Florence is one of the best home bases for exploring Tuscany and nearby cities. The most popular day trips from Florence are conveniently accessible by train, with destinations like Pisa, Lucca, Bologna, Arezzo, and Siena just one to two hours away. Renting a car or joining a guided tour provides access to Tuscan hill towns, Chianti wineries, and the scenic landscapes of Val d’Orcia.
We’ve visited Florence and Tuscany multiple times and have personally done every day trip in this guide, some more than once. That includes the easy train trips, the famous Tuscan hill towns, the wine regions, and the longer days to places like the Cinque Terre, Milan, Assisi, and Orvieto.
In this guide, we will help you choose the right day trip based on your travel style and how much time you have. If this is your first trip to Florence, Siena is our top overall pick. For wine and scenery, choose Chianti or the Val d’Orcia. For the easiest train day, pair Pisa and Lucca. And if food is your priority, Bologna is hard to beat.
We have lots of information to share with you, so let’s get started.
At a Glance: Which Florence Day Trip Should You Choose?
| If you want… | Best Pick | How to Go | Time from Florence |
| The best all-around first trip | Siena | Bus or train | ~1.5 hrs |
| Wine, scenery, and rolling hills | Chianti or Val d’Orcia | Car or tour | ~1–1.5 hrs |
| The easiest train day | Pisa + Lucca | Train | ~1 hr (Pisa) |
| Italy’s best food city | Bologna | High-speed train | ~40 min |
| Dramatic coastal scenery | Cinque Terre | Train | ~2 hrs |
| Classic Tuscan hill towns | San Gimignano + Siena | Tour or car | ~1–1.5 hrs |
| Off the beaten path | Volterra or Cortona | Car | ~1.5–2 hrs |
| A big Italian city escape | Milan | High-speed train | ~2 hrs |
| A short half-day escape | Arezzo | Train | ~1 hr |
Getting to Your Florence Day Trip: Train, Car, Bus & Tour
When planning your day trips from Florence, one of the biggest factors to consider is how you will get around.
Florence is well connected to other major Italian cities by bus and train. There are also numerous buses and trains that connect Florence to nearby Tuscan towns. In addition to the buses and trains, you also have the option to rent a car, hire a driver, or join a tour. These all have advantages and disadvantages.
By Train
The train is the fastest and most convenient option for most day trips from Florence. Within an hour you can reach Bologna and Arezzo; Pisa, Lucca, Siena, and Cinque Terre are all within two hours.
One thing to keep in mind: Italy has two types of trains, high-speed trains like the Frecciarossa, and slower regional trains. Most connections to Tuscan towns run on regional trains, but for longer trips like Bologna or Milan, the high-speed train is worth the extra cost. We book train tickets directly through Trenitalia.
Best for: Pisa, Lucca, Bologna, Arezzo, Cinque Terre, Milan, Orvieto, Assisi
By Bus
The bus is the cheapest option but also the slowest and least reliable. On our first trip to Florence, we tried getting around by bus and had a frustrating experience. Buses ran over an hour late, transferred in unexpected places, and a lot of time was spent waiting at stations instead of exploring. We eventually rented a car and never looked back. The one exception worth noting: the direct bus from Florence to Siena is fast, affordable, and genuinely easy.
Best for: Siena
Palazzo Communale in Montepulciano
By Car
A rental car gives you the most flexibility and is the best way to explore the southern Tuscan hill towns (Montepulciano, Pienza, Montalcino, and the Val d’Orcia), which are difficult to reach efficiently any other way.
The main thing to plan around: avoid driving into central Florence itself. Pick up your car at the train station or airport to stay out of the ZTL zone, and research parking before you arrive in each hill town, as most require paid lots on the outskirts of the historic center. We have parking tips included in each of our individual town guides.
Best for: Chianti, Val d’Orcia, Montepulciano, Pienza, Montalcino, Volterra, Cortona, San Gimignano
Getting Around By Private Driver
If you want the freedom of the rental car but don’t want the hassle of driving and parking, hiring a driver is the way to go. This is the most expensive way to travel, but it eliminates most of the headaches and hassles…no long waits for a bus, no need to research where to park in advance, and you can drink as much wine as you like without having to later get behind the wheel of a car.
Each of the day trips below can be done with a private driver.
Getting Around on a Tour
A guided tour is the smartest choice if you want to visit multiple Tuscan hill towns in a single day without the logistics of driving and parking. Tours handle the transportation, include a knowledgeable guide, and many add a winery visit or cooking class. This is especially worth considering for San Gimignano, Chianti, and the Val d’Orcia, where stringing multiple stops together independently requires careful planning.
Best for: Multi-stop Tuscany days, Chianti wine tours, Val d’Orcia
Best Day Trips from Florence
Here is a map showing the location of the cities and hill towns that make great day trips from Florence.
How to Use This Map: Click the icons on the map to get more information about each point of interest. To take this map with you, click the star next to the title of the map which adds it to your Google account. Next, within your Google Maps app, select ‘Saved’ and then select ‘Maps’. This map title will now appear in your list.
1. Siena: The Best Overall Day Trip from Florence
Best for: First-time visitors, medieval streets, cathedral, classic Tuscany
Best way to get there: Bus or tour
Travel time from Florence: About 1 hour 15 minutes
How much time you need: Full day
Our take: The best overall day trip from Florence: easy to reach by direct bus, stunning cathedral, beautiful piazza, and everything Tuscany promises in one walled city
Of all the Tuscan hill towns you can visit from Florence, Siena is the one we keep coming back to, literally. We fell in love with it on our first trip to Italy and made a point of staying here for multiple nights on a later visit. As a day trip, it delivers everything: one of the most beautiful cathedrals in Italy, a stunning medieval piazza, walkable medieval streets, and a direct bus from Florence that takes just over an hour.
