Best Cities Near Florence Italy That Are Worth Visiting

Best Cities Near Florence That Are Worth Visiting

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Florence is a great base to explore some of Tuscany’s most beautiful cities and towns.

You can enjoy medieval towns on hilltops, stroll through the small cobblestone streets, and enjoy the local food and wine.

While some of the best cities near Florence are reachable by train, the best way to experience the small hilltop towns is by joining a guided tour or if you’re comfortable by driving.

Visiting Florence and the hilltop cities in Tuscany is one of the best things to do in Italy. Especially if you visit Florence in 3 days, you can spend day 3 by exploring one of the nearby cities.

Our Top Picks for Cities Near Florence

Siena
San Gimignano
Volterra
Montepulciano
Pisa

1. Siena 

Piazza del Campo in Siena, Italy, viewed from a narrow side street. The medieval square is dominated by the Torre del Mangia and the Palazzo Pubblico with its Gothic architecture. The space is open and dotted with visitors.
Piazza del Campo and Palazzo Vecchio in Siena

Siena, a city with a rich medieval history, is known for its stunning Gothic architecture and vibrant local culture. The city’s centerpiece is the Piazza del Campo, famous for the Palio horse race.

Distance from Florence: 50 miles / 80 km

Things To See:

  • Piazza del Campo: One of Europe’s greatest medieval squares.
  • Siena Cathedral: An architectural masterpiece with intricate details.
  • Palio di Siena: Experience this historic horse race if you’re visiting in July or August.

Siena’s narrow streets and beautiful buildings make it a captivating destination that complements any Tuscan itinerary. The city is very popular and is one of the best cities to visit in Italy for first-timers.

⭐️ Are you planning a trip to Italy soon? Download our free Italy travel checklist, and check out our free Italy trip budget calculator!

2. Volterra 

Volterra is one of the hidden gems in Tuscany and among the best small towns
Volterra

Volterra, a hilltop medieval town, is one of our personal favorites.

The ancient walls and stunning vistas make it feel like you’ve stepped back in time.

Staying at a nearby agriturismo added to the charm, waking up to birdsong and fresh Tuscan air. The best way to visit Volterra is by car.

Read our guide on tips for driving in Italy for the first time to make your visit to Tuscany as smooth as possible.

Distance from Florence: 39 miles / 63 km

Highlights:

  • Etruscan Museum: Showcases fascinating artifacts from the Roman era.
  • Roman Theatre: A well-preserved site worth visiting.
  • Shopping: Local workshops sell exquisite hand-carved alabaster pieces, perfect for souvenirs.

Volterra isn’t as crowded as San Gimignano or Siena, making it one of the best small towns in Tuscany, and a peaceful retreat where you can truly soak in Tuscany’s beauty.

😱 Travel Tip: Read our how to avoid tourist scams in Italy article! We witnessed these in Florence as well!

3. San Gimignano 

The historic skyline of San Gimignano, Italy, known for its well-preserved medieval towers and surrounding countryside. The towers rise above the town, against a backdrop of rolling hills and a dramatic sky.
view of San Gimignano

Often referred to as the medieval Manhattan, San Gimignano is known for its towering skyline.

Climb the Torre del Podesá for breathtaking views of the Tuscan hills.

The town is also home to incredible historical art, such as the frescos in the La Collegiata church.

Distance from Florence: 35 miles / 57 km

Must-Do’s:

  • Gelateria Dondoli: Don’t miss tasting what many claim to be the world’s best gelato.
  • Fonti Medievali: A hidden gem just outside the historical center.
  • Piazza Moments: Enjoy a coffee in the main piazza, where you might witness an authentic Italian wedding.

San Gimignano is magical in the early morning or late afternoon when the light is soft and the crowds are thin.

4. Montepulciano 

Christina in front of the Pozzo dei Grifi e dei Leoni fountain in Montepulciano
Christina in front of the Pozzo dei Grifi e dei Leoni fountain in Montepulciano

Montepulciano is a dream destination for wine lovers.

Known for its Vino Nobile, this town offers rich, full-bodied red wines best enjoyed in a local bar with family or during a wine tasting in a historic wine cellar.

Distance from Florence: 68 miles / 110 km

Things To See:

  • Palazzo Comunale: An architectural marvel.
  • City Walls: Walk to the western part for stunning views of the Tuscan landscape.
  • Tempio di San Biagio: A picturesque church standing alone in a scenic field.

Explore the wine cellars within and outside the city walls for the best tasting experiences. Montepulciano blends culture, relaxation, and breathtaking views seamlessly.

5. Pisa

The Leaning Tower of Pisa and the adjacent Pisa Cathedral under a soft, cloudy sky at. The white and gray marbled exteriors of both the tower and the cathedral exhibit intricate architectural details and Romanesque styling.
The Leaning Tower of Pisa and Duomo Santa Maria Assunta

Pisa is famous for the Leaning Tower, the Piazza dei Miracoli, and the Duomo Santa Maria Assunta.

