Planning a trip to Tuscany can feel confusing at first. Many travelers run into the same problems: Which towns are actually worth visiting? Should you stay in Florence or in the countryside? Is it better to rent a car or rely on trains? Tuscany looks small on the map, but once you start planning, the number of places quickly becomes overwhelming.
I remember planning my first trip to Tuscany and feeling unsure about where to start. Florence alone could take several days. Then I continued reading about Siena, San Gimignano, the wine villages of Chianti, and the scenic hills of Val d’Orcia. It became clear that Tuscany is not one single destination. It is a region filled with different towns, landscapes, and food experiences.
When I finally visited Tuscany, what helped most was combining famous cities with smaller countryside towns. That balance made the trip feel relaxed instead of rushed. This guide shares the best things to do in Tuscany, Italy, from historic landmarks, scenic drives, wine regions, and local food experiences.
Quick Takeaways for Visiting Tuscany
| Topic | Best Place |
| Best city for art | Florence |
| Best medieval town | San Gimignano |
| Best wine region | Chianti |
| Best scenic landscapes | Val d’Orcia |
| Best relaxing town | Montepulciano |
| Best beach town | Viareggio |
Things to Do in Tuscany – City, Coast and Countryside
Tuscany offers many different travel experiences.
Some travelers focus on:
- historic cities
- museums
- famous landmarks
Others explore:
- countryside villages
- vineyards
- scenic drives
Florence is known for Renaissance art and architecture. Siena offers medieval streets and strong traditions. San Gimignano is famous for its tall stone towers.
Beyond the cities, the countryside reveals the landscape many travelers imagine when they think about Tuscany:
- rolling hills
- vineyards
- olive groves
- hilltop villages
When I first drove through the Tuscan countryside, the view felt exactly like the photos I had seen before visiting.
Long roads lined with cypress trees and quiet farms appear almost everywhere once you leave the big cities. For couples and slow travelers, Tuscany is also a peaceful destination.
Many visitors spend their days:
- driving scenic roads
- visiting wineries
- relaxing in small villages
Visit Pisa and the Leaning Tower
Pisa is one of the most famous destinations in Tuscany. The city is known for the Leaning Tower of Pisa, one of the most recognisable landmarks in the world. The tower stands in Piazza dei Miracoli, a historic square that also includes:
- Pisa Cathedral
- the Baptistery
Many visitors climb the Leaning Tower. From the top you can see:
- the city of Pisa
- the surrounding countryside
When I visited, the square was larger than I expected. The bright white marble buildings and the leaning tower together create one of the most iconic scenes in Italy. For first-time travelers in Tuscany, Pisa is one of the easiest day trips from Florence.
Lucca
Lucca is a charming city surrounded by Renaissance walls. These walls are still fully intact and today serve as a:
- walking path
- cycling route
around the historic center. Many travelers rent bikes and ride along the walls. From here you can see:
- church towers
- rooftops
- gardens across the city
Inside the walls, Lucca feels relaxed and welcoming. Narrow streets lead to:
- cafes
- bakeries
- small piazzas
One of the most famous squares is Piazza dell’Anfiteatro, built on the site of an ancient Roman amphitheatre. When I walked through this square, it quickly became one of my favorite spots in the city. Small restaurants and cafes surround the oval plaza. Lucca is also popular with:
- families
- couples
because the city is easy to walk and has a calm atmosphere.
Where to Stay in Lucca
Accommodation options include:
- hotels inside the historic walls
- countryside villas outside the city
Staying outside the city often offers peaceful vineyard views.
Truffle Hunting In San Miniato
- San Miniato sits between Florence and Pisa.
- The town is famous for white truffles, one of the most prized ingredients in Italian cooking.
- A popular activity here is truffle hunting.
Local guides take visitors into nearby forests with trained dogs that search for truffles underground.
Watching the dogs search for truffles was one of the most interesting local experiences during my trip. After the hunt, many tours include a meal where guests taste dishes made with fresh truffles. Food travelers often add San Miniato to their Tuscany itinerary because it offers a unique local experience.
Where to Stay in San Miniato
Popular options include:
- boutique hotels
- countryside farmhouses
- agriturismo stays
These places often offer views of vineyards and olive groves.
San Gimignano
San Gimignano is one of the most famous hill towns in Tuscany. The town is known for its medieval towers. During the Middle Ages, wealthy families built towers to show their power and status. Today several towers remain, creating the town’s unique skyline.
The historic center has:
- narrow streets
- stone buildings
- local shops
Piazza della Cisterna is the heart of the town. Many travelers relax here with:
- coffee
- gelato
I still remember sitting in this square with gelato while looking up at the tall stone towers. It feels like stepping back into medieval Italy. San Gimignano is also known for award-winning gelato shops.
