Make this trip your own
Create your own free, personalized itinerary in seconds — then sign up to save and edit it.
Create my version

7-Day Tuscany Road-Trip: Florence, Chianti, Siena, Val d'Orcia, Montalcino, San Gimignano, Pisa & Lucca

Viewed by 878 travelers

Day 1: Classic Florence

Florence, Italy on August 13, 2025

8:30am

Breakfast at Caffè Gilli

Historic café on Via Roma serving pastries and cappuccino to start your Florentine day; good for people-watching near Piazza della Repubblica. Check opening hours (often opens ~7:30–8:00).
EUR8, 0h30m

9:30am

Duomo Complex: Cathedral, Baptistery & Brunelleschi's Dome

Climb Brunelleschi's Dome for panoramic views and visit the Duomo and Baptistery to appreciate Renaissance art and architecture; reservation strongly recommended. Typical hours vary by season (often 8:15–19:00 for visits).
EUR18, 2h0m

12:00pm

Lunch at Trattoria Mario

Casual, traditional Tuscan trattoria near Mercato Centrale serving hearty Tuscan dishes (open for lunch, often closes mid-afternoon). Arrive early to avoid queues.
EUR20, 1h0m

1:30pm

Uffizi Gallery

World-class collection of Renaissance masterpieces (Botticelli, Leonardo, Michelangelo); pre-book timed ticket — usual hours around 8:15–6:30pm but check seasonal schedules.
EUR25, 2h0m

4:00pm

Boboli Gardens & Pitti Palace (optional)

Relax in expansive Renaissance gardens with sculptures and views over Florence; gardens typically open mid-morning to late afternoon (hours vary by season).
EUR10, 1h30m

6:30pm

Sunset at Piazzale Michelangelo

Short drive or uphill walk to the panoramic terrace for classic sunset views over Florence — free and popular, so arrive early for a good spot.
EUR0, 0h45m

8:00pm

Dinner at La Giostra

Romantic restaurant famous for Tuscan specialties and friendly service; reservations recommended, dinner hours typically from 7pm.
EUR45, 1h30m

Day 2: Chianti to Siena

Chianti region → Siena, Italy on August 14, 2025

8:00am

Breakfast at Hotel or Café in Florence

Quick breakfast before departing Florence for the Chianti hills — many cafés open early; pack water for the drive through rural roads.
EUR8, 0h30m

9:00am

Drive to Greve in Chianti (approx 45–60 min)

Scenic drive into the Chianti wine region; Greve is a good first stop for a wine shop and piazza exploration. Roads are narrow — drive carefully.
EUR0, 1h0m

10:00am

Castello/Winery visit and tasting (e.g., Castello di Verrazzano or a local estate)

Guided tasting and short tour of vineyards and cellars to understand Chianti Classico production; most wineries require reservations and have tastings around 10am–4pm.
EUR35, 1h30m

12:30pm

Lunch at Enoteca Falorni (Greve)

Historic enoteca with charcuterie, local cheeses, and seasonal dishes — ideal for sampling Chianti pairings; typically open 12:00–15:00 for lunch.
EUR25, 1h0m

2:00pm

Drive through Castellina and Radda (scenic stops)

Short stops in hilltop villages for photos, viewpoints, and a coffee; small museums and shops may be open 10:00–18:00 depending on season.
EUR0, 1h30m

4:00pm

Arrive Siena — Piazza del Campo stroll

Explore Siena’s famous shell-shaped square and visit surrounding medieval streets; many attractions and shops close earlier in the evening — check specific opening times.
EUR0, 0h45m

6:00pm

Check into hotel in Siena

Settle into centrally located lodging to walk Siena’s streets easily and enjoy evening ambiance.
EUR0, 0h30m

8:00pm

Dinner at La Taverna di San Giuseppe

Traditional Sienese cuisine served in a wine-cellar setting; reservations recommended, typical dinner hours 7:30–10:30pm.
EUR40, 1h30m

Day 3: Siena deep-dive

Siena, Italy on August 15, 2025

8:30am

Breakfast at Pasticceria Nannini

Local bakery known for pastries and cantucci; they open early and supply robust breakfasts for a day of walking.
EUR7, 0h30m

