EN

Florence · Siena · Tuscany

Chianti Wine Tastings

The vineyard hills between Florence and Siena, home of Sangiovese and the black rooster of Chianti Classico. Walk the rows with the family that farms them, taste a Riserva in a cool stone cellar, then mop up the olive oil with warm bread.

  • Half or full day
  • Transport included
  • Free cancellation

Independent guideTickets and experiences hand-picked by our editors.

Tours from$56per person ↓
Where the wine is fromClassico zone or not, tour by tour
Wines countedWineries, pours and food, spelled out
Free cancellationUp to 24 hours before on almost every tour
Nobody drives tipsyTransport from Florence or Siena included

Tours

Choose your Chianti wine tour

In the centre, the half-day coach trip to two family wineries that most people book from Florence. Either side, a full day that mixes Siena and San Gimignano with one tasting, and a small-van day with a long lunch at the estate.

Siena, San Gimignano & a Chianti Winery Towns + wine ★ 4.710.5 hoursFree cancellation

Siena, San Gimignano & a Chianti Winery

Full day3 towns1 winery

A guided walk in Siena, free time in San Gimignano and Monteriggioni, and one Chianti estate with two or three wines. More sightseeing than tasting, and lunch is extra.

What's included
  • Guided Siena walk with headsets
  • Free time in San Gimignano and Monteriggioni
  • One winery with 2 to 3 wines and snacks
  • Coach from Piazzale Montelungo and back
  • Free cancellation up to 24 hours before
Full tour details
From$74per person Reserve
Semi-Private Chianti & San Gimignano Day Top rated ★ 4.98.5 hoursFree cancellation

Semi-Private Chianti & San Gimignano Day

Small vanLunchHotel pickup

A small van, a long lunch at a winery near San Casciano with its wines and olive oil, and time in San Gimignano. Hotel pickup in central Florence is included.

What's included
  • Winery visit with wine and olive oil tasting
  • Lunch with wine at the estate
  • Hotel pickup in Florence's central zone
  • Small air-conditioned van with Wi-Fi
  • Free cancellation up to 24 hours before
Full tour details
From$237per person Reserve

More ways to taste Chianti

All tours

Compare

Which tour suits which traveller

Three questions sort it out. How much wine do you want, and how much sightseeing? Does a real Chianti Classico estate matter to you? And do you want lunch at a farm, or just snacks with the glasses?

TourWhereWineries & winesBest forLengthFrom
Half-Day Chianti Tasting at Two WineriesVia Chiantigiana, by coach from Florence2 wineries, 6 to 8 winesA classic first tasting, evening free5.5 hours$62Book
Siena, San Gimignano & a Chianti WinerySiena, San Gimignano, Monteriggioni + one estate1 winery, 2 to 3 winesSeeing Siena and San Gimignano too10.5 hours$74Book
Semi-Private Chianti & San Gimignano DaySan Casciano and San Gimignano, small van2 wineries, lunchSmall group, lunch, hotel pickup8.5 hours$237Book
Chianti Vespa Tour with Tasting & LunchChianti hills, van to the start point1 winery, lunchRide a Vespa through the hills, then lunch and wine at a farm6.5 hours$118Book
Small-Group Chianti Classico Half DaySR222 Chiantigiana, 8-seat minivan2 Classico estates, up to 7Two Classico estates, up to 7 wines, 8 people at most5 hours$170Book
Chianti E-Bike Tour with Lunch & TastingsHills around Impruneta, from FlorenceLunch + 2 tastingsPedal-assisted hills; the guided option adds lunch and two tastings6 hours$51Book
Chianti Wine & Olive Oil Trail with LunchThree wineries and an oil mill, minibus3 wineries, oil millThree wineries, an olive mill and a three-course lunch7 hours$122Book
Vintage Fiat 500 Tour with Lunch & WineStarts in Certaldo, west of the Chianti hills2 tastings, lunchA vintage Fiat 500 convoy to a farm lunch and two tastings7 hours$170Book
Chianti Half Day from SienaCastellina in Chianti and two wineries2 wineriesStaying in Siena: Castellina and two tastings in half a day5 hours$56Book
Private Chianti Wine Tour with LunchStrada in Chianti and Mercatale estates, hotel pickup2 estates, lunchYour own driver, two Classico estates and lunch5 hours$487Book

Under-18s pay less on most tours but are not served wine. Every tour here cancels free up to 24 hours before, except the private tour, which is non-refundable. Lunch is not included on the half-day coach trip or the town tour.

