The 10 Best Tuscan Winery Tours from Florence, Italy (2026)
You’re planning a trip to Florence – and honestly, one of the best decisions you can make is spending a day in the Tuscan countryside.
Walking through the Uffizi and standing under the Duomo is unforgettable, sure. But a glass of Chianti Classico at a family-run estate, with cypress trees rolling out into the hills?
That’s a different kind of magic. We’ve done a lot of wine tours through Tuscany ourselves over the years. From Chianti to Montalcino, from San Gimignano to Bolgheri – we keep coming back, and every single visit teaches us something new about Italian wine.
For this guide, we hand-picked the best Tuscan winery tours from Florence, Italy – covering everything from half-day Chianti escapes to full-day Brunello tastings, from intimate boutique cellars to legendary Super Tuscan estates.
Whether you’re a serious wine lover or simply curious about what makes Tuscan wines world-famous – a winery tour from Florence will be one of the most memorable days of your entire trip. Here are our personal favorites.
- Updated on
At a Glance: Our Top 3 Tuscan Winery Tours
Most popular wine tour via GetYourGuide: Small Group Wine Tour – from €89 per person
Most popular wine tour via Winalist: Malenchini Wine Estate — Villa Medicea di Lilliano – from €40 / €95 per person
3rd Best via Winalist: Castello di Oliveto — A 1424 Florentine Castle – from €25 / €35 per person
Small Group Wine Tasting Tour to Tuscany (Chianti Classico)
Rating:
Duration: 4.5 hours
One of the most popular wine tours – and for good reason.
This 4.5-hour escape into the Chianti Classico region pairs two contrasting wineries in a single afternoon, which is exactly the right length if you only have one free day in Florence.
You travel by air-conditioned minibus from Piazzale Montelungo through the cypress-lined back roads, sample three wines per estate, and taste the fresh-pressed olive oil that most tour operators forget to include. Cheese, salami, and bruschetta are paired with each pour. Group size stays small enough that you can actually talk to the winemakers, not just watch them pour.
- English-speaking driver-guide, air-conditioned minibus
- Three wines per estate plus olive oil, cheese, salami, bruschetta
- Two Chianti Classico wineries, one tour comparing both cellar techniques
- Price: €89 per person
- Free cancellation up to 24 hours in advance
You might also like:
Small Group Tuscany Wine Safari with Lunch or Dinner
Rating:
Duration: 7.5 – 8 hours
If you want the full Tuscan day — not just a quick tasting — the Wine Safari version is the most rewarding format we have found on GetYourGuide. You visit two or three authentic wineries depending on the option you pick, and lunch (or sunset dinner) is served at the vineyard, not at a roadside restaurant.
The afternoon-into-evening departure is the sleeper choice: you arrive at the second estate during golden hour, when the cypress shadows stretch across the rows of Sangiovese. Group sizes cap at 25, so it never feels like a coach tour.
- 2 or 3 organic wineries with lunch or dinner included
- Duration: 7.5–8 hours, full day or golden-hour afternoon option
- Small group (max 25 guests), departs from Florence
- Price: €149 per person
- Wines paired with multi-course traditional Tuscan menu
- Free cancellation up to 24 hours before start
Tuscany Wine Tour with San Gimignano & 7 Wines
Rating:
Duration: 7 hours
The clever thing about this tour is the structure: you taste at a dedicated wine school first — four reference Tuscan wines including Brunello di Montalcino and a Super Tuscan — before visiting actual producers.
That sequence trains your palate so the vineyard tastings later make more sense. You also get a 30-year-old balsamic and truffle olive oil thrown in. Afternoon is spent wandering San Gimignano’s medieval lanes at your own pace, with stops for gelato at the world champion gelateria on Piazza della Cisterna. Back in Florence by 5 PM.
- Up to 7 wines across 2 wineries + wine school session
- Includes 30-year aged balsamic and truffle olive oil tasting
- Free time in San Gimignano (UNESCO medieval town)
- Price: €90 per person
- 8-seater minivan, intimate small group format
- 9:45 AM departure from Piazza della Calza
You might also like:
Chianti Wineries Tour with Wine Tasting (Half-Day)
Raiting:
Duration: 5 – 5.5 hours
Short on time? This is the half-day option we point people toward when they have a packed Florence itinerary but still want to taste Chianti at the source. Two genuine cantine in the rolling Chianti hills, a coach with commentary about the landmarks along the SR222 Chiantigiana, and tastings paired with cheese, olive oil, and regional charcuterie.
The two wineries are deliberately contrasting — typically one larger family-run operation and one smaller boutique producer — so you get a feel for how different scales of Chianti producers actually work.
Why we love it: It is the rare wine tour that leaves Florence after lunch (some departures) and gets you back by aperitivo hour — a smart move if you want to keep your evening in Florence free for dinner at a proper trattoria.
