10 Best Places to Visit in Tuscany

Town of Pienza in Tuscany, Italy

Town of Pienza in Tuscany, Italy

The best places to visit in Tuscany capture legendary beauty and remarkable history that you can discover during your Italy trip. The region’s finest destinations emerge like fairy tales through medieval towns clinging to hilltops, terraced vineyards texturing the landscape, and Renaissance art reflecting the world's beauty back at you. Tuscany offers living history, with streets that act as open-air museums you can stroll through at your leisure.

Whether you are interested in sensational cuisine, delicious wines, unforgettable vistas, or remarkable villas, our list of the best places in Tuscany to visit will immerse you in the idyllic world of Italian heritage and history.

Extraordinary travel begins with a human touch, and our destination specialists design every journey with care, insight, and personal attention. As you consider a visit to Tuscany, use this insight as a guide before connecting with our travel experts to help you plan your trip.

1. Florence

Palazzo Vecchio, Florence, Italy
Palazzo Vecchio, Florence, Italy

Florence is a treasure trove of medieval and Renaissance wonder, with masterful architecture and art that underline the power of the human spirit. A warren of cobblestone streets circles opulent churches, connects to the ancient Ponte Vecchio bridge, and hides beneath the looming dome of the renowned cathedral. The city is home to the Uffizi and Accademia galleries, which house famous works like Botticelli’s Birth of Venus and Michelangelo’s David. It's also a hub for culinary experiences, where you can find some of the best cooking classes in Tuscany. Illustrious designs often trace Medici family history and boutique shops provide fascinating displays that lure even the most dispassionate shopper.

Historical Immersion

  • Birthplace of the Renaissance: Florence was the epicenter of the Renaissance, a cultural movement that profoundly shaped European art, science, and philosophy.
  • The Medici Dynasty: The city's golden age was largely funded and influenced by the powerful Medici banking family, whose patronage supported artists like Michelangelo, Leonardo da Vinci, and Botticelli.
  • Architectural Innovation: Home to Filippo Brunelleschi's magnificent dome on the cathedral, a feat of engineering that remains an architectural marvel.
  • Artistic Epicenter: Its galleries, the Uffizi and Accademia, hold one of the world's most important collections of Western art, cementing its status as a global art capital.

What to Expect

  • Immerse yourself in the overwhelming beauty of Renaissance art and architecture, where every street and piazza feels like part of a living museum.
  • Feel the smooth, cool marble of Michelangelo's David, the ancient cobblestones underfoot, and the vibrant energy of Piazza della Signoria.
  • Taste the classic Bistecca alla Fiorentina, a hearty lampredotto sandwich from a street cart, and sip on world-class Chianti wine.
  • Hear the resounding chime of the Campanile di Giotto, the lively chatter echoing through the Mercato Centrale, and the soft strum of a guitar on the Ponte Vecchio.
  • See the breathtaking panoramic view of the city from Piazzale Michelangelo, the intricate details of Ghiberti's Gates of Paradise, and the sun setting over the Arno River.

Where to Enjoy Your Visit

  • Cathedral of Santa Maria del Fiore: Marvel at Brunelleschi's iconic dome and climb to the top for stunning city views.
  • Uffizi Gallery: Explore one of the world's greatest art museums, with masterpieces by Renaissance artists.
  • Accademia Gallery: Witness the perfection of Michelangelo's David, the ultimate symbol of Florentine artistry.
  • Ponte Vecchio: Stroll across Florence's oldest bridge, famous for the glittering jewelry shops built along it.
  • Palazzo Pitti and Boboli Gardens: Discover the vast former palace of the Medici rulers and wander through its magnificent Italianate gardens.

Recommended length of stay: 3-4 days

Embark on one of our Florence, Venice, and Milan Itineraries and Tours for a spectacular introduction to Florence.