Before you book

Chianti is a big word. Classico is the heart.

"Chianti" covers a large slice of Tuscany, split into eight subzones from the hills of Arezzo to Pisa. The Chianti Classico zone is the old core between Florence and Siena: all of Greve, Castellina, Radda and Gaiole, and parts of four more towns. Its bottles carry the black rooster seal and must hold at least 80% Sangiovese.

Tour titles rarely tell you which one you get. Two of the cheapest half days from Florence taste at an estate near San Gimignano, outside the Classico zone. The Gray Line coach drives the Chiantigiana through Greve, but guests name its second estate as Poggio ai Laghi near Monteriggioni, just outside the line. None of this is a scam: the wine near San Gimignano can be very good. Just read the stops on the tour pages if the rooster on the label matters to you.

80%

The minimum share of Sangiovese in a Chianti Classico. Gran Selezione, the top tier, moves to 90% with native grapes only from the 2027 vintage.

Chianti ClassicoChianti Colli SenesiVernacciaSuper Tuscan
A vaulted brick wine cellar with oak barrels and three glasses of red wine on a tasting table
Riserva rests at least 24 months before release, Gran Selezione at least 30.
01

How many wines?

Six to eight on a two-winery half day, two or three on the town tour.

02

Is lunch included?

Snacks on the coach half day. A real lunch on the Vespa, e-bike, olive oil and small-van days.

03

Can I drive myself?

Italy's limit is 0.5 g/l, zero for new drivers. Two tastings will put most people over it.

04

Who should skip it?

Anyone who wants a single famous estate: tours pick the wineries, often small family farms.

Your day

How a tasting tour runs

About five and a half hours on the classic half day from Florence. This is the shape of it.

01

Meet in Florence

Coaches leave from Piazzale Montelungo by Santa Maria Novella; small vans pick up at a hotel or a city gate.

15 minutes early
02

Into the hills

South on the SR222 Chiantigiana past olive groves and cypress rows, with the guide talking wine and history.

45 to 60 minutes
03

Cellar and glass

A walk through the vines and the barrel room, then three or four wines with pecorino, salami and oil on bread.

About 75 minutes
04

Second estate

Another family, another style. Shops ship to the US and Europe if you fall for a bottle.

About 75 minutes

Plan your trip

Plan your Chianti day

Season, prices, age and alcohol rules, and what a tasting includes: one tab each.

  • April to June: green vines, wild flowers and mild days. Our favourite time to go.
  • July and August: hot in the hills; pick a morning tour or one with a shaded lunch.
  • Mid-September to early October: the Sangiovese harvest. Busy cellars, crates of grapes, golden light.
  • November: olive harvest and new oil; vines turn red and gold.
  • December to March: quieter, cooler, fewer departures. Some estates shorten their hours.
  • E-bike day: from $51 self-guided; the guided option adds the winery lunch and tastings.
  • Half-day coach tour, two wineries: from $62 (on sale for $53 until 31 October 2026).
  • Full day with Siena and San Gimignano: from $74.
  • Vespa, olive oil trail, small-group Classico and Fiat 500: $118 to $170.
  • Semi-private day with lunch $237; private car and driver $487 per person.
  • You must be 18 to be served wine in Italy. Children join most tours at a lower price.
  • Italy's blood alcohol limit is 0.5 g/l, and zero for drivers with a licence under three years.
  • Vespa drivers must be 18 with a car licence; passengers from 12 or 13 depending on the option.
  • Wineries sit on hills with gravel paths: the Gray Line half day is listed as not wheelchair accessible.
  • Most tastings pour a young Chianti Classico, a Riserva and often a Super Tuscan blend.
  • Pours are small, around a few sips each. Six to eight make a relaxed afternoon, not a party.
  • Food is usually pecorino, salami, bruschetta and the estate's olive oil.
  • Vin Santo with cantucci sometimes closes the tasting. More in the price and tasting guide.
Greve in ChiantiAbout 45 minThe Chianti Classico market town on the SR222, with wine shops around its arcaded square.
CastellinaAbout 30 minA walled hill town on the Siena side of the zone, the first stop on the half day from Siena.
San GimignanoAbout 1 hourMedieval towers and white Vernaccia, outside the Classico zone.
In the glass6 to 8 winesThe number to compare on a half day, not just the trip length.
IncludedTransportEvery tour here except the Greve winery visit includes the ride to the wineries.
Refund24 hoursFree cancellation a day before, except on the private tour.

