5 Days in Tuscany: Florence to San Gimignano Wine Road Trip

Five days is the sweet spot for Tuscany. Enough time to explore the major wine zones without rushing, enough meals to fall in love with the cooking, and enough vineyard sunsets to understand why people upend their lives to move here. This itinerary takes you from Florence through the Chianti hills, south to Brunello country around Montalcino, east to Montepulciano, and finishes with the medieval towers of San Gimignano.

You will drink Sangiovese in four different expressions -- Chianti Classico, Brunello di Montalcino, Vino Nobile di Montepulciano, and Vernaccia di San Gimignano (a white, for contrast). You will eat wild boar ragu, hand-rolled pici, bistecca alla fiorentina, and pecorino aged in caves. And you will stay in an agriturismo where the olive oil on your breakfast table was pressed from the trees outside your window.

Budget estimate: EUR 240-700/day per person depending on accommodation and dining choices.

Best time to visit: April-June or September-October. Avoid August -- half of Italy is on vacation, prices spike, and the heat in southern Tuscany is punishing.

Before You Go

• Rent a car. There is no way around this. Tuscan wine country has almost no useful public transport between villages. Pick up at Florence airport (FLR) or the main train station (Firenze SMN). Manual transmission is cheaper; specify automatic if you need it.
• Book agriturismo stays early. The best farm stays book out months ahead for May-June and September. Aim for one near Montalcino or Pienza as your countryside base for nights 2-4.
• Winery appointments are less formal than Napa or Bordeaux. Many Tuscan estates welcome walk-ins, but the top names (Biondi-Santi, Castello di Ama, Antinori) require reservations. Book a week ahead to be safe.
• Bring cash. Smaller wineries, village trattorias, and parking meters often do not accept cards.
• Driving tips: Roads are narrow and winding, especially the SR222 through Chianti. White roads (strade bianche -- unpaved gravel) are common and usually fine for normal cars in dry weather. Do not attempt them after heavy rain. Speed cameras are everywhere in villages; the fines arrive months later by mail.

Day 1: Florence & Chianti Classico

Morning

Arrive in Florence and drop your bags at a hotel in the centro storico. You are only here one night, so make it count. Walk to Piazza della Signoria, past the Uffizi, across the Ponte Vecchio, and into the Oltrarno neighborhood.

Coffee at Ditta Artigianale on Via dei Neri -- Florence's best specialty coffee, and you will need it before the drive ahead.

Late Morning

Pick up your rental car and drive south on the SR222, the Chiantigiana. This road from Florence to Siena through the heart of Chianti Classico is one of the most beautiful drives in Europe. Cypress-lined ridges, vineyard-covered hills, stone farmhouses -- the scenery delivers immediately.

First stop: Castello di Verrazzano near Greve in Chianti. This 1,000-year-old estate offers tours of historic cellars, olive oil production, and a tasting of 4-5 wines paired with estate-made salumi and pecorino. EUR 28-38 per person. Book ahead.

Afternoon

Drive 10 minutes to Greve in Chianti for lunch. Park in the main piazza and head to Antica Macelleria Falorni, the legendary butcher shop operating since 1729. They serve tasting boards of finocchiona, prosciutto, lardo di Colonnata, and sopressata alongside Chianti Classico by the glass. EUR 15-22 for a full tasting.

After lunch, drive south to Castello di Ama near Gaiole in Chianti. This estate produces benchmark Chianti Classico Gran Selezione and doubles as a contemporary art gallery with site-specific installations scattered through the vineyards -- works by Daniel Buren, Anish Kapoor, and others among the vines. Tasting EUR 25-40 by appointment.

Evening

Continue south toward your agriturismo. Check in, unpack, and breathe. A good agriturismo in the Montalcino area to look for: Agriturismo Il Rigo near San Quirico d'Orcia (farm-to-table dinners, pool, Val d'Orcia views, EUR 120-180/night), Podere Salicotto near Buonconvento (intimate, design-forward, EUR 150-250/night), or Fattoria del Colle near Trequanda (working wine estate with apartments, EUR 100-160/night).

Most agriturismo kitchens serve home-cooked dinner using their own produce -- typically a multi-course meal with wine for EUR 25-40 per person. This is one of the essential Tuscan experiences. Take it.

Pro tip: The stretch of SR222 between Greve and Castellina in Chianti is gorgeous but slow. Budget 45 minutes for what looks like 25 minutes on the map. The curves are tight and tractors appear without warning.