2. Siena

Piazza del Campo in Siena, Italy
Piazza del Campo in Siena, Italy

Siena is a perfect example of an open-air museum, with architecture celebrating the Gothic style. Buildings soar into the sky and narrow cobblestone alleys open to the magnificent Piazza del Campo. The city once rivaled Florence for supremacy over the Tuscan region, a rivalry demonstrated in the remarkable artistry gracing its structural designs, artisanal boutiques, and famous pastry shops. Siena is a feast for the senses, where restaurants serve traditional cuisine and the world-famous Palio horse race takes place each summer.

Historical Immersion

  • Medieval Powerhouse: Siena was a fiercely independent and powerful city-state during the Middle Ages, a major rival to its neighbor, Florence.
  • Gothic Masterpiece: The city is a quintessential example of medieval Gothic urban planning and architecture, beautifully preserved to this day.
  • The Palio: Home to the historic Palio horse race, a passionate and dramatic event held twice a year in the Piazza del Campo, with roots stretching back to the medieval era.
  • Unique Central Piazza: The fan-shaped Piazza del Campo is one of Europe's greatest medieval squares, designed as the civic and social heart of the city.

What to Expect

  • Immerse yourself in the perfectly preserved medieval atmosphere, where time seems to stand still in the winding brick alleys and grand public spaces.
  • Feel the unique concave slope of the Piazza del Campo beneath your feet, the sun warming the ancient bricks and the electric atmosphere on a Palio race day.
  • Taste the traditional spiced fruitcake, delicate almond cookies, and handmade pici pasta, all Sienese specialties. Find more culinary inspiration on our Italy food and wine tours.
  • Hear the murmur of the crowd around the Fonte Gaia, the tolling of the bell from the Torre del Mangia, and the echoes of history in its narrow streets.
  • See the stunning black-and-white striped Duomo, the panoramic vista of the city and countryside from the Torre del Mangia, and the vibrant flags of the city's districts.

Where to Enjoy Your Visit

  • Piazza del Campo: Relax in the heart of Siena, a unique shell-shaped square that hosts the Palio and is surrounded by historic buildings.
  • Cathedral of Santa Maria Assunta: Explore this breathtaking example of Italian Gothic architecture, inside and out, including its Piccolomini Library.
  • Torre del Mangia: Climb the 400 steps of this slender tower for an unforgettable panoramic view of Siena and the surrounding Tuscan hills.
  • Palazzo Pubblico: Visit the town hall, which houses the Civic Museum and magnificent frescoes depicting Sienese life and government.

Recommended length of stay: 2-3 days

Plan your trip to Siena after taking a look at our sample Historical Immersion Tour of Tuscany: Siena and Florence.

3. Pisa

Leaning Tower of Pisa in Italy
Leaning Tower, Pisa, Italy

The glory of Pisa stretches far beyond its legendary Leaning Tower. The former maritime republic once rivaled the prestige of Genoa and Venice, a power still reflected in the regal architectural accomplishments crowning the Piazza dei Miracoli. Even after its naval power faded, education has influenced the local economy since the 15th century, giving the ancient city a modern, vibrant ambiance. It's filled with lively cafés and restaurants woven into the fabric of Romanesque buildings and Gothic churches.

Historical Immersion

  • Maritime Republic: Pisa was one of the four great Maritime Republics of Italy, a naval and trading powerhouse during the late Middle Ages.
  • Piazza dei Miracoli: This "Square of Miracles," a UNESCO World Heritage Site, is a testament to Pisan glory, containing the cathedral, baptistery, cemetery, and the famous tower.
  • Center of Learning: Home to one of Italy's oldest and most prestigious universities, founded in 1343, which gives the city a youthful and intellectual energy.
  • Architectural Marvel and Mishap: The Leaning Tower, a freestanding bell tower, is world-famous for its unintentional tilt, a result of an unstable foundation.

What to Expect

  • Immerse yourself in the awe-inspiring architectural splendor of the Piazza dei Miracoli and the lively, authentic atmosphere of a historic university town.
  • Feel the smooth, cool marble of the grand cathedral, the soft grass of the "Square of Miracles" underfoot, and the vibrant buzz of student life along the Arno River.
  • Taste traditional Pisan dishes like cecina, a chickpea flour pancake, and enjoy an aperitivo at a café.
  • Hear the constant click of cameras capturing the iconic tower, the majestic peal of the cathedral bells, and lively conversations flowing from bustling trattorias.
  • See the iconic Leaning Tower in all its glory, the intricate Romanesque facade of the Cathedral, the enormous dome of the Baptistery, and the beautiful frescoes of the Campo Santo.

