23 most beautiful places in Tuscany
Last updated on June 3rd, 2026.
Tuscany's most beautiful places span three distinct types: Renaissance cities (Florence, Siena, Pisa), hilltop towns (San Gimignano, Montepulciano, Volterra, Cortona) and the Val d'Orcia valley villages (Pienza, Montalcino, Montepulciano). For first-time visitors, Florence and Siena are essential. For the iconic rolling hill scenery, the Val d'Orcia in spring offers the most photographed Tuscany views. Most visitors need 5 to 7 days to meaningfully cover the highlights.
Tuscany is the region most people picture when they dream about Italy.
Rolling green hills, slender cypress trees, hilltop villages and Renaissance cities: it delivers on every expectation.
Romantic, wild and inspiring, it's one of the most rewarding regions in the country to explore.
In this guide I'll be sharing 23 of the most beautiful, most picturesque and most scenic places in Tuscany, from iconic cities to lesser-known hilltop towns.
Whether you're planning a weekend in Florence, a slow drive through the Val d'Orcia or a Tuscany road trip, you'll find the right destination here.
Perfect material for your Italy bucket list, use this post to help plan your trip to Italy.
Tuscany at a glance
TL;DR: If you only have a few days, focus on Florence for art, Siena for medieval history and Val d'Orcia (Pienza/Montepulciano) for iconic rolling hill views.
Deciding which part of the region to visit can be overwhelming, as each town offers a completely different experience.
To help narrow down your itinerary, I’ve summarized the most beautiful places in Tuscany in the comparison table below. It highlights what each destination is best for and a quick local tip for your visit.
| Destination | Best for | What is it like? | Travel tip |
| Florence | First-timers | Busy, touristy, renaissance architecture | Book Uffizi Gallery and Accademia tickets months in advance |
| Siena | First-timers | Atmospheric and majestic | Visit for the Palio (horse race) in July/August |
| San Gimignano | Slow travel | 'Manhattan of the Middle Ages' | Climb Torre Grossa for the best panoramic views |
| Montepulciano | Wine lovers | Historic hilltop | Book a vino nobile cellar tour |
| Pitigliano | Off-the-beaten path travel | 'Small Jerusalem' vibes and incredible views | Explore the Jewish Ghetto and Vie Caves |
| Pienza | Couples and slow travel | Romantic views and outdoor dining | Walk the panoramic city walls |
Planning a route? Check out my 5-day Tuscany itinerary to see how to link these together.
Interactive map of Tuscany: the 23 most beautiful places
To help visualize your trip, I’ve created this interactive map of the most beautiful places in Tuscany.
I’ve organized the destinations into four easy-to-navigate layers: major cities, hilltop towns, Tuscan villages and coastal escapes.
Click the icon in the top-left corner of the map to toggle these layers on and off and plan your perfect Tuscan route.
Want to see these locations in motion? Take a 4K virtual walk through Florence, Siena and Lucca to get a true feel for the Tuscan atmosphere.
Where is Tuscany?
Tuscany is a region in central Italy. It’s surrounded by Liguria to the north, Emilia-Romagna to the east and Umbria and Lazio to the south.
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23 most beautiful places in Tuscany
Pretty Tuscany cities
Immerse yourself in the rich history, art and architecture embodied in Tuscany’s cities. With plenty of attractions to fill a 5 days in Tuscany itinerary, the hardest part is deciding which ones you’d like to visit.
Most travelers start their Tuscany journey by flying into Pisa or Florence. See which one is cheaper in my Italy international airports guide.
1. Florence
The capital city of Tuscany, you don’t want to miss the opportunity to visit Florence.
Home of Renaissance art and architecture, the city offers plenty with its museums in Florence and its historic landmarks. Whether you choose to spend 1 or 2 days in Florence, it’s a Tuscan city that you shouldn’t miss.
Best attractions in Florence
The Duomo: climb Brunelleschi’s iconic red-tiled dome for the best city views.
Uffizi Gallery: home to the world’s greatest collection of Italian Renaissance art.
Ponte Vecchio: the famous medieval stone bridge lined with glittering jewelry shops.
📌 How to get there: High-speed train (Frecciarossa) from Rome (1.5hrs) or Milan (1hr 45mins). If flying, use Florence Peretola (FLR) or Pisa (PSA) for more budget options.
2. Siena
One of the most beautiful places in Tuscany, Siena has all the characteristics that make the perfect Tuscan city.
At its center is the jaw-dropping Duomo (Cattedrale di Santa Maria Assunta) and one of Europe’s greatest medieval squares and gothic town hall, Palazzo Pubblico.
