15 best day trips from Florence

Florence  has more than enough to keep you busy, but part of its charm is how easy it is to slip away for the day. Trains and buses connect the city to medieval hill towns, vineyard-covered countryside, and even the coast, all within a couple of hours. Here's our pick of the 15 best day trips to take from Florence during your trip. 

1. Pisa day trip from Florence

Most people head to Pisa for the Leaning Tower when planning their Italy itinerary, but the city’s history goes well beyond that famous landmark. Pisa was once a powerful maritime republic, and you can still see traces of that wealth in its churches, palaces, and squares along the Arno.

The main draw is the Campo dei Miracoli, where the tower, Duomo, and Baptistery stand together as a remarkable example of Romanesque architecture. You should also make time for Knights' Square, which was once the political center of Pisa and is now home to the Scuola Normale Superiore, one of Italy’s most respected universities. The historic center is small enough to cover in a day.

What to see and do in Pisa

• Climb the Leaning Tower’s 294 steps for wide views across the city
• Visit the Baptistery, known for its acoustics and detailed Gothic design
• Walk through Knights' Square and check out the Palazzo della Carovana with its decorated façade

How to get to Pisa from Florence

• Train: Getting from Florence to Pisa is easy. Regional trains leave Santa Maria Novella about every 30 minutes. The ride takes 50 to 80 minutes depending on stops, and tickets are around €9 each way.
• Bus: Flixbus runs from Villa Costanza coach station, which you can reach by tram. The trip takes about 1 hour 15 minutes and costs about the same as the train. Buses arrive at Pisa Airport rather than the city center.
• Car: Driving on the A11 autostrada or the SS67 takes around 1 hour 15 minutes. Free parking is available at Via Pietrasantina, while paid lots are closer to the tower. Parking can be tricky in summer. 

Best time to visit Pisa

The Leaning Tower gets busy, so aim for early morning before 10am or late afternoon after 4pm. Spring and autumn are comfortable for walking around, while winter is much quieter, though some places have shorter hours.

If you want to climb the tower in summer, book tickets online ahead of time.

Florence day trip travel tip: Skip the restaurants around the Campo dei Miracoli. Head to Via San Martino instead, where you’ll find trattorias popular with students; they serve better food and at lower prices. See our guide to how to plan a trip to Italy for more tips.

2. Siena day trip from Florence

In Siena you’re sure to feel the weight of history in every street. The city is famous for its Gothic architecture, the shell-shaped Piazza del Campo, and its fierce neighborhood rivalries.

Twice a year the Palio horse race takes over the main square, with each of Siena’s 17 contrade competing for pride as much as victory. The striped marble cathedral is a highlight, with Romanesque and Gothic details and works by Michelangelo, Donatello, and Bernini. Inside the Palazzo Pubblico, Lorenzetti’s frescoes show what life under good and bad government looked like in the 14th century.

Away from the big landmarks, the winding streets are filled with workshops, pastry shops selling ricciarelli and panforte, and wine bars serving Chianti Classico from the surrounding hills. You could easily spend a week-long Italy itinerary here alone. 

What to see and do in Siena

• Spend some time in Piazza del Campo, one of Europe’s most distinctive medieval squares
• Visit the striped marble Duomo with its detailed floor mosaics and the Piccolomini Library
• Climb Torre del Mangia for views over Siena’s rooftops and the Tuscan countryside

How to get to Siena from Florence

• Bus: The 131R Rapida leaves hourly from Florence’s bus station near Santa Maria Novella. The ride takes about 1 hour 15 minutes and ends at Piazza Gramsci inside Siena’s walls. Tickets are cheaper at the station rather than when you buy them on board.
• Train: Direct trains from Santa Maria Novella take around 1.5 hours. They arrive at Siena’s station outside the walls, with an escalator system or local buses connecting to the center.
• Car: Driving takes between 1.5 and 2 hours. The SR222 Chiantigiana route winds through vineyards, while the faster superstrada gets you there more directly. You’ll need to park in lots outside the walls, as the historic center is restricted to residents.