Where to Enjoy Your Visit

  • Leaning Tower of Pisa: Climb the iconic tower for a unique experience and a great view of the piazza.
  • Cathedral of Santa Maria Assunta: Admire the magnificent Pisan-Romanesque architecture and the impressive pulpit by Giovanni Pisano.
  • Baptistery of St. John: Visit the largest baptistery in Italy, renowned for its incredible acoustics, which are often demonstrated by the guards.
  • Campo Santo Monumentale: Walk through this serene monumental cemetery, known for its beautiful Gothic arcades and restored frescoes.
  • Museum of Ancient Ships: Discover remarkably preserved Roman ships and artifacts unearthed in Pisa, showcasing its ancient maritime heritage.

Recommended length of stay: 1-2 days

With our travel experts, plan your Best of Tuscany in a Week Itinerary: Lucca, Pisa, San Gimignano, Siena, and Florence.

4. San Gimignano

Aerial view of Torre Grossa and medieval village in San Gimignano, Italy
View of Torre Grossa and medieval village in San Gimignano, Italy

Quiet but powerful, San Gimignano is the embodiment of a traditional Tuscan medieval town. The remains of what were once 72 towers continue to loom large over the surrounding hills, earning it the nickname "Medieval Manhattan." These towers provide fantastic views of nearby vineyards, villas, and olive groves. The streets and walls date back to the late 12th century, creating a palpable ambiance of tangible history. This UNESCO World Heritage Site is famous for its unique skyline and its crisp Vernaccia white wine.

Historical Immersion

  • Town of Fine Towers: Known as the "Medieval Manhattan" for its impressive skyline of well-preserved tower houses, built by rival families as symbols of wealth and power.
  • Pilgrimage Stop: It was a crucial stopping point for Catholic pilgrims on the Via Francigena, a route to Rome, which contributed to its wealth and development.
  • UNESCO World Heritage Site: Recognized for its perfectly preserved medieval architecture and iconic towers, offering a remarkable glimpse into feudal Italy.
  • Vernaccia Wine: The area is renowned for Vernaccia di San Gimignano, a white wine celebrated since the Renaissance and one of Italy's finest.

What to Expect

  • Immerse yourself in a fairy-tale medieval hill town, where ancient stone towers pierce the sky and every corner offers a view of the rolling Tuscan countryside.
  • Feel the cool, ancient stone of the towers, the wind at the top of Torre Grossa, and the smooth, chilled glass of a Vernaccia wine in your hand.
  • Taste the crisp, floral notes of Vernaccia di San Gimignano, savor saffron-infused dishes, and try the local wild boar salami from an artisanal shop.
  • Hear the wind whistling between the ancient towers, the distant chimes from the Collegiata church, and the cheerful bustle of visitors in the Piazza della Cisterna.
  • See the unforgettable skyline from the surrounding roads, the stunning 14th-century frescoes inside the main church, and the panoramic 360-degree view of Tuscany from its tallest tower.

Where to Enjoy Your Visit

  • Torre Grossa: Climb the tallest of the remaining towers for the most spectacular views of the town and the beautiful landscape.
  • Piazza della Cisterna: A charming triangular piazza with a medieval well, lined with tower houses and artisan shops.
  • Cathedral of Santa Maria Assunta: Discover the stunning, colorful frescoes depicting Old and New Testament stories that cover the interior walls.
  • La Rocca di Montestaffoli: Explore the ruins of this 14th-century fortress, now a public park with excellent viewpoints and an olive grove.
  • Palazzo Comunale: Visit the town hall, which houses the Civic Museum and provides access to the Torre Grossa.

Recommended length of stay: 1-2 days

Explore San Gimignano on our 7-Day Food and Wine Tour of Tuscany.

