Best Wine Tours from Florence: Chianti, Montalcino and Montepulciano Compared

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Florence is the easiest base in Italy for a wine day trip. Chianti starts where the city ends, and Montalcino and Montepulciano, home of Brunello and Vino Nobile, are close enough for a long day out. The question is not whether to go, but which tour fits the time you have and the wines you want to taste.

This guide compares four well-organised group tours that leave from central Florence, from a relaxed afternoon in Chianti to a full day in the Val d’Orcia, and explains when it is worth going on your own instead.

Tuscan Wine in Two Minutes

Almost every tour from Florence revolves around one grape: Sangiovese. What changes is where it grows and how it is made.

• Chianti Classico: the historic heart of Chianti between Florence and Siena, recognisable by the black rooster on the bottle neck. Bright, savoury reds made mainly from Sangiovese.
• Chianti: the wider appellation around the Classico zone, including sub-zones such as Rùfina, east of Florence.
• Brunello di Montalcino: made entirely from Sangiovese in the hills around Montalcino and aged for several years before release. Powerful, long-lived and one of Italy’s most prestigious reds.
• Vino Nobile di Montepulciano: based on Sangiovese, grown around the hill town of Montepulciano. Often softer and more approachable young than Brunello.
• Vin Santo: Tuscany’s traditional sweet wine, made from dried grapes and served at the end of a meal, often with cantucci almond biscuits.

Our overview of Tuscany’s wine country goes into each zone in more detail.

The Four Tours Compared

Tour	Duration	Meeting point	Wine	Food
Chianti afternoon, 7 wines	about 5 hours, from 14:00	Santa Maria Novella station	7 wines incl. sparkling and vin santo, plus olive oil	Tasting plates, no lunch
Chianti afternoon, two wineries	about 5.5 hours, from 14:45	Villa Costanza coach station (tram T1)	Tasting with local products	No lunch
Montalcino, Pienza and Montepulciano	about 11.5 hours, from 07:45	Piazzale Montelungo	Brunello and Vino Nobile at two wineries	Pecorino tasting, lunch not included
Siena, San Gimignano and Pisa	about 12 hours, from 08:00	Santa Maria Novella station	Local wines at a winery near San Gimignano	Tuscan lunch included

All four are shared group tours with a guide and air-conditioned transport. Prices change by season and date, so check the current rate on the booking page.

Chianti in an Afternoon

If you have one free afternoon, go to Chianti. It is the closest wine region to Florence, and an afternoon tour leaves your morning free for the Uffizi or the Duomo. For background on the region before you go, read our guide to Chianti Classico.

The 7-wine tour meets inside Santa Maria Novella station, which makes it the simplest option if you are staying in the centre. It starts with a glass of sparkling wine and a guided walk through the vineyard, continues with a visit to a cellar producing balsamic vinegar and vin santo, and ends with a seated tasting of seven wines, from white and sparkling to red and vin santo, paired with cured meats, cheese and olive oil. Departure times are strict, so arrive 20 minutes early. Book here: Chianti wine tour with tasting from Florence.

The two-winery tour meets at the Villa Costanza coach station in Scandicci, about 20 minutes from the centre on tram T1. The first stop is a small, lesser-known estate with a cellar visit; the second is a medieval hamlet in the Chianti hills, with time to walk and buy local products. Cancellation is free up to 24 hours before. Book here: Chianti day trip with two wineries.

Brunello and Vino Nobile in One Day

For wine lovers, this is the tour that matters. Brunello di Montalcino is made entirely from Sangiovese and is one of Italy’s most collected red wines; Vino Nobile di Montepulciano, also based on Sangiovese, is its softer, often better-value neighbour. Our guides to Montalcino and Montepulciano explain the difference in detail.

The Val d’Orcia day trip from Florence leaves Piazzale Montelungo, a short walk from Santa Maria Novella, at 07:45. After about two hours on the road it reaches Montalcino for a guided cellar visit and Brunello tasting, then continues to Pienza for free time and its local pecorino cheese, and finishes in Montepulciano with a winery visit and a Vino Nobile tasting. You are back in Florence in the evening. Lunch is not included, so plan it during the free time in Pienza. Cancellation is free up to 72 hours before.

It is a long day with a lot of driving, but it is an efficient way to taste both of southern Tuscany’s great reds in one trip without a car.