We fell in love with Siena from the moment when we first visited on our Italy road trip. A UNESCO World Heritage Site city, it’s a true Tuscan gem.
Best attractions in Siena
Piazza del Campo: the shell-shaped main square, home to the Palio horse race.
Siena Cathedral (Duomo): a Gothic masterpiece with an inlaid marble floor.
Torre del Mangia: climb the 400 steps of this 14th-century tower for a bird's-eye view.
📌 How to get there: Itabus is the fastest, and cheapest, way to travel from Florence to Siena. Ticket prices start from €6.90* with an average journey time of 1 hour. Trains take longer and include a train change, bus and a walk.
3. Pisa
A city made famous by its leaning tower, Pisa continues to draw visitors in their masses to see the structure. Buy tickets to climb to the top of the tower to enjoy panoramic views of Pisa and the Tuscan countryside.
Located in the aptly named Square of Miracles (Piazza dei Miracoli), the bell tower sits alongside other historical landmarks.
They include Pisa Cathedral (Duomo di Pisa), the baptistery (Battistero di San Giovanni) and the cemetery (Camposanto). Get a combined ticket to visit all the landmarks in the Square of Miracles.
Battistero di San Giovanni, Camposanto, Piazza del Duomo
How to get from Florence to Pisa
There are two ways to get from Florence to Pisa. If renting a car, the journey takes around 1hr and 24mins and will take you past towns like San Miniato Basso.
Best attractions in Pisa
Leaning Tower: the world’s most famous architectural mistake in the Piazza dei Miracoli.
Pisa Baptistery: known for its acoustics and striking Romanesque-Gothic design.
Camposanto Monumentale: a peaceful cloistered cemetery with ancient frescoes.
📌 How to get there: Direct trains run every 30 minutes from Florence (approximately 1hr 10mins) to Pisa. From Pisa Centrale, it’s about a 20-minute walk or a quick bus ride to the Leaning Tower.
Before you book your Tuscany trip
Tuscany in August is beautiful, but brutally hot and heavily crowded. Read my honest guide on when to visit Italy and the 17 biggest Italy planning mistakes to get your timing and logistics right.
4. Lucca
Lucca is a city renowned for its well-preserved medieval walls that encircle the city center. They were never breached or torn down, making Lucca one of the few Italian cities with fully preserved city walls.
Main attractions in Lucca’s city center include the Piazza dell'Anfiteatro, a unique oval-shaped square filled with bars and shops.
Also nearby is Torre Guinigi, a tower with oak trees on its rooftop offering panoramic views.
One of the most beautiful places in Tuscany, come to Lucca for its renaissance walls, picturesque views and the music scene.
Best attractions in Lucca
The renaissance walls: a 4km loop of preserved walls, ideal for walking or cycling.
Guinigi Tower: a medieval tower topped with ancient holm oak trees.
Piazza dell'Anfiteatro: a circular square built on the ruins of an ancient Roman amphitheater.
📌 How to get there: easy direct train from Florence SMN station (1hr 15mins). The station is right outside the historic walls, making it a perfect car-free day trip.
5. Arezzo
One of the less touristy Tuscany cities, Arezzo has plenty of travel potential. As you walk around the town and streets, you absorb the different historical influences.
At its heart is Piazza Grande, a large medieval square seemingly frozen in time.
Surrounded by 16th century stone buildings, cafes and antique shops, Arezzo makes an ideal day trip from Florence.
Best attractions in Arezzo
Piazza Grande: a medieval square famous as the setting for the movie 'Life is Beautiful'.
Basilica of San Francesco: home to the legendary Piero della Francesca fresco cycle.
Monthly antiques fair: Italy’s oldest and largest market (first Sunday of every month).
📌 How to get there: Frequent direct trains from Florence (around 50 minutes). The historic center is a short walk up the hill from the station. By car, the journey time is around 1 hour.
Tuscany is best explored by car. If you're nervous about driving in Italy, read my guide on 'Renting a car in Italy' and how to avoid 'ZTL Tuscany fines'.
6. Livorno
The coastal city of Livorno is known for being one of the largest and busiest ports in Italy.
Livorno's architectural style reflects its history of multiculturalism and different cultural influences.
Within the city is a mix of Renaissance, Baroque, Neoclassical and Art Nouveau architecture. Visit the Central Market (Mercato Centrale) to see an example of 19th-century iron and glass architecture.
Another neighborhood worth visiting is the Venetian Quarter (Venezia Nuova). It was named after Venice given its network of canals and colorful buildings lining the waterways.
