Updated December 6, 2023
Whether you're taking your first trip to Italy or a seasoned explorer, Florence is an ideal base for exploring Tuscany.
Beyond its fame as the birthplace of the Renaissance and its treasures of art and architecture, its strategic location makes it the perfect launchpad for an unforgettable day trip.
As you set off on these day trips from Florence Italy, you'll discover entirely new experiences from those in the city's heart. You'll have the chance to immerse yourself in the essence of Italian history and culture.
These day trips range from historic cities that will transport you back in time to coastal villages caressed by turquoise waves. Wander through untouched medieval towns, savoring delectable Tuscan delicacies and sipping world-renowned wines amidst rolling vineyards.
So sit back, grab an espresso - or better yet, a glass of Chianti - and get ready to wander through the alluring landscapes of Tuscany.
Disclosure: This post may contain affiliate links, meaning I may get a small commission if you decide to make a purchase through my links, at no cost to you.
Siena
Just an hour's drive from Florence, in the heart of Tuscany, Siena has left an indelible mark on Italian history. The city welcomes you with a treasure trove of fantastic architecture, superb art, and a horse race that makes the Kentucky Derby look like child's play.
Part of Siena's appeal is that it feels like it's frozen in time. Its historic center is one of Europe's best-surviving examples of a medieval town.
Siena's breathtaking Cathedral, the Duomo of Santa Maria Assunta, is a Gothic masterpiece. It was built between 1215 and 1263, making it older than the Duomo of Florence. It houses spellbinding works by Pisano, Donatello, and Michelangelo and a beautiful mosaic floor. Also, take the time to visit the Piccolomini Library, with spectacular frescos by Pinturicchio.
A stone's throw away from the Cathedral is the Torre del Mangia, the tallest tower in Siena. At 335 feet tall, it's the third tallest tower in Italy. The 14th-century building offers a spectacular view if you can conquer its more than 400 steps.
One of the city's most famous traditions is the Palio. This frantic and exhilarating horse race transforms the main square, Piazza del Campo, into a race course. It's a thrilling tradition of passion, color, and age-old rivalry.
Taking place twice a year, on July 2 and August 16th, 10 of the 17 contrade, or districts, of Siena compete in a bareback race. A 4-day event that culminates with the race, the Palio is a spectacle of parades, historically costumed locals, and even a special mass.
Ten horses complete three laps around the very narrow course, and the first horse across the finish line, with or without its jockey onboard, wins. It's an exhilarating experience!
How to get to Siena from Florence
You can reach Siena by train in about 1.5 hours, and direct trains depart Firenze Santa Maria Novella (Firenze SMN) every hour. Direct return trains also run every hour.
Once you arrive in Siena you can take a bus from the train station to the town center or take an escalator up the hill from the train station to Viale Vittorio Emanuele II. From there, it's about a 20-minute walk to the Siena Cathedral.
To make the most of your day, consider a guided tour of Siena to see the highlights before exploring on your own.
Private tours from Florence are also easy to arrange, eliminating the need to get to Siena on your own. Your driver/guide will pick you up from your lodging in Florence, and they take care of all the details to ensure you make the most of your time in Siena.
Where to stay in Siena
If you'd like to extend your Siena day trip with an overnight stay, I recommend the Grand Hotel Continental. The hotel is in a beautiful 17th-century palazzo within walking distance of the Piazza del Campo and the Duomo di Siena.
Pisa
While it's best known for the world-famous Leaning Tower of Pisa, this Tuscan city offers much more than just the perfect "holding up the leaning tower" shot for your Instagram feed.
The Piazza dei Miracoli, or Square of Miracles, is home to the Leaning Tower, the stunning Pisa Cathedral, and the largest Baptistery in Italy.
Just beyond the bustling piazza, the streets of Pisa unwind into an assortment of ancient buildings, vintage shops, comfortable cafes, vibrant markets, and a crowd with significantly fewer tourists.
Take time to immerse yourself in some of Pisa's less-known sights. The Museo dell'Opera del Duomo houses sacred art and architectural fragments once part of the Cathedral. The Museo delle Sinopie displays preparatory drawings created by fresco painters working in the Camposanto, the large graveyard in the Piazza dei Miracoli.
How to get to Pisa from Florence
Direct trains depart Firenze SMN and Pisa Centrale every thirty minutes, and the trip takes an hour.
Once you arrive in Pisa, it takes about 20-25 minutes to walk to the Piazza dei Miracoli.
Pisa also has a well-connected airport, with more flights than Florence. If you're catching a connecting flight through Europe, check for flights to Pisa. You may find a better flight, and you can spend a night or two in Pisa to get through the jet lag and see the sights before continuing to another destination in Italy.