The Siena Duomo alone is worth the trip. It’s arguably more ornate than Florence’s, with a black-and-white striped facade and a rooftop walkway most visitors don’t know exists. Il Campo, the shell-shaped main piazza, is where you’ll want to linger over lunch before climbing the Torre del Mangia for sweeping views over the rooftops and countryside. A full day here goes quickly.
If you’re traveling by car or tour, Monteriggioni, a tiny, perfectly preserved walled village, is just 15 minutes away and worth a quick stop before or after Siena.
Piazza del Campo and Palazzo Pubblico
The view of Siena from Torre del Mangia
Inside the Siena Cathedral
Plan Your Siena Day Trip from Florence
HOW MUCH TIME DO YOU NEED: Siena is a large Tuscan hill town and for the best experience, plan on spending one full day here.
TRANSPORTATION: The best ways to travel from Florence to Siena are by bus, train, rental car, and private driver. Line 131R by Autolinee Toscane, travel time approximately 1 hour 15 to 20 minutes, around €7.80 in advance or €10 to €12 on board. Flixbus departs from Piazzale Montelungo or Villa Costanza, travel time approximately 50 minutes to 1 hour, prices starting around €14 to €16.
You can also travel by train, with a travel time of 1.5 to 2 hours and a cost of €10 one way. There is a regional train with a travel time of 1.5 hours with no transfers.
If you will have a rental car, one of the most convenient places to park in Siena is Parcheggio San Franceso. It is located just outside of the city center. You will ride up a long series of escalators, coming out next to Basilica di San Francesco. It is a 15-minute walk to the city center.
PLANNING YOUR TIME: Siena is one of the largest Tuscan hill towns and it is easy to fill your day with the top sites here. To help you plan your time, read our article One Perfect Day in Siena ↓
One Perfect Day in Siena, Italy | A Detailed Itinerary
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2. Monteriggioni: Tuscany’s Most Perfectly Preserved Medieval Village
Best for: Medieval walls, quick stop, combining with Siena or San Gimignano
Best way to get there: Car or tour
Travel time from Florence: About 45 minutes
How much time you need: 2 to 3 hours (best combined with another stop)
Our take: Too small to justify a standalone day trip, but one of the most perfectly intact medieval villages in Tuscany; pair it with Siena for an ideal day
Monteriggioni is one of those places that catches you off guard. You come around a bend in the road and suddenly the medieval walls are just there, rising intact from the Tuscan landscape, looking exactly as they did in the 13th century. We visited on a day trip from Siena and that first glimpse of Monteriggioni is startling.
There isn’t a long list of things to do here, and that’s part of the appeal. Stroll through the small village center, then walk the walls, which are the real highlight and offer lovely views over the surrounding countryside. An hour or two is plenty, making it an easy and worthwhile addition to a Siena day.
Monteriggioni
Plan Your Monteriggioni Day Trip from Florence
HOW MUCH TIME DO YOU NEED: If you simply want to walk the walls, take a stroll through town, and visit the museum, an hour is all you need. With more time, you can sit down to lunch or dinner.
TRANSPORTATION: There is no train station in town but there are buses that run frequently from Siena. Here is a link to the timetable (select “GLI Orari Autobus da Siena a Monteriggioni). You can also get here by rental car. It is a 1 hour drive from Florence to Monteriggioni and a 20-minute drive from Siena to Monteriggioni.
PLANNING YOUR TIME: This town is tiny. Take a stroll through the center of town (it takes less than 10 minutes to walk from one end to the other) and then walk the walls for the best views. A visit here lasts about 2 hours.
Monteriggioni: Best Things to Do, Photos, and Helpful Tips
How to plan your day trip to Monteriggioni.3. San Gimignano: Medieval Towers and Hilltop Views
Best for: Medieval towers, hilltop scenery, wine tasting, gelato
Best way to get there: Car or tour (no direct train)
Travel time from Florence: About 1 hour 15 minutes by car
How much time you need: Half day to full day
Our take: Crowded but completely worth it. The towers, the views over the Tuscan countryside, and Gelateria Dondoli alone justify the trip
San Gimignano is one of the most visited day trips from Florence, and for good reason.
We’ve been twice, and both visits felt completely different. The first time, we arrived by bus from Siena on a busy morning with our kids, climbed Torre Grossa for views over the rooftops and rolling Tuscan hills, ate wild boar stew for lunch, and took some of our all-time favorite family photos on a quiet street at the edge of town. The second visit, Tim and I drove in on a relaxed afternoon, explored the Torri Salvucci tower house, and spent more time than planned in the shops.
Fair warning: San Gimignano is one of the most touristy towns in Tuscany. It gets crowded, especially midmorning when tour buses arrive. If you prefer something quieter, Cortona or Montalcino will suit you better. But if you can go early or stay into the late afternoon, San Gimignano earns its reputation. The towers, the views, the food, and the gelato at Gelateria Dondoli are genuinely worth it.
It pairs well with Volterra, Siena, or Pisa if you want to combine two stops in one day.
San Gimignano
San Gimigano
Plan Your San Gimignano Day Trip
HOW MUCH TIME DO YOU NEED: San Gimignano can be visited in half a day, which means you can pair it with another Tuscan hill town or return to Florence in the afternoon.
TRANSPORTATION: You can travel to San Gimignano by bus, train, car, and on a tour. There are no direct buses. Buses run approximately every hour with a transfer in Poggibonsi, for a total travel time of 1.5 to 2 hours (take bus 131 from Florence to Poggibonsi and bus 130 or 133 from Poggibonsi to San Gimignano).
