A private villa in Florence Countryside and Chianti
The Hidden Voyage guide

Florence Countryside and Chianti

Vineyards, cypresses and stone farmhouses between Florence and Siena.

Best months
May, Jun, Sep, Oct
Ideal stay
7 nights
Fly into
FLR · PSA · BLQ · FCO
Getting around
Car essential, or driver for tasting days
Our villas here
94 private villas
Why go

Why choose Florence Countryside and Chianti

Between Florence and Siena lies the landscape most people picture when they dream of Tuscany: vine rows combed across the slopes, silver olive groves, cypress avenues leading to stone farmhouses and castle estates that have made wine for centuries. The Chianti Classico hills are close enough to Florence for an evening at the opera, yet the nights are dark, quiet and scented with rosemary.

This is country for slow days. Mornings start with a walk between vineyards, afternoons with a tasting in a cellar beneath a medieval tower, and evenings with dinner under a pergola. It suits families gathering for a milestone, friends who love wine and food, and anyone who wants Florence and Siena within easy reach of a private retreat.

Ideal for: Large families and groups, Weddings, Food and wine · Relaxed, rural and wine focused

Our villas of the month · October 2026

Chosen this month by our team

Getting there

Airports and arrivals

FLR
Florence Airport (Amerigo Vespucci, Peretola)
about 40 minutes by car to Greve in Chianti

closest airport to the northern Chianti villages

PSA
Pisa International (Galileo Galilei)
about 1h30 by car to Greve in Chianti

wide choice of European and seasonal routes

BLQ
Bologna Guglielmo Marconi
about 1h45 by car to Greve in Chianti

good for long haul connections

FCO
Rome Fiumicino (Leonardo da Vinci)
about 3h by car to southern Chianti

practical when combining Rome and Tuscany

  • High speed trains reach Firenze Santa Maria Novella from Rome in about 1h35 and from Milan in just under 2h, with a car or driver then needed to reach the hills.
  • The SR222 Chiantigiana road links Florence with Siena through Greve, Panzano and Castellina in Chianti.
  • The Florence to Siena motorway (Raccordo Autostradale) offers a faster route to the western side of the region.
  • Private transfers by car with driver are recommended, especially for wine tasting days.

We arrange private transfers, drivers, boats and helicopters for every villa.

Where to stay

Choosing your base

Greve in Chianti
Families, first time visitors

A lively market town with an arcaded, funnel shaped piazza and the region's main wine fair.

Panzano in Chianti
Food lovers, couples

A small hilltop village above the Conca d'Oro, a natural amphitheatre of vineyards with some of the finest Sangiovese.

Radda in Chianti
Walkers, wine enthusiasts

A compact walled village at the heart of the old Chianti League, cool in summer and surrounded by woods.

Castellina in Chianti
Couples, touring Siena and Chianti

A fortified village with a covered medieval passageway along its walls, well placed for Siena.

Gaiole in Chianti
Privacy, cyclists, castle lovers

Gateway to the castles of Brolio, Meleto and Vertine, set among thick oak forests.

San Casciano and the Florentine hills
Families, short transfers to Florence

Gentle countryside just south of Florence, ideal for combining villa life with city days.

Positions are approximate: the exact address is shared once your stay is confirmed.

What to see

The highlights

01
Piazza Matteotti, Greve in Chianti

The town's triangular arcaded square is lined with butchers, wine shops and cafés. Saturday morning brings the weekly market.

02
Badia a Passignano

An eleventh century Vallombrosan abbey rising from vineyards, with towers and cypresses that look almost theatrical. The monastery refectory holds a Last Supper fresco by Domenico and Davide Ghirlandaio.

03
Castello di Brolio

The ancestral seat of the Ricasoli family, where Baron Bettino Ricasoli set down an early formula for Chianti wine in the nineteenth century. The gardens and ramparts look out over vineyards towards Siena.

04
Volpaia

A tiny fortified hamlet above Radda, where cellars and a winery are hidden inside medieval buildings and a deconsecrated church.

05
Montefioralle

A ring shaped walled hamlet above Greve, among the best preserved in the region and wonderful for a short evening stroll.

06
Conca d'Oro, Panzano

A golden bowl of vineyards below Panzano, at its most beautiful in October when leaves turn copper and amber.

07
San Gimignano

On the western edge of the region, this UNESCO listed town preserves fourteen of its medieval towers. Visit late in the day once coach groups have left.

What to do

Experiences worth planning for

Private cellar tastings

Tour historic estates and small family wineries, tasting Chianti Classico Riserva and Gran Selezione with the people who make them.

Olive oil harvest

Join the pressing in late October and November and taste peppery new oil straight from the mill on toasted bread.

Truffle hunting with a trufflehunter and dog

Search the woods for seasonal truffles, then cook them simply with eggs or fresh pasta.

Cycling the white roads

Ride the gravel strade bianche between villages on an e bike or road bike, with luggage and tastings arranged along the way.

Hot air balloon at dawn

Drift above vineyards and castles as the morning mist lifts from the valleys.

Butchery and grill masterclass

Learn the art of the Florentine steak from a local butcher and grill it yourself over olive wood.

Outdoors

Nature and walks

Montefioralle to Pieve di San Cresci walk

A short, gentle hike from Greve's hilltop hamlet to a Romanesque parish church.

Radda to Volpaia path

A woodland and vineyard trail linking two of the most atmospheric villages.

Monti del Chianti

The wooded ridge east of Greve and Radda, cool in summer and rich in wild boar and chestnut trees.

Bosco di Sant'Agnese

Ancient woodland near Castellina with marked trails and quiet clearings.

