7 Days in Tuscany — Deep-Dive Wine Itinerary (2026)
Deep-dive Tuscany — all four major DOCGs across one week. Chianti Classico, Brunello, Vino Nobile, Bolgheri Super Tuscans.
Last reviewed May 2026
Seven days is the trip length that finally lets Tuscany breathe. You can taste all four major DOCGs — Chianti Classico, Brunello di Montalcino, Vino Nobile di Montepulciano, and Bolgheri's Bordeaux-blend Super Tuscans — without ever rushing a meal. The structure is three bases: two nights in Florence at the start, three nights in a Val d'Orcia or Montalcino agriturismo for the southern Tuscany middle, and two nights in Bolgheri for the coastal-Cabernet finale. This is also enough time to slot a non-wine day (the Pienza pecorino-and-truffle day on Day 4) without the trip feeling thin. The deal-breaker visits — Tenuta San Guido (Sassicaia) and Biondi-Santi — both need 4–8 weeks notice; book before the rest of the trip.
- Length
- 7 days
- Best for
- Serious oenophiles and second-time visitors
- Cost estimate
- From €3,200 per person (mid-range, double occupancy across three bases, 12 tastings + 7 dinners + rental car for 6 days — excludes flights and the Sassicaia vertical)
- Sub-regions
- Florence · Greve in Chianti · Panzano · Antinori nel Chianti Classico (Bargino) · Castello di Brolio (Gaiole) · Montalcino · Sant'Antimo Abbey · Pienza · Montepulciano · San Gimignano · Bolgheri · Castagneto Carducci
Deliberately skipping: Maremma (southern coastal Tuscany), Cortona / eastern hilltop towns, Massa-Carrara / northern Apennines, Pisa beyond an airport stop. See the longer itineraries if you want to fit these in.
Book ahead
- Tenuta San Guido (Sassicaia, Day 6) — book 6–8 weeks ahead via tenutasanguido.com; €75 for the Sassicaia vertical, capped at 8 guests
- Biondi-Santi (Day 3) — book 4 weeks ahead via biondisanti.com; €60–€120 vintage Brunello tasting on the terrace
- Ornellaia (Day 6) — book 4–6 weeks ahead via ornellaia.com; €60–€90 with art installations as part of the cellar tour
- Antinori nel Chianti Classico (Day 2) — 2–3 weeks ahead via antinori.it; €35–€60 + Osteria di Passignano dinner (Michelin-starred, book 6+ weeks)
- Castello di Brolio (Day 2 alternative or Day 1 afternoon) — 1–2 weeks ahead via ricasoli.com; €25–€35
- Avignonesi in Montepulciano (Day 5) — 1–2 weeks ahead via avignonesi.it; €30–€50 for Vino Nobile and Vin Santo, biodynamic estate
- Casanova di Neri or Il Poggione in Montalcino (Day 3 second visit) — 2 weeks ahead via the winery website
- Florence hotels for nights 1–2 (Hotel Lungarno, Hotel Brunelleschi, or NH Collection Porta Rossa) — 2+ months ahead in peak season
- Val d'Orcia agriturismo for nights 3–5 (La Bandita Townhouse, La Foce, or Castiglion del Bosco) — 2+ months ahead
- Bolgheri hotel for nights 6–7 (Hotel Le Caselle or B&B Podere il Castellaccio) — 2+ months ahead
- Rental car at Florence (pick up Day 2, drop at Pisa Airport Day 8) — 4 weeks ahead via Sixt or Hertz
Day 1 — Florence orientation
Base: FlorenceOn foot. No driving today.
- Morning
- Arrive Florence (Amerigo Vespucci Airport or by train to Santa Maria Novella). Check in to your central hotel. Walk the Duomo and Baptistery — they're the orientation that makes the rest of the trip make sense. If you've booked a 10am Uffizi slot, do it now while you're freshest; otherwise save it for Day 8 on the way out.
- Afternoon
- Lunch at Trattoria Cammillo or Trattoria Sabatino (both unfussy Florentine, both serve a textbook bistecca alla Fiorentina with Chianti Classico). Walk the Oltrarno in the afternoon — Piazza Santo Spirito, the Pitti Palace gardens, the leather workshops on Via Maggio. Today is for the city, not the wine.
- Evening
- Aperitivo at Le Volpi e l'Uva (a Sangiovese-focused wine bar near the Ponte Vecchio) — the by-the-glass list is the best way to calibrate your palate to the Chianti Classico style before tomorrow's estate visits. Dinner at Il Latini (Florentine, group tables, well-aged Chianti) or Cibreo (more refined, book ahead).
Day 2 — Pick up car, Antinori nel Chianti Classico
Base: Florence (last night)Florence → Antinori Bargino: 30 min. Antinori → Panzano: 15 min. Panzano → Florence: 45 min.