Where to Stay in San Gimignano
Visitors can stay:
- inside the historic town
- in countryside villas nearby
Many countryside accommodations offer vineyard views.
Siena
Siena is one of the most historic cities in Tuscany. The heart of the city is Piazza del Campo, a large shell-shaped square where the famous Palio horse race takes place twice each year. Siena Cathedral is another highlight.
The cathedral is known for:
- detailed marble floors
- impressive artwork
Standing in Piazza del Campo, it becomes easy to imagine the famous horse race happening in the square. History lovers enjoy exploring Siena’s medieval streets and neighborhoods.
Where to Stay in Siena
Many visitors stay in:
- hotels inside the old city walls
This location allows easy access to major attractions.
Val d’Orcia
Val d’Orcia is one of the most scenic areas in Tuscany. The landscape includes rolling hills, vineyards, and roads lined with cypress trees. Many of the iconic photographs of Tuscany come from this region. Small towns such as Pienza and Montalcino sit on hilltops overlooking the countryside.
When I drove through this region near sunset, the golden light across the hills created one of the most memorable landscapes I saw during my trip.
Val d’Orcia is also recognised as a UNESCO World Heritage landscape because of its historic farming traditions and natural beauty. Couples and photographers often visit this area for peaceful scenery and sunset views.
Bagni San Filippo (San Filippo Thermal Springs)
Bagni San Filippo is known for natural hot springs. Warm mineral water flows through white limestone formations. The most famous formation is called the White Whale, created by mineral deposits.
Visitors relax in natural pools surrounded by forest. The water stays warm throughout the year, making it a relaxing stop after visiting nearby hill towns. Many travelers combine this stop with nearby villages in Val d’Orcia.
Montepulciano
- Montepulciano is a hill town known for wine and Renaissance architecture.
- Stone streets lead to historic squares, churches, and wine cellars.
- Wine lovers visit Montepulciano to taste Vino Nobile di Montepulciano, one of the region’s most respected wines.
- Many wine cellars are located beneath the town.
- Walking down the steep streets of Montepulciano often leads to underground wine cellars where visitors can taste local wines.
Volterra
- Volterra is another historic hill town in Tuscany.
- The town dates back to the Etruscan civilization. Visitors can still see parts of the ancient city walls and a Roman theater.
- Volterra is also known for alabaster crafts. Local workshops produce art from this soft white stone.
- Compared with some Tuscan towns, Volterra feels quieter and less crowded.
Get a Taste of Chianti with My Favourite Tour in Tuscany
- Chianti lies between Florence and Siena and is one of Italy’s most famous wine regions.
- Wine tours allow visitors to explore vineyards and learn how local wine is produced.
- Many tours include tastings of wine, olive oil, cheese, and traditional Tuscan dishes.
- Driving through Chianti was one of the highlights of my Tuscany trip because the countryside views change constantly along the road.
Take a Tuscan Cooking Class
- Cooking classes are a popular activity in Tuscany.
- Visitors learn how to prepare traditional dishes such as fresh pasta, bruschetta, and tiramisu.
- Many classes take place in countryside villas or farmhouses.
- Travelers cook together and enjoy the meal with local wine.
- Food lovers often consider this one of the most memorable experiences in Tuscany.
A 8 Day Easy to follow Plan According to My Trip
Days 1–2: Historic, Art and Cultural Things to Do in Florence
Florence is the cultural center of Tuscany. The Florence Cathedral is one of the most famous landmarks in Italy. Visitors can climb the dome for views across the city.
The Uffizi Gallery displays masterpieces by artists such as Leonardo da Vinci and Botticelli. Another famous attraction is Ponte Vecchio, a historic bridge lined with jewelry shops. Walking through Florence reveals markets, historic palaces, and lively squares.
Day 3: City of Horses and History – Trot Around Siena
After Florence, many travelers visit Siena.
Spend time exploring Piazza del Campo and Siena Cathedral. Walking through the streets reveals bakeries, cafes, and historic buildings. Siena offers a strong sense of history and local tradition.
Day 4: Great Gelato in a Towering Town – What to See in San Gimignano
- San Gimignano makes a great day trip.
- Visitors climb Torre Grossa for views across the countryside.
- After exploring the towers and streets, many travelers stop for gelato in the main square.
Day 5: A Fine Vintage – One of the Coolest Things to Do in Tuscany
- Day five often focuses on the Chianti wine region.
- Visitors travel through vineyard landscapes and small villages.