Mercato Centrale, Via Buontalenti
Best attractions in Livorno
Terrazza Mascagni: a black-and-white checkered seaside terrace.
Quartiere Venezia: a district of canals and bridges inspired by Venice.
Mercato Centrale: one of Europe’s largest indoor food markets with plenty of fresh seafood.
📌 How to get there: very easy to reach by direct train from Florence (1hr 18mins) or Pisa (13 minutes). From Livorno Centrale station, take bus no. 1+ (20 minutes) to reach Terrazza Mascagni and the seafront.
Beautiful Tuscan towns
Discover some of the most beautiful hilltop towns in Tuscany and get lost in the beauty and splendor.
7. Montepulciano
The small hilltop town of Montepulciano is famous for its namesake wine and beautiful views of the Tuscany countryside.
Its town center is well preserved and boasts a 16th century cathedral, historic churches, palaces and a grand piazza. Come here to stroll through its pretty streets and to sample the local Vino Nobile di Montepulciano.
Best attractions in Montepulciano
Piazza Grande: the main square dominated by the Palazzo Comunale.
Underground wine cellars: deep, vaulted caves where Vino Nobile has aged for centuries.
San Biagio Church: a honey-colored Renaissance church sitting outside the walls.
📌 How to get there: The most efficient way is by car (1hr 15mins from Siena). By public transport, take a train from Siena to Chiusi-Chianciano Terme (1hr) followed by a local bus (FN1) for 20 minutes.
8. San Gimignano
Tucked away in central Tuscany is the picturesque small hilltop town of San Gimignano.
Renowned for its many medieval towers, they were built by wealthy families during the 14th and 15th centuries.
A UNESCO World Heritage site, San Gimignano has several notable attractions. Alongside exploring its quaint streets, visit its cathedral (Duomo di San Gimignano) and the art museum (Palazzo Comunale Pinacoteca).
For panoramic views of the Tuscany countryside, climb to the top of one of the town's remaining towers.
⏩️ Visit San Gimignano plus Pisa and Siena on this day trip from Florence with lunch included.
Duomo di San Gimignano, Piazza delle Erbe
Palazzo Comunale Pinacoteca, Piazza Duomo, 2
Best attractions in San Gimignano
Medieval Towers: 14 surviving 'skyscrapers' that create Tuscany’s most famous skyline.
Piazza della Cisterna: a triangular square with a 13th-century well.
Torre Grossa: the tallest tower in town, offering 360° views of the vineyards.
📌 How to get there: there's no direct train. Take the train to Poggibonsi from Firenze Rifredi. From here, catch bus no.130 (20 mins) which drops you right at the city gate.
9. Certaldo
Get lost in the charming streets and architecture of Certaldo in central Tuscany.
We visited as part of our 4-day Tuscany road trip and it was easily one of our highlights.
Divided into two parts, Upper Certaldo (Certaldo Alto) and Lower Certaldo (Certaldo Basso), the town makes for an interesting visit.
Certaldo Alto is the medieval part of the town, while Certaldo Basso is the more modern quarter.
The former is where you’ll find Palazzo Pretorio (museum) and the House of Boccaccio (Casa di Boccaccio). Once home to Italian writer Giovanni Boccaccio, the 14th century house is now a museum dedicated to his work.
Palazzo Pretorio, Piazzetta del Vicariato, 4
Casa di Boccaccio, Via Giovanni Boccaccio, 18
Best attractions in Certaldo
Palazzo Pretorio: a brick fortress decorated with the colorful coats of arms of past governors.
Casa Boccaccio: the former home of poet Giovanni Boccaccio.
The funicular: a cable car ride connecting the new town to the medieval top.
📌 How to get there: take a direct train from Florence (1 hour) or Siena (35 minutes) to Certaldo station. From the modern lower town, take the funicular (€1.40)* up to the medieval hilltop center.
10. Cortona
Overlooking the Chiana Valley (Val di Chiana) in eastern Tuscany is the hilltop town of Cortona.
Visitors come to Cortona to walk the Etruscan city walls and to enjoy the views from the impressive Girifalco Fortress.
Other top attractions in Cortona include the Captain’s Palace (Palazzo del Capitano), Republic Square (Piazza della Repubblica) and its churches.
To learn more about Cortona’s rich history, include the Museum of the Etruscan Academy (Museo dell'Accademia Etrusca) to your itinerary.
Palazzo del Capitano, Via Roma, 4
Fortezza del Girifalco, Via di Fortezza
Museo dell'Accademia Etrusca e della città di Cortona (MAEC), Piazza Luca Signorelli, 9
Best attractions in Cortona
Piazza della Repubblica: the heart of town with its iconic stone staircase.