- Morning
- Pick up the rental from the city centre Avis or Sixt depot (cheaper than the airport for a 5–6 day rental). Drive 30 minutes south to Antinori nel Chianti Classico in Bargino — the family's flagship winery, terraced into the hillside. The €35–€60 tour walks the cantina and barrel hall and ends with a 4–6 wine flight typically including Tignanello and Solaia. The Antinori family has been making wine since 1385.
- Afternoon
- Lunch at Osteria di Passignano on the Antinori property (Michelin-starred, book 6+ weeks ahead) or at Solociccia in Panzano (Dario Cecchini's meat-focused trattoria, cheaper and less precious). Afternoon visit at Fontodi in Panzano — the benchmark 100% Sangiovese Super Tuscan operation. €25–€30 for the four-wine flight including Flaccianello della Pieve.
- Evening
- Drive back to Florence (40 minutes) for the second city night. Dinner at Trattoria Mario near the Mercato Centrale — the bistecca portion sizes are notorious, the wine list is short and good, no reservations (queue at 12:30 or 7:30).
Day 3 — Florence to Montalcino via Castello di Brolio
Base: Val d'Orcia / Montalcino agriturismoFlorence → Brolio: 75 min. Brolio → Montalcino: 75 min via Siena + SP14.
- Morning
- Check out of Florence. Drive south on the Florence-Siena motorway, exit at Siena and continue south-east on the SP484 to Castello di Brolio (about 75 minutes from Florence). The 12th-century castle is the spiritual home of Chianti Classico — Bettino Ricasoli formalised the original formula here in 1872. €25–€35 for the historic-cellar visit ending with the Castello di Brolio Gran Selezione and Colledilà single-vineyard. Lunch at Osteria del Castello on the estate.
- Afternoon
- Drive south to Montalcino — about 75 minutes via Siena bypass + SP14. Check in at your Val d'Orcia agriturismo. The afternoon Brunello visit is Biondi-Santi (the founding 1888 estate) — €60–€120 vintage tasting on the terrace, including library vintages. This is the appointment you booked 4 weeks ago; budget 2 hours and stay sober enough to drive to dinner.
- Evening
- Dinner at Re di Macchia or Boccon di Vino in Montalcino village. Both pour deep on Brunello and the staff will sell you bottles to take back to the agriturismo. Or eat at your agriturismo if it's a half-board property like La Foce — Tuscan agriturismo dinners are part of the experience.
Day 4 — Val d'Orcia non-wine day (Pienza + Sant'Antimo)
Base: Val d'Orcia / Montalcino agriturismoMontalcino → Pienza: 30 min via SP146. Pienza → Sant'Antimo: 20 min. Sant'Antimo → Montalcino: 20 min.
- Morning
- Drive 30 minutes to Pienza — the Renaissance hilltop town that produces the most famous pecorino in Italy. The town itself takes 90 minutes to walk; the pecorino tasting at Caseificio Cugusi or Pienza's main piazza shops is the food highlight of the week. October–December adds white truffle hunting around San Miniato (book ahead through Savini or a local truffle company).
- Afternoon
- Drive 20 minutes south to Sant'Antimo Abbey — the 12th-century Romanesque abbey is one of the most photographed buildings in Tuscany. The Gregorian chants at the late-afternoon office (4:45pm) are worth timing. From Sant'Antimo, drive 30 minutes back toward Montalcino and stop for the afternoon at a second Brunello estate — Casanova di Neri (Tenuta Nuova is the bottle to taste) or Il Poggione if Casanova is fully booked. €40–€60 for either.
- Evening
- Back at the agriturismo. Easy dinner — the second day is the right time for an agriturismo half-board dinner with the property's own wine.
Day 5 — Montepulciano (Vino Nobile)
Base: Val d'Orcia / Montalcino agriturismo (last night)Montalcino → Montepulciano: 30 min via SP146. Montepulciano → Montalcino: 30 min.
- Morning
- Drive 30 minutes east to Montepulciano — a Renaissance hilltop town that is materially less visited than San Gimignano and substantially more pleasant. Walk the Piazza Grande and the Duomo before the appointment. Avignonesi is the estate to visit — Italy's leading biodynamic operation, with a Vin Santo programme that's the most serious in Tuscany. €30–€50 for the Vino Nobile + Vin Santo tasting.
- Afternoon
- Lunch at La Grotta in Montepulciano (book ahead) or up the road at Le Logge del Vignola. Afternoon visit at Poliziano or Salcheto — both serious mid-range Vino Nobile producers in town. €25–€40. Then drive back via Pienza for a second pecorino stop if you haven't bought enough on Day 4. Last night at the Val d'Orcia agriturismo.
- Evening
- Dinner at the agriturismo or back in Montalcino. Tomorrow's drive to Bolgheri is the longest of the trip — early dinner, early night.
