Badelle Vino Nobile di Montepulciano
- Vin Santo di Montepulciano.
Vintages, formats and prices change; confirm the current list directly with Avignonesi.
2. Fattoria Santa Vittoria (Arezzo Province)
Fattoria Santa Vittoria gave us a quieter countryside wine stop in the Valdichiana area. We enjoyed the setting and its food and wine pairing. Ask the estate what tasting and dining experiences are currently offered before you build it into your route.
Our tasting here was generous, and the food pairing made the visit feel like more than a quick stop. The wines we noted were Leopoldo IGT Rosso, Canapone and Conforta Toscana. Their vintages and prices can change; confirm the current selection and reservation details with the estate.
3. Fattoria di Luiano (Chianti)
In the Chianti hills near San Casciano in Val di Pesa, Fattoria di Luiano gave us a relaxed way to pair local wine with food. We especially enjoyed its “Tasty Tasting” pairing. Check Luiano’s current tasting options and reserve ahead; menus and prices can change.
- In the glass: Chianti Classico and other Sangiovese-led wines were the draw for us.
- Our visit: The food pairing at Luiano made the tasting especially enjoyable. Ask about the current “Tasty Tasting” menu and available tours when booking.
PLP Top Picks
- LUI
- Chianti Classico Riserva
- Chianti Classico Annata
Choose a current vintage with the team at Fattoria di Luiano.
4. IVITI (Cortona)
IVITI was one of our most personal winery visits near Cortona. Our host Elisa welcomed us with a charcuterie board and had juice and snacks ready for the kids. The tour, tasting room and vineyard views made it an easy stop to recommend for families traveling together.
We would pair this tasting with time in town. Our Cortona day trip guide covers the places we enjoyed visiting, eating and staying nearby.
- Our visit: Elisa’s welcome, the charcuterie pairing and the thoughtful snacks for the children stood out. We enjoyed the tour, views and tasting room.
- Before you go: Check IVITI’s current visits for reservation times, family arrangements and the wines being poured.
PLP Top Picks
- Cortona Cabernet Sauvignon
- Iugero Cabernet Franc
Ask the winery about current vintages and availability.
Getting There
These four wineries are spread across Chianti, Montepulciano, the Valdichiana and Cortona. A rental car or private driver makes it easier to connect stops; use each winery’s booking confirmation for the exact address and arrival instructions. If you plan to taste, arrange a designated driver or tour.
Allow plenty of travel time on rural roads and avoid packing all four into a single day. Consider grouping Montepulciano and the Valdichiana, or Cortona with a nearby stop.
Luiano is near San Casciano in Val di Pesa. Avignonesi is located near Montepulciano. Fattoria Santa Vittoria is in the Valdichiana area, and IVITI is near Cortona.
Confirm your route with the estates before leaving. If you are relying on rail, arrange the final taxi or transfer in advance; countryside wineries are rarely a simple walk from a station.
What to Know Before You Go
Reserve each tasting directly and confirm the language, duration, food options, accessibility and cancellation terms. Mention children when booking; IVITI made our family feel especially welcome, but arrangements vary.
- Book ahead, especially for food pairings and harvest dates.
- Leave time between appointments for the drive and an unhurried visit.
- Confirm opening days, parking and the current tasting price directly with each winery.
Ask what the visit actually includes: a seated tasting, vineyard walk, cellar tour and lunch are different experiences. Availability can change with vineyard and cellar work.
Best Time of Year to Visit
Spring can be mild and green, while summer can be hot. Check each estate’s opening days.
September–October harvest season: Tuscany’s vendemmia often falls in these months, but timing depends on the grape variety, site and weather. Vineyards and cellars may be especially active, and regular tour schedules can change. Book early and ask if a harvest-focused visit is offered; do not assume guests can join picking or grape pressing.
Late autumn and winter tend to be quieter, with fewer outdoor activities.
PLP Practical Tips
Bring a payment card and a little cash, and check accepted payment methods when booking. Wear comfortable shoes if your visit includes vineyard paths. A food pairing is worth reserving explicitly if you want time to linger over the wines.
Our Favorite Tuscany Wine Experiences
Each stop gave us a different memory: Avignonesi’s organized estate tasting and shipment experience, Santa Vittoria’s generous food pairing, Luiano’s “Tasty Tasting,” and Elisa’s welcome to our family at IVITI. Choose the experiences that fit your route and confirm current offerings with the wineries.
We loved how food changed the tasting at Santa Vittoria, Luiano and IVITI. If that matters to you, book a pairing explicitly; a standard tasting may not include one. For a different hands-on food experience, see our Tuscany cooking experiences.
Plan your Tuscany stay: Compare Tuscany hotels for your dates. If you book through it, we may earn a commission at no extra cost to you. Reserve winery tastings with each estate separately.
Read More from Pure Life Podcast
- Our Cortona day trip guide — what to see, eat and where to stay near IVITI.
- Tuscany cooking experiences — another way to enjoy the region’s food culture.
- Italy One Day at a Time: 8 Itineraries, Day Trips & Food Experiences Worth the Detour — our eight-detour roundup for a longer Italy trip.
Every Journey, Once in a Lifetime.
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