The best wineries to visit in Tuscany are not always the most famous ones, and a prize does not guarantee an open door. Gambero Rosso’s Italian Wines 2027 guide gave its top award, Tre Bicchieri, to 100 Tuscan wines. We went through the winners and kept the estates that actually welcome visitors, with a published tasting program and, at six of the eight, rooms on the property.
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- The award
- Tre Bicchieri, Gambero Rosso Italian Wines 2027
- Tuscan winners
- 100 wines, the most of any Italian region
- This list
- 8 estates with a public visit or tasting program
- Rooms on site
- 6 of the 8
- Areas covered
- Chianti Classico, Carmignano, the Valdarno, Montalcino, Montepulciano, the Maremma
- Booking
- Always ahead, directly with the estate
In this article
What Tre Bicchieri actually rewards
Tre Bicchieri, “three glasses,” is the highest mark in Gambero Rosso’s guide to Italian wine, presented in Rome on October 25, 2026 for the 2027 edition. The national list counts 540 wines, and Tuscany leads every region with 100 of them in the official tally (the guide’s own Tuscan list, in Italian, shows a few more). Chianti Classico takes the biggest share, followed by Brunello di Montalcino and Bolgheri.
Two rules matter when you use the list to plan a trip. The award goes to one specific wine from one vintage, not to the estate as a whole, and only one wine per winery can win it. So a Tre Bicchieri tells you a cellar is making wine at the very top of its category right now; it tells you nothing about whether you can visit. Our report on the Gambero Rosso Italian Wines 2027 winners covers the full results, the Special Awards and what changed from last year.
How we chose the best wineries to visit in Tuscany
We started from the Tuscan winners and kept only the estates that publish a way in: a bookable tour or tasting, with prices or a booking contact on the estate’s own website. Several of the most celebrated names on the list fell out at that stage, because they do not receive visitors or only open to the trade.
From what was left, we picked eight that cover Tuscany’s main wine areas and give a traveler something more than a glass at a counter: art, architecture, a historic village, a cellar dug into the rock. We favored estates where you can also spend the night, and six of the eight have rooms. The order is geographic, not a ranking. Formats and prices change through the year, so confirm the details with the estate when you book.
Chianti Classico
1. Castello di Ama — Gaiole in Chianti
Award-winning wine: Chianti Classico Ama 2024. Castello di Ama is a hamlet in the hills above Gaiole, and the reason to come is as much the art as the wine: the estate has commissioned site-specific works from contemporary artists for years, and they are scattered through the cellars, the chapel and the gardens. It is the most memorable visit on this list if you care about both.
Every visit is booked in advance on the estate’s website. The entry format, Journey to Ama, lasts about 90 minutes in a group of up to seven and pours three Chianti Classico wines for €90 per person; a private tasting of older vintages runs to €279. Il Ristoro serves lunch, and five suites in the eighteenth-century Villa Ricucci mean you can stay the night inside the estate.
2. Castello di Volpaia — Radda in Chianti
Award-winning wine: Chianti Classico 2024. Volpaia is a fortified village first recorded in 1172, high above Radda, and the winery lives inside it: the cellars are hidden inside the walls of the village, and the vineyards, about 45 hectares farmed organically, sit above 400 meters. It is one of the cooler corners of the Classico zone, which shows in wines that are fresh rather than heavy.
Visits and tastings are booked through the estate’s website or by email. Volpaia is also a place to stay, with villas, apartments and rooms in the village itself, an osteria, a bakery and cooking classes. If you want to explore the rest of the area from here, our guide on where to stay in Chianti covers Radda and Gaiole.
3. San Felice — Castelnuovo Berardenga
Award-winning wine: Chianti Classico Borgo 2024. In the southern Chianti Classico, near Siena, San Felice farms about 150 hectares of vineyards, most of them Sangiovese, around a medieval hamlet that has been turned into Borgo San Felice, which describes itself as the first Relais & Châteaux hotel in Chianti Classico. Few estates in Tuscany combine a serious cellar and a full luxury hotel this completely.
The winery offers several levels of tasting, including a barrel tasting in the cellar, booked online or by email. The hotel has rooms, suites and two separate villas, and its restaurant, Poggio Rosso, is listed by the estate with a Michelin star and a green star. It works best as a base for two or three nights, with Siena a short drive away.
Book it
Sleep at a Tre Bicchieri winery
Borgo San Felice is a Relais & Châteaux hotel inside the San Felice estate in Chianti Classico. Compare dates and rates, then book the cellar tasting with the winery.
Around Florence: Carmignano and the Valdarno
4. Tenuta di Capezzana — Carmignano
Award-winning wine: Vin Santo di Carmignano Riserva 2018. West of Florence, Capezzana has a history on paper that goes back to a parchment dated 804, and the Contini Bonacossi family has owned it since 1900. Carmignano is one of Tuscany’s smallest and oldest appellations, and the estate’s prize-winning Vin Santo is a good reason to taste the sweet wine of Tuscany at its source.