Day 6 — Drive to Bolgheri + Sassicaia
Base: BolgheriMontalcino → Bolgheri: 2.5 hr via SS1 Aurelia.
- Morning
- Check out and drive west to Bolgheri — about 2.5 hours via the SS1 Aurelia coastal road. The drive itself includes the Viale dei Cipressi — the cypress boulevard into Bolgheri village that you'll have seen in a hundred photographs and a few films. Check in at your Bolgheri hotel. Lunch in Bolgheri village (Osteria Magona for the bistecca or Enoteca Tognoni for a more wine-focused meal).
- Afternoon
- The big appointment: Tenuta San Guido for the Sassicaia visit (you booked this 6–8 weeks ago). €75 for the Sassicaia vertical, capped at 8 guests, includes the current vintage and one or two library vintages. The estate doesn't look like a Bolgheri showpiece — it's a working farm — and the visit is more conversational than choreographed. This is the wine that started the Super Tuscan story in the 1940s.
- Evening
- Dinner at Enoteca Tognoni in Bolgheri village. The wine list is the deepest in Bolgheri for Sassicaia, Ornellaia, Masseto and the rest. Book ahead. Walk back to the hotel.
Day 7 — Ornellaia + Castagneto Carducci
Base: Bolgheri (last night)Bolgheri → Ornellaia: 10 min within the appellation. Bolgheri → Castagneto Carducci: 10 min.
- Morning
- Ornellaia is the morning appointment — €60–€90 for the cellar tour with art installations as centrepieces (the Vendemmia d'Artista series commissions a different artist to label each vintage). The wine programme covers Ornellaia, Le Serre Nuove (the second wine) and Le Volte for value. The cellar is theatrical in a way Tenuta San Guido is not.
- Afternoon
- Lunch in Castagneto Carducci (Trattoria La Tana del Pirata for grilled fish, or Caconero for a more elevated set menu). Castagneto is the hilltop town above Bolgheri and worth 90 minutes of walking — the Carducci poet museum, the views down to the sea. Afternoon free for a beach stop at Marina di Castagneto or one more visit at Guado al Tasso (Antinori's Bolgheri property, €40 four-wine tasting, less hard to book than Sassicaia or Ornellaia).
- Evening
- Last dinner at Osteria Magona in Bolgheri or back at your hotel. Pack out.
Frequently asked
Is 7 days too long for Tuscany?
Not if you cover all four DOCGs. Two days in Chianti, three in southern Tuscany (Montalcino + Vino Nobile + non-wine Val d'Orcia day), two in Bolgheri is exactly the right shape for tasting all four styles without rushing meals. If you have less appetite for Super Tuscans (Bolgheri's Bordeaux-blend style is materially different from Sangiovese-led Chianti and Brunello), drop the Bolgheri leg and add a Florence city day plus a San Gimignano half-day — that's the 6-day Tuscany trip without coastal Cabernet.
Why pick Sassicaia + Ornellaia and not Masseto or Solaia?
Three reasons. One: Sassicaia and Ornellaia run published visit programmes; Masseto does not (it's allocation-list only). Two: Sassicaia is the historical hinge of the Super Tuscan movement — visiting Tenuta San Guido contextualises everything else in Bolgheri. Three: Ornellaia's art programme is genuinely engaging and the cellar visit is worth the price. Solaia is Antinori-made in Chianti Classico, which you taste at Antinori nel Chianti Classico on Day 2 — no need to repeat in Bolgheri.
Can I do this trip by train instead of renting a car?
Florence → Siena → Montalcino is workable by bus but the timetables don't fit the estate appointments. Bolgheri requires a car — there is no public transport to the estates. A pre-booked driver for the wine days (5 days × €450/day = €2,250) is more expensive than renting a car (€60/day) and using one designated driver. The math only works for a couple where neither person wants to drive, which is unusual. Rent the car.
When is the absolute best week to do this trip?
Second week of October. Vendemmia is finishing in Bolgheri but mostly done in Chianti and Montalcino — you get harvest-energy still in the cellars without August's crowds or heat. Temperatures are 16–22°C and the Val d'Orcia colour palette (cypress green + ploughed terracotta + golden hilltop) is at its photographic peak. The trade-off: Brunello estates are tasting the 2020 vintage by then, so library vintages matter more than the current release. Avoid August (40°C, staff holidays) and avoid Easter week (every estate fully booked).
Where should I fly into and out of?
In via Florence Amerigo Vespucci, out via Pisa Galileo Galilei. Florence is closer to Day 1's Florence base; Pisa is 30 minutes from Bolgheri, where the trip ends. Drop the rental at Pisa Airport on Day 8 morning. If you can only fly in/out of one airport, Florence works either way but adds 90 minutes from Bolgheri to Florence Airport at the end of Day 7.
Want to customise this itinerary?
Use the trip planner to mix-and-match days, or read the full Tuscany guide.
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