16 small-group food tours in 12 destinations

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Autumn vines running down to a stone farmhouse among cypresses in the Chianti hills of Tuscany

Italy · 1 tour

Florence food tours, then Chianti and Montalcino

Lampredotto at a Florence market kiosk, a bistecca in Panzano, Chianti Classico and Brunello in the cellars where they age, and pici rolled by hand near Pienza. Seven days from the city to the Val d’Orcia.

Tours
1, from $4,190
Places we eat
4
Best months
April to June and September to November
Group size
12 guests at most

Chianti vineyards in autumn

Overview

Eating in Tuscany with us

Tuscan food is country food: unsalted bread, beans, green olive oil, grilled beef, sheep’s cheese and pasta rolled by hand. The wine is mostly Sangiovese, and it changes character from the hills of Chianti to the warmer slopes of Montalcino. Nothing about it is complicated, which is why the quality of each ingredient matters so much.

Our tour starts in the markets of Florence, then moves to Panzano, a hill village in the heart of Chianti Classico, and south to Montalcino and Pienza in the Val d’Orcia. Chiara Bertini, a Florentine who trained as a cook and worked harvests in both wine zones, hosts.

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1 tour · prices per person

Tuscany food tours for 2026 and 2027

All 16 tours
Sliced rare bistecca alla fiorentina with rosemary, white beans and red wine in Tuscany

Tuscany

Tuscany: Florence, Chianti and Brunello Country

  • 7 days
  • 12 guests max
  • Easy pace

Florence · Panzano · Montalcino · Pienza

  • Florence markets, lampredotto and schiacciata
  • Bistecca in Panzano and Chianti Classico tastings
  • Brunello in Montalcino and a pici class near Pienza

WineCookingProducers

From$4,190per person, double room, most meals

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4 places

Where we eat in Tuscany: the stops

Artichokes, cavolo nero, mushrooms and persimmons on a produce stall in the Mercato Centrale, Florence
Mercato Centrale, Florence

01

Florence: lampredotto and the market halls

Florence eats at its markets. The Mercato Centrale in San Lorenzo, a cast-iron hall from 1874, has butchers, tripe sellers and cheese stalls on the ground floor, and Sant’Ambrogio across town is where Florentines buy their vegetables. The city’s street food is lampredotto, the fourth stomach of the cow, simmered with herbs and served in a roll with green sauce from a kiosk. Bakeries sell schiacciata, flat, oily bread, filled with finocchiona salami. Look for the small wine windows in old palazzo walls, once used to sell wine by the flask. Our tour spends two nights here, near Santa Croce.

  • Lampredotto from a tripe kiosk
  • The Mercato Centrale and Sant’Ambrogio market
  • Schiacciata with finocchiona

Best monthsApril to June, September to November

Tours that visit Florence

The hill village of Panzano in Chianti above morning mist, with grapevines in the foreground
Panzano in Chianti

02

Chianti and Panzano: bistecca and Chianti Classico

Chianti is the hill country between Florence and Siena, with woods, olive groves and vineyards on the slopes, and stone villages along the Chiantigiana road. Chianti Classico, with the black rooster on the neck, must be at least 80 percent Sangiovese and comes only from this zone. Greve has an arcaded market square, and Panzano sits above the Conca d’Oro, a bowl of vineyards facing south. The village is also known for its butchers, and a bistecca alla fiorentina, cut thick and cooked rare over coals, is the classic lunch here. Our tour spends two nights in Chianti, with an olive oil farm and two estates.

  • Bistecca alla fiorentina in Panzano
  • Chianti Classico in the Conca d’Oro
  • An olive oil farm and mill

Best monthsMay, June, September and October

Tours that visit Chianti and Panzano

Montalcino and its fortress on a hilltop above olive groves and autumn vineyards at sunset
Montalcino, Brunello country

03

Montalcino: Brunello estates

Montalcino is a walled hilltop town south of Siena, with a fortress at the top and vineyards on every side. Brunello di Montalcino is made from Sangiovese alone and released no sooner than five years after the harvest, with at least two of those years in wood. Rosso di Montalcino, from the same grape, is younger and easier to drink with lunch. The estates range from large houses to small family cellars, and we visit one of each. Nearby is the Romanesque abbey of Sant’Antimo, where monks still sing the offices. Harvest is usually late September to mid-October.