Best time to visit Siena

Unless you want to experience the Palio, it’s best to avoid July 2 and August 16 when the city is crowded and prices spike. Spring and early autumn are good for walking the city, while winter is quieter and often has a fog that adds atmosphere to the hills (see our guide to the best time to visit Italy for more tips).

Florence day trip travel tip: If you arrive by train, use Porta Camollia to enter the city. From there it’s an easy downhill walk into the center and saves you a tough climb. 
 

Chianti day trip from Florence

Chianti lies between Florence and Siena, a landscape of vineyards, olive groves, and small medieval towns. It has been recognized as a wine region since 1716, when Cosimo III de’ Medici set its boundaries. The best-known wine here is Chianti Classico, marked by the black rooster symbol, made mostly from Sangiovese grapes and often aged in cool cellars beneath old farmhouses. Visiting here is one of the best things to do in Tuscany.  

The Via Chiantigiana is the main road through the region. It passes cypress-lined hills, farmhouses, and villages worth stopping for.

Greve has a triangular piazza lined with arcades and wine shops, Castellina hides medieval passageways under its streets, and Montefioralle, a tiny walled hamlet above Greve, is one of the quietest places to walk around and look out over the vineyards.

Along the way you’ll come across family-run wineries, where tastings often include pecorino cheese, wild boar salami, and fresh olive oil.

What to see and do in Chianti

• Taste Chianti Classico at family-run wineries with centuries-old cellars
• Stop in Greve’s triangular piazza to browse wine shops and local food 
• Wander Montefioralle’s cobbled lanes with vineyard views all around

How to get to Chianti from Florence

• Organized tours: Half-day tours leave daily from Piazzale Montelungo near Santa Maria Novella. They usually visit two or three wineries, include tastings and transport, and last 4 to 6 hours.
• Bus and local transport: Bus 365 connects Florence to Greve in about an hour, but services are limited and most wineries are not reachable without a car or taxi. Tastings need to be booked in advance.
• Car: Driving gives the most flexibility. The SR222 takes about 45 minutes to Greve, and you can stop at wineries along the way marked with “vendita diretta” signs. That said be careful not to drink and drive.

Best time to visit Chianti

September and October bring harvest season, with activity in the vineyards and autumn colors across the hills. Spring has mild weather and wildflowers. August is quieter since many family-run businesses close for holidays. Winter is calm, with fewer visitors and more relaxed tastings.

Florence day trip travel tip: Plan for a winery lunch at an agriturismo. Many serve set menus of local dishes paired with their own wines, usually around €35, often with wide views across the countryside. And don't miss our guide to the best food in Florence for when you're in town.

4. Bologna day trip from Florence

Bologna has a very different feel from Florence. Locals call it la dotta, la rossa, la grassa (the learned, the red, the fat), nicknames that reflect its long academic history, terracotta architecture, and fantastic food.

The university here dates back to 1088, making it the oldest in Europe, and you’ll still notice the student energy around town. Much of the city is shaded by its 24 miles (38 kilometers) of porticoes, now UNESCO-listed, which connect markets, cafés, and bookshops.

Walking through the center, you’ll see the leaning Asinelli and Garisenda towers, the vast Piazza Maggiore with San Petronio Basilica, and even a few canals hidden between the streets. Food is at the heart of daily life here, from tortellini in brodo to tagliatelle al ragù, better known abroad as “Bolognese,” along with mortadella and a glass of local Pignoletto wine. 

What to see and do in Bologna

• Climb the 498 steps of Torre degli Asinelli for wide views over the city
• Walk the medieval market streets of the Quadrilatero and try mortadella or Parmigiano-Reggiano
• Visit the Santo Stefano complex, a group of seven connected churches

How to get to Bologna from Florence

• High-speed train: Frecciarossa and Italo trains leave Santa Maria Novella about every 30 minutes. The trip takes 37 minutes to Bologna Centrale, with tickets ranging from €10–40 depending on time and class. Booking ahead helps with price.
• Regional train: The Regionale trains take 1.5–2 hours and cost around €7–10. They run through the Apennines and stop at smaller stations. No reservations are needed, though they can be crowded during peak hours.
• Bus: FlixBus runs from Villa Costanza to Bologna in about 1 hour 15 minutes. Tickets usually cost €7–19. It can be cheaper than trains but travel times depend on traffic, and luggage space is limited on busy days.

