Every time I return to Tuscany, I get that same flutter of excitement driving through those rolling hills. The last time I visited, I found myself pulling over constantly just to stare at the perfectly aligned cypress trees and endless vineyards. Standing in front of Siena’s marble-striped cathedral at sunset, watching the facade glow golden, I realized why the beautiful places in Tuscany have captivated artists and dreamers for centuries.
From sipping Brunello in Montalcino’s medieval squares to watching the sun set behind Florence’s Duomo from Piazzale Michelangelo, each moment here feels almost surreal. After countless plates of pici pasta and way too many scoops of gelato, I’ve gathered my favorite spots across this incredible slice of Italy. Let me show you the places that keep drawing me back year after year.
Enchanting Places to Visit in Tuscany
Looking to explore Tuscany’s most beautiful places? From the rolling hills of Val d’Orcia to the historic streets of Florence, Tuscany is packed with stunning scenery. Stroll through the charming town of Siena, marvel at the art in Pisa, or explore the cultural richness of Lucca. Discover the serene allure of San Gimignano, the tranquil vineyards of Chianti, or the breathtaking views from Cortona. Whether you’re into history, art, or wine country, here are 12 of Tuscany’s most breathtaking spots!
1. The Old Town of Florence
Florence hits you like a Renaissance brick to the face, and honestly, that’s exactly what makes it so damn incredible. I’ve wandered these cobblestone streets more times than I can count, and it still gets me every single time – you literally can’t walk 10 steps without bumping into something Michelangelo or da Vinci touched.
The Uffizi Gallery currently runs about €25 for advance tickets (totally worth it to skip those insane lines), and the Accademia where Michelangelo’s David lives costs around €16. Pro tip: get the Firenze Card for €85 if you’re staying three days – it covers 72 museums and you’ll definitely save money. The Duomo climb costs €30 but those 360-degree views over terracotta rooftops are pretty spectacular.
Piazzale Michelangelo at sunset is tourist central, but there’s a reason everyone goes – it’s actually stunning and completely free. I always tell people to grab a bottle of wine and some cheese from a local shop and make it a proper picnic. The crowds thin out after 8 PM, and that golden hour light hitting the city is pure magic.
Food-wise, skip the touristy spots around major attractions where a mediocre pasta will run you €18. Head to Santa Croce neighborhood where locals eat – family-run places serve incredible meals for half the price. Hotels in central Florence are pricey right now (€200-400/night in 2025), but anything within walking distance of the Duomo saves you transportation costs.
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2. The Old Town of Siena
Siena feels like someone pressed pause on the 14th century and forgot to hit play again. The whole UNESCO-protected center revolves around that incredible shell-shaped Piazza del Campo, and trust me, it’s way more impressive than any photo can capture.
The Palio horse race happens July 2nd and August 16th every year, and 2025 tickets are already selling like crazy. I watched from the center of the piazza for free last time (you just stand there for about 4 hours in the sun), but balcony tickets run €500-800 now. Hotels jack up prices by 50-100% during Palio, so book at least 6 months ahead or stay in nearby Monteriggioni and bus in.
Siena Cathedral entry is €10, but the floor is only fully uncovered during Palio season – those marble inlay panels are actually incredible when you can see them all. The Torre del Mangia climb costs €12 and it’s worth every euro for views over Tuscany’s rolling hills.
The city’s 17 contrade (neighborhoods) each have their own fierce identity and museums. I spent an afternoon in the Oca (Goose) contrada museum learning about centuries of rivalry and tradition – it’s way more fascinating than it sounds. Each district throws massive outdoor dinners the night before Palio that feel like the world’s most intense block party.
Don’t miss the underground passages and ancient Fonte Gaia fountain. The atmosphere here is completely different from Florence – more intimate, authentic, and honestly a bit magical. Plus parking outside the walls costs about €1/hour versus Florence’s €3-5.
3. San Gimignano
This place looks like someone built a medieval Manhattan on a hilltop and then froze it in time. San Gimignano‘s 14 remaining towers (down from 72 originally) create one of the most dramatic skylines I’ve ever seen, especially when you’re driving up through Tuscan countryside and it just appears on the horizon.
Torre Grossa entry costs €8 and the climb is totally manageable – about 200 steps to views that’ll make your Instagram followers hate you. The medieval streets are packed during peak season, but early morning or late afternoon gives you those magical golden hour shots without fighting crowds.
The Vernaccia di San Gimignano wine tastings here are actually legit – this isn’t tourist trap stuff, it’s been produced since the 13th century. I tried about six different producers last visit and spent maybe €25 total. Gelateria Dondoli has world champion gelato (literally, they won competitions), and yeah, it lives up to the hype.