5. Arezzo

Medieval shields at the Piazza Grande in Arezzo, Italy
Medieval shields at the Piazza Grande in Arezzo, Italy

Arezzo is a city where art has always flourished, inspired by the countryside's grandeur and timeless beauty. The city's foundations rise from a former Etruscan trading post, with churches creating a glamorous ambiance. Visit museums representing famous works by the likes of Pisano and harking back to the poems of Petrarch. It is exciting to discover the terra cottas in the 13th-century Duomo, the Romanesque features of Santa Maria della Pieve, or the National Archeological Museum.

Historical Immersion

  • Etruscan Origins: Arezzo was one of the most important cities in the Etruscan federation before becoming a strategic Roman settlement.
  • Home of Masters: The birthplace of influential cultural figures like the poet Petrarch, the artist and art historian Giorgio Vasari, and Guido of Arezzo, the inventor of modern musical notation.
  • Piero della Francesca's Masterpiece: The Basilica of San Francesco houses The Legend of the True Cross, a breathtaking fresco cycle by Piero della Francesca, considered one of the greatest masterpieces of the early Renaissance.
  • Antiques Capital: Hosts Italy's most famous and largest monthly antique fair, drawing collectors and enthusiasts from all over the world.

What to Expect

  • Immerse yourself in a city of profound artistic and historical depth, offering a more tranquil and authentic experience than its more famous Tuscan neighbors.
  • Feel the unique, dramatic slope of the Piazza Grande, the hushed reverence as you stand before Piero della Francesca's frescoes, and the thrill of discovering a treasure at the antique market.
  • Taste authentic Aretine cuisine in a traditional osteria, enjoying local specialties like Pappa al Pomodor, a thick bread and tomato soup,  accompanied by regional wines. Explore other Tuscan culinary delights on our In-Depth Tour of Tuscan Gourmet Cuisine.
  • Hear the lively bargaining and chatter during the bustling monthly antique fair and the peaceful silence within the city’s magnificent churches.
  • See the vibrant colors of The Legend of the True Cross, the eclectic mix of architecture on the Piazza Grande, the uniquely curved apse of Santa Maria della Pieve, and the remains of a Roman Amphitheater.

Where to Enjoy Your Visit

  • Piazza Grande: Discover the sloping main square, surrounded by a wonderful mix of medieval towers and loggias designed by Vasari.
  • Basilica of San Francesco: Witness Piero della Francesca's stunning fresco cycle, The Legend of the True Cross.
  • Arezzo Cathedral: Admire the Gothic architecture and beautiful stained-glass windows by Guillaume de Marcillat.
  • Santa Maria della Pieve: Visit this beautiful Romanesque church, known for its intricate facade with dozens of columns and a tall bell tower.
  • Casa Vasari: Explore the former home of Giorgio Vasari, which he designed and decorated himself with impressive frescoes.

Recommended length of stay: 2-3 days

Embark on a tour of Arezzo after contacting our travel experts to help you plan your trip.

6. Elba

Wine tasting at a vineyard in Elba, Italy
Wine tasting at a vineyard in Elba, Italy

Elba is a serene island paradise, with coves opening to gorgeous beaches, vineyards hidden amid inland mountains, and azure waters sparkling in the Mediterranean sun. Views over the sea and landscape are enchanting and the island's history, dating back to the 3rd century BC, is most famously known as the place of Napoleon's first exile. Local gastronomy highlights the treasures of the sea, while wineries embrace the distinctive characteristics of the soil.

Historical Immersion

  • Napoleonic Exile: Most famously known as the island where Napoleon Bonaparte was exiled in 1814, his presence is still felt in the two villas he occupied.
  • Ancient Iron Mines: For centuries, Elba's economy was dominated by iron mining, a resource exploited by the Etruscans and Romans.
  • Tuscan Archipelago National Park: The island is the largest in this protected marine park, preserving its rich biodiversity, pristine waters, and natural landscapes.
  • Strategic Location: Its position in the Tyrrhenian Sea made it historically significant for maritime control, attracting various powers throughout the centuries.

