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Tuscany Wine Itinerary — 5 Days Through Chianti, Brunello & Vino Nobile

Florence, Chianti Classico, Brunello di Montalcino, Vino Nobile di Montepulciano and a San Gimignano finish — a five-day route you can actually book.

Or read the whole plan below — it’s all on this page.

Five days is the sweet spot for a first serious Tuscany wine trip. It is long enough to taste three of the four major appellations without rushing a single lunch — Chianti Classico in the hills south of Florence, Brunello di Montalcino, and Vino Nobile di Montepulciano — and it leaves room for one slower, non-wine afternoon in the Val d’Orcia. The shape is two bases: Florence for the first night, then a Montalcino or Val d’Orcia agriturismo for the southern Tuscany core.

Rent a car for days 2 to 5 — the estates are rural and the timetabled buses do not fit tasting appointments. Book the marquee cellars first: Antinori nel Chianti Classico and any Brunello visit (Biondi-Santi is the founding 1888 estate) want two to four weeks notice, more in autumn. Everything below is a real place you can reserve; each day carries a where-to-stay link and a wine-tours link so you can lock in lodging and a guided tasting as you read.

At a glance

Best months

April to October. Harvest energy in September and October; second week of October is the photographic peak.

Nearest airport

Florence (FLR) to start; Pisa (PSA) is handy if you continue to the coast. Both are about an hour from Chianti.

Getting around

Rental car for days 2–5 (pick up in Florence). One designated driver, or a hired wine-day driver for a couple who would rather not drive.

Budget

Roughly €130–220 per day mid-range, €70–110 budget, €350+ luxury, before flights.

Book these before you go

  • Antinori nel Chianti Classico (Day 2) — 2–3 weeks ahead via antinori.it; €35–€60 cellar tour and flight, often including Tignanello.
  • A Brunello estate in Montalcino (Day 3) — Biondi-Santi (the founding 1888 estate) takes ~4 weeks; €60–€120 vintage tasting on the terrace. Casanova di Neri or Il Poggione are 2-week alternatives.
  • Avignonesi in Montepulciano (Day 4) — 1–2 weeks ahead via avignonesi.it; €30–€50 for Vino Nobile and Vin Santo at Italy’s leading biodynamic estate.
  • Florence hotel for night 1 and a Val d’Orcia / Montalcino agriturismo for nights 2–4 — 2+ months ahead in peak season.
  • Rental car at Florence, picked up Day 2 — around 4 weeks ahead via Sixt, Hertz or Avis (the city depot is cheaper than the airport for a multi-day rental).

The 5 days plan

Day 1

Florence — orientation & a Sangiovese warm-up

Base: FlorenceOn foot — no driving today.

Land, settle into the city, and calibrate your palate to the Chianti Classico style before the estate visits begin.

  1. Duomo & the Oltrarno. Walk the Duomo and Baptistery to get your bearings, then cross to the Oltrarno for Piazza Santo Spirito and the Via Maggio leather workshops — today is for the city, not the wine.

  2. Le Volpi e l’Uva. Aperitivo at this Sangiovese-focused wine bar near the Ponte Vecchio; the by-the-glass list is the best way to learn the Chianti Classico style before tomorrow.

  3. Dinner with a bistecca. Il Latini or Trattoria Mario near the Mercato Centrale for a textbook bistecca alla Fiorentina and a short, well-aged Chianti list.

Where to stayFlorence (city centre)Wine tours & tastingsFlorence food & wine walks

Day 2

Chianti Classico — Greve, Panzano & the Antinori flagship

Base: Florence (last night) or first agriturismo nightFlorence → Antinori (Bargino) 30 min; → Panzano 15 min. Sleep in Florence again, or push on toward Montalcino if you prefer two southern nights.

Pick up the car and drop into the heart of Chianti Classico along the SR222, the road that strings the appellation together.

  1. Antinori nel Chianti Classico (Bargino). The family’s hillside flagship, 30 minutes south of Florence. The cellar tour ends with a flight that typically includes Tignanello; the Antinori family has made wine here since 1385.

  2. Panzano & Dario Cecchini. Lunch at Solociccia or Officina della Bistecca, the legendary Panzano butcher’s meat-focused tables — less precious than the Michelin route and a Chianti institution.

  3. Fontodi, Panzano. Afternoon visit to the benchmark 100% Sangiovese estate; the flight includes Flaccianello della Pieve, one of the original Super Tuscans.

Where to stayGreve in Chianti / PanzanoWine tours & tastingsChianti winery day trips

Day 3

Montalcino — Brunello & the Castello di Brolio crossing

Base: Val d’Orcia / Montalcino agriturismoFlorence area → Brolio ~75 min; Brolio → Montalcino ~75 min via the Siena bypass and SP14.