Where to stay in Pisa
For a lovely, centrally located stay, consider the Rinascimento Bed & Breakfast. With only six rooms in the heart of Pisa, you'll feel like you've found a home away from home.
San Gimignano
San Gimignano, "the Manhattan of Tuscany," boasts enchanting streets and medieval towers that make the town visible for miles around. This gem has earned its spot on the UNESCO World Heritage list.
There are 14 towers still standing. Originally there were between 70 and 100 towers built in San Gimignano. Feuding families created them as a way to both protect their household and show their wealth and status. In the middle ages, the family tower's size reflected the family's wealth and power. The taller the tower, the richer you must be!
In the center of town, you'll find the Piazza del Duomo. Step inside the Collegiata di San Gimignano, or Duomo of San Gimignano, to see the 14th-century frescoes that cover the walls.
From the town, you have views across Tuscany. Vineyards stretch as far as the eye can see, and the golden sun paints the landscape. For the best views, visit the Palazzo Comunale, the town hall, and climb the Torre Grossa (Great Tower). The tallest tower in San Gimignano and the only one you can climb, you'll be rewarded at the top with views 200 feet above the hilltop city streets.
While you're in San Gimignano, sample the Vernaccia di San Gimignano. The only DOCG (Denominazione di Origine Controllata e Garantita, the highest classified wine in Italy) rated white wine in Tuscany.
How to get to San Gimignano from Florence
San Gimignano doesn't have a train station and is only reachable by bus or car. If you prefer to have the driving done for you, a small group tour is a great option. Many excursions to San Gimignano also have stops in Pisa, Siena, or Volterra, allowing you to see multiple sights in one day.
Where to stay in San Gimignano
There are few hotel options in San Gimignano, so if you're interested in staying the night in the area, renting a car and staying at one of the hotels in the surrounding countryside is best. Borgo Pignano, about 30 minutes from San Gimignano, is one of my favorite hotels in Tuscany.
Lucca
The medieval, fortified city of Lucca is best known for its perfectly preserved Renaissance walls. Built in the 16th century, the walls protected the town from invaders. Today you'll find a park on top of the walls that wraps around the city, providing beautiful views of the town and the surrounding countryside.
When you hear "town walls," you probably think of something tall but narrow. Not the walls of Lucca! They're so large that the park on top of them is part of Lucca's yearly marathon course. For a fun couple of hours, take a walk or rent a bike and ride around them to see the town from all sides.
Lucca is also home to beautiful churches and cathedrals, like the Cathedral of San Martino and the Church of San Michele in Foro, which feature stunning art and architecture.
Aside from the walls, some of the most iconic sites of Lucca are its towers. In medieval Lucca, there were as many as 250 towers in the city. Today only a few remain.
The most famous is the Torre Guinigi, which features a garden at the top filled with oak trees. You can climb the tower (about 20 flights of stairs) and take in stunning views of Lucca and the surrounding hills from the top.
In the center of town, you'll find the Piazza dell'Anfiteatro, built on the ruins of the ancient Roman amphitheater. The oval shape of the piazza and the curved façades of the surrounding buildings still reflect the original structure of the arena.
The piazza is a popular spot for locals and tourists alike to meet up, grab a drink or a bite to eat, and enjoy the lively atmosphere. The square is surrounded by restaurants, cafes, and shops, making it a great place to browse or relax during a trip to Lucca.
Lucca is also famous as the birthplace of world-renowned composer Giacomo Puccini. Puccini was born in Lucca in 1858 and lived there until he moved to Milan to study music. His family had been prominent in Lucca for centuries, and his father had served as a choirmaster in the local Cathedral.
How to get to Lucca from Florence
Direct trains between Florence SMN and Lucca run 2-3 times per hour. The trip takes about an hour and twenty minutes. Other trains connect in Pisa with a journey time of about 2 hours.
Where to stay in Lucca
For an overnight stay in Lucca, I recommend the Grand Universe Lucca, now a member of Marriott's Autograph collection. Located in a beautifully restored palazzo, it is the only luxury hotel within the city walls.
The Chianti Wine Region
Wine lovers will want to take a day trip to the Chianti wine region to sample vintages from the many historic wineries that dot the landscape.
Nestled between Florence and Siena, the rolling Tuscan countryside is a treat for the eyes and the tastebuds. With endless rows of grapes growing in the vineyards and picturesque towns and villages dotting the hilltops, you may never want to leave.
Wander through the vineyards, discover the ancient art of winemaking, and learn all about tasting and pairing some of the world's most outstanding wines.
Don't worry if you're not a wine expert. The passionate winemakers will guide you through the nuances of each vintage.