What to Expect

  • Immerse yourself in a stunning natural paradise that perfectly blends beautiful beaches, rugged mountains, and fascinating European history.
  • Feel the warm, soft sand between your toes on a secluded beach, the refreshing spray of the sea on a boat tour, and the invigorating challenge of a hike to the summit of Monte Capanne.
  • Taste exceptionally fresh seafood drizzled with local olive oil and savor a glass of Aleatico, a sweet red dessert wine unique to the island.
  • Hear the gentle lapping of turquoise waves against the shore, the cries of gulls circling overhead, and the peaceful hum of cicadas in the Mediterranean scrub.
  • See the crystal-clear waters of beaches like Sansone and Fetovaia, the panoramic views from the top of Monte Capanne, charming fishing villages, and Napoleon’s historic residences.

Where to Enjoy Your Visit

  • Napoleon's Residences: Visit the Villa dei Mulini in Portoferraio and his more secluded summer home, the Villa di San Martino.
  • Monte Capanne: Take the thrilling cable car or hike to the island's highest peak for breathtaking 360-degree views of Elba and the surrounding sea.
  • Spiaggia di Sansone: Relax on one of Elba's most beautiful white-pebble beaches, known for its incredibly clear, turquoise water. It’s perfect for snorkeling.
  • Tuscan Archipelago National Park: Explore the protected natural beauty of the island through its numerous hiking and biking trails.
  • Active Excursions: Enjoy water sports like kayaking, sailing, and diving, or explore the island's rugged interior on foot or by mountain bike.

Recommended length of stay: 3-4 days

Visit Elba when you embark on Zicasso’s Splendors of the Italian Coastline: Elba and Cinque Terre Tour.

7. Prato

Pretorio Palace in Prato, Italy
Pretorio Palace in Prato, Italy

Whether looking for historical inspiration or contemporary creations, Prato has always celebrated art in all its forms, focusing on the textile industry and archeological discoveries that pre-date Etruscan colonization. Explore the city’s beauty and how it exudes diverse cultural influences that have changed with the shifting aesthetics of power, from the Byzantines to the united Italian Kingdom. Adventure can take on a different form here, allowing you to indulge in history around the Duomo or witness the medieval architecture of the Emperor’s Castle.

Historical Immersion

  • Textile Capital: Prato has been a major center for textile production since the Middle Ages, a heritage that continues today and is celebrated in its Textile Museum.
  • The Holy Belt: The Prato Cathedral houses a revered relic, the Sacra Cintola, or Holy Belt of the Virgin Mary, which is displayed to the public five times a year from a special external pulpit by Donatello.
  • Imperial Castle: Home to the impressive Castello dell'Imperatore, a rare example of Swabian imperial architecture in Northern and Central Italy, built by Emperor Frederick II.
  • Contemporary Hub: The city embraces the modern with the Luigi Pecci Centre for Contemporary Art and one of Italy's largest and most established Chinese communities.

What to Expect

  • Immerse yourself in an off-the-beaten-path city that fascinatingly blends a powerful industrial heritage with priceless religious art and a vibrant contemporary culture.
  • Feel the quality of fine wool and cashmere fabrics in a local shop, the cool, imposing stone of the Emperor's Castle, and the creative energy of a modern art exhibit.
  • Taste the city's famous almond biscuits, biscotti di Prato, and its unique Slow Food presidium, mortadella di Prato.
  • Hear the hum of a city at work, blending its industrial pulse with the historic chimes of its church bells.
  • See the magnificent outdoor pulpit by Donatello and Michelozzo on the cathedral facade, the formidable walls of the Castello dell'Imperatore, and thought-provoking modern works at the Pecci Centre.

Where to Enjoy Your Visit

  • Prato Cathedral: Admire the green-and-white striped facade, the outdoor pulpit, and the beautiful frescoes by Filippo Lippi inside.
  • Castello dell'Imperatore: Explore this imposing medieval fortress and walk along its ramparts for views of the city.
  • Palazzo Pretorio: Visit Prato's main art gallery, housed in a stunning medieval palace, featuring works by local masters.
  • Textile Museum: Delve into Prato's most important industry with a collection that spans centuries of textile history and design.
  • Luigi Pecci Centre for Contemporary Art: Discover cutting-edge exhibitions of painting, sculpture, and design at this renowned modern art center.