MAEC Museum: houses a collection of Etruscan treasures and art.
Santa Margherita Sanctuary: a high-point basilica with views of Lake Trasimeno.
📌 How to get there: take the train to Camucia-Cortona station (1hr 12mins from Florence). From here, catch the local SU4 bus (10 minutes) that climbs the steep hill to the town center.
11. Pitigliano
One of the most beautiful places in Tuscany, the hilltop town of Pitigliano is unmissable.
Located in the Grosseto region in southern Tuscany, get lost in the labyrinth of its magnificent cobblestone streets.
Known as 'little Jerusalem’, Pitigliano has had a Jewish community and presence for centuries. As you walk around the small Tuscan town, take note of its synagogue and its Jewish shops.
My travel guide on the best things to do in Pitigliano covers the Tuscan borgo in greater detail.
Best attractions in Pitigliano
The Jewish Ghetto: known as little Jerusalem, featuring a historic synagogue and carved cellars.
Orsini Fortress: a grand defensive structure guarding the town’s only entrance.
Vie Cave: deep pathways carved into the tufa rock by the Etruscans.
📌 How to get there: as it’s deep in the Maremma region, a car is essential (2hrs 50mins from Florence or 2hrs 18mins from Rome). There are no direct train links.
12. Sorano
Sorano is a medieval town carved directly into a high volcanic tufa cliff.
Walking through its ancient gates feels like stepping into a subterranean labyrinth. The streets are narrow, steep and carved with Vie Cave (ancient Etruscan pathways).
It feels wilder and more untamed compared to the rest of Tuscany, making it perfect if you want to escape the typical tourist trail.
Best attractions in Sorano
Fortezza Orsini: a 14th century fortress dominating the town, with a maze of underground passages and incredible panoramic views.
Masso Leopoldino: a giant, fortified rock that acts as a natural terrace overlooking the green valley below.
Vie Cave di Sorano: ancient, deep-cut paths carved into the rock by the Etruscans that lead you through a forest landscape.
📌 How to get there: a car is essential given its location (approximately 1.5hrs from Grosseto or 2.5 hours from Florence). There are no direct trains and local buses are very infrequent.
13. Volterra
Discover a charming medieval town in western Tuscany where time has seemingly stopped.
Volterra's medieval character is evident in its well-preserved city walls, narrow cobblestone streets and historic buildings.
A town center teeming with remnants of its Etruscan past, come to Volterra to visit its historical sites. Several noteworthy ones include the Palace of the Priory (Palazzo dei Priori), its jaw-dropping cathedral and the Medici Fortress.
⏩️ Visit Volterra and San Gimignano on a day trip from Florence (food and wine included).
Palazzo dei Priori, Piazza dei Priori, 20
Cattedrale di Santa Maria Assunta, Piazza San Giovanni
Fortezza Medice
Best attractions in Volterra
Roman theatre: one of the best-preserved ancient theaters in all of Italy.
Palazzo dei Priori: the oldest town hall in Tuscany (the model for Florence’s Palazzo Vecchio).
Alabaster workshops: watch local artisans carve the translucent stone the town is famous for.
📌 How to get there: take bus no.770 from Colle di Val d'Elsa (connected to Florence and Siena by bus line 130). It’s a winding, scenic road that’s best done by car if possible.
14. Pienza
Known as 'the Ideal City' (La Città Ideale), Pienza is a picturesque Tuscan town in the south of the region.
Originally known as Corsignano, Pienza was the birthplace of Pope Pius II. In the 15th century, he transformed his birthplace into an 'ideal' renaissance town, which lead to the new Pienza.
Pienza’s most famous architectural sites include Piccolomini Palace (Palazzo Piccolomini di Pienza) and Pienza Cathedral (Duomo di Santa Maria Assunta).
The surrounding views of the Val d'Orcia Tuscan countryside make Pienza one of the most beautiful places in Tuscany.
Palazzo Piccolomini di Pienza, Piazza Pio II, 2
Duomo di Santa Maria Assunta, Piazza Pio II, 2
Best attractions in Pienza
Piazza Pio II: a prime example of ideal Renaissance urban planning.
Piccolomini Palace: features a beautiful hanging garden overlooking the Val d'Orcia.
Via dell'Amore: a tiny, romantic street with views of the rolling hills.
📌 How to get there: by car, via the scenic SS2, is the most convenient way to reach Pienza from Siena (around 1 hour). By bus, take no.112 from Siena via Buonconvento (approximately 1hr 40mins).
15. Bagno Vignoni
Bagno Vignoni is one of the most unique villages in the world.