Where to stay

Private villas in Florence Countryside and Chianti

See all 94 villas in Florence Countryside and Chianti

At the table

Food and wine

What to eat

Finocchiona IGP

A soft Tuscan salami flavoured with wild fennel seeds, sliced thickly on unsalted bread.

Bistecca alla fiorentina

The great Tuscan steak, served rare and generously shared at the table.

Chianti Classico DOP olive oil

Grassy, peppery extra virgin oil, at its finest when freshly pressed in November.

Cinta Senese

A native breed of black and white pig reared semi wild in the woods, prized for its cured meats.

Pappardelle al cinghiale

Wide ribbons of fresh pasta with a slow cooked wild boar sauce.

Peposo

A rustic, pepper rich beef stew traditionally cooked with red wine, linked to the kilns of Impruneta.

What to drink

Chianti Classico DOCG

Sangiovese at its most expressive, identified by the black rooster seal, with Annata, Riserva and Gran Selezione tiers.

Vin Santo del Chianti Classico DOC

A rich, amber sweet wine from dried grapes, the traditional close to a Tuscan meal.

Vernaccia di San Gimignano DOCG

A crisp white from the towered town on the region's western edge, Italy's first DOC wine in 1966.

Super Tuscans (Toscana IGT)

Many Chianti estates also produce celebrated blends with Cabernet or Merlot outside the DOCG rules.

Beyond the villa

Day trips

Florence
about 40 minutes by car from Greve

Renaissance masterpieces, artisan workshops and the Duomo.

Siena
about 40 minutes by car from Castellina

A Gothic city with one of Italy's most beautiful squares.

San Gimignano
about 45 minutes by car from Castellina

Medieval towers and Vernaccia wine on a ridge above the Val d'Elsa.

Monteriggioni
about 25 minutes by car from Castellina

A perfectly circular walled village crowned with towers, on the Via Francigena.

Volterra
about 1h15 by car from Castellina

An Etruscan city famous for alabaster carving and dramatic hilltop views.

When to go

The year, season by season

May, June, September and October. The harvest in September and October is magical. July and August are hot and perfect for life around the pool.

Spring

April and May bring wildflowers, poppies and fresh green vines, with cool evenings and quiet roads. It is ideal for walking and cycling.

Summer

Long, hot days are best spent by the pool, with tastings in the cool of the cellars and dinners outdoors. Hilltop villages stay pleasantly breezy at night.

Autumn

The harvest season is the region's finest moment, with golden light, busy cellars and new olive oil from late October. Book early for September and October.

Winter

Quiet and atmospheric, with misty mornings, fireplaces and hearty cooking. Some restaurants and wineries close or reduce hours between January and March.

Weather month by month

3h11°Jan4h13°Feb5h16°Mar6h20°Apr8h24°May9h29°Jun10h32°Jul9h32°Aug7h27°Sep5h22°Oct3h16°Nov3h11°Dec

Bars: hours of sunshine a day. Above: average daytime high. Shaded: the best months.

Full weather table
MonthJanFebMarAprMayJunJulAugSepOctNovDec
Daytime high, °C111316202429323227221611
Night low, °C235812161819151163
Sunshine, hours a day3456891097533
Rainy days87798534691010
Dry days242124212325282724222021

Air: averages 1991 to 2020, Florence Peretola weather station. Dry days have less than 1 mm of rain.

Events through the year

September
Expo del Chianti Classico
Greve's main square fills with producers pouring their wines over a long weekend, usually in the second week of September.
Early October
L'Eroica
A celebrated vintage cycling event based in Gaiole, where riders on period bikes and dress tackle the white gravel roads.
September and October
Grape harvest
The vendemmia transforms the estates, with picking, pressing and harvest lunches across the region.
Late May
Cantine Aperte
On this national open cellars weekend, many Chianti estates welcome visitors for tastings and tours.

Planning Florence Countryside and Chianti?

Tell us your dates and the group: we reply with availability and the full price, usually within one working day, and arrange transfers, chefs and boats.

See the villasPlan my stay
Good to know

Practical tips

  1. A car is essential; roads are winding and narrow, so allow more time than satellite navigation suggests and avoid driving after tastings by booking a driver.
  2. Most wineries require advance booking for tours and tastings, even small estates.
  3. Greve, Radda and Castellina have paid car parks just outside their centres; village cores are often restricted to residents.
  4. Supermarkets and shops are limited in the villages; stock up in Greve or on the outskirts of Florence and Siena.
  5. Sunday lunch is a long affair in Tuscany, and many country restaurants close on one weekday, so reserve ahead.
  6. Several villages also apply a small municipal tourist tax per person per night, collected by the property.
Questions

Florence Countryside and Chianti: frequently asked

What is the difference between Chianti and Chianti Classico?

Chianti Classico is the historic heartland between Florence and Siena, with its own DOCG and black rooster seal. Chianti DOCG covers a much wider area of Tuscany with different rules and several subzones.

Where is the best place to stay in Chianti?

Greve and Panzano are central and lively, Radda and Gaiole feel more remote and wooded, and Castellina is well placed for Siena. The countryside around San Casciano is ideal if you want frequent days in Florence.

How far is Chianti from Florence?

Greve in Chianti is about 40 minutes by car from Florence. The southern villages such as Gaiole and Castellina are around an hour away.

When is the best time to visit Chianti?

May, June, September and October are ideal. Autumn adds the grape harvest and the new olive oil season.

Can you visit wineries without a booking?

A few estates have wine shops open to walk in visitors, but most tours and seated tastings need a reservation, ideally several days ahead in high season.

Travel advisors, wedding and event planners

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