By train, take the regional train from Florence to Poggibonsi, transfer to bus 130 or 133 to San Gimignano for a travel time of 1.5 to 2 hours.
If you have a rental car or driver, it takes just over one hour to drive from Florence to San Gimignano, making this the fastest mode of transportation.
PLANNING YOUR TIME: With half of a day in San Gimignano, stroll the city streets, climb one or two towers for views of the town, go shopping, and have lunch or dinner.
Best Things to Do in San Gimignano (Tips from Two Visits)
Things to do, where to eat, and how to plan your day trip to San Gimignano.Tours of San Gimignano
San Gimignano is one of the easiest Tuscan hill towns to visit on a tour. This small group tour combines San Gimignano and Volterra together.
This highly rated tour includes Pisa, Siena, and San Gimignano.
And this full day tour includes Pisa, San Gimignano, Siena, plus lunch in a winery in Chianti. It packs a lot in, so you don’t have much time in any one place, but you do get to see a lot on this tour.
4. Lucca: The Most Underrated City in Tuscany
Best for: Walking the city walls, laid-back atmosphere, fewer crowds than the hill towns
Best way to get there: Train
Travel time from Florence: About 1 hour 30 minutes by train
How much time you need: Half day to full day
Our take: One of our favorite easy train days from Florence: beautiful, walkable, and far less crowded than the more famous Tuscan towns. Pairs well with Pisa.
Lucca tends to get overlooked in favor of Florence and the famous Tuscan hill towns, which is exactly why we love it. While everyone else is queuing at the Uffizi or jostling for position at the Leaning Tower, Lucca rewards visitors with Renaissance walls, medieval towers, and a piazza built inside a Roman amphitheater,an d far fewer crowds than you’d expect for a city this beautiful.
We visited on a day trip from Florence and spent our time walking the walls, climbing Torre Guinigi for views over the rooftops, and having lunch in Piazza dell’Anfiteatro, which is as charming a place to eat as anywhere in Tuscany. What struck us most was how compact and walkable it is. Even with a half day, you can cover the highlights quite comfortably.
Lucca pairs naturally with Pisa as a combined day trip from Florence. Both are easy by train, both have a short but satisfying list of sights, and together they make for a full and well-balanced day.
Lucca
Outdoor restaurants on Piazza dell’Anfiteatro
Plan Your Lucca Day Trip from Florence
HOW MUCH TIME DO YOU NEED: You need a half to a full day to visit Lucca.
TRANSPORTATION: The best way to get to Lucca is by train. From Florence, it takes about an hour and fifteen minutes to travel to Lucca by train. The Lucca train station sits just outside of the walls and it is a very short walk to the city center.
PLANNING YOUR TIME: Take a morning train to Lucca and spend the day exploring the city. You also have the option to combine Lucca and Pisa together in a day trip from Florence, which we outline in our article One Day in Pisa and Lucca.
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5. Pisa: Beyond the Leaning Tower (Though That’s Worth It Too)
Best for: The Leaning Tower, the Cathedral complex, combining with Lucca
Best way to get there: Train
Travel time from Florence: About 1 hour by train
How much time you need: Half day
Our take: The tower and cathedral complex are genuinely impressive. Pair it with Lucca rather than doing it as a standalone day.
Pisa isn’t the most well-rounded day trip, but it has one of the most iconic landmarks in Italy and that alone justifies the visit. We stopped here with our kids while en route to the Cinque Terre, and even knowing exactly what to expect, taking the obligatory photos with the Leaning Tower was more fun than we anticipated. For kids especially, it’s one of those rare landmarks they actually recognize, which makes the reaction when they see it in person genuinely memorable.
Beyond the tower, the cathedral complex is beautiful and worth more time than most visitors give it. But the list of must-dos here is short, which is why Pisa works best as a half-day stop rather than a full day on its own. Pair it with Lucca, just 30 minutes away by train, and you have a very satisfying full day in western Tuscany.
The Leaning Tower of Pisa
Pisa
Plan Your Pisa Day Trip
HOW MUCH TIME DO YOU NEED:A visit to Pisa takes 2 to 3 hours. This includes your time to walk to and from the train station to the Leaning Tower, plus time for photos, to climb the tower, and to visit the other monuments in the duomo complex.
TRANSPORTATION: The best way to travel from Florence to Pisa is by train. Trains run frequently throughout the day with a travel time of one hour. By car, it takes an hour and a half to drive here. If you prefer to take a tour, this highly rated tour of Pisa also includes San Gimignano and Siena.
PLANNING YOUR TIME:For details on how to plan your day trip and how to visit the Leaning Tower of Pisa and the duomo, read our article How to Plan a Day Trip to Pisa. It’s also very easy to combine Pisa and Lucca together. Learn how to do this in our article One Day in Pisa and Lucca.
6. Cinque Terre: Dramatic Coastline and the Most Spectacular Long Day from Florence
Best for: Colorful coastal villages, hiking, scenery, seafood, photography
Best way to get there: Train
Travel time from Florence: About 2 hours to the first village
How much time you need: Full day (plan for a long one)
Our take: One of the most beautiful places in Italy. Commit to the full day, go early, and book the Cinque Terre card in advance
The Cinque Terre is one of the most spectacular places in Italy. Five colorful villages clinging to a dramatic stretch of Ligurian coastline, connected by hiking trails, ferries, and a local train line. It’s a UNESCO World Heritage Site, and the kind of place that looks exactly like the photos and somehow still exceeds expectations.
We spent two days here: one hiking between the villages, one relaxing on the beach at Monterosso. As a day trip from Florence, it’s absolutely doable, but if you can spend a night, you’ll be glad you did. The crowds thin out in the evening and the villages take on a completely different feel.