Wine with the Highlights: Siena, San Gimignano and Pisa

If this is your first time in Tuscany and wine is only part of the plan, the Siena, San Gimignano and Pisa day trip with lunch at a winery covers the region’s best-known towns and still gives you a proper tasting. The day starts with a two-hour guided visit to Siena, including Piazza del Campo and the Duomo, then stops at a winery near San Gimignano for a tasting and a Tuscan lunch with homemade pasta, cured meats and cheese. After free time in San Gimignano, the tour ends with an hour and a quarter in Pisa for the Leaning Tower. Expect a 12-hour day.

More Ways to Taste: Dinner Tours and San Gimignano

Two other formats are worth knowing about. Evening tours, such as the Chianti day trip with dinner at a vineyard, leave Florence in the afternoon and end with a meal among the vines, a good choice in summer when the days are long and hot. And if you are drawn more to towns than to cellars, the San Gimignano day trip with wine tasting and lunch combines the famous medieval towers with a winery stop and a Tuscan lunch; San Gimignano is also known for its white wine, Vernaccia di San Gimignano.

What to Expect at a Tasting

A typical winery visit starts outdoors among the vines, moves into the cellar, often with barrels of different sizes and sometimes an old vinsantaia where grapes dry for Vin Santo, and ends at a table with three to seven wines and local food: pecorino, salami, finocchiona, bread and new-season olive oil. Pours are small, but they add up over two wineries, so eat what is offered and drink water between glasses.

Do not feel obliged to buy, but if you find a wine you love, small producers often sell bottles that are hard to find at home, and many can ship abroad.

Group Tour, Private Tour or Driver?

• Group tour: the best value and the least planning. You share the bus and the tasting room, and the wineries are chosen for you.
• Private tour: a guide and driver for your group alone, with wineries chosen around your taste. Ideal for couples celebrating or serious wine lovers.
• Private driver only: you book the wineries yourself and the driver takes care of the roads. The most flexible option if you already know which estates you want to visit.

Should You Go Without a Tour?

Many Chianti estates accept visitors by appointment, and driving the roads between Greve, Panzano and Castellina is part of the pleasure. The problem is the tasting: someone has to drive. A tour solves that, and the larger estates on the group itineraries are usually well set up for visitors. If you prefer small family producers or want to taste Chianti Rùfina, which few group tours cover, hire a private driver for the day and book the wineries directly.

Tips for Your Wine Day

• Afternoon or full day: the Chianti tours suit a short stay; the Montalcino and Montepulciano tour is worth a dedicated day.
• Check the meeting point: the tours leave from three different places, and only one meets inside Santa Maria Novella station. Allow time to get there.
• Eat before the tasting: the afternoon tours serve tasting plates, not a meal.
• Shipping wine home: many wineries ship abroad. Ask at the tasting rather than carrying bottles all day.

Visiting the north as well? Our guide to Franciacorta wine tours from Milan covers Italy’s answer to Champagne.

For a powerful red to compare with Brunello, read our guide to Amarone and the Valpolicella.

Frequently Asked Questions

Which wine region is closest to Florence?

Chianti. The vineyards begin a short drive south of the city, which is why half-day Chianti tours are possible.

Is Montalcino too far for a day trip?

No, but it is a long day. Expect around two hours on the road each way, which is why the Val d’Orcia tours leave early and return in the evening.

Should I choose Chianti or Brunello?

For a first taste of Tuscan wine and a shorter day, choose Chianti. If you already love Italian red wine and want to taste its most famous expression, go to Montalcino.

When is the best time for a wine tour?

Spring and autumn are the most pleasant. September and October bring the harvest, when the vineyards are at their busiest and most atmospheric.

Are wine tours suitable for non-drinkers?

Yes. The vineyards, villages and food are half the experience, and many tastings include olive oil and local products.

Plan the Rest of Your Stay

Arriving by air? A pre-booked private transfer from Florence Airport gets you to your hotel without a taxi queue, and an eSIM for Italy keeps you connected for maps and tickets. For where to stay, see our guide to the best luxury hotels in Florence, and for wine in the city itself, read Florence and wine. Our overview of Tuscany’s wine country and the complete guide to Italian wine regions put each of these areas in context.

Related guides: read our articles on Florence museum tickets, the best day trips from Florence, a Val d’Orcia road trip and San Gimignano.

Golfers should also read our guide to golf in Tuscany.

Hungry? See our guide to where and what to eat in Florence.