10 Best Places to Visit in Tuscany

Florence is a treasure trove of medieval and Renaissance wonder, with masterful architecture and art that speak to the power of the human spirit.

A warren of cobblestone streets circles opulent churches, connects to the ancient Ponte Vecchio bridge, hides beneath the looming dome of the renowned cathedral, and leads to the doors of the Uffizi Gallery and Accademia, home to famous works of art, including Botticelli’s Birth of Venus and Michelangelo’s David.

Illustrious architectural designs often trace Medici family history and boutique shops provide fascinating window displays that lure even the most dispassionate shopper. Florence is famous for its culinary history, with delicious flavors adding to the cultural heritage that you can find in the 5 dishes to try on your trip to Florence.

Highlights: Ponte Vecchio • Cathedral of Santa Maria dei Fiore • Uffizi Gallery • Accademia Gallery • Pitti Palace • Basilica of Santa Croce • Palazzo Vecchio

Recommended length of stay: 3-4 days

Siena is a perfect example of an open-air museum, with architecture celebrating the Gothic perspective that has buildings soaring into the sky and narrow cobblestone alleys opening to wide boulevards.

The city once rivaled Florence for supremacy over the Tuscan region, demonstrated in the remarkable artistry gracing structural design, artisanal boutiques, and famous pastry shops.

Siena is a feast for the senses, where restaurants serve traditional Tuscan cuisine, gelaterie dish up large scoops, and, during summer, the world-famous Palio horse race takes place in the central plaza, accentuating the picturesque charm of the Tuscan hills. You can explore Siena and its surroundings with a sample 14-day Tuscany itinerary.

Highlights: Cathedral of Santa Maria Assunta • Mangia Tower • Piazza del Campo • Pubblico Palace

Recommended length of stay: 2-3 days

The glory of Pisa travels far beyond the legendary Leaning Tower, with the former navy once rivaling and exceeding the prestige of Genoa and Venice. Pisa retains its historic symbols in the form of regal architectural accomplishments, with a cathedral, baptistry, and tower crowning the Piazza dei Miracoli.

Even after the naval powers faded, education has influenced the local economy since the 15th century, giving the antique city a modern ambiance. It is filled with vibrant cafes and restaurants woven into the fabric of Romanesque buildings and Gothic churches. Locals primarily fill the city outside of the views of the Leaning Tower, providing an authentic connection to Tuscan history and contemporary life.

Highlights: Leaning Tower • Cathedral of Santa Maria Assunta • Baptistery • Campo Santo • Cathedral Museum • Arsenals and Museum of Ancient Ships

Recommended length of stay: 1-2 days

Quiet but powerful, San Gimignano is the embodiment of a traditional Tuscan medieval town. The remains of what once amounted to 72 towers continue to loom large over the surrounding hills, providing fantastic views of nearby vineyards, villas, and olive groves.

The streets and walls date back to the late 12th century, creating a palpable ambiance through tangible history that connects winding streets to mesmerizing views of the countryside.

Whether visiting for the notable Vernaccia wine, eager to visit the serene churches, or interested in the unique skyline punctuated by the rival towers, you can find more ideas on how to best enjoy San Gimignano and where to go in Tuscany with our 7-Day Tuscany itineraries.

Highlights: Torre Grossa • La Rocca di Montestaffoli • Cathedral of Santa Maria Assunta • Popolo Palace

Recommended length of stay: 1-2 days

Arezzo is a city where art has always flourished, inspired by the countryside's grandeur, charm, and timeless beauty, which is reflected in the architecture and design. The central piazza has been featured in films and the foundations of the overall city rise out of a former Etruscan trading post.

Churches create a glamorous ambiance and connect to small museums representing famous works by the likes of Pisano, harking back to the poems of Petrarch, or showcasing the masterful stained-glass artist Guillaume de Marcillat.

It is exciting to discover the terra cottas in the 13th-century Duomo or the Romanesque features of Santa Maria della Pieve, or to visit Vasari house or explore the National Archeological Museum and Roman Amphitheater to get a sense of ancient life.

Highlights: Piazza Grande • Arezzo cathedral • Santa Maria della Pieve • Casa Vasari • National Museum of Medieval and Modern Art

Recommended length of stay: 2-3 days

Elba is a serene island paradise, with coves opening to gorgeous beaches, vineyards hidden amid the inland mountains, and azure waters sparkling beneath the Mediterranean sunlight. Views over the sea or landscape are enchanting and the island’s history dates back to approximately the 3rd century BC. It is known as the place to which Napoleon was exiled.