- Expert English-speaking guide
- Duration: 5–5.5 hours, half-day format
- 2 contrasting Chianti wineries with cellar tours
- Price: from $24 / €20 per person
- Local food pairings: pecorino, olive oil, cured meats
- Private option and pickup available on request
Siena, San Gimignano, Pisa & Winery Lunch (Full-Day Combo)
Raiting:
Duration: 12 hours (full-day)
If this is your only day outside Florence, this combo tour does the heavy lifting. You see Siena’s Piazza del Campo, the towers of San Gimignano, and the Leaning Tower of Pisa, plus a long lunch at a Chianti farmhouse with unlimited wine — all in one day. Yes, it is ambitious.
But the wine stop is where the day really lands: a working fattoria in the Chianti hills serving multiple courses of Tuscan staples with house Chianti flowing freely. The optional wine-and-lunch package is the one worth booking; without it, you skip the highlight.
- Full day (~12 hours) covering 3 UNESCO-related sites + winery
- Optional Tuscan farmhouse lunch with unlimited wine
- Free time in Siena, San Gimignano, and Pisa
- Price: €95 per person
- Live multilingual guide and coach transport
- Most-booked Tuscany combo tour from Florence
Please note: Winalist tours work differently than GetYourGuide The experiences below are booked directly with each Tuscan winery via Winalist. A few important differences to keep in mind:
- No transport included — you’ll need your own rental car, a private driver, or a taxi to reach the estate
- Smaller, more personal groups — many tastings are led by the owner, winemaker, or a family member
- Payment — some hosts offer “book & pay on arrival” without requiring a credit card upfront
- Distance from Florence — the wineries we’ve selected are between 20 minutes and 1 hour drive from the city center
Below are the top 5 wine tours through Winalist.
Malenchini Wine Estate — Villa Medicea di Lilliano
Raiting:
Duration: 1.5 hours
Owned by the Malenchini family since 1830, this estate sits inside the former Villa Medicea di Lilliano on the outskirts of Florence — close enough that you can technically reach it without leaving the city’s southern hills.
The wines are Chianti and Chianti Superiore, the olive oil is exceptional, and the optional vineyard picnic is the version of this estate you should book if you can. A 4.9 rating across 60 reviews is unusually consistent. The villa setting is the bit guests rarely expect: you taste inside a property with documented Medici history.
- Just outside Florence — closest "Tuscany feel" without going far
- Chianti and Chianti Superiore appellations
- Multiple tasting formats including vineyard picnic and lunch
- Price range: roughly €40–€95
- Organic certification, family-owned since 1830
Castello di Oliveto — A 1424 Florentine Castle
Raiting:
Duration: 1.5 hours
Built in 1424 by the Pucci family of Florence, Castello di Oliveto is one of those Tuscan estates where the building itself is half the reason to go.
The tastings are reasonably priced (under €40 for the basic option, around €40 for the light lunch version) and consistently rated 4.8 across 62 reviews. The wine focus here is Vin Santo and Tuscan reds, but the experience is really about drinking inside a properly preserved 15th-century castle that has somehow stayed off the mainstream tourist track.
Worth knowing: The cantaloupe-yellow tone of the stone in late afternoon light is the photograph you will actually want to keep — better than most “famous” Chianti castles that get more Instagram traffic.
- 15th-century Pucci family castle, sustainably farmed
- Vin Santo specialty plus Tuscan red blends
- Approximately 30 minutes south of Florence by car
- Tastings from €29; light lunch option around €40
Castello di Monterinaldi — Etruscan Roots, Off-Road Option
Raiting:
Duration: Between 1 – 4 hours (depending on the tour)
This one is for travellers who want to do more than swirl and sip. Castello di Monterinaldi sits on land continuously inhabited since the Etruscan era, and the estate offers wine tastings plus off-road 4×4 tours through Chianti Classico, hiking routes, and a “Winemaker for a Day” experience.
The tasting menu pairs Chianti Classico and Vin Santo with the estate’s own olive oil and balsamic. A wide price spread (€17 for a basic tasting up to multi-thousand-euro private formats) makes it accessible, whether you want something casual or a serious cellar dive.
- Organic Chianti Classico and Vin Santo
- 4x4 off-road Chianti tour available (rare offering)
- Tuscan cooking course and "Winemaker for a Day" experiences
- Tastings from €17; full lunch with tasting available
Tenuta Casenuove — Boutique Chianti Classico in Panzano
Raiting:
Duration: approx. 1.5 – 2.5 hours
Tenuta Casenuove is in Panzano in Chianti, in what locals call the Conca d’Oro (Golden Shell) — arguably the best soil pocket in all of Chianti Classico.
The estate produces a small, focused range of Chianti Classico wines using organic methods, and the Grand Tour with light lunch is the experience to book if you want time with the team rather than a rushed pour. 59 reviews and a 4.7 rating reflect the consistency. Pricing sits in the middle of the Winalist Florence range at €35–€80.
- Located in Panzano's celebrated Conca d'Oro area
- Organic Chianti Classico specialist
- Grand Tour with private light lunch option
- Price: from $35 to €80 per person
- Around 1 hour drive south of Florence
Marchesi Gondi — Tenuta Bossi (Chianti Rufina)
Raiting:
Duration: 1.5 hours
This is the Florence-area pick for travellers who already know Chianti Classico and want something different. Tenuta Bossi is in Chianti Rufina — the smaller, cooler, higher-altitude DOCG north-east of Florence — and the estate has been in the Gondi family since the 16th century, making them one of the oldest documented Florentine winemaking families still active.