Day 2: Montalcino & Brunello

Morning

Drive to Montalcino, the hilltop fortress town that produces Brunello -- Italy's most prestigious and age-worthy red wine, made from 100% Sangiovese.

Start at Biondi-Santi, the estate that created Brunello di Montalcino in the 1800s. Franco Biondi-Santi's Riservas from the 1950s and 1960s are among Italy's most legendary wines. Their historical tasting (EUR 50-80) walks you through decades of Sangiovese aging. Book 2-3 weeks ahead -- this is Montalcino's most in-demand visit.

For a more approachable alternative (or a second morning stop), visit Casanova di Neri on the southeast slope. Winemaker Giacomo Neri makes modern, concentrated Brunello that has earned perfect scores from critics. Tasting EUR 25-40.

Afternoon

Lunch in Montalcino town at Ristorante Re di Macchia -- wild boar ragu over handmade pici pasta is the house specialty and the dish this town is built on. Mains EUR 12-20. Pair it with a young Rosso di Montalcino (the baby Brunello, aged two years instead of five).

After lunch, walk to the Fortezza di Montalcino. The 14th-century fortress houses an enoteca inside its walls where you can taste Brunello from dozens of producers by the glass (EUR 5-15 per pour). This is the most efficient way to compare styles across the appellation. The fortress ramparts give panoramic views of the surrounding valleys.

Late afternoon visit: Poggio Antico, one of Montalcino's highest estates at 480 meters. Their Brunello is elegant and structured, and the vineyard views toward Monte Amiata are stunning. Tasting EUR 20-35.

Evening

Dinner at Osteria di Porta al Cassero in Montalcino -- refined Tuscan cooking with one of the deepest Brunello lists in town. Try the hand-cut tagliatelle with white truffle (seasonal, October-December) or the guinea fowl with Brunello reduction. Mains EUR 16-28.

Return to your agriturismo.

Pro tip: Rosso di Montalcino (the same grape, same vineyards, less aging) costs EUR 12-20 per bottle versus EUR 35-100+ for Brunello. Buy Rosso for drinking this year and Brunello for cellaring. Many producers make better Rosso than their neighbors make Brunello.

Day 3: Val d'Orcia & Montepulciano

Morning

Today is as much about landscape as wine. Drive south through the Val d'Orcia, the UNESCO World Heritage landscape of rolling wheat fields, solitary cypress trees, and medieval villages perched on ridges. This is the Tuscany of postcards and desktop wallpapers.

Stop first at Pienza, a tiny Renaissance town rebuilt by Pope Pius II in the 1460s as his vision of the ideal city. The main street, Corso il Rossellino, is lined with shops selling pecorino cheese aged in every style imaginable -- in walnut leaves, in ash, in hay, with truffles. Zazzeri lets you taste before buying. Walk to the viewpoint behind the cathedral for one of the finest panoramas in Italy.

Afternoon

Continue east to Montepulciano, a dramatic hilltop town producing Vino Nobile -- made from the same Sangiovese grape (locally called Prugnolo Gentile) as Brunello, but in a rounder, more approachable style.

Visit Contucci in the Piazza Grande at the top of the town. The Contucci family has made wine here since the 11th century, and their cellars sit directly beneath the Renaissance palazzo. Tastings are free and poured by family members. This is old-school Tuscan hospitality.

Walk downhill to Cantina De' Ricci, where the tasting room and cellars occupy an extraordinary network of underground chambers carved from volcanic tufa rock. The architecture alone is worth the visit. Tastings EUR 10-15.

Lunch (late) at La Grotta just outside the Porta al Prato gate. The restaurant occupies a former church with a garden terrace overlooking the valley. Seasonal Tuscan cooking with a creative touch. Mains EUR 14-24. The handmade ravioli with pecorino and pear is outstanding.

Evening

Drive back to your agriturismo through the Val d'Orcia. If you time it right, the sunset over the rolling hills from the road between Pienza and San Quirico is one of the great drives in wine country.

Dinner at the agriturismo tonight -- you have earned a quiet evening.

Pro tip: Vino Nobile di Montepulciano delivers roughly 80% of Brunello's quality at 40% of the price. Bottles at the cellar door run EUR 12-25 versus Brunello's EUR 35-100+. Stock up here.

Day 4: San Gimignano & Vernaccia

Morning

Drive west to San Gimignano, the medieval town famous for its 14 surviving tower-houses (there were once 72). Arrive by 9:30 AM -- day-trip buses from Florence start arriving around 11, and the town transforms from magical to crowded.