Instead of a traditional stone piazza at its center, it features a 16th century thermal pool fed by volcanic springs.
While it’s closed to the public, the steam rising from the turquoise water at sunrise is hauntingly beautiful.
This tiny hamlet in the heart of the Val d'Orcia is the ultimate slow travel destination and one that rightly deserves a place on this list.
Should you want to bathe in the thermal springs, these baths are free and open to the public:
- Parco dei Mulini
- Antiche Terme Romane Libere
Nearby are also several spa hotels, which make an ideal spa weekend getaway.
Best attractions in Bagno Vignoni
Piazza delle Sorgenti: the iconic rectangular pool that serves as the town’s main square, surrounded by renaissance buildings and cafes.
Parco dei Mulini: an open-air park of mills just below the village where you can see ancient stone channels and dip your feet in free thermal streams.
Hortus Leonini: located a few minutes’ drive in San Quirico d’Orcia are classic Italian Renaissance gardens perfect for a stroll.
📌How to get there: by car is the best way to reach Bagno Vignoni. (about 1 hour drive from Siena). There’s plenty of parking by the village entrance, providing you arrive early enough! The center is entirely pedestrianized.
16. Colle di Val d'Elsa
Situated on a hill overlooking the Elsa River valley is the town of Colle di Val d'Elsa.
Known to the locals as 'Colle', Colle di Val d'Elsa consists of narrow, winding streets and medieval buildings.
The upper part is known as Colle Alta. It’s a step into the past, offering visitors a glimpse of the town’s medieval influences. Walk up the cobblestone streets to reach the top or take the modern-day elevator.
From Colle Alta, admire the panoramic views, stroll through its streets, visit its cathedral and walk through Palazzo Campana.
Palazzo Campana, Via Francesco Campana, 47
Best attractions in Colle di Val d'Elsa
Crystal Museum: explore the history of Italy's Crystal City.
Sentierelsa trail: a turquoise river walk with waterfalls and swimming spots.
Via del Castello: a long, historic street lined with medieval palaces and glass shops.
📌 How to get there: take bus no.130 or 131 from Florence (1.5hrs) or Siena (25 minutes). It stops in the lower town, where you can take a public elevator up to the historic Colle Alta district.
17. Montalcino
The ancient hilltop town of Montalcino is best known for two things: wine and the Montalcino Fortress (Fortezza di Montalcino).
Montalcino is renowned for producing Brunello di Montalcino wine.
Unsurprisingly, Montalcino is surrounded by picturesque vineyards which only add to its appeal. A popular destination among wine enthusiasts, this tour combines wine tasting and lunch in a Tuscan castle.
Best attractions in Montalcino
The Fortress (la Fortezza): a 14th-century castle where you can taste Brunello wine.
Abbey of Sant'Antimo: a beautiful Romanesque abbey set in a valley of olive trees.
Civic Museum: a small but rich collection of Sienese religious art.
📌 How to get there: a 55-minute drive south of Siena. If using public transport, take bus #114 from Siena (approx. 2 hours). You can also take a train from Siena to Buonconvento. However, it involves taking a further two more buses (nos. 112 and 114).
18. Pistoia
The small town of Pistoia in northern Tuscany is approximately 30kms (19mi) northwest of Florence.
At its heart are its medieval architectural structures and landmarks. In Cathedral Square (Piazza del Duomo) is the 10th century Romanesque-Gothic Pistoia Cathedral (Cattedrale di San Zeno).
Nearby is the magnificent Baptistery (Battistero di San Giovanni in corte). The former gothic-style baptistery with multicolored marble external cladding today hosts cultural events.
Just steps away from the two landmarks is the 13th century Palazzo Commune. The impressive stone facade building houses a collection of paintings from the civic museum.
Cattedrale di San Zeno, Battistero di San Giovanni in corte, Palazzo Commune, Piazza del Duomo
Best attractions in Pistoia
Piazza Duomo: a quiet square that rivals the beauty of Florence.
Ospedale del Ceppo: famous for its colorful 16th-century terracotta frieze.
Pistoia Underground: a guided tour through the city's ancient hidden tunnels.
📌 How to get there: a perfect car-free trip; frequent direct trains run from Florence Rifredi station (30 minutes) and Lucca (40 minutes). Pistoia station is a 14-minute walk from the main cathedral square.
19. Monteriggioni
The beautiful Tuscan village of Monteriggioni draws you in long before you step inside.
Its circular fortress wall, which encloses the entire village, has 11 imposing towers, something you can see clearer from afar.
Its well-preserved medieval walls were built by the Republic of Siena during the 13th century to defend against Florence.