Best time to visit Bologna

The city feels lively during the university term from October to May. September is a good time for food festivals. In August many restaurants close, though you’ll find fewer visitors. Graduation season in July can push up accommodation prices.

Florence day trip travel tip: How many days in Florence you need depends on how many day trips you want to take.

5. San Gimignano day trip from Florence

San Gimignano is found above the Val d’Elsa with its cluster of medieval towers. Fourteen are still standing today, though in the 1200s there were more than seventy, each built by wealthy families competing to outdo each other.

The town became prosperous as a stop on the Via Francigena pilgrimage route, and wandering its streets gives you a real sense of that history. You’ll come across workshops making saffron and Vernaccia wine, the Collegiate Church with frescoes showing dramatic scenes of heaven and hell, and the central Piazza della Cisterna, where Dante once addressed the townspeople. 

Away from the main square, the quieter streets lead to artisan studios and a gelateria known for regional flavors like saffron and Vernaccia.

What to see and do in San Gimignano

• Climb Torre Grossa for views across the Tuscan countryside and the town’s remaining towers
• Taste Vernaccia di San Gimignano, the town’s signature white wine, in one of the historic cellars
• Step inside the Collegiate Church to see frescoes that illustrate paradise, hell, and biblical stories

How to get to San Gimignano from Florence

• Bus via Poggibonsi: From Florence bus station, take line 131 to Poggibonsi (about 50 minutes), then switch to line 130 for San Gimignano (20 minutes). Buses are regular on weekdays but less so on weekends (see our guide to the perfect weekend in Florence).
• Train + bus: From Santa Maria Novella, take the train to Poggibonsi-San Gimignano station (1 hour), then catch bus 130 outside the station entrance. The journey takes about 1.5 hours in total. The train is more comfortable, but you’ll need to match its schedule with the bus.
• Car: The drive takes about 1 hour 15 minutes via Poggibonsi on SP1 and SP47. You’ll need to park outside the town walls (€2 per hour) since the center is pedestrian-only. In summer, arrive early because parking fills quickly.

Best time to visit San Gimignano

Arrive early in the morning before 10am or later in the evening after 5pm to miss the heaviest crowds. Spring brings wildflowers, autumn brings the grape harvest, and winter weekdays can be very quiet.

Florence day trip travel tip: See our sample Tuscany itinerary for ideas on how to split up your time while you are here.

6. Val d'Orcia day trip from Florence

The Val d'Orcia is the kind of landscape people imagine when they think of Tuscany. Rolling hills stretch out in every direction, cut by winding roads lined with cypress trees, and hill towns rise above the valleys.

It is a UNESCO World Heritage site with a mix of wine, Renaissance history, and thermal springs. Montalcino and Montepulciano are known for their wines, Pienza is famous for pecorino cheese aged in underground caves, and Bagno Vignoni has long been a place to soak in natural hot water. 

Smaller villages like Monticchiello and San Quirico d'Orcia still keep a strong rural character. Out in the countryside, you will find the small Vitaleta Chapel and the winding road near La Foce, both instantly recognizable from countless postcards.