Where it happens

Where the wineries are

South of Florence, north of Siena

Coach tours: Piazzale Montelungo, beside Santa Maria Novella station, Florence

The Chianti Classico hills start about 20 km south of Florence and run almost to the walls of Siena. The SR222 Chiantigiana road threads through them via Greve, Panzano and Castellina. Tours from Florence reach the first estates in 40 to 60 minutes; from Siena, Castellina is about half an hour away.

  • Florence to Greve in Chianti: about 45 minutes
  • Siena to Castellina in Chianti: about 30 minutes
  • Florence to San Gimignano: about 1 hour
Getting there without a tour

Around your trip

Everything else worth knowing

Timing, what guests wish they had known, the Classico question and the fine print.

  • Late September: harvest week in many estates. Book early; it is the busiest time.
  • May and June: long, mild days and green hills. The best light for photos.
  • Afternoon departures: the half days often leave after lunch and come back for dinner in Florence.
  • Expo del Chianti Classico: Greve's wine fair in early September (10 to 13 September in 2026).
  • Eat before a half day: snacks come with the wine, but it is not lunch.
  • Use the bathroom before the coach leaves; the ride is about an hour each way, guests warn.
  • Want to buy wine? Most estates ship. Ask the price of shipping before you fill a box.
  • Wear flat shoes. Wineries sit on hilltops and the visit often starts with a walk down the rows.
  • Small vans fill first in September. Book two to three weeks ahead for harvest dates.
  • Chianti Classico: the zone between Florence and Siena, black rooster seal, at least 80% Sangiovese.
  • Chianti: a wider area with eight subzones, such as Colli Senesi near San Gimignano and Rufina east of Florence.
  • San Gimignano's own wine is the white Vernaccia; Super Tuscans are blends sold as Toscana IGT.
  • Full story in Chianti vs Chianti Classico.
  • Almost every tour here cancels free up to 24 hours before. The private tour does not.
  • Tastings run in light rain; a cellar is the best place to be in a shower.
  • The Vespa and e-bike days depend on dry roads; the operator moves or refunds you if it is unsafe.
  • Summer afternoons reach the low 30s °C in the hills. Bring water and a hat for the vineyard walk.

Chianti, Tuscany

Cypress, vines and a glass of Sangiovese.

Pick the tour, then pick your date.

Check availability

Guest reviews

What tasters say

4.5 ★★★★★
4,763 reviews · Half-day Chianti tasting at two wineries
Viator and Tripadvisor rating
★★★★★

Great experience in Toscana, the tour guide Alessandra was great, we visited two vineyards, test wines and food, and the beautiful landscape of Chianti.

Jorge · Half-day tasting at two wineries, Oct 2025
★★★★★

We visited 2 wineries and found the level of information, food/lunch superb and wines extremely interesting. We also visited San Girimingao loved it. Couldn’t ask for a better trip.

Joanne · Semi-private Chianti day, Feb 2026
★★★★★

A truly fantastic tour! Giulia was so knowledgeable, friendly, and made the whole experience great from start to finish. This was very well organized and a highlight of our time in Florence.

Christine · Chianti Vespa tour, Jul 2025
★★★★★

Love the 3 cities we visited and the wine tasting was marvellous. The day went by so smooth and in each city we had time to explore, eat and felt no rush.