If you’re coming for the day, plan for an early start and a full day. The hike between the villages is the highlight, and you can cover as much or as little of it as you like, using the local train to skip sections if needed. Book your Cinque Terre card in advance and check trail conditions before you go, as some sections close seasonally.
Vernazza
Riomaggiore
Plan Your Cinque Terre Day Trip from Florence
HOW MUCH TIME DO YOU NEED: Plan on spending one full day on the Cinque Terre. Take an early morning train and late evening train to give yourself as much time as possible here. Sunsets are beautiful so if you can, plan to board the return train to Florence in the evening.
TRANSPORTATION: The best way to get from Florence to the Cinque Terre is by train. There is no direct train. You will travel from Florence to Le Spezia and then transfer to the regional train for the Cinque Terre, with an average travel time of 2.5 hours. You can also visit Pisa on the way to the Cinque Terre and we cover how to do this in our Pisa Day Trip guide.
If you have a car, it takes about 2.5 hours to drive to the Cinque Terre.
This highly rated tour covers your transportation to and from the Cinque Terre with the option to add on a short hike.
PLANNING YOUR TIME: Take an early morning train to the Cinque Terre. Spend the day visiting the five towns, either hiking or taking the regional train from town to town. Have dinner, watch the sunset, and then return to Florence by train.
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7. Chianti Wine Region: Rolling Hills & Vineyard Estates
Best for: Wine tasting, scenic drives, olive oil, vineyard estates
Best way to get there: Car or tour
Travel time from Florence: About 30 to 45 minutes
How much time you need: Full day
Our take: The quintessential Tuscan countryside experience; best done by tour so you can actually drink the wine
The Chianti wine region stretches through the rolling hills between Florence and Siena, and a day spent driving through it, past cypress-lined roads, stone farmhouses, and vineyard estates that have been producing wine for centuries, is one of the most quintessentially Tuscan experiences you can have.
Unlike the hill towns, Chianti isn’t about a single destination, it’s about the drive itself and the estates along the way. A rental car gives you the freedom to stop where you like, but a guided tour is the smarter choice if wine tasting is the priority, so no one has to stay sober behind the wheel. Look for tours that include a visit to a working vineyard and a sit-down lunch.
Overlooking the Chianti wine region from San Gimignano
Plan Your Chianti Wine Region Day Trip
HOW MUCH TIME DO YOU NEED: With one day, visit one or two of the towns located in the Chianti wine region or take a tour of the Chianti vineyards.
TRANSPORTATION: This depends on where you plan to go. Some towns are easily accessible by bus (such as Siena) whereas others are easier to reach by car or driver.
Tours of the Chianti Wine Region
One of the best ways to visit the Chianti wine region is on a tour.
This highly rated tour includes a visit to two wineries in the Chianti Classico region with food and wine pairings.
On this half day tour from Florence, visit two wineries in the Chianti wine region.
You can also tour the Chianti wine region on a Vespa.
8. Val d’Orcia: The Most Beautiful Scenery in All of Tuscany
Best for: Postcard landscapes, Pienza, Montepulciano, Montalcino, Brunello wine
Best way to get there: Car or tour
Travel time from Florence: About 1 hour 30 minutes to 2 hours
How much time you need: Full day
Our take: The most beautiful scenery in Tuscany. You need a car or tour to make the most of it, but the rolling hills, stone villages, and Brunello wine make it one of the best days you can spend in Italy
Of all the places on this list, Val d’Orcia is our favorite. This is the Tuscany of postcards: rolling hills, cypress-lined roads, ancient stone farmhouses, and hilltop towns that look the same as they did centuries ago. When you see those iconic images of the Tuscan countryside, there’s a good chance they were taken here.
We’ve been twice. The first time we drove out from Florence with our kids by rental car, spending the day in Montalcino, Pienza, and Montepulciano. We liked it so much that on our next trip to Tuscany, we based ourselves in a villa just outside Montalcino, revisited all three towns at a slower pace, and spent time driving the landscapes and exploring San Quirico d’Orcia. Both visits were wonderful, and we’d go back again without hesitation.
This is also prime wine country. Brunello di Montalcino and Vino Nobile di Montepulciano are both produced here, and visiting a local cantina is worth building into your day.
A rental car is essential for this day trip. The towns are spread out, the scenery between them is half the experience, and there’s no realistic way to do it justice by bus or train. If you’d rather not drive, a guided tour that covers multiple towns is the next best option.
Wine tasting in Montalcino
Plan Your Val d’Orcia Day Trip from Florence
HOW MUCH TIME DO YOU NEED: With one busy day, you can explore the trio of Montalcino, Pienza, and Montepulciano. If you prefer to slow down the visit, choose two of these towns.
TRANSPORTATION: The best way to get here is by rental car or driver. It is possible to travel from Florence to Val d’Orcia by bus or train, but with limited schedules and multiple transfers, most of your day will be spent traveling, rather than visiting the hill towns. If you don’t plan to rent a car, you can hire a private driver, visit Val d’Orcia on a private tour, or visit Montepulciano, Montalcino and Pienza on a group tour.
PLANNING YOUR TIME: If you plan to rent a car or hire a driver, get an early start. It takes 2 hours to drive from Florence to Montepulciano. Spend a few hours in Montepulciano, drive to Pienza and have lunch, and spend the afternoon in Montalcino. From Montalcino, it is a 2-hour drive back to Florence. You can also do this in the opposite order (Montalcino to Pienza to Montepulciano) and take out a town for a more leisurely experience.