Local gastronomy highlights the natural treasures of the sea, wineries embrace the distinctive characteristics of the soil, and visitors indulge in the combination of relaxing coastline and dramatic landscape, where they can hike, kayak, sail, or sample the delicious harvest of grapes and olives. The island can feel like an untouched paradise.

Highlights: Spiaggia di Sansone • Toscano Archipelago National Park • Monte Capanne • Wine tasting • watersports • Active excursions

Recommended length of stay: 3-4 days

Whether looking for historical inspiration or contemporary creations, Prato has always been a city that celebrates art in all forms, focusing on the textile industry and archeological discoveries pre-dating Etruscan colonization.

You can search for the best time to visit Italy to explore the beauty of Prato and how the city exudes diverse cultural influences that have changed with the shifting aesthetics of power, from the Byzantines to the Lombards, the Medici to the united Italian Kingdom.

Adventure can take on a different form when visiting Prato, allowing travelers to explore the layers of history around the Duomo, uncover the fantastic art in the Pretorio Palace, witness the medieval architecture of the Emperor’s Castle, or wander along the shores of the Bilancino Lake.

Highlights: Prato Duomo • Pretorio Palace • Church of Santa Maria delle Carceri • Pitturo Murale Museum

Recommended length of stay: 1-2 days

Volterra’s incredible history dates back to the 8th century BC as an Etruscan town and prominent manufacturer of alabaster, complimenting any Italy tour & vacation. Winding cobbled streets unveil Roman history and move through medieval buildings decorated with artisanal designs and displays of shimmering alabaster.

The tower houses decorating the historic city center date back to the 12th century and the Roman Theater north of its walls could hold up to 2,000 spectators as early as the 1st century AD.

Visit the Etruscan Museum for insight into the former settlement, with fascinating artifacts that bring the past to life, and enjoy the views sweeping across the Tuscan countryside for a unique perspective that blends skyline, rural landscapes, and the beauty that has inspired art in the city for millennia.

Highlights: Roman theater • Etruscan museum • Viti Palace • Priori Palace • Porta all’Arco

Recommended length of stay: 2-3 days

While nearby Siena, Val d’Orcia is its own destination. Flush with farmlands brimming with olive groves and fields of grain, the valley embodies the quintessential image of Tuscany. Hills gently roll to the horizon, cypress trees line country roads, and vineyards spread across the lush floors or terraces of rising terrain.

Val d’Orcia is a perfect region in Tuscany for exploring by bike, car, or on foot to visit the traditional Tuscan hill towns and embrace the Unesco World Heritage sites. Discover grand abbeys, walk along medieval cobblestone lanes, and witness the wonders of Renaissance architecture and design in the town of Pienza, birthplace of Pope Pius II.

You can embrace the rich history and marvelous culture of the valley or enjoy the local flavors during an Italy food & wine tour.

Highlights: Abbey of Sant’Antimo • Montepulciano • Montalcino • Pienza • Vitaleta Chapel

Recommended length of stay: 2-3 days

Lucca has an endearing ambiance, where imposing Renaissance walls hide the medieval city center, promenades provide the perfect place for a stroll, restaurants brim with the aromas of Tuscan favorites, and historic villas open a window to an opulent past.

The Roman Amphitheater has become the main piazza and within the town walls, once built to protect the city from invaders, there’s a public park and garden, making it a perfect escape by foot or bike to enjoy the edging countryside. 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.

Food, wine, and panoramas sweeping across the traditional rolling hills only add to the city’s luster and you can explore it with our sample 10-Day Tuscany itineraries.

Highlights: Guinigi Tower • Roman amphitheater • Defensive Walls • Lucca cathedral • San Michele in Foro

Recommended length of stay: 1-2 days

From the Renaissance architecture of Florence to the dramatic walls of Lucca, the famous Leaning Tower of Pisa to the 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 found in quiet towns and the delicious cuisine you can enjoy with 5 dishes to try on your trip to Tuscany.

Find inspiration for your perfect trip with our sample Tuscany tour & vacation itineraries or find new ideas for activities you can enjoy by exploring the top 7 things to do in Tuscany. For more information on when to go and what to try during your trip, visit our Tuscany travel guide.