- Wine tastings introduce travelers to local grape varieties and wine traditions.
- Lunch at a vineyard is often part of the experience.
Day 6: Walk on the Wall Side with These Things to Do in Lucca
- Lucca offers a relaxed travel day.
- Cycling along the city walls is one of the most popular activities.
- Inside the city center, visitors enjoy slow walks, cafes, and small shops.
Days 7–8: Relax in Stylish Viareggio One of the Finest Tuscany Beaches
- Viareggio is a coastal town known for long sandy beaches.
- Visitors spend time swimming, relaxing under umbrellas, and walking along the seaside promenade.
- Restaurants along the coast serve fresh seafood and local wine.
Read also: 25 Best Things to Do in Minneapolis, Minnesota for Visitors
Best Tuscany Road Trip Route
Driving is one of the best ways to explore Tuscany.
A popular route is:
Florence → San Gimignano → Siena → Val d’Orcia → Montepulciano
This route passes vineyards, hill towns, and scenic countryside. Many travelers stop in small villages along the way for photos and local food.
Tuscany Photography Spots
Tuscany offers many famous photography locations.
One well-known spot is the cypress road near Agriturismo Baccoleno in Val d’Orcia. Another popular photo location is Cappella della Madonna di Vitaleta, a small chapel surrounded by rolling hills. Sunrise and sunset often create the best light for photography.
10 More Places to See in Tuscany – Small Towns for Your Travel Itinerary
1. Cortona
2. Anghiari
3. Montepulciano
4. Castelnuovo di Val di Cecina
5. Massa Marittima
6. Pienza
7. Barga
8. Castelnuovo Berardenga
9. Certaldo
10. Pitigliano
Tuscany Trip Planning Guide
| Days in Tuscany | Suggested Plan |
| 1–2 days | Explore Florence highlights |
| 3–4 days | Florence + Pisa + Siena |
| 5–6 days | Add San Gimignano and Chianti |
| 7+ days | Include Val d’Orcia and Montepulciano |
Tuscany Regions Overview
| Area | Known For |
| Florence | Renaissance art and museums |
| Chianti | Vineyards and wine tours |
| Val d’Orcia | Scenic landscapes |
| Lucca | Historic walls and cycling |
| Coastal Tuscany | Beaches and seaside towns |
Travel Tips for Tuscany
- Renting a car helps reach countryside towns.
- Start sightseeing early to avoid crowds.
- Hill towns often require walking uphill.
- Spring and fall usually offer the best weather.
Where to Stay in Tuscany – My Recommendation
- Travelers often stay in Florence, Siena, or the Chianti countryside.
- City hotels allow easy access to museums and landmarks.
- Countryside villas and agriturismo farms offer peaceful rural settings with local food and wine.
Tours of Tuscany
Guided tours help travelers explore Tuscany easily.
Popular tours include:
- wine tasting tours
- cooking classes
- cycling tours
- walking tours
These experiences provide insight into local culture.
Places to Visit in Tuscany – Map of the Region’s Highlights from City to Country and Coast
- Florence sits in northern Tuscany.
- Siena and Chianti lie further south.
- Val d’Orcia spreads across the southern countryside.
- Coastal towns such as Viareggio sit along the Tyrrhenian Sea.
- Understanding this layout helps travelers plan their route.
How to Get to Tuscany
- Most travelers arrive through Florence or Pisa. Florence has an international airport and strong train connections.
- Pisa airport serves many European flights. Trains connect major cities, while renting a car makes countryside travel easier.
Conclusion
After spending time exploring Tuscany, one thing becomes clear. The region offers far more than famous landmarks. Some of the best memories come from simple moments. Driving through the hills of Val d’Orcia at sunset. Sitting in a small town square with local food and wine. Walking quiet streets in places like Montepulciano or Pienza.
Florence and Siena provide history and art, but the countryside often creates the most memorable experiences. Tuscany rewards travelers who slow down and explore beyond the main cities. The landscapes, food, and historic towns leave a lasting impression long after the trip ends.
FAQs About Visiting Tuscany
How many days are enough for Tuscany?
Most travelers spend 5 to 7 days in Tuscany. This allows time to explore Florence, Siena, and several countryside towns.
Is Tuscany better explored by car or train?
Trains work well between major cities like Florence and Pisa. However, renting a car makes it much easier to reach hill towns and rural villages.
What is the most beautiful town in Tuscany?
Many travelers consider San Gimignano, Montepulciano, and Pienza among the most beautiful towns because of their hilltop views and historic streets.
What is the best month to visit Tuscany?
Spring and early fall are usually the best months because the weather is comfortable and crowds are smaller than in summer.