9:30am

Siena Cathedral (Duomo) & Piccolomini Library

Imposing Romanesque-Gothic cathedral with frescoes and the ornate Piccolomini Library; check opening hours (often 10:00–19:00) and ticket combos with baptistery/museum.
EUR12, 1h30m

11:30am

Climb Torre del Mangia

Climb for commanding views over Siena and the surrounding countryside — typically open ~10:30–18:30, limited capacity so arrive early or book a slot.
EUR10, 0h45m

1:00pm

Lunch at Osteria Le Logge

Refined local cuisine a short walk from Piazza del Campo, offering seasonal Sienese dishes; lunch hours often 12:00–14:30.
EUR30, 1h0m

2:30pm

Walk the Contrade & Museo Civico

Learn about Siena's neighborhood system, Palio history, and view civic art in the Museo Civico located on Piazza del Campo; museum hours vary (often 10:00–17:30).
EUR8, 1h30m

5:00pm

Leisure time / shopping

Stroll medieval lanes for ceramics, leather goods, and local wine shops; many small boutiques close ~7–8pm.
EUR0, 1h30m

8:00pm

Dinner at Ristorante il Bandierino

Warm trattoria serving Sienese classics; friendly service and typical dinner hours 7:00–10:30pm.
EUR35, 1h30m

Day 4: Pienza & Val d'Orcia

Pienza → Bagno Vignoni → Montepulciano, Italy on August 16, 2025

7:45am

Breakfast and depart Siena

Early breakfast and drive southeast into the Val d'Orcia to maximize daylight and photo opportunities on the rolling hills.
EUR8, 0h30m

9:30am

Explore Pienza & Pecorino tasting

Charming Renaissance town famed for Pecorino cheese and panoramic viewpoints of the Orcia valley; shops and tasting rooms open mid-morning (check specific hours).
EUR10, 1h30m

11:30am

Drive to Bagno Vignoni and visit the thermal square

Unique village built around a large thermal water pool in the square; the public thermal square is free to view, but bathing options require reservations at nearby spas (hours vary).
EUR0, 0h45m

1:00pm

Lunch at La Porta (Monticchiello) or local trattoria

Light, countryside lunch in a tiny hill town with great views; many family-run places serve lunch around 12:00–15:00.
EUR25, 1h0m

3:00pm

Drive to Montepulciano & wine cellar tour (Cantina Contucci or similar)

Historic hill town known for Vino Nobile di Montepulciano; book a cellar tour and tasting (most open 10:00–18:00 but require booking for tastings).
EUR30, 1h30m

5:30pm

Stroll Montepulciano streets and sunset viewpoint

Walk Piazza Grande, visit local shops, and enjoy sunset views over Val d'Orcia; many attractions start closing around 7–8pm.
EUR0, 0h45m

8:00pm

Dinner at Osteria Acquacheta (Montepulciano)

Rustic spot famed for bistecca alla Fiorentina and Tuscan cooking; arrive early or reserve as it gets busy (dinner hours ~7:00–10:00pm).
EUR40, 1h30m

Day 5: Montalcino & Sant'Antimo

Montalcino & Castelnuovo dell'Abate, Italy on August 17, 2025

8:00am

Breakfast in Montepulciano then depart for Montalcino (~1h drive)

Enjoy a quick breakfast and scenic drive into Brunello country; roads are rural and winding so allow time for photo stops.
EUR8, 1h0m

10:00am

Abbey of Sant'Antimo visit

Beautiful Romanesque abbey near Montalcino with serene setting and occasional Gregorian chant services; check visiting hours (often morning/afternoon) and service times if you wish to attend.
EUR0, 0h45m

11:30am

Winery tour & Brunello tasting (e.g., Caparzo, Poggio di Sotto or small producer)

Reserve a guided tasting of Brunello di Montalcino and a cellar tour — many wineries operate tastings by appointment, typically mid-morning to late afternoon.
EUR40, 1h30m

1:30pm

Lunch at Osteria Le Logge di Bacco or local trattoria

Simple, hearty lunch paired with local Brunello or Rosso di Montalcino; lunch hours commonly 12:00–14:30.
EUR30, 1h0m

