9 of the Best Weekend Getaways from Florence

Stretching from Florence south to Siena, the iconic Chianti hills are one of the best weekend trips from Florence, offering plenty to do for everyone from foodies to outdoor enthusiasts. Take two days to visit its vineyards with a wine tour, explore the scenic trails with a hiking or cycling excursion, and stroll through its walled hill towns that haven’t changed since the Middle Ages.

Tiny hamlets such as Greve in Chianti, Castellina in Chianti, Radda in Chianti, Montefioralle, and Panzano are delightful spots for an overnight base to explore the surrounding area, or you can book one of Chianti’s many wine resorts or farm stays (known as an agriturismo). Other highlights include the Brolio Castle and Castle of Meleto, plus the A-list town of San Gimignano, just to the west of Chianti.

Recognized by UNESCO as a World Heritage Site and home to the lively Palio historic festival, Siena is one of the top nearby destinations from Florence for both culture lovers and foodies. Admire Siena Historic Center highlights including the Piazza del Campo, Mangia Tower, and the Siena Cathedral (Duomo) on a walking tour; marvel at Ambrogio Lorenzetti's massive 14th-century fresco cycle The Allegory of Good and Bad Government in the Civic Museum inside the Pubblico Palace; and dedicate time to exploring the old town’s excellent shops and restaurants.

Siena is also a perfect base for exploring the nearby hills with a wine tour or truffle hunt, or for exploring serene gems such as the walled hamlet of Monteriggioni and Abbey of Sant’Antimo.

The dreamy, cypress-lined hills of Tuscany’s Val d’Orcia are among the top weekend getaways in Tuscany for lovers of idyllic views. But exploring the countryside on foot, by bike, or by car isn’t the only draw. This Tuscan enclave is also home to the Montalcino and Montepulciano wine countries, where Brunello di Montalcino and Vino Nobile di Montepulciano dominate area wine tours. Admire Renaissance architecture and sample artisan Pecorino (sheep milk) cheese in Pienza, snap a photo of the hilltop Vitaleta Chapel, and luxuriate in the relaxed vibe far from the Florentine crowds.

Pisa is among the most popular day trips from Florence, but this culture-rich city has plenty to fill an entire weekend. The gems in Piazza dei Miracoli (also known as the Campo dei Miracoli or Piazza Duomo)—including the Leaning Tower of Pisa, Pisa Cathedral (Duomo), Pisa Baptistery, and Monumental Cemetery of Pisa (Camposanto Monumentale)—are the city headliners, but the atmospheric old town is crowded with cultural treasures, bustling squares, an array of shops, and authentic Tuscan dining. Once you’ve visited the Church of Santa Maria della Spina and Knights’ Square, head outside the city to tour the Carrara Marble Quarry.

Though Lucca is one of the best places to visit near Florence, this charming walled old town flies under the radar of most visitors to Tuscany. You’ll come across the occasional tourist, but the streets of this inviting town bustle mainly with locals going about their day on foot and by bike. Get an overview of the main sights in the old town with a sightseeing tour that covers highlights such as the Lucca Cathedral (Duomo di Lucca) and Church of San Michele in Foro (Chiesa di San Michele in Foro), browse the smart shops along Via Fillungo, and pause over an aperitivo in lively Piazza dell’Anfiteatro.

Once you’ve covered the sights, Lucca is the perfect city in which to spend your second day learning how to prepare classic Tuscan dishes with a hands-on cooking class or sipping wine in the vineyard-covered surrounding hills on a wine tour.

No Florence weekend travel guide would be complete without mentioning the Cinque Terre National Park, a major seaside destination from the Tuscan capital. Stay in one of the five villages—Riomaggiore, Manarola, Corniglia, Vernazza, and Monterosso al Mare—and make it your base for visiting the towns on foot or by train with a guided tour. Lovers of outdoor adventure can also explore the coastline along its many trails, including the scenic Via dell’Amore, which has recently reopened after years of restoration.

Insider tip: Weekends are crowded on the Cinque Terre, so escape the throngs by heading out to sea on a boat tour or explore the towns just outside the overflowing national park, including Portovenere, Portofino, Santa Margherita Ligure, Camogli, and Sestri Levante.

Experience the verve of an Italian city without the inescapable tourist presence in Florence by hopping on a high-speed train and travel just 30 minutes north to spend a few days exploring Bologna. This handsome city, home to the oldest university in the Western world, has become a more popular tourist destination over the past few years, but locals and students still dominate the urban scene.

The city is great for lovers of art and architecture: A grand network of UNESCO–listed porticoes connect the city to the hilltop Sanctuary of the Madonna of San Luca, and cultural gems from the San Petronio Basilica in Piazza Maggiore to the Basilica of Santo Stefano. But it’s the local cuisine that really impresses, with fresh pasta, rich ragù, and an endless array of local cheeses and cold cuts to feast on during a food tour.

Lovers of Italian cuisine can set their sights on Food Valley, a stretch of fertile farmland and vineyards around the Emilian cities of Modena and Parma where some of the country’s most iconic gourmet specialties are produced. Join a food tour to discover the artisan makers of Parmigiano Reggiano cheese and Prosciutto di Parma ham, stopping to visit farms and indulge in plenty of tastings along the way. Then move toward Modena to sample authentic balsamic vinegar and bubbly Lambrusco wine with another culinary itinerary, paired with a walking tour through the charming old town.

It's not all about the food, though: Car enthusiasts will also want to spend some time exploring the area’s Motor Valley, home to the Enzo Ferrari Museum (Museo Casa Enzo Ferrari) and Ferrari Museum in nearby Maranello.

If Florence’s go-go pace of sightseeing, shopping, and dining feels overwhelming, the quiet region of Umbria just south of Tuscany offers a welcome respite. Home to the pink-hued medieval hill town of Assisi—birthplace of St. Francis of Assisi, entombed beneath the UNESCO–listed Basilica of St. Francis—and the handsome perches of Perugia and Orvieto, this largely unsung corner of Italy sees just a fraction of the tourists of its famous neighbor to the north. Stroll through its pretty towns overlooking the Umbria valley, sip wine in the vineyards of Montefalco, hike or bike though the unspoiled countryside, and experience Italy’s heartland just two hours from Florence.