What to see and do in Val d'Orcia

• Stop at La Foce for the winding cypress road and take in the view of the Vitaleta Chapel standing alone in the fields
• Visit Montalcino to sample Brunello wines inside the old fortress with wide views of the valley
• Walk through Pienza’s Renaissance streets and try pecorino cheese in cellars that have been used for centuries

How to get to Val d'Orcia from Florence

• Organized tours: Full-day tours usually include Montalcino, Pienza, and Montepulciano with wine tastings and lunch. They leave from Piazzale Montelungo in Florence and last around 10 to 12 hours.
• Public transport: Reaching the Val d'Orcia by bus is possible but not very practical. First, you take a bus to Siena which takes about 1 hour 15 minutes. From there, infrequent buses run to towns like Montalcino or Pienza. Lines 112 and 114 connect some villages, but the schedules make it difficult to see more than one place in a day.
• Car: Driving yourself gives the most flexibility. Take the A1 south to the Valdichiana exit, then continue on the smaller country roads. From Florence it is about 2 hours to Montalcino and 1.5 hours to Pienza. The drives between the towns are scenic but winding, so take your time.

Best time to visit Val d'Orcia

In May the hills are green with wildflowers. July is when the wheat fields turn golden before the harvest. October brings grape harvests and colorful vineyards. Winter often brings fog that drifts through the valleys,though many wineries keep shorter hours.

Florence day trip travel tip: If you are driving, take the SP146 between Pienza and San Quirico d'Orcia in the late afternoon. The light across the hills makes this one of the most memorable stretches of road in Tuscany.
 

7. Lucca day trip from Florence

Lucca is known for its Renaissance walls, which completely circle the old town and now function as a wide, tree-lined park. Locals use the paths for walking and cycling, and it’s one of the best ways to get a feel for the city, with views over the rooftops as you go. Inside the walls, you’ll find the oval Piazza Anfiteatro, built on the foundations of a Roman arena; the Guinigi Tower, crowned with oak trees; and San Michele church, with its ornate Romanesque façade.

The city also has a strong musical connection as the birthplace of composer Puccini, and concerts are still held in historic venues. The medieval streets are easy to explore on foot or by bike, with small workshops, pastry shops selling buccellato, and independent boutiques around every corner. Unlike many Tuscan hill towns, Lucca is flat and pedestrian-friendly. 

What to see and do in Lucca

• Walk or cycle the 2 mile (4 km) tree-lined ramparts around the old town
• Climb 230 steps up Guinigi Tower to see oak trees growing on its roof
• Visit Piazza Anfiteatro, an unusual oval square built into Roman amphitheater remains

How to get to Lucca from Florence

• Train: Regional trains leave Santa Maria Novella about once an hour, taking around 1 hour 20 minutes. The station is just inside the walls at Piazza Ricasoli, a short walk through Porta San Pietro to the center.
• Bus: Autolinee Toscane buses run from Piazzale Montelungo in Florence to Piazzale Verdi in Lucca every two hours. The trip takes about 55 minutes and drops you inside the walls near the center.
• Car: Take the A11 autostrada toward Pisa and exit at Lucca Est or Lucca Ovest. The drive is about an hour. Cars are restricted in the historic center, so plan to park outside the walls in city lots, which cost about €1–2 per hour.

Best time to visit Lucca

September brings the Lucca Comics festival, which transforms the city but also draws huge crowds. Summer evenings are often filled with concerts. Spring and early autumn are good for cycling the walls, while winter is quieter and has a more atmospheric feel.

Florence day trip travel tip: You can rent a bike near the train station for about €3 an hour. Cycling the walls at sunset is an easy way to take in the views without having to walk the whole loop.
 

8. Cortona day trip from Florence

Cortona clings to the slopes of Mount Sant’Egidio, looking out over the Valdichiana plain and Lake Trasimeno. Its history runs deep. In fact, part of the Etruscan walls still surrounds parts of the town. 

The Etruscan Academy Museum (MAEC) has artifacts dating back three millennia, including an intricate bronze chandelier that is well worth a visit. The town itself is compact but steep, with winding medieval lanes, Renaissance palaces, and small piazzas that keep a lived-in feel despite its fame from Under the Tuscan Sun.

The main square, Piazza della Repubblica, is anchored by the Palazzo Comunale, while higher up the hill the Basilica di Santa Margherita rewards the climb with wide views across Tuscany and into Umbria.

