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.
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
What to Expect
Where to Enjoy Your Visit
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.
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
What to Expect
Where to Enjoy Your Visit
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.
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
What to Expect
Where to Enjoy Your Visit
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.
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
What to Expect
Where to Enjoy Your Visit
Recommended length of stay: 1-2 days
Explore San Gimignano on our 7-Day Food and Wine Tour of Tuscany.
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
What to Expect
Where to Enjoy Your Visit
Recommended length of stay: 2-3 days
Embark on a tour of Arezzo after contacting our travel experts to help you plan your trip.
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
What to Expect
Where to Enjoy Your Visit
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.
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
What to Expect
Where to Enjoy Your Visit
Recommended length of stay: 1-2 days
Add Prato to your itinerary when organizing a Wonders of the Italian Renaissance Tour: Past and Present.
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
What to Expect
Where to Enjoy Your Visit
Recommended length of stay: 2-3 days
Include Volterra on an Explore Tuscany Tour: Ancient Towns, Coastlines, Snorkeling, and Trekking.
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
What to Expect
Where to Enjoy Your Visit
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.
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
What to Expect
Where to Enjoy Your Visit
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.
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.
Tuscany for Every Traveler
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.
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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