Within the walls of Monteriggioni is a central square (Piazza Roma) lined with bars, restaurants and shops. The main church, Chiesa di Santa Maria Assunta, is also located in the village square.
One of the most beautiful places in Tuscany, don’t miss out on seeing Monteriggioni for yourself.
Best attractions in Monteriggioni
The medieval walls: walk the perimeter of this tiny, circular fortified village.
Arme Museum: a small museum featuring authentic medieval and Renaissance armor.
Church of Santa Maria Assunta: a simple, beautiful 13th-century stone church.
📌 How to get there: a 16-minute bus ride (no.130) or 26-minute drive from Siena. It’s located off the main Florence-Siena highway.
20. Asciano
The countryside surrounding Asciano epitomizes the classic Tuscan landscape: rolling hills, vineyards, olive groves and cypress trees.
What makes Asciano stand out however is its location.
The small town in the province of Siena is at the center of the Crete Senesi. 'Crete' means clay or chalk in Italian and refers to the soil in the Crete Senesi which contains clay.
It gives the soil a pale, almost white or gray appearance, especially when the sun shines on it. Add to this, winding roads, hills and slender cypress trees and you’ve got one spectacular Tuscan scene.
Best attractions in Asciano
Palazzo Corboli Museum: often cited as one of the best small art museums in Italy.
Abbey of Monte Oliveto Maggiore: a brick monastery famous for its frescoes.
Crete Senesi views: the gateway to the most iconic moon-like landscapes in Tuscany.
📌 How to get there: located in the heart of the Crete Senesi, by car is best to enjoy the views. However, there’s a direct local train from Siena that only takes 22 minutes, dropping you right near the town center.
21. Montemerano
Walking into the small village in Tuscany of Montemerano is like walking into a real-life oil painting.
The small borgo is rated one of the most beautiful in Italy and it’s easy to see why.
Traditional Tuscan stone houses decorated by vines, flowers and plants add to the romance of it all. As you explore further down the narrow streets, you’ll come across small churches and spectacular piazzas.
Montemerano, in the province of Grosseto in southern Tuscany, doesn’t have many attractions to its name. But it does have that authentic Tuscan charm that many visitors come to the region to experience.
Best attractions in Montemerano
Piazza del Castello: a perfectly preserved, s-shaped medieval square.
Church of San Giorgio: houses the famous Madonna of the Cat Renaissance painting.
📌 How to get there: deep in the Maremma countryside, a car is essential (approximately 2hrs 50mins from Florence or 2rs 15mins from Rome). Montemerano is located 10 minutes from the famous Saturnia hot springs, making them a perfect pair for a day trip.
22. Castiglione della Pescaia
If you’re looking for a hilltop fortress combined with a sandy beach, Castiglione della Pescaia is it.
The Upper Town is a fortified medieval citadel with sweeping views of the Tyrrhenian Sea. In contrast, the Lower Town is a chic seaside resort with some of Italy’s cleanest Blue Flag beaches.
It’s a favorite vacation spot for Italian families and travelers seeking good quality seafood and a clean, sandy beach.
Best things to do and see in Castiglione della Pescaia
The castello: a beautifully-preserved medieval castle that sits at the highest point of the town. While you can’t enter (private property), the walk around its walls offers the best sunsets.
Diaccia Botrona Nature Reserve: a vast wetland area just outside town, perfect for birdwatching and seeing pink flamingos in the wild.
📌 How to get there: Take a direct bus (no.49D) from Grosseto (25 mins). If driving, it’s roughly 2hrs 16mins from Florence or 1hr 20mins from Siena.
23. Elba
Should you want to swap the Tuscan towns and villages for an island, a visit to Elba makes an ideal getaway.
The island in Tuscany is one where many Italians come to vacation and for good reason.
Elba has a picturesque town center, beautiful beaches, a national park and historical sites. The third-largest island in Italy was home to Napoleon Bonaparte who was exiled to Elba in 1814.
His former residences, Palazzina Napoleonica dei Mulini and Villa San Martino, are both open to the public.
Best attractions in Elba
Portoferraio: historic harbor town with Napoleonic residences.
Fetovaia Beach: turquoise-water cove considered one of Italy's best.
Mount Capanne: take the cable car to the highest peak for island views.
📌 How to get there: take a train from Livorno Centrale to Campiglia Marittima (47 minutes). From here, take bus no.200 to Piombino (20 minutes). Lastly, take the ferry (Moby or Toremar) for Portoferraio (1 hour).
Planning a road trip through these hilltop towns can be tricky. This video breaks down essential things to know before you visit, from navigating ZTL driving zones to finding the best agriturismos.