The Diocesan Museum is worth a stop if you want to see Fra Angelico’s Annunciation and paintings by Luca Signorelli, who was born here. On Saturdays, the market spreads through the streets with fresh produce and antiques. This is one of the best things to do in Tuscany.

What to see and do in Cortona

• MAEC Etruscan Museum, home to the bronze chandelier and other rare artifacts
• Basilica di Santa Margherita for sweeping views, especially at sunset
• Diocesan Museum to see Fra Angelico’s Annunciation and Signorelli’s paintings

How to get to Cortona from Florence

Train to Camucia-Cortona: Trains from Santa Maria Novella take about 1.5 hours with a change in Arezzo, or just under 2 hours direct. From Camucia station, buses run roughly once an hour and reach Piazza Garibaldi in about 15 minutes.

Train to Terontola-Cortona: This route takes about 1 hour 45 minutes. From the station, you’ll need a taxi or an infrequent bus up to town. It can work well depending on schedules, but it’s less reliable.

By car: The drive takes around 1.5 hours via the A1 south to the Valdichiana exit. Parking is available near Porta Santa Maria and Santo Spirito. From there, you can walk or use escalators to reach the upper town.

Best time to visit Cortona

Spring and autumn are the most pleasant, with flowers or harvest colors in the hills and comfortable weather for climbing. Winter weekdays are quieter and give you more of the town to yourself. August is worth skipping unless you specifically want to attend the Tuscan Sun Festival, as the heat and crowds make it less enjoyable.

Florence day trip travel tip: If you park at Piazzale del Mercato, take the escalator. It brings you close to the main piazza and saves energy for exploring the streets above.

9. Fiesole day trip from Florence

Fiesole is only 5 miles (8 kilometers) above Florence. This hill town is known for its wide views and slower rhythm compared to the city. It predates Florence by centuries, starting as an Etruscan settlement, and you can still see traces of its past.

The Roman theater is still in use for summer performances, and the surrounding area has remains of baths, walls, and temple foundations set among olive groves.

The town center is compact, with Piazza Mino and the cathedral at its core. The Bandini Museum nearby holds della Robbia ceramics and early Renaissance works. If you continue uphill, you reach the San Francesco monastery, where terraces open out over Florence and on clear days you can see as far as the Apennines. Writers and artists have been coming here for centuries, drawn by the quiet and the quality of light. 

What to see and do in Fiesole

• Visit the Roman theater and archaeological area with Etruscan walls and temple remains
• Walk up to San Francesco monastery for wide views and quiet cloisters
• Step into the Bandini Museum for medieval and Renaissance art in small galleries

How to get to Fiesole from Florence

• Bus: The number 7 bus runs every 15–20 minutes from Piazza San Marco or Santa Maria Novella station and reaches Piazza Mino in around half an hour. A regular city ticket covers the round trip.
• Car: Driving takes about 20 minutes. Parking in Piazza Mino (€1/hour) is limited and fills quickly, so you may need to leave the car further down and walk.
• Walking: If you like a climb, trails lead from Florence through olive groves and take between one and two hours. One option is starting from Piazza San Marco and following Via degli Artisti uphill.

Best time to visit Fiesole

In summer the Roman theater hosts evening concerts. Spring and autumn bring the clearest views, and mornings are the quietest time to arrive. Winter is colder but peaceful, with very few visitors around.

Florence day trip travel tip: See our favorite museums in Florence for a good idea of what to see while you're in town.
 

10. Perugia day trip from Florence

Perugia, the capital of Umbria, feels both historic and lively thanks to its deep Etruscan roots, medieval streets, and large student population. 

Walking through the city, you’ll notice layers of history everywhere: an Etruscan arch built into the medieval walls, the Gothic Palazzo dei Priori that now houses the National Gallery of Umbria, and Renaissance frescoes tucked inside the Collegio del Cambio.

The main street, Corso Vannucci, is the heart of the city and always filled with people. On some weekends, squares fill with antiques and curios at the monthly market.

On weekends, you might catch the antique market in one of the main squares. Perugia is also known for chocolate, especially its famous Baci, and every October the Eurochocolate festival takes over the city.