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9. Volterra: Atmospheric, Ancient, and Refreshingly Uncrowded
Best for: Etruscan history, alabaster crafts, hilltop atmosphere, fewer crowds
Best way to get there: Car
Travel time from Florence: About 1 hour 30 minutes by car
How much time you need: Half day to full day
Our take: One of the most dramatic hilltop settings in Tuscany and significantly less crowded than San Gimignano
Volterra is one of the most historically rich hill towns in Tuscany, and one of the least crowded. While San Gimignano draws tour buses by the dozen, Volterra rewards the extra effort it takes to get here with a long list of archaeological sites, medieval streets, and museums that can easily fill a full day.
We climbed the tower of Palazzo dei Priori for a 360-degree view of the surrounding countryside, walked a Roman theater that dates back to the 1st century AD, and climbed Torre del Maschio with a guide and just two other visitors, the kind of experience that’s hard to find in the more famous Tuscan towns. We also had some of the best paninis of the entire trip on Piazza dei Priori, which is reason enough to linger.
View from the tower of Palazzo dei Priori
Volterra
Plan Your Volterra Day Trip
HOW MUCH TIME DO YOU NEED: With half of a day, you can stroll the streets, climb to the top of the town hall tower for a bird’s eye view of Volterra, visit a museum that is of interest to you, have lunch, and do a little shopping. With more time, visit the Roman Theater and visit another museum or two.
TRANSPORTATION: The easiest way to get to Volterra by car. From Florence, it takes an hour and a half to drive here. The best place to park is Parcheggio La Dogana Srl. The closest train station to Volterra is Volterra Saline – Pomerance, which is 10 km outside of town. From the train station, you will need to take a bus or taxi to get into town. By bus, transfer in Colle di Val d’Elsa. This highly rated tour includes San Gimignano and Volterra.
PLANNING YOUR TIME: For a list of things to do and for a one day itinerary, read our Guide to Volterra ↓
Volterra, Italy: Best Things to Do, Map & Tips
Best things to do in Volterra and how to plan your day trip.10. Arezzo: A Classic Tuscan City That’s Easy to Reach by Train
Best for: Renaissance frescoes, antique markets, beautiful piazza, off-the-beaten-path feel
Best way to get there: Train
Travel time from Florence: About 1 hour by train
How much time you need: Half day to full day
Our take: One of the most underrated cities in Tuscany. Easy by train, rewarding to explore, and far less crowded than the famous hill towns.
Arezzo was one of the last Tuscan hill towns we visited, and we arrived on a Sunday in early October not quite sure what to expect. What we found was one of the most distinctive main squares in all of Italy. Piazza Grande is ringed with colorful medieval shields, each representing a different house of the city. It’s bold and vivid in a way that sets Arezzo apart from every other town we visited in Tuscany.
Beyond the piazza, Arezzo is small, walkable, and easy to spend a full day in. The Renaissance frescoes by Piero della Francesca in the Basilica of San Francesco alone are worth the trip, and the hilltop fortress offers sweeping views over the surrounding countryside. There’s also a well-regarded antique market that fills Piazza Grande on the first Sunday of each month if your timing lines up.
For those who prefer a quieter, more local atmosphere than the heavily toured hill towns, Arezzo consistently delivers. And since it’s one of the easiest Tuscan cities to reach by train from Florence, about an hour on a regional train, it’s one of the lowest-effort, highest-reward day trips on this list.
Arezzo is located near Cortona, making these two towns a natural pairing for a full day in southeastern Tuscany.
Piazza Grande in Arezzo
Corso Italia
Lunch in Arezzo
Overlooking Piazza Grande from the clock tower
Plan Your Arezzo Day Trip from Florence
HOW MUCH TIME DO YOU NEED: With a half of a day, you can see the highlights of Arezzo, if you move very quickly. A full day is ideal, to get to everything, plus have lunch and/or dinner in Arezzo.
TRANSPORTATION: From Florence, there are frequent trains to Arezzo and the journey takes 1 hour to 1 and a half hours from Florence to Arezzo, depending on the speed of the train. It’s a bit slower and trickier to get from Florence to Arezzo by bus, so if you plan to use public transportation, the train is the way to go. By car, it takes an hour and fifteen minutes to drive to Arezzo.
PLANNING YOUR TIME: In the morning, drive or take the train to Arezzo. Spend the day in Arezzo. In the afternoon, you have the option to add on Cortona, but this is best done with a rental car, since it can be tricky to get between these two towns using public transportation.
Best Things to Do in Arezzo, Tuscany (+ Map, Tips & Itinerary)
Best things to do, where to eat, and everything you need to know to plan your day trip.11. Cortona: A Quiet Hilltop Town with Big Views
Best for: Hilltop views, quiet atmosphere, medieval streets, fewer tourists
Best way to get there: Train to Camucia-Cortona, then taxi or bus; or by car
Travel time from Florence: About 1 hour 30 minutes
How much time you need: Half day to full day
Our take: Quieter than most Tuscan hill towns with sweeping views toward Lake Trasimeno. A good choice if you want something a step off the main tourist circuit.
Cortona is the kind of Tuscan hill town that rewards slow, aimless wandering. We walked the medieval streets, ducked into wine shops along Via Nazionale, stumbled into a small art gallery we almost walked past, and finished the day wine tasting at a vineyard just outside of town. It was one of the most relaxed and enjoyable days we had in Tuscany.
If you’ve seen Under the Tuscan Sun, Cortona will feel familiar. The film was set here, and the town absolutely lives up to its on-screen charm. But what makes it worth visiting is how genuinely quiet it is compared to the more famous stops on the Tuscan tourist trail. You can actually hear yourself think here.
The to-do list is short, which makes Cortona an ideal half-day stop or a natural pairing with Arezzo, just 30 minutes away.