Which is the most beautiful town in Tuscany for you?
With so many beautiful locations, it's impossible to see them all in one trip.
Use the comparison below to match your travel style to the right Tuscany destination, whether you're after art, medieval history, wine, romance or hilltop views.
| If you want... | Choose this city/town | What to expect | Extra tip |
| Renaissance art | Florence | High energy and crowds | Book popular gallery tickets and attractions months in advance |
| A medieval city to see with kids | Siena | Atmospheric and fairy-tale like | Visit in July and August to see the Palio race |
| Thermal springs | Bagno Vignoni | Slow and serene | Bathe in the free thermal baths close to the center |
| A 'wow' factor | Pitigliano | Historic, quiet and local | Tour the small, but historic, Jewish Ghetto |
| Sandy beaches | Castiglione della Pescaia | A coastal hilltop town | Hike up the castle at sunset |
| Fewer crowds | Colle Val d'Elsa | Authentic Tuscan town, peaceful streets | Take the modern elevator to skip the slight incline |
| To drink Tuscan wine | Montepulciano | Pretty with plenty of history | Join an underground cellar wine tour |
| An island escape | Elba | Mediterranean getaway | Rent a scooter to explore the sights |
FAQs about Tuscany
It depends on what you're after. For iconic rolling hills, the Val d'Orcia around Pienza is the most photographed landscape in the region. Florence for art and architecture. For medieval atmosphere with fewer crowds, Siena. For hilltop drama, San Gimignano.
San Gimignano has 14 medieval towers rising above the Chianti hills, visible for miles. Pienza is close behind for pure village charm. If you can only visit one Tuscan hill town, make it San Gimignano.
Five to seven days covers the highlights: Florence, Siena, one or two hill towns and a drive through the Val d'Orcia. Ten days lets you add the coast, Lucca or the less-visited south. See my 5-day Tuscany itinerary for a suggested route.
April to June and September to October. Warm, manageable crowds and the most beautiful light. May is particularly beautiful in the Val d'Orcia. Avoid August if possible, as it’s very hot, crowded and more expensive.
Florence, Siena, Pisa and Lucca are all well-served by train. For hill towns like San Gimignano, Montepulciano, Pienza and Pitigliano, a car is almost essential. If your itinerary mixes both, rent a car from day three once you've finished with Florence.
Renaissance art (Florence), wine (Chianti, Brunello, Vino Nobile), the iconic cypress-lined rolling hills and some of Italy's finest cuisine. Bistecca alla Fiorentina, ribollita and pici pasta are among some of the most well-known dishes.
Final thoughts
Which of these most beautiful places to visit in Tuscany is at the top of your list? If you can't decide, my 4-day Tuscany road trip covers the absolute highlights. Let me know in the comments below.
Disclosure: This post may contain affiliate links, which means I may receive a commission if you click a link and purchase something that I’ve recommended. Thank you for your support.
*information correct at the time of publishing.
Written by Lisa Rivera: Italy traveler and resident for 10+ years. First-hand researched for 2026.
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Ah! Tuscany is so lovely. I was just there in June, although I didn't get to all these sites. Livorno wasn't my favorite, as it was a little commercial, but I adored Lucca! If I go back, I'd love to experience the quaint, medieval town of Colle di Val d’Els as it looks so lovely. I really enjoy wandering and discovering. Of course, the mountains and seaside are lovely, too. I hope to get back someday b/c Italy is amazing!
I really hope you do too! Colle is really pretty and not touristy at all, I highly recommend it
I love that you have included Arezzo! We got married in Arezzo last year in the medieval courthouse. The fact it felt stuck in time and less touristy really drew us in too. We were hoping to get to lucca but got a bit caught up. We also heard great things about Pienza cathedral and plazza but hadn’t seen
Pictures of there until yours here. It looks stunning.
What a beautiful place to get married! It really is less touristy and the architecture here is amazing. Pienza is really charming too 🙂
All this time I thought Tuscany was a small town with miles of sunflower beds outside the town. I was so wrong! lol. I'm glad you wrote about this, so I have an understanding of Tuscany. So many beautiful towns to visit, but the street in Pienza is very pretty. No wonder it became the best town in Tuscany.
It's a big region here! I'm glad I cleared it up for you 🙂 Pienza is very pretty
Tuscany is beautiful!
Thanks for documenting
You're welcome
Awesome recommendation, I want to visit Val d'Orcia again and San Gimignano..
Thank you, they're both beautiful
Some really nice looking places. I like the designs of the buildings, look similar to the Colosseum building which makes it easy to recognize the country. Great post.