Climb the Torre Grossa (EUR 9, the only tower open to the public) for 360-degree views across the Tuscan hills. On clear days you can see all the way to the coast.

Walk the walls and visit the Collegiate Church (EUR 4) for its astonishing 14th-century frescoes -- Old Testament scenes on the left wall, New Testament on the right, and a Last Judgment at the back that rivals anything in Florence.

Late Morning

San Gimignano has its own wine, and it is white: Vernaccia di San Gimignano, Tuscany's only DOCG white. After days of Sangiovese, this is a palate cleanser.

Visit Fattoria Poggio Alloro just outside town. This organic estate produces Vernaccia alongside olive oil and saffron (San Gimignano has grown saffron since the Middle Ages). Tasting with vineyard tour EUR 18-25. Their Riserva Vernaccia aged in oak has unexpected depth.

Afternoon

Lunch at Dulcisinfundo on Via degli Innocenti -- creative Tuscan cooking in a medieval vaulted room. Try the saffron risotto (the local specialty) or the rabbit with Vernaccia sauce. Mains EUR 14-20.

After lunch, browse the artisan shops on Via San Giovanni. Gelateria Dondoli on the main piazza has won the Gelato World Championship multiple times -- the Vernaccia and saffron gelato flavors are unique to San Gimignano.

Evening

Drive north to Florence for your final night. Check into a hotel near the train station or airport for easy departure tomorrow.

Dinner at Trattoria Mario near the Mercato Centrale (no reservations, communal tables, cash only, open for lunch only -- if you miss it, go to Il Latini instead for the communal table experience with free-flowing house Chianti). For a more refined final meal, Buca Mario on Piazza degli Ottaviani has served Florentine classics since 1886. The bistecca alla fiorentina here is a proper farewell to Tuscany. EUR 35-55 per person.

Pro tip: San Gimignano's main piazza has free Wi-Fi and a public water fountain with drinking water. Small things, but useful when you have been driving all morning.

Day 5: Slow Morning & Departure

Morning

No agenda. Sleep in. Walk to a cafe for a final cappuccino and cornetto (filled croissant). If you have time before your flight, two options:

Option A: Florence culture. The Uffizi (book timed entry, EUR 25) for 2 hours of Botticelli, Raphael, and Caravaggio. Or the Accademia (EUR 16) to see Michelangelo's David -- book ahead, it takes 30-45 minutes.

Option B: One last winery. Drive 30 minutes south to Antinori nel Chianti Classico in Bargino. This spectacular modernist winery is built into a hillside, with the roof planted as a vineyard. The architecture alone justifies the trip. Tours EUR 25-40, tastings EUR 15-30.

Afternoon

Return your rental car at Florence airport (FLR) or Pisa airport (PSA, 90 minutes west). Depart.

Where to Stay: Agriturismo Recommendations

Most agriturismo properties have a 2-night minimum in peak season. Book directly for the best rates -- aggregator sites add 15-20% markups.

Driving Tips

• Fuel: Fill up in towns. Gas stations in the countryside close for lunch (1-3 PM) and on Sundays. Self-service pumps accept cards but sometimes only Italian ones; carry cash as backup.
• ZTL zones: Florence, Siena, Montalcino, Montepulciano, and San Gimignano all have ZTL (zona traffico limitato) zones in their historic centers. Drive in without a permit and you will receive a EUR 80-100 fine by mail. Park at lots outside the walls and walk in.
• White roads: The strade bianche (unpaved white gravel roads) are scenic and sometimes unavoidable. They are fine in dry weather for normal cars. Avoid after rain. Drive slowly -- 30-40 km/h is about right.
• Tolls: The autostrada (A1) from Florence south has tolls. Budget EUR 5-15 per segment. Alternatively, take the free superstrada (SGC) or scenic state roads, which are slower but more beautiful.
• Parking: EUR 1.50-3/hour in hilltop town lots. Many are free after 8 PM and on Sundays. Blue lines = paid parking. White lines = free. Yellow lines = residents only.

Budget Summary

More Tuscany Wine Travel Guides

• Tuscany Wine Region Overview
• Chianti Guide
• Montalcino Guide
• Montepulciano Guide
• Tuscany vs Bordeaux Comparison
• Italy Wine Regions

Word Count: ~1,950

Last Updated: January 2026

Author: WineTravelGuides Editorial Team