Besides these world-renowned attractions, Pisa also has beaches to offer. If you want to spend some time at the sea, Pisa is a good choice for you.

In case you experience Florence in the rain, Pisa might be a great choice for a day trip.

Distance from Florence: 50 miles / 80 km

Things To See:

6. Cortona 

Best Cities Near Florence Italy

Famous from the book and movie “Under the Tuscan Sun,” Cortona’s charm is undeniable. Walking its streets, you’ll understand why the city and a bike tour through the Val di Chiana is so special.

Distance from Florence: 72 miles / 116 km

Must-Sees:

  • Museo Diocesano: Features beautiful religious art.
  • MAEC: Ideal for Etruscan artifact fans.
  • Belvedere at Piazza Garibaldi: Offers spectacular views of the surrounding landscape.

7. Castellina in Chianti 

Author Christina at a terrace overlooking the rolling hills of Tuscany during a breakfast in a agriturismo in Castellina in Chianti
Breakfast with a view in Castellina in Chianti

Nestled in the Chianti wine region, Castellina in Chianti is perfect for relaxing amidst serene woodlands with a glass of wine. Once an important Florentine outpost, it retains a sense of its historical significance.

Distance from Florence: 30 miles/48 km

Key Attractions:

  • La Rocca: Now the town hall, featuring an archaeological museum.
  • Wine Shops: Plenty of options for wine tasting and shopping.

Strolling through Castellina feels like stepping back into the 15th century, making it a great escape.

Tips for Exploring Cities Near Florence

Getting There

Most towns are just a one to two-hour drive from Florence.

Renting a car with Discovercars is the best way to explore these charming villages at your own pace. We explored the cities close to Florence during a Tuscany road trip. 

Learn more about what you need to know and how to save money in our guide about renting a car in Italy.

Driving around the Tuscan countryside is amazing and one of the many reasons to visit Italy.

Guided Tours

If you prefer convenience, our favorite list of day trips from Florence to Tuscany offers guided experiences that cover multiple highlights in one day.

Where To Stay

Beautiful agriturismo near Volterra with a pool and the golden hills of Tuscany in the back.
Agriturismo near Volterra with a view of the golden hills of Tuscany.

Many great options exist, from boutique hotels in town centers to countryside agriturismos. Waking up amidst vineyards and olive groves in Castellina in Chianti and close to Volterra was our favorite experience

Best Time to Visit The Towns

Spring (April to June) and fall (September to October) offer mild weather and fewer crowds.

Summer is peak season, so expect high temperatures and more tourists, especially in Siena and San Gimignano.

Final Thoughts About The Best Cities To Visit Near Florence

While Florence and Siena are essential stops, the nearby small towns offer unique experiences. Volterra, Montepulciano, and San Gimignano are our favorites, especially if you’re Italy travel itinerary is tight. 

You might also enjoy our Florence In One Day Itinerary
2 Days In Florence: The Perfect Itinerary
Is Florence Worth Visiting? Reasons For A Trip
How Many Days In Florence? This Is What You Need To Know
The Best Day Trips From Florence To Tuscany
Food Guide For Florence
Best Secret Spots In Florence

PLAN YOUR CITY TRIP TO ITALY

✈️ Compare and book flights to Italy with Expedia
🚅 Book train tickets and find timetables with Omio
🚗 Rent a car with DiscoverCars

🏨 Find the best rates for hotels and accommodations with Booking or Expedia
🎒 Find budget hotels and hostels in Italy at Hostelworld

📱Get a SIM card for Italy at DrimSim to avoid high roaming fees
📈 Get Travel Insurance for Italy
🎟 Find the best tours and activities at GetYourGuide or Viator

Is your flight delayed or canceled? Airhelp helps you to receive compensation. You can check them out here.

PLAN YOUR TRIP TO FLORENCE

✈️ Compare and book flights to Florence airport with Expedia
🚅 Book train tickets to Florence with Omio
🚗 Rent a car and explore Tuscany with DiscoverCars

🏨 Book your Florence hotel with Booking or Expedia
🎒 Find budget hotels and hostels in Florence at Hostelworld

📱Get a SIM card for Italy at DrimSim to avoid high roaming fees
📈 Get Travel Insurance for Italy 

🗺 Buy a Florence City Card for public transportation and access to the main attractions
🎟 Find tours and activities for Florence at GetYourGuide or Viator

Is your flight delayed or canceled? Airhelp helps you to receive compensation. You can check them out here.

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About The Author

Christina Leutner is the founder of ItalyThingsToDo. She has a profound love for Italy, having made her first trip to the Italian seaside at the age of two.

As a travel expert, author, and content creator, Christina shares invaluable travel planning tips, detailed itineraries, and comprehensive guides to ensure you have the perfect trip to Italy.

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