Cortona
Plan Your Cortona Day Trip from Florence
HOW MUCH TIME DO YOU NEED: If you want to stroll the city streets, go shopping, have a bite to eat, and visit museum or church or two, you will need 2 to 3 hours in Cortona. In order to visit the sites that sit outside of the city center, add on another 2 to 4 hours, which means that your visit to Cortona will last about one full day.
TRANSPORTATION: The fastest, most convenient way to get to Cortona is by car (it is an hour and a half drive from Florence). By train, there are frequent trains from Florence to the Terontola-Cortona station with travel times ranging from an hour to 1.75 hours, some direct and some with a transfer. From the Camuccia-Cortona station, take a bus or taxi to the city center.
You can visit Cortona on this private tour that also includes Montepulciano and this full day tour that includes Cortona, Montepulciano, and Siena.
PLANNING YOUR TIME: Cortona needs about 3 to 4 hours to see the highlights.
Cortona, Italy: Things to Do in This Underrated Hill Town
Complete guide to Cortona: best things to do, how to get here, where to stay, and more.12. Bologna: The Best Day Trip from Florence for Food Lovers
Best for: World-class food, porticoes, towers, university city energy
Best way to get there: High-speed train
Travel time from Florence: About 40 minutes by high-speed train
How much time you need: Full day
Our take: The closest major city to Florence and arguably the best food city in Italy. An easy, rewarding day that feels completely different from Tuscany.
Bologna didn’t make it onto our Italy itinerary until our sixth trip. We’d been to Rome, Florence, Venice, the Amalfi Coast, Tuscany, and the Dolomites, and somehow kept skipping over it. That was a mistake we won’t be making again.
We arrived to find one of the most captivating food cities in Europe: the Quadrilatero market overflowing with fresh pasta and wine bars, kilometers of beautiful porticoes winding through the medieval city center, and a food scene that made us wonder how we’d overlooked it for so long. We spent three days in the end, touring the top sights, taking a cooking class, eating our way through as many restaurants and wine bars as we could manage, and day tripping out to the Ferrari, Lamborghini, and Pagani museums.
As a day trip from Florence, Bologna is almost absurdly easy. It’s just 40 minutes on the high-speed train, no transfers, and you step out into one of Italy’s most rewarding cities. If food is your priority, this is the day trip to choose. The porticoes alone are worth the trip, a UNESCO-listed network of covered walkways that stretch for kilometers through the medieval center and are unlike anything else in Italy.
Plan Your Bologna Day Trip from Florence
HOW MUCH TIME DO YOU NEED: Plan on spending one full day in Bologna, to tour the city center, climb a tower or two, take a food tour, and for those with an interest in cars, tour the Lamborghini and Ferrari museums.
TRANSPORTATION: The best way to get to Bologna is by train. By direct high-speed train, it takes just 40 minutes to travel to Bologna. You can save a little money by taking a regional train with a transfer for a travel time of just under 2 hours.
PLANNING YOUR TIME: Take an early morning train and spend the day exploring Bologna. Taking a food tour or a cooking class is one of the best things to do on a visit to Bologna. We took this cooking class and had a great experience. After dinner, return to Florence by train. Plan your time with our One Day in Bologna Itinerary ↓
1 to 2 Days in Bologna: The Best Itinerary for First Timers
Bologna didn’t make it onto our Italy itinerary until our sixth trip. We’d visited Rome, Florence, Venice, the Amalfi Coast, Tuscany, and the Dolomites, and somehow kept skipping over this city in northern Italy. Once we finally arrived, Tim and I were instantly captivated: the busy, bustling Quadrilatero with its wine bars and shops overflowing […]
20 Best Things to Do in Bologna, Italy
Bologna doesn’t get the attention it deserves. The best things to do in Bologna revolve around food, from rolling fresh pasta in a cooking class, wandering the Quadrilatero while cheese wheels and cured meats hang in every doorway, and sitting at a wine bar long enough to understand why locals call this city La Grassa, […]
13. Milan: Art, Fashion, the Duomo, & the Last Supper
Best for: The Duomo, the Last Supper, Galleria Vittorio Emanuele II, big city energy
Best way to get there: High-speed train
Travel time from Florence: About 2 hours by high-speed train
How much time you need: Full day
Our take: A long but doable day and best for travelers who won’t otherwise make it to Milan.
Milan looks far from Florence on a map, but the high-speed train connects the two cities in about two hours, making it a legitimate day trip for travelers who want a taste of Italy’s most cosmopolitan city.
We passed through Milan in transit between the Cinque Terre and Venice, spending a good chunk of the day here with our kids. We saw the Duomo, which is as spectacular as advertised, and made it to the Last Supper, which is the main reason most people come. That was enough for a satisfying day, and the city’s energy felt completely different from anything else on our Italy itinerary.
Milan works best as a day trip if your goal is the highlights: the Duomo, the Galleria Vittorio Emanuele II, and the Last Supper. If you want to go deeper, visiting the fashion district, the Brera art gallery, the Castello Sforzesco, you’ll need more time. One thing is non-negotiable: book your Last Supper tickets well in advance. We’re talking months, not days. It’s one of the most visited attractions in Italy and availability disappears fast.
Duomo di Milan
Plan Your Milan Day Trip
HOW MUCH TIME DO YOU NEED: You need 4 to 5 hours in Milan to tour the duomo, see The Last Supper, go shopping, and have lunch.
TRANSPORTATION: A direct, high-speed train to Milan takes 1 hour and 55 minutes, making the train the best way to day trip to Milan (by car it takes 3.5 hours).
PLANNING YOUR TIME: Take a morning train to Milan, spend the day touring the main sites, and return to Florence in the evening. For the best experience, it is best to book your duomo tickets and tickets to see The Last Supper in advance.
