One Week in Tuscany: Wine, Food & History

A week in Tuscany is the trip wine lovers dream about -- and it delivers. Seven days lets you explore Chianti's rolling hills, taste Brunello in Montalcino, compare Vino Nobile in Montepulciano, and still have time for the Renaissance masterpieces in Florence and the medieval towers of San Gimignano.

This itinerary uses a two-base strategy: Florence for the first two nights (culture plus easy access to Chianti), then a countryside base near Montalcino for the remaining five nights. This minimizes driving while maximizing the diversity of what you see, taste, and eat.

Budget estimate: $180-350/day per person (mid-range). Tuscany offers exceptional value compared to Napa or Bordeaux.

Best time to visit: April-June or September-October. Avoid August when Italians vacation and prices spike.

Base Recommendations

Option A: Florence + Countryside (Recommended)

• Nights 1-2: Florence -- walkable city, museums, Chianti day trip
• Nights 3-7: Agriturismo near Montalcino or Pienza -- central to all southern Tuscany wine towns

Option B: Full Countryside

• All 7 nights: Single agriturismo between Siena and Montalcino. More relaxing, but you will need to drive to Florence (90 minutes each way).

Option C: Multi-Base

• Nights 1-2: Florence, Nights 3-4: Greve in Chianti, Nights 5-7: Montalcino. Most immersive but requires two hotel changes.

Day 1: Arrive in Florence

Afternoon

Fly into Florence (FLR) or Pisa (PSA, then 90-minute train to Florence). Check into your hotel in the historic center. Drop your bags and walk to Piazza della Signoria -- the open-air museum of Renaissance sculpture.

Visit the Mercato Centrale (Central Market) on the upper floor for lunch. The food hall has excellent pasta, pizza, and wine by the glass from Tuscan producers. Budget EUR 15-25.

Evening

Walk across the Ponte Vecchio at sunset, then continue to the Oltrarno neighborhood for dinner. Trattoria dell'Orto serves honest Florentine cooking at fair prices -- the ribollita (bread and vegetable soup) and bistecca alla fiorentina are essential. Mains EUR 14-25.

Stop at Le Volpi e l'Uva, a tiny wine bar near Ponte Vecchio, for a post-dinner glass. They specialize in small Tuscan producers you will not find elsewhere. Glasses EUR 5-10.

Day 2: Florence Art & Wine

Morning

Uffizi Gallery first thing (book timed entry online, EUR 25). Even if you are here for wine, the Botticelli rooms and Caravaggio pieces deserve 2 hours.

Afternoon

Lunch at All'Antico Vinaio (the famous sandwich shop on Via dei Neri). The line looks intimidating but moves fast. Sandwiches EUR 5-8 -- some of the best EUR 5 you will ever spend.

Afternoon wine education at Enoteca Pitti Gola e Cantina in the Oltrarno, or take a 30-minute bus to Antinori nel Chianti Classico in Bargino -- a stunning modernist winery built into a hillside. Tours EUR 25-40, tastings EUR 15-30.

Evening

Dinner at Buca Mario (since 1886) for traditional Florentine fare, or Il Latini for the full communal table experience with free-flowing house Chianti. Budget EUR 35-50 per person.

Pro tip: Book Uffizi tickets for 8:15 AM entry. The crowds arrive around 10 AM. You will have the Botticelli rooms nearly to yourself at opening.

Day 3: Chianti Classico

Morning

Pick up your rental car and drive south into Chianti Classico. The SR222 (Chiantigiana) from Florence to Greve is one of the most beautiful drives in Italy -- cypress-lined roads through vineyard-covered hills.

First stop: Castello di Verrazzano near Greve in Chianti. The estate tour covers their historic cellars, olive oil production, and a tasting of 4-5 wines with local salumi and cheese. EUR 25-35. Book ahead.

Afternoon

Lunch in Greve in Chianti at the main piazza. Antica Macelleria Falorni is a legendary butcher shop that also serves tastings -- prosciutto, finocchiona, and lardo with Chianti Classico. EUR 12-20.

Drive to Castello di Ama near Gaiole for an afternoon tasting. Their Chianti Classico Gran Selezione is outstanding, and the estate doubles as a contemporary art gallery (site-specific installations throughout the vineyards). Tasting EUR 25-40.

Evening

Continue south to your countryside base near Montalcino. Check into your agriturismo (farm stay). Many serve home-cooked dinner using their own olive oil, vegetables, and wine -- an experience you cannot replicate in a restaurant. Dinner typically EUR 25-35 per person, wine included.

Pro tip: An agriturismo with a pool is worth the small premium in Tuscany. After a day of wine tasting and driving, floating in a pool overlooking the Val d'Orcia at sunset is restorative in ways hotels cannot match.