Beyond the main sights, you can explore the underground passages of the Rocca Paolina fortress or relax in gardens overlooking the Umbrian countryside of sunflower fields.

What to see and do in Perugia

• Look for Perugino’s Renaissance frescoes in the Collegio del Cambio, painted in small, atmospheric chambers
• Walk through the underground streets of the Rocca Paolina, a medieval quarter buried beneath the city
• Spend time in the National Gallery of Umbria, which has regional art from the Byzantine period through the Renaissance

How to get to Perugia from Florence

• Train: Direct regional trains run from Santa Maria Novella to Perugia 3 to 4 times a day. The trip takes about 2 hours 15 minutes. Some services require a change at Terontola-Cortona. From Perugia station, the MiniMetro tram takes you straight to the historic center.
• High-speed plus regional: Take a Frecciarossa to Arezzo, a 35-minute ride, then connect to a regional train for another 1.5 hours. It takes about 2.5 hours total and gives you more departure options.
• Car: Driving takes about 1 hour 45 minutes via the A1 to Valdichiana, then the E45 to Perugia. You can park at Pian di Massiano and take the MiniMetro into town, or use paid parking at Pellini or Mercato Coperto, both connected to the center by escalators.

Best time to visit Perugia

In July, the Umbria Jazz Festival brings music and plenty of visitors, while October is all about Eurochocolate. If you’d prefer a quieter trip, spring is a good time, with mild weather and countryside views filled with flowers.

Florence day trip travel tip:  The Perugia City Museum Card costs €15 and covers several main sights as well as public transport. Even the short ride on the MiniMetro gives you sweeping views of the surrounding hills.

11. Cinque Terre day trip from Florence

Cinque Terre is made up of five villages built along the cliffs of the Ligurian coast.

Monterosso has a sandy Italy beach and lemon groves, Vernazza curves around a small harbor, Corniglia is perched high above the sea, Manarola is known for cliff diving, and Riomaggiore has steep streets running straight down to the water. Terraced vineyards surround the towns, where families have produced Sciacchetrà wine for centuries.

There are a lot of things to do in Cinque Terre. You can move between the villages by train or on foot. Hiking paths wind across the cliffs and connect the towns, while local trains run regularly and only take a few minutes between stops.

Even with the heavy flow of visitors, you still see signs of traditional life, like fishermen working in the harbors or restaurants serving fresh anchovies and pesto made with locally grown basil.

What to see and do in Cinque Terre

• Walk the coastal trails for wide sea views and vineyard-covered hillsides
• Swim at Monterosso’s beach or jump from the rocks at Manarola
• Watch the sunset from Vernazza’s harbor walls or from Corniglia’s terrace above the sea

How to get to Cinque Terre from Florence

• Train via La Spezia: Getting to Cinque Terre from Florence is easy. Take a high-speed or Intercity train to Pisa in about an hour, then continue by regional train to La Spezia, which takes another hour. From La Spezia, local trains reach the villages in 10 to 25 minutes. At La Spezia, you can buy the Cinque Terre Train Card for unlimited village trains.
• Organized tours: Tours leave Florence early in the morning and return in the evening. They usually include transport and a guide, and some also add a boat ride between villages. They cost more but save you from managing multiple train connections, which can be stressful in peak summer when trains are overcrowded.

Best time to visit Cinque Terre

July and August bring crowds, hot weather, and occasional trail closures. Late September and October are easier for travel, with warm sea temperatures and the grape harvest underway. May is good for hiking, with comfortable weather and wildflowers along the paths. In winter, the villages are quieter, though many restaurants are closed.

Florence day trip travel tip: Begin in Monterosso and move through the villages in the opposite direction of most visitors. This way you avoid the biggest crowds later in the day.
 

12. Arezzo day trip from Florence

The heart of Arezzo is Piazza Grande, a sloping square edged with medieval towers and Renaissance palaces. On the first weekend of the month it fills with one of Italy’s most important antique markets, spilling into the surrounding streets.

