Are you looking for how to spend 7 days in Tuscany with all must-visit places? Then read this detailed blog on Tuscany road trip itinerary. Tuscany is one of the most beautiful regions in Italy, famous for its rolling vineyards, medieval hilltop towns, world-class wines, and historic cities. Whether you’re a history lover, a foodie, or simply someone who enjoys stunning landscapes, Tuscany offers something magical every day.
You may also like👉🏼 Best Italy Itinerary 7 Days From Rome With 2 Unique Options – One Week In Italy
The region’s charm lies in its timeless beauty, from Florence’s grand Renaissance architecture to the serene countryside dotted with charming villages.
Tuscany Itinerary 7 Days – Things to do in Tuscany
This detailed day-by-day Tuscany road trip itinerary covers the must-visit places, how to travel between them, mid-budget accommodations, and useful tips to make your journey smooth and memorable. Every town tells a story, every road leads to breathtaking vistas, and every meal celebrates local flavors.
Day 1: Florence – The Renaissance City
Fly into Florence Airport or take a train from Rome (1.5 hours) or Milan (2 hours). Florence is compact, and you can explore the city on foot.
You may also like👉🏼Best One Day In Florence Itinerary (Things To Do )
Florence, the capital of Tuscany, is the birthplace of the Renaissance, home to incredible art, architecture, and culture. Walking through its streets feels like stepping back in time, where every corner reveals an artistic masterpiece. The city’s iconic landmarks, such as the Duomo and Ponte Vecchio, are historic sites and symbols of human creativity and innovation.
Things to Do
- Visit the Duomo (Cathedral of Santa Maria del Fiore) – Climb to the top of Brunelleschi’s Dome for breathtaking city views.
- Explore the Uffizi Gallery – See masterpieces by Leonardo da Vinci, Michelangelo, and Botticelli.
- Walk Across Ponte Vecchio – This medieval bridge is lined with charming jewelry shops.
- Visit the Accademia Gallery – Home to Michelangelo’s famous statue of David.
- Sunset at Piazzale Michelangelo – A must-do for panoramic views of Florence.
Hotel Stay – Hotel Balestri – A charming hotel near the Arno River with stunning city views.
Florence is also a paradise for art lovers, boasting world-famous museums filled with works by Michelangelo, Botticelli, and Leonardo da Vinci. The city’s lively atmosphere, charming cafés, and scenic viewpoints make it an unmissable destination in Tuscany.
You may also like👉🏼7 Best Day Trips From Florence, Italy – Weekend Trips & Beautiful Places
Day 2: Chianti Wine Region – Vineyards & Wine Tasting
Commuting Options
- Car – Drive from Florence (30-40 minutes). Renting a car is recommended to explore at your own pace.
- Route: Florence → Greve in Chianti → Radda in Chianti.
- By Public Transport: Buses run from Florence to Greve in Chianti, but service is limited. Public transport is not ideal for exploring multiple villages in one day.
Tuscany is synonymous with world-class wines, and Chianti is at the heart of it. It’s a dreamy region filled with picturesque vineyards and charming villages. The rolling hills covered in vineyards and olive groves create an idyllic landscape, perfect for those who appreciate nature and fine wine. Chianti’s centuries-old winemaking traditions, combined with its warm hospitality, make every visit feel special.
Things to Do
- Wine Tasting in Greve in Chianti – Visit family-run wineries to taste authentic Chianti Classico.
- Explore Radda in Chianti – A scenic hilltop town with cobblestone streets and panoramic views.
- Lunch at a Vineyard – Enjoy a farm-to-table meal with a wine pairing.
- Drive the Chiantigiana Road (SR222) – One of the most scenic drives in Italy.
Hotel Stay – Villa Le Barone – A charming countryside villa in Radda in Chianti.
Whether you’re sipping a glass of Chianti Classico at a family-run winery or exploring quaint villages, you’ll be immersed in an authentic Tuscan experience.
Day 3: San Gimignano & Volterra – Medieval Tuscany
Commuting Options
- Car – Drive from Radda in Chianti (1 hour). Renting a car is best.
- Route: Radda → San Gimignano → Volterra.
- By Public Transport: A combination of train and bus is required, making travel time-consuming.
San Gimignano, known as the “Town of Fine Towers,” and Volterra, a historic Etruscan town, take you to an immersive medieval experience. These towns transport visitors to a bygone era with their well-preserved walls, ancient streets, and stunning architecture.
Things to Do
- Climb Torre Grossa in San Gimignano – Enjoy spectacular views.
- Visit Gelateria Dondoli – Taste world-champion gelato.
- Explore Volterra’s Roman Theater – A stunning historical site.
- Visit the Alabaster Workshops – Watch artisans craft unique souvenirs.
Hotel Stay – Hotel La Cisterna – Located in San Gimignano’s main square.
San Gimignano’s skyline, dominated by medieval towers, is a breathtaking sight, while Volterra’s Etruscan heritage and artistic culture make it a fascinating stop. Both towns boast spectacular views of the surrounding countryside, delightful trattorias, and rich local traditions.
Day 4: Siena – Gothic Splendor
Commuting Options
- Car – Drive from San Gimignano (45 minutes). Route: Volterra → Siena.