Day 4: Montalcino & Brunello

Morning

Drive to Montalcino, the hilltop town that produces Brunello -- one of Italy's most age-worthy and prestigious reds.

Start at Biondi-Santi, the estate that invented Brunello di Montalcino in the 1800s. Their historical vertical tasting (EUR 50-75) is a masterclass in how Sangiovese ages. Book weeks ahead.

Afternoon

Lunch in Montalcino town at Ristorante Re di Macchia -- wild boar ragu with handmade pici pasta is the local specialty. Mains EUR 12-18.

After lunch, visit Poggio Antico or Casanova di Neri for a contrasting modern Brunello experience. Tastings EUR 20-35. Both estates have panoramic views of the surrounding valleys.

Walk the walls of the Fortezza di Montalcino (EUR 6 entry). The fortress enoteca inside sells Brunello from dozens of producers by the glass -- an efficient way to sample broadly. Glasses EUR 5-15.

Evening

Dinner at Osteria di Porta al Cassero in Montalcino -- refined Tuscan cooking with an outstanding Brunello list. Mains EUR 16-28.

Day 5: Val d'Orcia & Montepulciano

Morning

Drive through the Val d'Orcia, a UNESCO World Heritage landscape of rolling wheat fields, isolated cypress trees, and medieval villages. Stop at Pienza first -- a tiny Renaissance town famous for pecorino cheese. Buy some at Zazzeri on the main street (they let you taste) and walk to the viewpoint behind the cathedral for one of the best panoramas in Tuscany.

Afternoon

Continue to Montepulciano, a hilltop town producing Vino Nobile -- made from the same Sangiovese grape as Brunello but in a different style. The town itself is gorgeous, with Renaissance palaces climbing a steep ridge.

Visit Contucci in the Piazza Grande -- the oldest winery in Montepulciano, with cellars under the medieval palazzo. Free tastings. Then walk downhill to De' Ricci, where the underground cellars carved into the town's volcanic rock are spectacular.

Lunch (late) at La Grotta just outside the town walls -- seasonal Tuscan cooking with a garden terrace. Mains EUR 14-22.

Evening

Return to your base. This is a good night to eat at the agriturismo or cook your own meal with ingredients from Pienza and Montepulciano markets.

Pro tip: Vino Nobile di Montepulciano offers 80% of Brunello's quality at 40% of the price. Stock up here.

Day 6: San Gimignano & Vernaccia

Morning

Drive west to San Gimignano, the medieval town famous for its 14 surviving towers. Arrive by 9:30 AM to beat the day-trip crowds from Florence (they arrive around 11 AM).

Climb the Torre Grossa (EUR 9) for 360-degree views of the Tuscan countryside. Walk the town walls and visit the Collegiate Church for its stunning 14th-century frescoes.

Afternoon

San Gimignano has its own wine: Vernaccia di San Gimignano, Tuscany's best white. Visit Fattoria Poggio Alloro just outside town -- organic Vernaccia tasting with vineyard views. EUR 15-25.

Lunch at Dulcisinfundo for creative Tuscan dishes (mains EUR 12-18), or pick up ingredients at the shops along Via San Giovanni for a picnic outside the town walls.

Evening

Drive back via the scenic route through Volterra if time allows (adds 45 minutes). Dinner at your agriturismo or in Montalcino.

Day 7: Slow Morning & Departure

Morning

Sleep in. Have a long breakfast at your agriturismo -- fresh bread, local honey, homemade jam, pecorino, and a final espresso overlooking the vineyards.

If you have time before your departure, stop at one last estate. Poggio di Sotto near Montalcino makes some of the most traditional, elegant Brunello -- a quiet, beautiful farewell to Tuscany.

Afternoon

Drive to Florence airport (90 minutes from Montalcino) or Pisa airport (2 hours). Return your rental car and depart.

Transport Tips

• Rental car is essential. Tuscan wine country has minimal public transport outside Florence and Siena.
• Pick up at Florence airport, drop off there too. Train station pickup works but airport is easier for departures.
• Roads are narrow and winding. Drive during daylight, especially in Chianti. The beauty is part of the experience but requires attention.
• Parking: Most hilltop towns have parking lots at the base of the walls (EUR 1.50-3/hour, some free after 8 PM).
• Tolls: Autostrada (highway) from Florence south has tolls. Budget EUR 5-15 per trip segment.
• Alternative: Guided day tours from Florence cover Chianti (EUR 70-120) and Montalcino/Montepulciano (EUR 100-150) if you prefer not to drive.

Budget Summary

More Tuscany Wine Travel Guides

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

Word Count: ~1,500

Last Updated: January 2026

Author: WineTravelGuides Editorial Team