The Chianti region is also known for its traditional Tuscan dishes, simple yet bursting with flavors. Try a savory ribollita (a hearty vegetable soup) or a plate of pici pasta (similar to a thick, hand-rolled spaghetti) with pesto. Prosciutto Toscana and creamy pecorino cheese are also excellent paired with a glass of Chianti.
How to get to the Chianti Wine Region from Florence
The easiest way to experience the region is to rent a car and drive. But if you'd like to do some wine tasting and no one wants to miss out by being the designated driver, an organized Florence day tour is the way to go.
Where to stay in the Chianti Wine Region
You can't go wrong with Belmond's Castello di Casole for the ultimate luxury experience. It's one of the best luxury hotels in Tuscany. Castello di Spaltenna, a member of Small Luxury Hotels, is also an excellent option in the heart of the Chianti wine region.
Cinque Terre
When you think of day trips from Florence, you may not consider heading to the coast. But it's only about an hour to the beaches near Pisa. North of Pisa you'll find some of Italy's most beautiful seaside towns, the Cinque Terre (Five Lands).
These five villages, strung like pearls along the Ligurian coast, are postcard-perfect. Gracefully clinging to cliffs that seem to drop straight into the ocean, tiny harbors filled with fishing boats and crystal clear coves make these villages special.
The villages of Monterosso al Mare, Vernazza, Corniglia, Manarola, and Riomaggiore all have beautiful views and vibrantly colorful houses. But each town is also has it's unique charm.
You can visit one village or hike the cliffside path between the towns and visit several of them. A train also runs between them, which can make for a quicker trip if you're trying to fit all five into one day.
Travel Tip: If you plan to hike between the villages, proper footwear (i.e., not sandals or flip-flops) is required. Wearing improper footwear can get you a stiff fine between €50 and €2,500.
How to get to Cinque Terre from Florence
The travel time from Florence to La Spezia is between 2 and 2.5 hours. From La Spezia you can catch the local train that stops at the villages. Many trains also connect through Pisa, so you can also take a direct train from Pisa to Monterosso and then take the local train from Monterosso to the other villages.
You can purchase a Cinque Terre Card from an information point or a train station. Some options give you unlimited access to the train and the trails running between the villages.
I recommend going on your own if you plan to spend a night or two in one of the villages. Otherwise, you spend more time getting there and back then you'll have in the towns. A guided Cinque Terre day trip from Florence is the best day trip option so you can make the most of your day at the coast.
Where to stay in Cinque Terre
For a 5-star experience near Cinque Terre, the Grand Hotel Portovenere is a good option, with ocean views overlooking the Gulf of Poets. You can catch the ferry to Cinque Terre from the harbor in front of the hotel.
If you prefer to stay in one of the towns, Monterosso al Mare has the best rail network access and doesn't have steps to get from the train station to town. If you are staying in Monterosso, I recommend the Hotel Margherita.
The Val d'Orcia
The Val d'Orcia epitomizes Tuscan landscapes and has inspired countless Renaissance artists. This UNESCO World Heritage site is home to rolling hills, cypress-lined avenues, and picturesque hilltop towns basking in the Tuscan sun.
Three of these towns are worth particular attention. The first is Montalcino, sitting atop a hill covered in olive groves and vineyards. It's best known for being the birthplace of Brunello di Montalcino, one of Italy's most loved red wines.
Pienza, known as the "Ideal City of the Renaissance," is the home of pecorino cheese. Its narrow streets, intimate piazzas, and delightful views over the surrounding countryside make it a lovely slice of Renaissance Italy.
Completing the trio is Montepulciano, a charming town famous for the wine that carries its name. A walk through its winding streets lined with Renaissance palaces and hidden wine cellars is a stroll to remember. If Montepulciano looks familiar, it's because much of it is a smaller version of Florence. The resemblance means it often stands in for Renaissance Florence in movies and television productions.
Then there's the real star of the show - the Val d'Orcia itself. The landscape views are like a painting and are a great reminder that nature paints the most beautiful pictures.
How to get to the Val d'Orcia from Florence
This area is best visited by car since it's challenging to get around by train or public transportation. If you're not renting a car, great Val d'Orcia day trips from Florence take you to the three towns.
Where to stay in the Val d'Orcia
Stay in Pienza, where you can explore the tiny town before the day trippers arrive or after they've departed. Book one of the 12 rooms at La Bandita Townhouse and feel like you've found your little slice of small-town Italian life.
The bottom line: The best day trips from Florence
Whether you drive the winding roads of the Val dOrcia, hike the seaside paths on Cinque Terre, or bike the walls of Lucca, you're sure to experience a different side of Italy when you head out on a Florence day trip.
It's time to plan a trip to Italy. Tuscany is waiting for you!