If you only see one thing here, make it Piero della Francesca’s Legend of the True Cross frescoes inside the Basilica di San Francesco, a highlight of Renaissance art. 

The city has deep Etruscan and Roman roots but still feels lived-in and local. You can visit Giorgio Vasari’s former home, walk through the Gothic cathedral with its stained glass windows, or step into goldsmith workshops that carry on traditions centuries old. Movie fans may recognize corners of the historic center from Life is Beautiful, which was filmed here.

What to see and do in Arezzo

• See Piero della Francesca’s Legend of the True Cross frescoes in the Basilica di San Francesco
• Browse the monthly antique market in Piazza Grande
• Visit Casa Vasari, the artist and historian’s decorated home and gardens

How to get to Arezzo from Florence

• Regional train: Direct trains leave Santa Maria Novella about once an hour. The ride takes around 1 hour 20 minutes.The station is a 10-minute walk from the center, or you can catch a local bus.
• High-speed train: Frecciarossa and Frecciargento trains reach Arezzo in 35 to 40 minutes. Tickets usually cost more than the regional train and come with reserved seats, which is helpful during the antique fair.
• Car: Driving the A1 south takes about an hour. You can park at Parcheggio Pietri near the station or at Eden Parking closer to the center. The historic core has ZTL restrictions, but once inside, it is easy to explore on foot.

Best time to visit Arezzo

The antique market brings big crowds on the first weekend of each month. In June, the Giostra del Saracino fills the city with parades and jousting in Piazza Grande. Autumn weekdays are quieter and a good time to combine the city with vineyard visits during the harvest.

Florence day trip travel tip: Reserve tickets online for the Basilica di San Francesco. Entry to the frescoes is limited to 25 people every half hour, and spaces fill quickly.
 

13. Montepulciano day trip from Florence

Montepulciano runs along a ridge between the Val d’Orcia and Valdichiana, with narrow medieval streets that climb toward Piazza Grande.

At the top, you’ll find the cathedral and Palazzo Comunale, whose tower has views across the Tuscan countryside. Beneath the town, centuries-old wine cellars carved into the rock store barrels of Vino Nobile di Montepulciano.

Walking up the main street, you pass wine shops, Renaissance palaces, and small churches before reaching terraces that look out over vineyards, olive groves, and even Lake Trasimeno in the distance.

The town has been used as a film location for Twilight and Under the Tuscan Sun, but daily life still feels centered on local workshops and family-run osterie where handmade pici pasta is a staple.

What to see and do in Montepulciano

• Visit underground cellars such as Contucci or Cantina del Redi, where tastings are often held among the barrels
• Climb the tower of Palazzo Comunale for wide views across the hills
• Walk down to San Biagio, a Renaissance church built in warm travertine stone below the town

How to get to Montepulciano from Florence

• Train and bus: From Santa Maria Novella, take a train to Chiusi-Chianciano Terme, which takes about 1.5 hours. From there, catch the bus to Montepulciano, around 40 minutes. The total trip is about 2.5 hours, but bus services are limited on weekends, so check ahead.
• Organized tours: Many day tours combine Montepulciano with towns like Pienza, often including wine tastings and lunch. Tours usually leave Piazzale Montelungo around 8am and return by 7pm.
• Car: Drive south on the A1 to the Valdichiana exit, then follow signs to Montepulciano. The drive takes about 1 hour 45 minutes. Cars are not allowed in the historic center, so park outside the gates at Porta al Prato or Porta delle Farine. From there you can walk up or use the orange shuttle buses.

Florence day trip travel tip:  If you want to avoid the steep uphill walk through town, start your visit at Porta al Prato and take your time wandering upward, stopping at wine shops and cafés along the way. By the time you reach Piazza Grande, you’ll have worked up an appetite for a plate of pici pasta at one of the osterie nearby.
 

14. Assisi day trip from Florence

Assisi runs down the slopes of Monte Subasio in pale pink and white stone, its medieval streets still carrying the presence of Saint Francis, who lived here eight centuries ago.