- By Public Transport: Direct buses from Florence take about 1.5 hours.
Siena is one of Tuscany’s most beautiful medieval cities, known for its stunning Gothic architecture, vibrant piazzas, and the famous Palio horse race.
Things to Do
- Visit Piazza del Campo – The heart of Siena and home to the famous Palio horse race.
- Explore Siena Cathedral (Duomo di Siena) – A gothic masterpiece.
- Walk the Medieval Streets – Discover hidden corners and artisan shops.
- Visit the Torre del Mangia – Climb for panoramic views.
Hotel Stay – Hotel Athena – Great views and a short walk to the center.
Day 5: Val d’Orcia – Picture-Perfect Tuscany
Commuting Options
- Car – Drive from Siena (1 hour).
- Route: Siena → Pienza → Montepulciano → Bagno Vignoni.
- By Public Transport: Buses are available but infrequent. Renting a car is recommended.
The rolling hills, cypress trees, and golden fields of Val d’Orcia define Tuscany’s postcard-perfect landscapes.
Things to Do
- Visit Pienza – A UNESCO-listed town famous for pecorino cheese.
- Explore Montepulciano – A Renaissance town known for Vino Nobile wine.
- Take Photos at the Chapel of Vitaleta – One of Tuscany’s most iconic spots.
- Relax in Bagno Vignoni’s Thermal Baths – A peaceful experience.
Hotel Stay – Agriturismo Poggio Piglia – A beautiful countryside farmhouse.
Day 6: Montalcino & Brunello Wine
Commuting Options
- Car – Drive from Val d’Orcia (45 minutes).
- Route: Val d’Orcia → Montalcino.
- By Public Transport: Take a train from Siena to Chiusi, then a bus to Montepulciano. Catch another bus to Cortona.
Montalcino is home to the world-famous Brunello wine and offers breathtaking views.
Things to Do
- Wine Tasting at Biondi Santi Winery – The birthplace of Brunello.
- Visit the Fortress of Montalcino – Enjoy panoramic countryside views.
- Explore Abbey of Sant’Antimo which is a peaceful Romanesque church.
Hotel Stay – Castello di Velona – A castle hotel with a view.
Day 7: Lucca & Pisa – A Grand Finale
Commuting Options
- Car – Drive from Montalcino to Lucca (2 hours), then to Pisa (30 minutes). Drop off your rental car in Pisa. Route: Montalcino → Lucca → Pisa.
- By Public Transport: Many trains connect Cortona to Lucca and Pisa easily.
Lucca is a hidden gem with well-preserved Renaissance walls, and Pisa’s Leaning Tower is iconic.
Things to Do
- Bike Along Lucca’s City Walls – A fun way to explore the town.
- Visit Piazza dell’Anfiteatro – A unique oval-shaped square.
- See the Leaning Tower of Pisa – A must-visit landmark.
Leaning Tower of Pisa
Hotel Stay – Hotel Relais dell’Orologio – A charming hotel in Pisa.
Helpful Tips for planning Tuscany Itinerary 7 Days
- Best Time to Visit: Spring (April–June) and fall (September–October) for pleasant weather.
- Getting Around: Renting a car is the best way to explore Tuscany’s countryside.
- Local Delicacies: Try pici pasta, ribollita soup, and bistecca alla fiorentina.
- Packing Tips: Comfortable walking shoes are essential for exploring cobblestone streets.
Driving Tips for Tuscany Road Trip – Places to Visit in Tuscany
Driving in Tuscany is one of the best ways to explore the countryside, but there are a few important tips to keep in mind.
- ZTL Zones (Limited Traffic Zones): Most historic town centers, including Florence, Siena, and Lucca, have ZTLs where only authorized vehicles can enter. Make sure to park outside these zones to avoid hefty fines.
- Narrow Roads: Many roads, especially in small villages, are narrow and winding. Drive cautiously and be prepared for tight turns.
- Toll Roads: Major highways (autostrade) have tolls. Keep some cash or a credit card ready for payment.
- Fuel Stations: Gas stations in rural areas may close early, so plan refueling accordingly.
- Parking: Free parking is often available outside town centers, with shuttle buses taking you in.
- Speed Limits & Cameras: Speed limits vary, and speed cameras are common. Always follow posted limits.
- Wine Tasting & Driving: If visiting wineries, consider hiring a driver or joining a guided tour to enjoy tastings responsibly.
Whether you’re a history lover, a foodie, or simply someone who enjoys stunning landscapes, Tuscany offers something magical daily. This 7-day Tuscany road trip itinerary takes you through the best of the Tuscan region, blending history, landscapes, and authentic experiences.
After reading this list of best places to visit in Tuscany, you know why Tuscany is one of the most beautiful regions in Italy, well-known for its rolling vineyards, medieval hilltop towns, world-class wines, and historic cities. Explore Tuscan adventures with this helpful Tuscany itinerary 7 days guide.
Picture Courtesy – CanvaPro
Follow more on social media channels at
Facebook, Twitter, Instagram, Pinterest
Read the Disclaimer, Affiliate & Cookie Policy by clicking here.
Discover more from Travel With Me 24 X 7
Subscribe to get the latest posts sent to your email.