Milan Day Trip: One Day Itinerary from Florence, Venice & Cinque Terre
Exactly how to plan a Milan day trip from Florence.14. Assisi: A Spiritual and Scenic Escape into Umbria
Best for: The Basilica of St. Francis, medieval hilltop town, art, peaceful atmosphere
Best way to get there: Train (may require a transfer)
Travel time from Florence: About 2 to 2.5 hours by train
How much time you need: Full day
Our take: One of the most peaceful and beautiful hilltop towns in central Italy. The Basilica of St. Francis alone is worth the journey.
Assisi is the longest day trip on this list. It’s in Umbria rather than Tuscany, and the train journey takes two to two and a half hours each way. We liked it enough to spend two nights here, which tells you something about what awaits.
Some of our favorite time in Assisi was spent simply wandering, ducking into narrow, flower-lined alleyways, getting pleasantly lost in the medieval streets, and learning about the life of St. Francis at every turn. The town is steeped in his story in a way that feels genuine rather than touristy, and the churches here are among the most beautiful we have seen anywhere in Italy.
The Basilica of St. Francis, with its famous Giotto frescoes in the upper church, is the centerpiece, but the Basilica of Santa Chiara and the smaller churches tucked throughout the city center are worth seeking out too.
As a day trip, Assisi is best suited to travelers with an interest in history, religious art, or simply wanting to explore beyond Tuscany. The journey is long, so go early and give yourself the full day.
St. Francis Basilica
The view from Rocca Maggiore
Taverna dei Consoli is a beautiful spot to have lunch
Piazza del Comune
Plan Your Assisi Day Trip from Florence
HOW MUCH TIME DO YOU NEED: For the best experience, plan on spending one full day here. That is almost impossible to do on a day trip from Florence, since it takes several hours to travel here, but you will still have enough time to see the highlights.
TRANSPORTATION: By car, it takes 2 hours to drive from Florence to Assisi. There is a direct train from Florence to Assisi that takes just over 2.5 hours. There are also train routes with one transfer that take 3 to 4 hours. To maximize your time in Assisi, pick the earliest train with a direct route to Assisi.
There is also a tour from Florence that includes Assisi and Orvieto.
PLANNING YOUR TIME: Plan your travel so that you arrive in Assisi as early as possible (by taking a direct train early in the morning or renting a car, leaving Florence around 7 am). Follow our One Day Assisi Itinerary that includes a walking tour of historic city center.
16 Wonderful Things to Do in Assisi (+ Helpful Tips & Map)
Located in Umbria, sitting on the slopes of Monte Subasio, is the beautiful city of Assisi. This city, which is the birthplace of St. Francis, is filled with spiritual treasures and works of art. There are many things to do in Assisi…visit the long list of churches and basilicas, stroll the picturesque streets, go shopping […]
One Day in Assisi, Italy: Walking Tour of the Historic City Center
With one day in Assisi, you have just enough time to visit the highlights of this beautiful city. In this guide, we provide an Assisi walking tour that covers the main sites within the historic city center. On this walking tour, visit the churches and important religious sites in Assisi, wander through picturesque streets, and […]
15. Orvieto: The Dramatic Clifftop Town Most Florence Visitors Miss
Best for: Clifftop setting, spectacular cathedral, underground caves, Umbrian wine
Best way to get there: Train
Travel time from Florence: About 2 hours by train
How much time you need: Half day to full day
Our take: Sitting on a volcanic plateau above the valley, Orvieto has one of the most dramatic settings of any town in central Italy, and a fraction of the crowds of the Tuscan destinations.
Orvieto sits on a volcanic plateau above the Umbrian valley, and the view of it rising from the landscape as you approach is one of the great first impressions in central Italy. Tim and I visited on a day trip from Tuscany in September, and what struck us most wasn’t just the setting, it was how much this town rewards curiosity.
Go underground into St. Patrick’s Well, where a double helix staircase spirals down to the water in one of the most remarkable pieces of engineering we’ve seen in Italy. Walk the ramparts of the Albornoz Fortress for sweeping views over Umbria. And don’t miss Il Labirinto Di Adriano, our favorite unexpected discovery of the day: part restaurant, part cave exploration, and far less touristy than it sounds.
Orvieto also has an extraordinary cathedral, Etruscan history around every corner, and a famous white wine that’s been produced here for centuries, but it’s the sense of adventure layered into an otherwise compact hilltop town that makes it memorable.
Orvieto sits roughly halfway between Florence and Rome, which makes it a natural stop if you’re traveling between the two cities by car or train.
Orvieto Cathedral
Lunch in Orvieto
The view from Albornoz Fortress
Plan Your Orvieto Day Trip
HOW MUCH TIME DO YOU NEED: This is a relatively large town so expect to spend a half to full day here.
TRANSPORTATION: Orvieto is located along the Rome – Florence – Milan train line, so it is very easy to get here by train. Travel times range from 2 to 2.5 hours. The train station is located just outside of the historic city center. To get to the city center, ride the funicular (the bottom station is located next to the train station) to Piazza Cahen.
PLANNING YOUR TIME: Take an early morning train from Florence, spend the day in Orvieto, and return to Florence in the evening by train.
Best Things to Do in Orvieto, Italy: A Guide to Umbria’s Hilltop Gem
How to see the best of Orvieto on a day trip from Florence.Best Florence Day Trips by Travel Style
First Visit to Tuscany
If this is your first time and you only have one day, go to Siena. It’s easy by direct bus, covers everything Tuscany promises, and you can add Monteriggioni as a quick stop if you’re driving.
If you prefer to travel on your own schedule, rent a car. Combining Montepulciano, Pienza, and Montalcino is a very long but memorable day, plus you get to see the iconic landscapes of Val d’Orcia.