Recommended length of stay: 1-2 days

Add Prato to your itinerary when organizing a Wonders of the Italian Renaissance Tour: Past and Present.

8. Volterra

Roman theater in Volterra, Tuscany, Italy
Roman theater in Volterra, Tuscany, Italy

Volterra’s incredible history dates back to the 8th century BC as an Etruscan town and a prominent manufacturer of alabaster. Winding cobbled streets unveil Roman history and move through medieval buildings decorated with artisanal designs and displays of shimmering alabaster. The tower houses in the historic city center date back to the 12th century and the Roman Theater could hold up to 2,000 spectators as early as the 1st century AD. A visit to the Etruscan Museum offers insight into the former settlement, with fascinating artifacts that bring the past to life.

Historical Immersion

  • Ancient Etruscan Power: Volterra was one of the 12 capital cities of the Etruscan League, a major civilization that predated the Romans in Tuscany.
  • Alabaster Craftsmanship: The city has been a center for alabaster carving for thousands of years, a craft that continues today in local workshops.
  • Layered History: The city showcases remarkable evidence of its long history, with an Etruscan gate, a Roman theater, and a perfectly preserved medieval town center.
  • Dramatic Location: Perched high on a steep hill, its dramatic and commanding position offers breathtaking views and has protected it for millennia.

What to Expect

  • Immerse yourself in a city with an almost tangible sense of deep time, where Etruscan, Roman, and medieval history coexist on a dramatic Tuscan hilltop.
  • Feel the cool, smooth, and translucent quality of expertly carved alabaster, the wind sweeping across the landscape from a panoramic viewpoint, and the weight of history in its ancient stones.
  • Taste local specialties that reflect the wild Tuscan landscape, such as dishes with truffles, wild boar, and local pecorino cheese.
  • Hear the gentle, rhythmic chipping of an artisan carving alabaster in a workshop and the eerie quiet within the ruins of the ancient Roman theater.
  • See the impressive ruins of the 1st-century BC Roman Theater, the priceless artifacts in the Guarnacci Etruscan Museum, the imposing medieval Priori Palace, and the rugged, cliff-like formations known as Le Balze.

Where to Enjoy Your Visit

  • Guarnacci Etruscan Museum: Discover one of Italy's most important collections of Etruscan artifacts, including the famous Shadow of the Evening sculpture.
  • Roman Theater: Explore the well-preserved ruins of the ancient theater and adjoining Roman baths.
  • Palazzo dei Priori: Admire the oldest town hall in Tuscany, located in the beautiful central piazza.
  • Porta all’Arco: See the impressive and ancient Etruscan gate, one of the few remaining examples of its kind.
  • Alabaster Workshops: Visit a local workshop to see artisans at work and purchase a unique, handcrafted souvenir.

Recommended length of stay: 2-3 days

Include Volterra on an Explore Tuscany Tour: Ancient Towns, Coastlines, Snorkeling, and Trekking.

9. Val d’Orcia

Town of Montepulciano in Tuscany, Italy
Town of Montepulciano, Tuscany, Italy

Flush with farmlands brimming with olive groves and fields of grain, Val d’Orcia embodies the quintessential image of Tuscany. Hills gently roll to the horizon, cypress trees line country roads, and vineyards spread across a lush landscape. This is a perfect region to explore by car or bike, visiting traditional Tuscan hill towns and embracing its UNESCO World Heritage status. Discover grand abbeys, walk along medieval cobblestone lanes in towns like Pienza, or relax in natural hot springs such as those in Bagno Vignoni.

Historical Immersion

  • UNESCO World Heritage Landscape: The entire valley is recognized as a cultural landscape that was redesigned in the Renaissance to reflect an idealized model of good governance and aesthetic beauty.
  • Quintessential Tuscany: This area is the source of the iconic Tuscan imagery seen in countless paintings and photographs—rolling hills, cypress trees, and charming farmhouses.
  • World-Class Wine Region: Home to the prestigious wine towns of Montalcino, which produces Brunello, and Montepulciano, which is famous for Vino Nobile.
  • Pienza, the "Ideal City": The town of Pienza was rebuilt by Pope Pius II to be the perfect embodiment of Renaissance humanist principles of urban design.