3:00pm

Explore Montalcino town and Fortezza

Visit the hilltop fortress for wine shops and panoramic views; fortress and shops typically open in afternoons as well.
EUR5, 1h0m

5:00pm

Check into agriturismo or hotel in Montalcino

Relax at a countryside property surrounded by vineyards for an authentic Tuscan evening.
EUR0, 0h30m

8:00pm

Dinner at Il Giglio (Montalcino)

Local restaurant with seasonal Tuscan dishes; ideal place to pair local wines with dinner (reservation recommended).
EUR45, 1h30m

Day 6: San Gimignano towers

San Gimignano, Italy on August 18, 2025

8:00am

Breakfast and depart Montalcino for San Gimignano (~1h45–2h drive)

Enjoy early morning countryside driving back north toward the medieval tower town of San Gimignano; allow extra time for narrow roads.
EUR8, 2h0m

10:30am

Visit Torre Grossa & Civic Museum

Climb Torre Grossa for panoramic views over the Val d'Elsa and explore the small civic museum; tower opening hours typically 10:00–19:00 (seasonal).
EUR10, 1h0m

12:00pm

Lunch at Cum Quibus (or local osteria)

One of the town’s notable restaurants offering refined local fare; reserve ahead as seats are limited and hours often 12:00–14:30 for lunch.
EUR35, 1h0m

1:30pm

Gelato at Gelateria Dondoli

World-famous gelateria in the main square — great stop to taste award-winning gelato; usually open from late morning through evening.
EUR4, 0h20m

2:00pm

Walk the medieval streets and defensive walls

Wander the UNESCO-listed town, browse artisan shops, and walk short stretches of the walls for views of the towers and surrounding countryside.
EUR0, 1h30m

4:30pm

Drive toward Pisa/Lucca area (optional early evening stop in Certaldo Alto)

If time allows, stop in Certaldo Alto — a well-preserved medieval hill town accessible by funicular; opening hours for museums vary so check ahead.
EUR0, 1h0m

8:00pm

Dinner and overnight in the Pisa/Lucca area or return to Florence

Choose a relaxed dinner near your next-day base; dinner hours usually 7:00–10:30pm. If you prefer less driving next day, stay near Lucca.
EUR35, 1h30m

Day 7: Pisa & Lucca

Pisa → Lucca → Florence, Italy on August 19, 2025

8:00am

Breakfast and drive to Pisa (if not already nearby)

Start early to beat crowds at the Leaning Tower complex; many cafés open early for breakfast.
EUR8, 0h30m

9:00am

Campo dei Miracoli: Leaning Tower, Cathedral & Baptistery

Iconic complex — climb the Leaning Tower (timed-entry tickets required) and visit the cathedral and baptistery; opening times often 9:00–20:00 but booking ahead is recommended.
EUR25, 1h30m

11:00am

Drive to Lucca (approx 30–45 min)

Short drive to the charming walled city of Lucca, famous for its intact Renaissance walls and relaxed atmosphere.
EUR0, 0h45m

12:00pm

Lunch in Lucca — Trattoria da Leo or Ristorante Giglio

Enjoy Luccan specialties near the historic center; many restaurants open 12:00–14:30 for lunch.
EUR25, 1h0m

1:30pm

Bike the Lucca city walls & visit Torre Guinigi

Rent a bike to cycle the scenic, tree-lined walls then climb Torre Guinigi with its rooftop garden for views of Lucca; rental and tower opening times vary (walls open always, tower often 9:00–19:00).
EUR12, 1h30m

3:30pm

Stroll Piazza Anfiteatro & shopping

Visit the oval Piazza Anfiteatro built on a Roman amphitheater and browse artisan shops for souvenirs; many shops close late afternoon — check individual hours.
EUR0, 1h0m

5:00pm

Return drive to Florence (approx 1h15–1h30)

Head back to Florence to conclude the loop; allow time for traffic and drop-off if you rented a car.
EUR0, 1h30m

8:00pm

Farewell dinner at Trattoria ZaZa (Florence) or nearby favorite

Enjoy one last Tuscan meal in Florence — book ahead, typical dinner hours 7:00–10:30pm.
EUR40, 1h30m
0
Like this trip? Make your own version.
A free, personalized itinerary in seconds — sign up to save and edit it.
Create my version