  • Two Brunello estates, one large and one family-run
  • The fortress of Montalcino
  • The abbey of Sant’Antimo

Best monthsMay, June, September and October

Tours that visit Montalcino

Wheels of pecorino with red, ash and leaf rinds on shelves in a Pienza shop
Pecorino shop, Pienza

04

Pienza: pecorino and hand-rolled pici

The Val d’Orcia is the Tuscany of postcards: bare rolling hills, cypress lines and farmhouses on the ridges, protected as a UNESCO World Heritage landscape. Pienza was rebuilt in the 1460s by Pope Pius II as an ideal Renaissance town, and today its streets smell of pecorino. The sheep’s cheese is sold fresh, semi-aged or aged under walnut leaves or ash. This is also pici country: thick, hand-rolled spaghetti made from flour and water, served with a garlicky tomato sauce or ragù. Our tour spends two nights in the valley, with a sheep farm visit and a pici class.

  • Pecorino at a sheep farm
  • A hands-on pici class
  • The UNESCO landscape of the Val d’Orcia

Best monthsMay, June, September and October

Tours that visit Pienza and the Val d’Orcia

Ways to go

Ways to eat Tuscany with us

01

Seven days, city to valley

Tuscany: Florence, Chianti and Brunello Country spends two nights each in Florence, Chianti and the Val d’Orcia, with the markets, a butcher’s lunch in Panzano, four estate tastings, a pecorino farm and a pici class.

02

Add Bologna

Bologna is under forty minutes from Florence by fast train. Arrive a day early or stay a day longer and join the Bologna Pasta Class and Market Walk, or follow the Tuscany tour with six days in Emilia-Romagna.

03

A private Tuscany

Groups of six or more can run the tour on their own dates, add a night in Siena or a truffle day in November, or stay longer in one farmhouse. Grant Mosley plans private groups.

What’s included

What our Tuscany tours include

The seven-day tour includes hotels in Florence, Chianti and the Val d’Orcia with breakfast, the lunches and dinners listed, the Florence market walk, four wine estate visits and wine with included meals for guests 18 and over, olive oil and pecorino farms, the pici class, the van and airport transfers at group times, and Chiara or another host.

  • Central hotels with breakfast daily on multi-day tours
  • A host from the first evening to the last morning
  • The meals, tastings and classes listed on each tour
  • Transport between stops and airport transfers at group times

Not included: flights to the start city, travel insurance, the meals not listed, tips. Alcohol only for guests 18 and over, the legal drinking age in Italy. Full list

When to go

When to eat in Tuscany

Spring and autumn are the best times for Tuscany. May and June bring green hills, poppies in the Val d’Orcia and long evenings for dinner outside. September and October are harvest months in Chianti and Montalcino, with grapes on the vines and cellars at work. November is quieter and cooler, with the olive harvest, new oil on every table and truffles in the Crete Senesi. July and August are hot and Florence is crowded, so we do not run then, and winter is cold in the hills.

  1. Jan: quieter or off season
  2. Feb: quieter or off season
  3. Mar: quieter or off season
  4. Apr: best months
  5. May: best months
  6. Jun: best months
  7. Jul: quieter or off season
  8. Aug: quieter or off season
  9. Sep: best months
  10. Oct: best months
  11. Nov: best months
  12. Dec: quieter or off season

Before you book

Tuscany food tour FAQs

Ask Lena directly

Lena Ortiz in reservations replies within one working day, Monday to Friday.

Which tour do you run in Tuscany?

Tuscany: Florence, Chianti and Brunello Country, seven days with two nights each in Florence, Chianti and the Val d’Orcia.

Is there a cooking class?

Yes. Day 6 is a hands-on pici class in a farmhouse near Pienza, and dinner that night is what you made.

Can I add a pasta class in Bologna?

Easily. Take a fast train to Bologna for the Bologna Pasta Class and Market Walk the day before or after the tour.

Is there time to see Florence’s museums?

Day 2 has a free afternoon, and the Uffizi and the Accademia are a short walk from the hotel. Book museum tickets online before you travel.

Can vegetarians join?

Yes. Tuscan food has bean soups, pecorino, pici and vegetable dishes, and we plan a separate plate at the butcher’s lunch.

Are wine tastings included?

Four estate tastings and wine with included meals, for guests 18 and over, always with a non-alcoholic option.

More destinations

After Tuscany: where to eat next

All 12 destinations

Dates and seats

Ask about Tuscany

Tell us which tour, roughly when and how many of you. Lena Ortiz in reservations replies within one working day with dates, seats, the price and how we can handle any dietary needs.

Lena, Grant and Priya, Charleston

To[email protected]

SubjectTuscany: Florence, Chianti and Brunello Country: dates and seats

Please include

  • Tour: Tuscany: Florence, Chianti and Brunello Country
  • Date
  • Guests (all 18 or over?)
  • Room type (double, twin or single)
  • Dietary needs or allergies
  • Message
  • Your name, email and a phone number
Write to Lena

Lena Ortiz in reservations replies within one working day. No payment now. A $300 deposit per person holds seats on a multi-day tour; day tours are paid when you book.

Ask about dates