Parking costs €2/hour but fills up fast, so arrive before 10 AM. The town gets absolutely slammed with tour buses between 11-4, so plan museum visits and serious exploring outside those hours. Stay overnight if possible – when the day-trippers leave, you get this whole magical medieval town almost to yourself.
The saffron here is ridiculously good and makes great gifts – local shops sell little containers for €8-15. Walk the ancient walls for free and don’t miss the hidden courtyards where local artisans still make ceramics the same way they did 800 years ago.
4. The Leaning Tower of Pisa
Yeah, it’s touristy as hell, but the Leaning Tower of Pisa is actually worth the chaos. Everyone comes for the obligatory “holding up the tower” photo, but climbing inside is the real experience – those sloping floors are genuinely disorienting and unlike anything else you’ll do in Italy.
Advance climb tickets cost €25 and sell out weeks ahead in summer 2025. Book online through the official site because third-party sellers charge double. The entire Piazza dei Miracoli (Square of Miracles) is a UNESCO site with the tower, cathedral, and baptistery all worth seeing.
The Pisa Cathedral is free and honestly more impressive inside than many places you pay for. That pulpit is 13th-century art at its finest. The Baptistery has incredible acoustics – they do demonstrations every 30 minutes that are pretty cool.
Here’s what nobody tells you: Pisa is actually a great base for exploring western Tuscany. Hotels are cheaper than Florence (€80-150/night), and you’re 20 minutes from beaches, 1 hour from Lucca, and 90 minutes from Florence. The train connections are excellent.
I spent a whole afternoon just wandering the Arno River area away from the tourist zone. Found amazing seafood restaurants where locals eat and prices are totally reasonable. The university students give the city a fun energy that’s missing in more tourist-focused places.
The tower leans about 4 degrees now – they stabilized it in the 1990s so it won’t fall over. Those 294 steps to the top are steep but manageable for most people. Views over the city and countryside are solid, though not as spectacular as some other Tuscan towers.
5. Val D’Orcia
This is the Tuscany everyone pictures in their heads – rolling hills, perfect cypress lines, golden wheat fields, and farmhouses positioned like someone arranged them specifically for postcards. Val d’Orcia is a UNESCO site and honestly lives up to every single Instagram photo you’ve ever seen.
Pienza (the “ideal Renaissance city”) is tiny but incredible – walk the whole town in 2 hours and try the pecorino cheese that made it famous. Local shops sell wheels for €15-25 that would cost double anywhere else. Montalcino produces Brunello wine, and tastings at family estates run €15-30 for seriously good stuff.
The most photographed road is near Podere Belvedere – arrive at sunrise (around 6 AM in summer) for that misty, magical light everyone captures. I’ve gone back three times because the landscape changes completely with seasons. Spring wildflowers, summer wheat, autumn harvest colors – each visit feels different.
Bagno Vignoni has natural thermal pools where you can soak for free. The ancient Romans used these same springs, and they’re still perfect for relaxing after hiking. Monticchiello is a hilltop village with maybe 200 people and some of the best views in Tuscany.
Driving here is essential – public transport is limited. Rental cars run €35-50/day, but you’ll cover way more ground. Gas stations are sparse, so fill up in larger towns. Many agriturismos offer cooking classes (€80-120) that include lunch and wine – totally worth it for the experience and meeting other travelers.
The Crete Senesi area has those weird gray clay hills that look almost lunar. It’s eerily beautiful and way less crowded than the main Val d’Orcia route. Perfect for photographers wanting something different from the typical cypress tree shots.
6. Lucca
Lucca has something no other Tuscan city can claim – you can bike on top of 16th-century city walls that are still completely intact. I rented a bike for €12/day and spent hours cycling this elevated 4km park with views over the city and countryside. It’s honestly one of my favorite urban experiences anywhere.
The Torre Guinigi has oak trees growing on top (seriously), and climbing up costs €5. Those rooftop gardens are bizarre and beautiful. Piazza dell’Anfiteatro is built on Roman amphitheater foundations – you can still see the oval shape, and it’s lined with cafes perfect for people-watching.
Puccini was born here, so there’s live music constantly. Churches host free concerts almost daily, and the Lucca Summer Festival brings major international acts inside the ancient walls. I caught a concert at San Giovanni church – the acoustics are incredible and tickets were only €15.
The local specialty buccellato (sweet bread with raisins and anise) is available at bakeries citywide. I’m not usually into sweet breads, but this stuff is actually amazing with morning coffee. Lucca feels way less touristy than Florence or Siena – locals still outnumber visitors even in summer.