There are. There's only one Colosseum but Tuscany has its own landmarks
Wonderful post. Italy is amazing. I also wrote a post about the most beautiful and romantic places in Italy.
Thank you, that sounds really nice
If given the choice, Italy is always my first option for a travel destination!
I'm glad to read that!
Every town is just stunning!
They are pretty
Beautiful place. Thanks for sharing!
My pleasure!
What a very informative post! As a Tuscan myself I think that your choice of towns is great. Great tips and great blog!
Grazie Claudia! I'm glad you enjoyed it 😀
I remember seeing under the Tuscan sun and just desperately wanting to visit Tuscany. I was a little girl but it's still my dream. What a stunning place and beautiful sights to check out 😀
The film has inspired many to come and visit Tuscany, it really is beautiful!
We love Tuscany! We visited Italy including Tuscany many years ago when our children were teenagers. You are right, the best cities of Pisa, Siena, Florence and San Gimignano are not to be missed. The rolling hills, natural scenic places, the history and architecture make Tuscany stand apart. I must do another trip to cover the rest of the places you have mentioned. 🙂
It's such a beautiful region! I'm glad you want to come back one day 🙂
Our boat stopped in Livorno on our cruise last year and we had fun exploring the area. The only other place on this list that we've been to (I think) is Pisa. So many places that I want to experience x
Tuscany really has many beautiful places to explore 🙂
Tuscany looks like such a lovely region with so many landmarks to see. Italy is such a beautiful country, it is definitely a must visit.
There is plenty to see here
I'd love to visit Florence one day! It's high on my bucket list. This was an awesome post, it really made me want to travel to Italy. Perhaps in 2024!
Thank you so much, I hope you visit one day 😀
Yes, these are indeed all beautiful. Though I am most interested in the small town of Pistoia. It would be nice to see the medieval architectural structures and landmarks up close.
Montemeramo and Elba are also on our bucket list. 🙂
Pistoia is truly beautiful, hope you visit one day
We spent 3 weeks travelling in Tuscanny during Corona what was wonderful - and not too touristy. During this time we visited about 50% of the places you mention in your post, but there are still enough left. Pistoia and Arrezo are two places we did some research about and in the end run out of time. Nice to find them on your list again - that means they are worth a visit.
That was the best time to be here honestly! Both are great towns in Tuscany, definitely come back to see them
I lived in Tuscany for a bit, a few years ago, and visited some of these towns. I had my own motorino, and I loved driving around on it, during the weekends. I was based in Montelupo Fiorentino, which is another very small but beautiful town. I drove one weekend from there to San Gimignano and to Certaldo, on the back roads, through vineyards and rolling hills. It felt like a scene from a romantic movie. Loved every minute of it.
That sounds wonderful! It really is so romantic, you can't help but fall in love with Tuscany
Tuscany truly encapsulates the Italian dream, and it's the region that often tops the list when people imagine their ideal Italian getaway. The picturesque Tuscan countryside, with its undulating green hills, charming villages, and iconic cypress trees, beckons travelers with its romantic and untamed beauty. It's no wonder so many are drawn to experience Tuscany's allure.
For those seeking to uncover the most enchanting corners of Tuscany, you're in for a treat. This guide unveils 20 of the region's most stunning places, spanning from vibrant Tuscan cities to quaint and inviting towns. With this comprehensive list, you'll have your Italy travel itinerary complete, making it an essential resource to plan your dream trip to Italy.
Thank you, I'm glad you enjoyed it
Tuscany sounds like a total dream! I mean, Florence with its Renaissance art, Siena's medieval charm, and the iconic leaning tower of Pisa – it's like a movie script waiting to happen! Those picturesque hilltop towns like Montepulciano, San Gimignano, and Pienza sound like straight out of a fairytale. I only visited Florence, but would love to come back and explore more.
There are so many incredible towns and villages to see and so dreamy too! I hope you come again one day 🙂
oh wow, Tuscany is gorgeous!!! I had no idea it is that beautiful. I've been to Italy but never made it to Tuscany...Soon I hope, soon...
There are so many beautiful places to see here 🙂
We visited Florence for only one day and saw a lot but know there is so much more to see. We loved Sienna and were happy we used that as a base for a few days and visited San Gimignano. But sadly we have missed Pisa on all of our trips. You have shown me there are many more places that we missed that are a little less touristy. The hill top towns could keep us wandering for weeks. I have also added a new island to my list. One day we will get to Elba! Lots of reasons to keep coming back to Italy.
Yes! There are so many hilltop towns in Tuscany, it's its own bucket list 😀