The menu is clear and well priced: Welcome to Capezzana takes 90 minutes, with the rose garden, the historic cellar and three wines plus the estate’s olive oil, for €30; The Capezzana Experience adds the vinsantaia and five wines in two hours for €45. There are also a jeep tour of the vineyards with lunch and cooking classes, and an agriturismo on the farm for overnight stays. Florence is well under an hour away.
5. Il Borro — San Giustino Valdarno
Award-winning wine: Valdarno di Sopra Petruna 2021. Il Borro is a medieval hamlet and a 1,100-hectare organic estate in the upper Arno valley, between Florence and Arezzo, restored from 1993 onward. It is less a winery with rooms than a village-sized resort with a winery at its center, and it is the most complete stay on this list.
Wine tours and tastings in the cellar are booked through the estate’s experiences page. The hotel, a Relais & Châteaux member, has suites in the hamlet and villas across the estate, plus several restaurants and a wine bar. If you only want the wine, a tour here pairs easily with a day in Arezzo; if you want the full stay, plan at least two nights.
Montalcino and Montepulciano
6. Poggio Antico — Montalcino
Award-winning wine: Brunello di Montalcino Vigna I Poggi 2021. Poggio Antico sits south of the town of Montalcino, and the estate describes its vineyards, above 550 meters, as the highest in the Brunello appellation. That altitude is what you taste: Brunello with more tension and perfume than the warmer, lower sites.
The tasting menu is unusually detailed: from four wines for €40 per person up to a private vertical of six for €200, all booked online. There are no rooms at the estate, so see the hotel suggestion below. For more cellar doors in the same zone, read our Brunello tastings in Montalcino.
7. Poderi Boscarelli — Montepulciano
Award-winning wine: Nobile di Montepulciano Il Nocio 2022. A family estate founded in the early 1960s, Boscarelli farms about 30 hectares in Cervognano, southeast of Montepulciano, and makes around 150,000 bottles a year. Il Nocio, its single-vineyard Nobile, is one of the wines that has kept Vino Nobile in the conversation alongside Brunello.
This is the most personal visit of the eight: a walk in the vineyard, the cellar and a tasting, by reservation only and mostly on weekends, arranged by email or through the form on the estate’s website. There are no rooms, so book a base in or near Montepulciano and keep the afternoon free for the town.
The Maremma
8. Rocca di Frassinello — Gavorrano
Award-winning wine: Maremma Toscana Merlot Baffonero 2023. In the hills of the Maremma, inland from the coast of Grosseto, Rocca di Frassinello is the winery Renzo Piano designed, built over a barrel room excavated in the rock that holds about 2,000 barrels. A small Etruscan exhibition shows finds from the nearby San Germano necropolis.
The Classic Tour lasts about 75 minutes and pours four wines for €30; the private Superior Tour adds Baffonero to five wines in 90 minutes for €60. Reservations are required. The estate’s guest house has four double rooms and two apartments with breakfast, which makes it an easy stop between Tuscany’s interior and the sea.
Where to stay near the Tre Bicchieri wineries
Six of the eight estates put you up themselves: Castello di Ama, Castello di Volpaia, San Felice, Capezzana, Il Borro and Rocca di Frassinello. For the other two, these are the hotels we would book, each within easy reach of the cellar door. Neither is part of the Gambero Rosso list; they are here for location and comfort.
For Poggio Antico: Castello Banfi, Il Borgo, the Relais & Châteaux hotel in the hamlet below the Poggio alle Mura castle, on the same southern side of Montalcino. Our Montalcino estates with rooms has more options around the town.
For Poderi Boscarelli: Villa Cicolina, a late sixteenth-century villa just outside Montepulciano on the Valdichiana side, with an infinity pool among the olive trees and a restaurant serving Tuscan food.
Hotels chosen for location; check rates and dates on Expedia. Prices are indicative and set by our booking partners.
Planning a route between them
| Estate | Area | Rooms on site |
|---|---|---|
| Castello di Ama | Gaiole in Chianti | Yes (5 suites) |
| Castello di Volpaia | Radda in Chianti | Yes |
| San Felice | Castelnuovo Berardenga | Yes (Borgo San Felice) |
| Tenuta di Capezzana | Carmignano | Yes (agriturismo) |
| Il Borro | San Giustino Valdarno | Yes |
| Poggio Antico | Montalcino | No |
| Poderi Boscarelli | Montepulciano | No |
| Rocca di Frassinello | Gavorrano | Yes (guest house) |
The eight estates stretch from Carmignano, west of Florence, to the Maremma near the coast: more than two hours by road end to end. The three Chianti Classico estates fit in a single base, and Poggio Antico and Boscarelli are under an hour apart. Two visits a day is a realistic pace. Our Tuscany wine country guide explains how the areas fit together, and the guide to renting a car for a wine trip covers the practical side, including Italy’s drink-driving limit.
If you have time for only one of these best wineries to visit in Tuscany, choose by what you want from the day. Castello di Ama is the one for art, Rocca di Frassinello for architecture, Poggio Antico for Brunello. For a single stop where the tasting, dinner and a room are all on the same estate, San Felice and Il Borro are the simplest answers.