At the heart of the lower town, the Basilica of San Francesco draws visitors with Giotto’s frescoes showing scenes from the saint’s life. Above the town, the Rocca Maggiore fortress looks out across the Umbrian valley.

As you move through Assisi, you’ll find traces of different eras layered together. Roman temples were turned into churches, medieval guild streets remain intact, and the Porziuncola chapel, where Francis founded his order, now stands inside the vast Santa Maria degli Angeli.

Despite its role as one of Christianity’s main pilgrimage towns, Assisi keeps its Umbrian character through family trattorias serving wild boar and truffle pasta and small artisan shops. 

What to see and do in Assisi

• Visit the Basilica of San Francesco to see Giotto’s frescoes of Saint Francis’s life
• Climb to Rocca Maggiore fortress for wide views over the valley and olive groves
• Step inside the Basilica of Santa Chiara, home to the San Damiano cross and Clare’s tomb

How to get to Assisi from Florence

• Train: From Santa Maria Novella, take the train to Assisi with a connection at Terontola-Cortona. The trip takes about 2.5 hours. From the station, buses run every 30 minutes to Piazza Matteotti in the historic center, or you can take a taxi for the 2 mile (4 km) ride.
• Train via Perugia: Another option is traveling through Perugia. The train to Perugia takes about 2 hours, followed by a 20-minute regional train to Assisi. This route can work better depending on schedules.
• Car: Driving takes about 2 hours. Take the A1 south toward Rome, exit at Valdichiana, and continue through the Umbrian countryside to Assisi. Use the Mojano or Giovanni Paolo II parking lots, then take escalators or a minibus into the center.

Best time to visit Assisi

Assisi is busiest at Easter and during other religious holidays. In May, the Calendimaggio festival fills the town with medieval parades and performances. Early mornings are the quietest time to walk the streets or visit the basilica. In December, nativity scenes appear across town.

Florence day trip travel tip:
 

15. Prato day trip from Florence

Prato is only 12 miles (20 km) from the city, which makes it an easy day trip from Florence but with a very different feel. The Duomo holds Filippo Lippi’s frescoes on the life of John the Baptist, works that influenced Botticelli. The cathedral also houses the relic of the Virgin Mary’s belt, still central to the city’s religious traditions.

Prato has long been a textile center and today is also known for its large Chinese community, the second biggest in Italy. This mix is part of what makes the city interesting. You can find dim sum restaurants on the same streets as Tuscan osterie serving mortadella di Prato and cantucci with Vin Santo.

The medieval center is small and easy to explore. You can see Frederick II’s Castello dell’Imperatore, admire the striped marble façade of the Duomo, and then head to Centro Pecci, a contemporary art museum with changing exhibitions. Because it is so close to Florence, many people combine Prato with a visit to the Medici villa at Poggio a Caiano or the nearby city of Pistoia. 

What to see and do in Prato

• Filippo Lippi’s frescoes in the Duomo
• Castello dell’Imperatore with its high walls and open terraces
• Contemporary exhibitions at Centro Pecci

How to get to Prato from Florence

• Train: Regional trains leave Santa Maria Novella every 15 to 20 minutes and reach Prato Centrale in about 20 minutes. From there it is a short walk through the old walls into the center.
• Prato Porta al Serraglio station: Some trains also stop here, which is even closer to the Duomo than Centrale. Check before you go.
• Car: Take the A11 autostrada toward Pistoia and exit at Prato Est or Ovest. The drive takes around 25 minutes. Parking is available at Piazza del Mercato Nuovo or Serraglio. The historic center is best explored on foot.

Best time to visit Prato

On September 8 the Virgin’s belt is displayed in a procession that fills the streets with medieval ceremony. Mondays bring a large market with both local produce and imported Chinese goods. For quieter museum visits, weekday mornings are ideal.

Florence day trip travel tip: Head to Via Pistoiese for lunch. Prato’s Chinese restaurants are some of the most authentic you will find in Italy, and the prices are usually very reasonable.