If you want to see multiple towns in one day without the logistics of driving, a guided that includes Siena and San Gimignano or a tour of Siena, Montepulciano, and Cortona are reliable and well-loved options.
Budget Travelers
The best budget day trips from Florence are Siena by direct bus, Arezzo by regional train, and the Pisa and Lucca combination, both accessible on regional train tickets. Bologna is slightly more expensive due to the high-speed train but still very affordable for what you get.
Families with Kids
Pisa is a natural choice because kids recognize the Leaning Tower and love it. The Cinque Terre is a longer day but our kids enjoyed hiking between the colorful coastal villages. Siena and Monteriggioni are both easy, walkable, and visually rewarding for younger travelers.
Wine Lovers
Val d’Orcia and the Chianti wine region are the top two picks. Val d’Orcia gives you Brunello di Montalcino and Vino Nobile di Montepulciano country alongside some of the most beautiful scenery in Italy. Chianti is closer to Florence and ideal for a more relaxed day of vineyard estates and tastings.
Wine shop in Montepulciano
How to Plan 1, 2, or 3 Day Trips from Florence
One day: Go to Siena. It’s the easiest, most rewarding single day trip from Florence regardless of how you’re traveling.
Two days: Siena on day one, Val d’Orcia on day two. Together they cover the best of both accessible Tuscany and the more remote southern hill towns.
Three days: Siena, Val d’Orcia, and either Pisa and Lucca by train or Chianti by car. That combination covers coastal western Tuscany, the iconic hill town experience, and the best of the Tuscan wine country.
If you don’t have a car: Siena by bus, Pisa and Lucca by train, and Bologna by high-speed train give you three very different and very satisfying days without ever needing to drive.
If wine is the priority: Chianti and Val d’Orcia together, ideally with a night somewhere between them.
If you have more than one day in Tuscany, take a look at our Tuscany Itinerary ↓
The Perfect Tuscany Itinerary for 3 Days, 5 Days & One Week
Get recommendations on how to plan your time, whether you have 1 day, 3 days, or an entire week.Day Trips from Florence We Would Skip
Rome: at two and a half hours each way on the high-speed train, you’re spending five hours in transit for a city that genuinely needs at least two days to do justice. Rome deserves its own trip, not a rushed day.
Venice: similar problem. Venice is two hours away by high-speed train, and the city is so dense with things to see that a day trip leaves most people feeling like they barely scratched the surface. If Venice is on your list, stay there.
Frequently Asked Questions
What is the best day trip from Florence?
Siena is our top pick for the best day trip from Florence. It’s easy to reach by direct bus, covers everything Tuscany promises, a stunning cathedral, a beautiful medieval piazza, and hilltop streets to explore, and can be done without a car or tour.
What is the easiest day trip from Florence by train?
Bologna is the easiest train day trip from Florence, just 40 minutes away on the high-speed train with no transfers. For Tuscany specifically, Arezzo and Pisa are both about an hour by regional train and require no advance booking.
What is the best day trip from Florence for first-time visitors?
For first-time visitors, Siena is the best overall day trip from Florence. If you want to see the iconic landscapes and a few hill towns, spending the day in Val d’Orcia and visiting Montalcino, Pienza, and Montepulciano is our top recommendation.
Can you do the Cinque Terre as a day trip from Florence?
Yes, the Cinque Terre is a doable day trip from Florence by train, though it is a long day. Plan to leave early and return late. The train takes about two hours to the first village. Hiking between the villages is the highlight, and you can use the local train to skip sections if needed.
Do I need a rental car for day trips from Florence?
A rental car is not necessary for every day trip, but it significantly expands your options. Siena, Bologna, Pisa, Lucca, and Arezzo are all easy by train or bus. However, Val d’Orcia, Chianti, Volterra, and San Gimignano are best by car or guided tour.
What are the best day trips from Florence without a car?
The best day trips from Florence without a car are Siena by direct bus, Bologna by high-speed train, Arezzo by regional train, and the Pisa and Lucca combination by train. The Cinque Terre is also accessible by train for those willing to commit to a full day.
Can you visit multiple Tuscan towns in one day from Florence?
Yes, but it requires a rental car or guided tour. The most popular combinations are Siena and Monteriggioni, Pisa and Lucca, and the Val d’Orcia towns of Montepulciano, Pienza, and Montalcino. Stringing towns together by bus is difficult due to infrequent schedules and unreliable timing.
Is Val d’Orcia worth visiting as a day trip from Florence?
Yes, Val d’Orcia is one of the most beautiful areas in all of Italy and absolutely worth a day trip from Florence. It requires a rental car or guided tour to visit multiple towns in one day, but the combination of Montepulciano, Pienza, and Montalcino against the backdrop of the iconic rolling Tuscan landscape makes it one of the best days you can spend in Italy.
Plan Your Time in Florence and Tuscany
If you’re still planning your time in Florence itself, our Things to Do in Florence post covers the 30 best things to do in the city, and our 2 Days in Florence Itinerary is the place to start if this is your first visit. It covers the Uffizi, the Duomo, Michelangelo’s David, and how to see it all without spending hours in line.
For the Tuscany side of your trip, our Tuscany Itinerary covers how to plan your time, whether you have three days, five days, or a full week in the region. And if you want the full picture of what to see and do across Tuscany beyond the day trips, our Best Things to Do in Tuscany is the guide to bookmark.
For a longer Italy trip, our 10 Days in Italy guide offers five itinerary options depending on which regions you want to prioritize, and our 14 Day Italy Itinerary is the starting point if you have two full weeks.
Everything else, Rome, Venice, the Amalfi Coast, the Dolomites, and beyond, is in our Italy Travel Guide.
If you have any questions about the best day trips from Florence, or if you want to share your experience, let us know in the comment section below.
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