Cross south through the spiritual home of Chianti Classico to the hilltop fortress town of Brunello.

  1. Castello di Brolio (Gaiole). A morning stop at the 12th-century castle where Bettino Ricasoli formalised the original Chianti formula in 1872; the historic-cellar visit ends with the Gran Selezione.

  2. Montalcino & its fortress. Check into your Val d’Orcia agriturismo, then walk the medieval fortress in town for the view over the Brunello vineyards.

  3. Biondi-Santi. The afternoon Brunello appointment you booked weeks ago — a vintage tasting on the terrace at the founding 1888 estate, including library vintages. Budget two hours and stay sober enough to drive to dinner.

Where to stayMontalcino / Val d’OrciaWine tours & tastingsMontalcino Brunello tastings

Day 4

Montepulciano — Vino Nobile, with a Val d’Orcia afternoon

Base: Val d’Orcia / Montalcino agriturismo (last night)Montalcino → Montepulciano 30 min via SP146; loop back via Pienza and Sant’Antimo.

The third appellation, plus the Renaissance towns and pecorino that make the Val d’Orcia a UNESCO landscape.

  1. Avignonesi, Montepulciano. Italy’s leading biodynamic estate, with the most serious Vin Santo programme in Tuscany; taste Vino Nobile alongside it after walking the Piazza Grande.

  2. Pienza pecorino. Drive 30 minutes to Pienza for the most famous pecorino in Italy — a tasting at the main-piazza shops is the food highlight of the trip.

  3. Sant’Antimo Abbey. On the way back, the 12th-century Romanesque abbey is one of the most photographed buildings in Tuscany; time it for the late-afternoon office.

Where to stayMontepulciano / PienzaWine tours & tastingsMontepulciano & Val d’Orcia tours

Day 5

San Gimignano — Vernaccia & towers on the way out

Base: San Gimignano, then Florence or Pisa airportMontalcino area → San Gimignano ~1.5 hr; San Gimignano → Pisa (PSA) ~1 hr or Florence (FLR) ~1 hr.

A white-wine coda and the towers everyone photographs, positioned for an easy run back to the airport.

  1. San Gimignano towers. The medieval skyline of surviving tower-houses; arrive early to walk the Piazza della Cisterna before the day-trip crowds.

  2. Vernaccia di San Gimignano. Taste the town’s crisp white — Italy’s first DOC — at a cellar in or just below the walls; a clean contrast after three days of Sangiovese reds.

  3. Drive to the airport. San Gimignano sits between the southern hills and the coast, so you are well placed for a late flight from either Florence (FLR) or Pisa (PSA).

Where to staySan GimignanoWine tours & tastingsSan Gimignano & Vernaccia tastings

Take this itinerary with you

Save the whole 5 days Tuscany plan as a clean PDF to print or read offline on the road.

Frequently asked

Is 5 days enough for a Tuscany wine trip?

Yes for a first serious visit. Five days lets you taste Chianti Classico, Brunello di Montalcino and Vino Nobile di Montepulciano — three of the four major appellations — at a two-visits-a-day pace, with one Val d’Orcia afternoon for pecorino and Renaissance towns. It deliberately skips the Bolgheri coast and its Super Tuscans (Sassicaia, Ornellaia); add two days for that if Bordeaux-blend reds are the reason you came.

Do I need a car, or can I do it by train and bus?

You need a car for days 2 to 5. Florence to Siena to Montalcino is workable by bus, but the timetables do not fit estate appointments, and there is no public transport to most cellars. A hired wine-day driver works for a couple where neither person wants to drive, but it costs far more than a rental plus one designated driver.

How far ahead do I book the wineries?

Two to four weeks for most estates, and four weeks or more for the marquee Brunello terrace tastings in autumn. Antinori nel Chianti Classico, Biondi-Santi and Avignonesi all take reservations through their own websites. Book lodging — a Florence hotel and a Val d’Orcia agriturismo — two months ahead in peak season.

When is the best time to go?

The second week of October. Harvest is finishing, so the cellars still have energy without August’s heat and crowds, temperatures sit around 16–22°C, and the Val d’Orcia colour palette of cypress, ploughed terracotta and golden hilltops peaks. Avoid August (very hot, many estates on holiday) and Easter week (everything books out).

Keep planning your Tuscany trip

Read the full region guide, browse more routes, or build a custom plan.

Tuscany region guide →More itinerariesBuild a custom trip

Last reviewed June 2026. Prices and booking lead times are guidance — confirm with each winery before you travel.

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