Grace · Siena, San Gimignano and Chianti day, Apr 2026
★★★★★

Phenomenal experience with 2 very different wineries. Would recommend this to anyone. Everything ran like clockwork and would definitely do this tour again.

John · Half-day tasting at two wineries, Oct 2024
★★★★★

Peter was wonderful & very kind. Knowledgeable and a wine lover. The three wineries we toured were full of charm and friendly staff & sommeliers.

Stephanie · Wine and olive oil trail, May 2025
★★★★★

We drove the Vespa’s to a few beautiful view points, stopped in a beautiful quaint town to explore, and enjoyed an amazing dinner at the winery after our wine and olive oil tasting.

Meghan · Chianti Vespa tour, Jul 2024
★★★★★

Excellent experience for seeing the Chianti countryside and vineyards. Top tier wine tour with a local guide eager to share Tuscan history.

Derek · Semi-private Chianti day, Sep 2024
★★★★★

Amazing! Wine tastings were great! Our driver, Tommaso, was charming, respectful & professional, highly recommend!

Already in the hills

Book the winery itself

Staying in a Chianti farmhouse, or riding the bus to Greve? A winery visit on its own is cheaper than any tour.

Greve in Chianti Winery Tour & Tasting

Greve in Chianti Winery Tour & Tasting

★ 4.7 · 1.5 hours

Staying in the hills, or happy to take the 365 bus to Greve? Skip the coach and book the winery itself. You get the cellar, the vineyard walk and the tasting, and you choose your own time to arrive.

Family estateCellar visitNo transport

From$57per personReserve

The guide

Chianti wine tasting, explained

Every Chianti tour photo shows the same cypress road and the same glass of red. The days behind them are quite different. Here is how to read them.

The wine

Chianti is Sangiovese country. In the Classico zone the grape makes up at least 80% of the blend, and many estates now go to 100%. Expect three levels at a tasting: the young Chianti Classico, released about a year after the harvest; the Riserva, aged at least 24 months; and sometimes a Gran Selezione, the top tier, aged at least 30 months and made from the estate's own grapes. Many wineries also pour a Super Tuscan, a blend with Cabernet or Merlot sold as Toscana IGT because it breaks the Chianti rules.

The black rooster on the neck of the bottle is the mark of the Chianti Classico consortium. The story goes back to a medieval race between horsemen from Florence and Siena; the zone's borders go back to a 1716 edict of Cosimo III de' Medici. If you see "Chianti" with no rooster, it comes from the wider area around it.

Large oak casks along a stone wall in a Chianti winery, with a glass of red wine on a barrel
Big old casks soften Sangiovese without the vanilla of new oak.

Two wineries, small pours

A half-day tour visits two estates, usually small family farms that host groups every day. At each you walk the vines and the barrel room for twenty minutes or so, then sit down to three or four wines with pecorino, salami, bruschetta and the farm's olive oil. Pours are tasting size. Six to eight of them over an afternoon is pleasant, not heavy, and you will not need dinner reservations moved. If you want lunch, choose a tour that says lunch: the Vespa day, the e-bike day, the olive oil trail or the small-van day.

The honest small print: "Chianti" in a tour title does not always mean the Chianti Classico zone. Two cheap half days from Florence taste near San Gimignano, and the town-hopping day spends most of its time in Siena and San Gimignano with a single tasting. Each of our tour pages lists the real stops.

Half day, full day, or on your own

A half day suits most people: two wineries, the drive through the hills, back for dinner in Florence. A full day adds either towns or a long lunch and a third winery. If you have a car and a sober driver, or you are happy to ride bus 365 to Greve in Chianti, you can book tastings straight with estates: Antinori's cellar at Bargino sells a four-wine tasting for EUR 30, and plenty of smaller farms charge less. Our half day or full day guide lays out each option.

A Tuscan farm lunch of pici pasta, salad, crostini and red wine on a terrace above the vineyards
Lunch at the farm is the main reason to pick a full day.