What to Expect

  • Immerse yourself in a living Renaissance painting, driving or cycling through one of the most beautiful and iconic landscapes in the world.
  • Feel the warmth of the Tuscan sun on your skin as you stand on a hilltop, the fine dust of the famous white gravel roads and the satisfying swirl of a world-class red wine in your glass.
  • Taste the bold, complex flavors of a Brunello di Montalcino, the rich taste of Pecorino di Pienza cheese, and the peppery notes of fresh-pressed olive oil.
  • Hear the gentle rustling of leaves in the vineyards, the peaceful silence of the countryside broken only by birdsong, and the clinking of glasses in a local enoteca.
  • See the iconic, solitary Vitaleta Chapel nestled between hills, endless rolling landscapes dotted with cypress trees, charming medieval towns, and vast, sprawling vineyards.

Where to Enjoy Your Visit

  • Pienza: Stroll through Pope Pius II's "ideal city," famous for its Renaissance architecture and delicious pecorino cheese.
  • Montalcino: Visit this classic hill town, explore its fortress, and sample the world-renowned Brunello di Montalcino wine at a local winery.
  • Montepulciano: Discover another stunning hill town, known for its elegant Renaissance palaces and its esteemed Vino Nobile wine.
  • Abbey of Sant’Antimo: Visit this beautiful and evocative Romanesque abbey, set in a peaceful olive grove.
  • Vitaleta Chapel: Seek out and photograph this iconic, picturesque chapel, perhaps the most famous symbol of the Val d'Orcia.

Recommended length of stay: 2-3 days

An Immersive Olive Oil Tour in Tuscany would not be complete without a visit to Val d’Orcia.

10. Lucca

Lucca cathedral in Tuscany, Italy
Lucca cathedral in Tuscany, Italy

Lucca has an endearing ambiance, where imposing Renaissance walls hide a medieval city center, promenades provide the perfect place for a stroll, and restaurants brim with Tuscan favorites. The former Roman Amphitheater has become the main piazza and within the town walls, there’s a public park and garden, making for a perfect escape by foot or bike. Art, connections to noble families and grand villas provide a fantastic introduction to Lucca’s marvels, punctuated by the unique contours of the Ponte della Maddalena.

Historical Immersion

  • Intact City Walls: Lucca is famous for its perfectly preserved Renaissance-era city walls, which have been transformed into a broad, tree-lined park and promenade.
  • Independent Republic: For almost 500 years, Lucca was a powerful and independent city-state, a history reflected in its proud and well-kept civic center.
  • Roman Footprint: The city's Roman origins are clearly visible in the grid-like pattern of its streets and the unique oval shape of the Piazza dell'Anfiteatro.
  • Home of Puccini: Lucca is the birthplace of the renowned opera composer Giacomo Puccini, and his legacy is celebrated throughout the city.

What to Expect

  • Immerse yourself in the relaxed and civilized charm of "the city of 100 churches," where you can ride a bike or walk atop massive, centuries-old walls.
  • Feel the gentle breeze as you cycle the 2.5-mile loop of the city walls, the lively atmosphere of the former Roman amphitheater, and the smooth keys of a piano in Puccini's birth home.
  • Taste buccellato, a traditional sweet bread with raisins and anise, and enjoy a leisurely meal in one of the many excellent trattorias.
  • Hear the cheerful ringing of bicycle bells, melodies from a Puccini opera wafting from a church concert, and the happy buzz of conversation from the cafes lining the piazza.
  • See the unique, tree-topped Guinigi Tower, the perfect oval of the Piazza dell'Anfiteatro, the intricate Romanesque facade of the Church of San Michele in Foro, and the locals enjoying their evening stroll.