Parking outside the walls costs €1/hour, and everything inside is walkable. Hotels here run €100-200/night, significantly cheaper than major cities. The train to Florence takes 90 minutes and costs €8, making this a great base for exploring without big city prices.
The walls have great running/jogging paths if you’re into that. Early morning or evening, you’ll see locals using it as their neighborhood gym. Car-free city center means kids can run around safely, making it very family-friendly.
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7. Sorano, Sovana, and Pitigliano
These three medieval towns perched on volcanic cliffs feel like secret discoveries even though they’re all pretty well-known. Pitigliano earned the nickname “Little Jerusalem” because of its historic Jewish community – the restored synagogue and museum are fascinating and cost €4 to visit.
The towns literally emerge from cliffside rock – Pitigliano especially looks like it grew organically from the stone. Sunset here is absolutely magical when the tufa rock glows golden. I probably took 200 photos trying to capture it properly.
Vie Cave are these mysterious sunken roads carved through rock by Etruscans 2,000+ years ago. They’re basically outdoor museums you can hike through for free. Some passages are 15 feet deep and create this incredible canyon effect. Sovana has the best-preserved Etruscan necropolis with tombs dating to 3rd century BCE.
Sorano has the most dramatic setting and great little cafes in medieval squares. I found this amazing family trattoria where lunch for two with wine cost €35 total. The old fortress offers panoramic views that stretch forever across Maremma countryside.
This area is about 2 hours from Florence, 1.5 from Rome – perfect for breaking up travel between the two cities. Accommodation is limited but charming. I stayed at a converted 11th-century fortress that was honestly one of the coolest hotels I’ve ever experienced.
The towns connect via hiking trails if you’re ambitious – about 6km between each. Road signs are sometimes confusing, so GPS is essential. Spring and fall are ideal because summer heat can be intense and winter weather unpredictable.
8. The Mountain Town of Cortona
Cortona sits 600 meters above sea level with views that literally made me pull over and stare the first time I drove up. This is “Under the Tuscan Sun” territory, and yeah, it absolutely lives up to the romantic reputation while somehow avoiding feeling like a movie set.
The Diocesan Museum houses Fra Angelico masterpieces and costs €8 – his Annunciation alone is worth the price. Etruscan Academy Museum has this incredible bronze chandelier from 5th century BCE that survived somehow. Entry is €12 and includes fascinating artifacts that predate Rome.
Local food is hearty and reasonably priced compared to coast cities. Pici pasta with wild boar ragù at family trattorias runs €12-15 and portions are huge. The Archidado Joust happens in June when locals dress in medieval costumes for crossbow competitions – it’s way more authentic-feeling than touristy festivals.
Streets are steep and cobblestoned, so comfortable shoes are essential. The walk from parking areas to the center is about 10 minutes uphill, but local shuttle buses run €1 if you’re not feeling it. Fortezza del Girifalco at the top offers incredible valley views for free.
Hotels here are mid-range expensive (€120-250/night) but you’re paying for location and views. Many have terraces overlooking Val di Chiana that are perfect for evening wine. The town empties out after day tours leave, so staying overnight gives you peaceful exploration time.
I always recommend timing visits for golden hour – the light hitting those stone buildings and countryside views is absolutely spectacular. Morning markets happen twice weekly where locals sell produce, cheese, and crafts.
9. The Coastal Beauty of Viareggio
Viareggio offers something completely different – 3km of excellent sandy beaches lined with Art Nouveau buildings painted in pastels. It’s Tuscany’s premier beach resort, and the promenade is honestly beautiful, especially at sunset.
The famous Carnival (February-March) features massive satirical floats up to 20 meters high that mock politicians and celebrities. I’ve never seen political satire this creative or gigantic – tickets run €18-25 and it’s absolutely worth experiencing. Hotels get expensive during Carnival, so book early.
Beach clubs charge €25-40/day for loungers and umbrellas, which includes shower access and sometimes lunch discounts. Free public beaches exist but get crowded. The Apuan Alps are visible from the shore and offer great hiking just 30 minutes inland.
Viareggio makes a good base for exploring northwest Tuscany. Lucca is 30 minutes away, Pisa 25 minutes, and Cinque Terre is about 90 minutes by train. Hotels run €100-300/night depending on season and sea views.
The boardwalk (Passeggiata) has excellent restaurants where seafood is fresh and reasonably priced. I found a place serving grilled fish for €20 that would cost double in Florence. Night life here is more relaxed than big cities – beach bars and casual wine spots rather than clubs.
Train connections are excellent – direct service to Florence takes 90 minutes and costs €12. Beach season runs May through September, but shoulder seasons offer better prices and fewer crowds while still having decent weather for walking and exploring.