Timing it

Late spring is green and mild. The harvest runs from mid-September into the first week of October, when cellars smell of crushed grapes and crates line the rows. November brings the olive harvest and new oil. July and August are hot, so a late-afternoon departure or a shady lunch helps. Whatever the month, book a few days ahead, and two to three weeks ahead for small vans in September.

Red crates full of dark Sangiovese grapes between vineyard rows at harvest time
Sangiovese ripens late: most of Chianti picks from mid-September.

Compare the tours

Guides

Plan it properly

In-depth guides to the questions people ask most before booking. See all guides.

From the blog

This season in Chianti

Season news, rule changes and what is new. All posts.

FAQ

Questions before you book

Straight answers to what people ask most about Chianti wine tours.

How much does a Chianti wine tour from Florence cost?

A shared half-day coach tour with two wineries starts at $62 per person online, and self-guided e-bikes at $51. Small-group minivan tours run $120 to $240, and a private car with driver about $490 per person. If you get to the estate yourself, a tasting alone costs roughly EUR 15 to 70. The price guide breaks it down.

What is the difference between Chianti and Chianti Classico?

Chianti Classico is the historic heart between Florence and Siena, around Greve, Panzano, Castellina, Radda and Gaiole, with the black rooster seal on every bottle and at least 80% Sangiovese. Plain Chianti comes from a much larger area around it, with eight subzones and looser rules. Read Chianti vs Chianti Classico.

Do Chianti wine tours actually go to the Chianti Classico area?

Not all of them. Some cheap half-days from Florence taste near San Gimignano, which is Vernaccia and Chianti Colli Senesi country, and the e-bike day rides the hills around Impruneta. The Gray Line half day drives the Chiantigiana through Greve, but guests name its second estate as Poggio ai Laghi near Monteriggioni, just outside. The private tour and the Fiat 500 lunch at Castellina stay inside. Check the stops on each tour page.

How many wines do you taste on a Chianti tour?

Usually six to eight. The two-winery half days pour three or four wines at each stop, with cheese, salami and bruschetta. The full-day Siena and San Gimignano tour has one winery and two or three wines. One guest summed it up: about 8 wines, all lovely.

Is lunch included on a Chianti wine tour?

Only on some. The half-day coach tours serve snacks with the tastings, not a meal, and the full-day town tour leaves lunch to you. The Vespa tour, the e-bike day, the semi-private day and the olive oil trail include a proper lunch at a farm or winery.

Half day or full day for Chianti?

A half day (five to five and a half hours) gives you two wineries and the drive through the hills, and leaves your evening in Florence free. A full day either adds towns like Siena and San Gimignano, with less wine, or adds a long lunch and a third estate. See half day or full day.

Can I visit Chianti wineries without a tour?

Yes. Autolinee Toscane bus 365 runs from Florence to Greve in Chianti, where you can taste at a wine shop or walk to a nearby estate, and some wineries such as Antinori in Bargino sell tastings online. Driving yourself is the hard part: Italy's limit is 0.5 g/l, and zero for drivers with a licence under three years. See Chianti without a car.

When is the best time for a Chianti wine tour?

May, June, September and October. The harvest runs from mid-September into early October, the hills are green in late spring, and July and August are hot. In winter most tours still run, but some estates cut their hours. More in the best time to go.

Where do Chianti tours from Florence start?

The coach tours meet at Piazzale Montelungo, a short walk from Santa Maria Novella station. The Vespa and olive oil tours meet at Via dei Vagellai near Santa Croce, the small-group Classico van at Porta Romana, and the semi-private and private tours pick you up at your hotel.

Can children join a Chianti wine tour?

On the coach tours, yes, with a child discount, but only adults taste: Italy does not serve alcohol to under-18s. A full day with three towns suits families better than a winery-only half day. On the Vespa tour drivers must be 18 with a car licence, and kids ride as passengers.

Can I cancel a Chianti wine tour?

Every tour here cancels free up to 24 hours before the start, except the private Chianti tour, which is non-refundable. Book that one only when your dates are fixed.

Ready to book

Pick your tour, pour the first glass.

Transport from Florence or Siena included, and free cancellation up to 24 hours before on almost every tour.

Some links are affiliate links; see our disclosure.