Where to Enjoy Your Visit

  • The City Walls: Rent a bike or walk along the top of the wide, tree-lined walls for unique views of the city's rooftops and gardens.
  • Piazza dell'Anfiteatro: Have a coffee or meal in this spectacular oval piazza, built on the ruins of a Roman amphitheater.
  • Guinigi Tower: Climb this iconic tower, famous for the holm oaks growing on its roof, for a fantastic view of Lucca.
  • Lucca Cathedral: Visit the city's cathedral, which houses the revered Volto Santo crucifix and the beautiful tomb of Ilaria del Carretto.
  • Church of San Michele in Foro: Admire one of the most beautiful Pisan-Romanesque facades in Tuscany, located on the site of the ancient Roman forum.

Recommended length of stay: 1-2 days

For more inspiration on visiting Lucca, take a look at Zicasso’s 8 Days in Puccini's Footsteps Tour: A Musical Pilgrimage Through Italy.

Planning Your Tuscan Adventure

The Medieval walls in Lucca at sunrise.
The Medieval walls in Lucca at sunrise.

Before diving into the specific destinations, let's answer some key questions to help you plan the perfect luxury trip. Capturing the essence of the region often means choosing the right home base and embracing the local way of getting around. For a detailed look at when to go, see our guide to the Best time to visit Tuscany.

Driving in Tuscany

To truly experience Tuscany, driving is a fundamental part of the adventure. Renting a car gives you the freedom to explore the winding country roads at your pace, stopping at will to admire a perfect view or a roadside winery. The scenic drives through the rolling hills of the Val d'Orcia and the world-famous Chianti region are destinations in themselves. For a truly Italian experience, consider a Vespa tour from Florence or Siena to zip through the cypress-lined lanes.

Where to Stay in Tuscany: Finding Your Home Base

Choosing the best base town in Tuscany depends on your travel style.

  • Florence is ideal for first-time visitors who want to be immersed in Renaissance art and have easy access to high-speed trains. However, it can be crowded and is less central for exploring the southern hill towns.
  • Siena, arguably, is the best all-around base. Its central location makes it perfect for day trips to San Gimignano, Montepulciano, and the Chianti region. Its medieval charm offers an authentic Tuscan experience after the day-trippers have left.

Tuscany for Every Traveler

  • Tuscany for couples or honeymooners: For ultimate romance, consider a rustic-luxe farm stay in the Val d’Orcia or a villa in Chianti. The privacy, stunning landscapes, and incredible food and wine create an unforgettable atmosphere.
  • Tuscany for families: Lucca is a fantastic choice. Its intact city walls are perfect for safe family bike rides and the flat city center is easy for little legs to navigate. Many farm stays also cater to families with pools and open spaces.
  • Tuscany for seniors: The region's relaxed pace and cultural richness make it an excellent destination. Consider spa towns like Montecatini Terme for wellness and a gentle atmosphere. The historic centers of Florence and Lucca are relatively flat and walkable. While many hill towns are steep, basing in an accessible countryside accommodation or using a private driver or day trips make seeing the stunning landscapes comfortable and stress-free.".

Is Lucca or Siena better?

This common question depends on what you're looking for. Siena offers a dramatic, Gothic, and quintessentially medieval experience. It's bustling and feels like the historic heart of Tuscany. Lucca is more relaxed and intimate, a place to slow down, ride bikes, and enjoy a more tranquil atmosphere within its famous Renaissance walls. If your goal is to explore the iconic southern hill towns, Siena is better. If you prefer a calmer base closer to Pisa and the coast, Lucca is the superior choice.

Explore the Best Places to Visit in Tuscany

 Val d’Orcia at sunrise in Tuscany, Italy
Val d’Orcia at sunrise in Tuscany, Italy

From the Renaissance architecture of Florence to the dramatic towers of San Gimignano, the famous Leaning Tower of Pisa to the celebrated wines of the Val d’Orcia, Tuscany is home to some of Italy’s most remarkable sites and experiences. Explore, discover, and embrace the beautiful scenery as you indulge in the historic culture and delicious cuisine that define this incredible region.

Find inspiration for your perfect trip with our sample Tuscany tours and travel packages. For further information on the region, see our Tuscany travel guide.

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