The Ultimate 7-Day Tuscany Wine Tour
Tuscany is Italy's wine heartland — and one of the world's most celebrated regions for serious red wine. This 7-day itinerary moves through three distinct zones: the rolling hills of Chianti Classico, the medieval hilltop town of Montalcino (home to Brunello), and the coastal powerhouses of Bolgheri where the Super Tuscan revolution began. Add Montepulciano and its Vino Nobile, and you have a week that covers the full depth of what Sangiovese can achieve — from perfumed, food-friendly Chianti to brooding, decades-long Brunello.
Day-by-Day Itinerary
Day 1: Arrival in Florence
- •Fly into Florence Airport (FLR) or Pisa (PSA) and transfer to your Florence hotel.
- •Settle in and take the evening drive up to Fiesole — the hilltop village above the city with sweeping views over the Arno valley.
- •Dinner at a Fiesole enoteca with a flight of Chianti Classico to set the tone for the week ahead.
Day 2: Chianti Classico — Antinori & Castello di Ama
- •Drive south from Florence into the Chianti Classico heartland (45 minutes).
- •Morning visit to Antinori nel Chianti Classico — one of Italy's most spectacular winery buildings, carved into the hillside at Bargino. Taste the Tignanello and Solaia alongside their estate Chianti Classico Gran Selezione.
- •Afternoon at Castello di Ama in Gaiole in Chianti — a family estate producing some of the zone's most refined, site-expressive Chianti Classico. Book a tasting tour in advance.
- •Return to Florence for the evening. Dinner in the Oltrarno neighbourhood.
Day 3: Chianti Classico — Barone Ricasoli & Fontodi
- •Morning visit to Barone Ricasoli at Brolio Castle in Gaiole — the historic home of Bettino Ricasoli, who invented the original Chianti formula in the 1870s. Tour the medieval castle and cellars.
- •Afternoon at Fontodi in Panzano in Chianti — a biodynamic estate famed for its Flaccianello (a single-vineyard Sangiovese). Their Chianti Classico Gran Selezione is benchmark.
- •Lunch at the Panzano butcher Dario Cecchini — a legendary Chianti institution.
- •Back to Florence for the final night before heading south tomorrow.
Day 4: Drive South to Montalcino — Biondi Santi & Banfi
- •Check out from Florence and drive south through the Val d'Orcia to Montalcino (90 minutes).
- •Afternoon visit to Biondi Santi at Tenuta Il Greppo — the historic estate where Brunello di Montalcino was created in the 1880s. The cellar holds vintages going back 80+ years. Pre-booking essential.
- •Late afternoon visit to Banfi Winery — the large, visitor-friendly estate in Poggio alle Mura castle with beautiful grounds and a full tasting menu.
- •Check in to your agriturismo in or around Montalcino. Dinner in the town.
Day 5: Montalcino Deep Dive — Casanova di Neri & Poggio Antico
- •Morning at Casanova di Neri — a family estate producing some of the most precise, age-worthy Brunello available. Their Cerretalto single-vineyard bottling is among Italy's greatest wines.
- •Afternoon at Poggio Antico — high-altitude estate with panoramic views of the Val d'Orcia. Excellent guided tasting with lunch available on the terrace.
- •Spend the evening exploring Montalcino town — the Fortezza, the Enoteca La Fortezza inside the castle walls, and a simple dinner at a local trattoria.
Day 6: Montepulciano & Vino Nobile
- •Morning drive east to Montepulciano (45 minutes) — a perfectly preserved Renaissance hilltop town and home of Vino Nobile.
- •Visit Avignonesi — Montepulciano's most internationally known estate, now certified biodynamic, with an outstanding Vino Nobile and a remarkable Vin Santo.
- •Afternoon at Poliziano — another top producer with deep roots in the commune. Elegant Vino Nobile di Montepulciano made from estate Prugnolo Gentile (a Sangiovese clone).
- •Walk the medieval streets of Montepulciano before heading back to your agriturismo. This is your last night in the south — make it count.
Day 7: Super Tuscans — Bolgheri, Depart via Pisa
- •Check out and drive west to the Bolgheri DOC on the Tuscan coast (90 minutes) — birthplace of the Super Tuscan revolution.
- •Drive the famous Viale dei Cipressi — the cypress-lined avenue to Bolgheri village — before visiting a producer in the Sassicaia or Ornellaia estates. Note: both require advance reservation and run limited tastings.
- •Lunch in Bolgheri village, then drive north to Pisa Airport (PSA) for departure. Alternatively, Livorno (LIV) is 45 minutes.
- •Travel note: if Sassicaia/Ornellaia bookings are unavailable, Le Macchiole and Guado al Tasso are outstanding alternatives with more flexible access.
Where to Stay
Florence (Days 1–3)
Base yourself in central Florence for the Chianti Classico days — the city is 30–45 minutes from most estates. The Oltrarno and Pitti neighbourhoods offer excellent local restaurants.
Find Florence HotelsMontalcino / Agriturismo (Days 4–6)
For the southern stretch, staying in Montalcino town or an agriturismo in the Val d'Orcia puts you close to the vineyards and makes early-morning winery appointments easy. Spectacular countryside.
Find Montalcino HotelsThe Wines You'll Taste
Chianti Classico
Sangiovese-dominant blends from the DOCG zone between Florence and Siena. Ranges from fresh and approachable Annata to complex, age-worthy Gran Selezione.
Brunello di Montalcino
100% Sangiovese Grosso (Brunello clone). The most powerful and longest-lived expression of Sangiovese — minimum 5 years aging before release.
Vino Nobile di Montepulciano
Prugnolo Gentile (a Sangiovese biotype) from the hilltop commune of Montepulciano. Elegant and food-friendly, with bright acidity and cherry fruit.
Super Tuscans
International varieties (Cabernet Sauvignon, Merlot, Syrah) blended with or without Sangiovese. Born in Bolgheri from estates like Sassicaia and Ornellaia.
Getting Around
A rental car is essential for this itinerary — Tuscany's wineries are spread across hilly terrain with limited public transport. Driving times between areas run 45–90 minutes. Florence to Montalcino is approximately 2 hours. Pick up your car at Florence Airport on arrival and drop it at Pisa Airport on Day 7. Roads in the Chianti Classico are scenic but can be narrow — a compact SUV is recommended for the white gravel roads (strade bianche) leading to many estates.
Best Time to Visit
September–October (Harvest)
The sagra season — village harvest festivals, Chianti crush, and Brunello estates at their most active. Some of Tuscany's greatest food-and-wine experiences happen here.
May–June (Roses & Ideal Weather)
Roses bloom across Chianti Classico. Perfect temperatures for driving the strade bianche. Full winery access before summer crowds arrive in July.
Month-by-Month
Want a deeper dive into the region? Read our full Tuscany wine region guide on WineTravelGuides.com