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10. Montepulciano
Montepulciano produces Vino Nobile, one of Italy’s finest red wines, and the town is basically built on wine cellars carved into limestone cliffs. Underground aging rooms extend deep into rock – touring them is like exploring wine caves that predate most European cities.
The main Piazza Grande has that unfinished cathedral and Palazzo Comunale you can climb for €5. Views stretch across Val d’Orcia to Monte Amiata – absolutely worth the stairs. San Biagio Church outside town walls is Renaissance architecture perfection and completely free to visit.
Wine tastings happen everywhere – family estates charge €15-25 for serious tastings with 4-5 wines plus local cheese and salami. I probably did 6 tastings over two days and learned more about wine than I expected. September-October during harvest is magical when you can watch grape picking.
The Bravio delle Botti festival in August features teams rolling huge barrels up steep medieval streets while crowds go crazy. It’s athletic, competitive, and way more entertaining than it sounds. Hotels fill up for this, so advance booking is essential.
Montepulciano sits at 605 meters elevation, so it’s cooler than valley towns even in summer. Stone buildings and narrow streets provide natural air conditioning. Parking is challenging – arrive early or use lots outside walls and walk up (about 10 minutes).
Restaurants serve hearty Tuscan food at reasonable prices. Osteria di Borgo had incredible wild boar stew for €16 that came with enough bread to feed three people. Local pecorino cheese aged in wine cellars has this amazing complex flavor you can’t find elsewhere.
11. Volterra
Volterra spans 3,000 years of history, from Etruscan origins through Roman rule to medieval glory. The Guarnacci Etruscan Museum has the most important Etruscan collection outside Rome, including that haunting “Shadow of the Evening” bronze statue – €16 entry and absolutely fascinating.
This is alabaster capital of the world, and watching artisans carve the translucent stone is mesmerizing. Workshops line medieval streets where families have practiced this craft for generations. You can buy pieces ranging from €15 souvenirs to museum-quality sculptures costing thousands.
Twilight fans recognize Volterra as the Volturi vampire headquarters, but honestly, the town’s actual history is way more interesting than fiction. The Roman Theater ruins are impressive and free to visit – you can see original stage structures and seating carved from rock.
The Balze clay cliffs at town’s edge are slowly eroding in this fascinating geological process. Walking to viewpoints is free and offers dramatic landscapes that look almost otherworldly. Medieval walls and towers provide excellent photography opportunities, especially during golden hour.
Volterra sits high enough (531 meters) that it catches cool breezes even in summer heat. Stone construction keeps buildings naturally cool. The town has great restaurants serving traditional Tuscan food – I found places charging €12-18 for full meals that would cost €25+ in Florence.
Hotels here are reasonably priced (€80-180/night) and many occupy historic buildings with authentic character. Parking costs €1.50/hour in town or use free lots about 10 minutes walk outside walls. The town stays lively with locals even after tourists leave, giving it authentic Italian atmosphere.
12. Chianti
Chianti wine country delivers every single Tuscan fantasy you’ve ever had – rolling hills covered with vineyards, cypress-lined roads, stone farmhouses, and medieval villages connected by scenic drives that photographers dream about.
Wine tastings at historic estates run €20-40 for serious sessions with 4-6 wines plus local food pairings. Castello di Brolio where modern Chianti was basically invented offers tours for €25 that include cellars, vineyards, and that dramatic castle. Many places offer cooking classes (€80-120) where you learn pasta-making and eat everything with their wines.
Greve in Chianti has the best Saturday market where local producers sell everything from wine to cheese to olive oil. Radda in Chianti and Castellina in Chianti are picture-perfect medieval villages where you can spend hours just wandering stone streets and stopping at wine bars.
Hot air balloon rides over Chianti cost around €200-250 and provide absolutely incredible aerial views of this landscape. Dawn flights offer the best light and calmest conditions. I did this last year and it honestly felt like floating over a Renaissance painting.
Driving here is essential since vineyards are scattered across countryside. Rental cars cost €35-50/day, and having designated drivers for wine tastings is smart planning. Many estates offer pickup services from Florence or Siena for €40-60 per person.
Agriturismo stays are perfect for experiencing authentic rural Tuscany. Family-owned properties serve incredible dinners using their own wine, olive oil, and produce. Rooms typically cost €120-200/night but include breakfast and often dinner. It’s way more authentic than hotel experiences.
Harvest season (September-October) is magical when you can participate in grape picking at many estates. Spring offers green landscapes with wildflowers, while summer brings those classic golden wheat field photos everyone wants.
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