The “Five Shades of Chianti Rufina” tasting is the signature: a vertical flight that shows how the same vineyard expresses itself across vintages. A perfect 5.0 average across 13 reviews tells you something.
- Chianti Rufina DOCG — cooler, age-worthy alternative to Classico
- Five Shades of Rufina vertical tasting (signature experience)
- Historic villa setting, 16th-century Florentine family
- Tastings from approximately €21 to €50
- Sustainable certification
Quick tip: GetYourGuide tours include transport from central Florence — book these if you do not want to drive. Winalist experiences need you to arrive at the estate yourself — book these if you have a rental car (or are willing to take a taxi out for ~€40–€60 each way) and want a more intimate, owner-led visit.
FAQ: Tuscany Wine Tours from Florence
How much does a Tuscany wine tour from Florence cost?
A Tuscany wine tour from Florence typically costs between €60 and €180 per person. Half-day group tours start around €60–€90, full-day tours with lunch range from €120–€180, and private tours or premium tastings at historic estates can exceed €250 per person.
How long does a wine tour from Florence to Tuscany take?
A wine tour from Florence to Tuscany takes between 4.5 hours and 12 hours, depending on the format. Half-day tours visit two wineries in about 5 hours, full-day tours include 2–3 wineries with lunch over 7–9 hours, and combo tours covering Siena and San Gimignano run roughly 11–12 hours.
What is the best wine region to visit from Florence?
The best wine region to visit from Florence is Chianti Classico, located directly between Florence and Siena. It is famous for Sangiovese-based wines marked with the Black Rooster (Gallo Nero) seal. Chianti Rufina, north-east of Florence, is a quieter, age-worthy alternative preferred by many locals.
Do I need to book a Tuscany wine tour in advance?
Yes, you should book a Tuscany wine tour from Florence at least 1–2 weeks in advance, especially between April and October. Small-group tours and popular wineries like Castello di Oliveto and Tenuta Casenuove sell out quickly. GetYourGuide and Winalist both offer free cancellation up to 24 hours before.
What is included in a Tuscany wine tour from Florence?
A typical Tuscany wine tour from Florence includes round-trip transport by minibus, visits to two or three wineries, guided cellar tours, tastings of 3–7 wines per estate, and local food pairings such as cheese, olive oil, salami, and bruschetta. Full-day tours add a traditional Tuscan lunch.
What is the difference between GetYourGuide and Winalist for Tuscany wine tours?
The difference between GetYourGuide and Winalist is the format. GetYourGuide offers group tours from Florence with transport and a guide included. Winalist connects you directly with the winery for a more personal, owner-led tasting — but you need to arrange your own transport to the estate.
What is the best time of year for a Tuscany wine tour?
The best time of year for a Tuscany wine tour from Florence is between May and October. September and early October are ideal, as you may witness the vendemmia (grape harvest). Spring offers green landscapes and fewer crowds, while summer brings the warmest weather and longest tasting hours.
Can you do a wine tour from Florence without a car?
Yes, you can do a wine tour from Florence without a car by booking a group tour with GetYourGuide, which includes round-trip transport from central Florence. Public transport to Chianti wineries is limited, so independent visits via Winalist require a rental car, taxi, or private driver.
How many wineries do you visit on a Tuscany wine tour from Florence?
On a Tuscany wine tour from Florence, you typically visit two wineries on half-day and standard full-day tours. Premium small-group tours and specialist operators visit three wineries, allowing you to compare different winemaking styles, scales, and estate philosophies across the Chianti region.
What wines will I taste on a Tuscany wine tour?
On a Tuscany wine tour from Florence, you will mainly taste Chianti Classico DOCG made from Sangiovese grapes. Premium tours also include Brunello di Montalcino, Vernaccia di San Gimignano, Super Tuscans, and Vin Santo dessert wine. Most tastings pair wines with extra virgin olive oil and local cheese.
Is a Tuscany wine tour from Florence worth it?
Yes, a Tuscany wine tour from Florence is worth it for anyone interested in wine, food, or Italian landscapes. You experience the Chianti countryside, meet winemakers, and taste wines you cannot find outside Italy. It is consistently rated as a highlight of visiting Tuscany.
What should I wear on a Tuscany wine tour?
On a Tuscany wine tour from Florence, wear comfortable layers and closed-toe shoes suitable for walking on gravel and uneven cellar floors. Bring sunglasses, a light jacket for cool cellars, and a sun hat in summer. Avoid strong perfumes, as they interfere with the wine tasting experience.
Author
Welcome!
My name is Allie.
Italy is one of my favorite countries to visit in Europe, especially Florence!
I love everything the city has to offer. From the architecture to the most delicious food and wine, Florence has it all. So, come with me on this beautiful journey through Florence.
Allie
Did you know that …
By purchasing through my links, you support me at no additional cost.
Thank you for your support. ♥️
via GetYourGuide
via Booking.com
Flights to Florence
via Skyscanner
Discover more guides: