12 fantastic day trips from Florence you and your family will love in 2025

Our selection of the best day trips from Florence by car, train and guided tour. From medieval towns to wineries and areas of great natural beauty in Tuscany, these are the best side-trips from Florence Italy

Florence is a fantastic home base to visit Italy.

Within a short distance from the city, you have beautiful countryside, stunning hilltop villages, soft sandy beaches and even UNESCO marvels such as Cinque Terre and Rome.

Planning side-trips from Florence is easy, thanks to the excellent road and train network in the area and the vast choice of guides tours available.

If you are in the city itself, you have easy access to train, buses and guided tours. If you are nearby, you can also use this list as all these places are all withing easy reach not just from Florence but the hills of Fiesole and Chianti.

I love this part of Tuscany. I love the whole of Tuscany, to be honest, but this part and Val d’Orcia I love more than most, as I find the option it gives for day trips are pretty much unparalleled. Where else can you enjoy one of the most stunning art cities in the world, yet also have on your doorstep jaw-droppingly beautiful countryside landscapes and our of this world coastline?

I go to Tuscany any time I can and never get tired of it! On this page, I share my favorite side trips from Florence, based on our hope experience. I hope you love them too!

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Best side trip from Florence: my selection at a glance

Destination	Type of Experience	Transport
Tenuta Chiudendone	Farm to table experience in the countryside	Train / Provided
Chianti	Wine tasting, country meals, farms	Own car to explore independently / tour available
Lucca	Pretty medieval town, option to get bikes	Train
Pisa	Famous for the tower, can be combined with Lucca	Train
Monteriggioni	Medieval hamlet (half day is sufficient)	Car / Tour (can be combined with Siena or San Gimignano)
Siena	Stunning Medieval Town	Car / bus / train / Tour
San Gimignano	Stunning Medieval Town, can be combined with wine tasting or Monteriggioni	Car / bus / Tour
Cortona	Medieval Town	Car
Horse Riding	Oudoords, wine tasting	Provided
Versilia beaches	Beaches	train/ car
Cinque Terre	Coastal beauty, boating	Train/ Tour
Rome	Rome 🙂	Train

This is my selection of the best day trips and best day tours from Florence, to take after you have enjoyed Florence’s must-see sites.

Best side-trips from Florence map

The best day trips from Florence Italy: our top picks

A day at Tenuta Chiudendone

If you are looking for a way to spend a day in the stunning Tuscany countryside, learn to cook and even have a dip in a swimming pool (a lifesaver, if in Tuscany in the summer!), then you will love the option of spending a day at Tenuta Chiudendone.

The Tenuta is a private family home owned by a your local family.

Isabella and Francesco, the owners, live here but they open their home to visitors and offer them the chance to spend the day with them and enjoy all their estate has to offer: stunning views, amazing food, olive oil and wine from the estate, and great chats – Isabella and Francesco’s English is perfect and they are great conversationalists!

The Tenuta is wonderful and this experience is a mix between a cooking class (it’s communal cooking rather than a full on lesson), a day with friends and a wine tasting trip.

I absolutely love it here and highly recommend it. This is my full review of the experience, with photos, if you want to see what it is all about.

Day trip from Florence to Chianti – the perfect day trip for wine lovers

The Chianti region is world-famous for its production of Chianti classico wine and it is a very easy area to visit from Florence.

Here, you are going to see beautiful countryside and will have your pick of wineries and restaurants to sample the local, amazing wood and see what this famous wine is all about.

The best way to visit this wine region is by car, if you have a designated driver in our party who will not partake in the wine tasting, or with a guided tour such as this one by LivTours which I personally love.

With your private driver, you will visit two wineries (one big, one small, so you can get a sense of different Tuscan producers – one is a castle!), walk the grounds, taste the wines, have a light lunch and enjoy the stunning rolling hills of this area.

This tour is a fantastic way to experience Tuscany without a car and it can be tailored to your needs and customized as required.

If, on the other hand, you have your own car, then you can make your own trip. Depending on what you love, you can visit stunning Verrazzano Castle and winery, Brolio, Castello di Ama, Volpaia, Cantina Antinori and the pretty village of Montefioralle.

If you love meat, Panzano and Dario Cecchini’s restaurants are here too. If you have kids, you can find several ideas such as kid-friendly wine tasting here

Catch a train to Lucca

Lucca is one of the prettiest small towns in Tuscany and a perfect day trip from Florence by train.

The town has intact medieval walls and a stunning historical center with plenty of beautiful churches, shops and restaurants, for a pleasant day of sightseeing.

Not to be missed in Lucca is the stunning Piazza dell’Anfiteatro, one of the most beautiful piazzas in Italy, the old city walls and the pretty Guinigi Tower but the city as one thing that adults and kids love: the option of taking bikes and cycle along the ancient walls (now a park)!

You can find our guide to spending a day in Lucca here.

Lucca is one of the easiest Tuscan cities to explore with small children.

The town’s ancient walls are now a park and they have a wonderful cycling trail easy to tackle at any age. Find our tips for visiting Lucca with kids here.

Lovely places for a nicer meal in Lucca are PepeRosa (despite the touristy location, it is a good one!, Il and Buca di Sant’Antonio although you won’t have issues finding local, delicious and informal food places here!

Top tip: Lucca is on the way between Florence and the coast and you can easily combine a trip here with time on the beach. You can find here >>> our handpicked selection of the best beaches near Lucca. Another popular solutions is to combine it with Pisa.

Monteriggioni

Monteriggioni is a tiny village perched on the top of a hill in the province of Siena, less than 50 km from Florence.

The town is still entirely surrounded by its imposing medieval walls and it is a wonderful example of a Tuscan castle, complete with a chapel, turrets and a stunning main square now filled with restaurants and pretty shops.

It is a super pretty place!

The village is tiny and can be visited in a couple of hours, reason why many plan it for the same day as San Gimignano. I personally love to stop here for aperitivo in the piazza!

Not to be missed is the walk on its bastions and food stop on the main square – a charcuterie platter in this setting is even more delicious!

Top tip! If you can, try and visit the city in early July when the Monteriggioni medieval festival takes place (bring water and a sun hat as Monteriggioni is hot in summer!).

Find our guide to Monteriggioni here.

Visit San Gimignano, UNESCO city of towers

San Gimignano is the best hilltop Tuscan village to visit as a day trip from Florence and one of the most popular destinations for day-trippers.

Perches on top of a beautiful hill, San Gimignano is a medieval walled town with a perfectly preserved old center, a staggering amount of medieval towers (it is not called ‘city of towers’ for nothing!) and it is also a lovely place for foodies.

As well as stunning churches and alleys, San Gimignano is famous for the production of saffron and the delicious vernaccia wine: vernaccia di San Gimignano!

You can visit San Gimignano on your own or by joining an organized tour.

Whatever you decide, prepare for crowds: during the day, San Gimignano gets a lot of tourism – escape to the smaller side roads for a respite from the crowds and some of the most beautiful corners of the city.

Find our guide to San Gimignano here or check out well-organized day trips from Florence to San Gimignano such as this one.

Cortona

Cortona is one of the prettiest and best-known towns in Tuscany, known to English speakers mostly as the backdrop of the best seller Under the Tuscan sun.

Perched on top of a beautiful hill surrounded by pretty countryside, Cortona is a delight and since it is about 1h further South than Florence, it is also a chance to see a slightly different part of the region. Tuscany is funny in that sense as different parts do have a slightly different feel, even if the description of ‘hilltop village and rolling hills’ may make them sound all the same!

Not to be missed here are its central square medieval and still perfectly preserved, its churches and museums and the nearby Eremo Le Celle (Hermitage) which dates back to St Francis’ times.

You can find our guide to what to see in Cortona here.

Top tip: make sure you have lunch in Cortona or at least aperitivo so you can try the local specialties such as the delightful ciaccia (local focaccia)!

Day tours from Florence to Cortona often include stops in other beautiful localities and can be a good option to explore more if you don’t have your own car.

Have a look at this beautiful day trip from Florence to Cortona and Montepulciano, which touches two of our favorite Tuscan towns!

Horse riding and wine Tasting in The Tuscan countryside

Another fantastic way to experience Tuscany, if experience and budget allows, is to have a day horse riding and wine tasting, two activities that more than most other get you in touch with the territory and give you a sense of what Tuscany is deeply about. 

I find the best and easiest way to do so is by joining this tour by LivTours: as well as taking care of all the logistics, they care about the suppliers they choose and this is to me even more important with animals involved. Their tour is expensive but really worth considering how special a memory a day such as this will be. 

Pisa

If you have always dreamed of seeing the Tower of Pisa and UNESCO’s Piazza del Miracoli (Square of miracles), then you’ll be happy to know that Pisa is easy to visit from Florence.

Regular trains connect Florence Santa Maria Novella station with Pisa Centrale and good buses lead you to the tower, which is where Pisa’s main attractions are.

Not to be missed here are the tower itself, a visit inside the cathedral and baptistry and a visit to the cemetery, which is a real gem and Pisa must-see.

The one problem you may have in Pisa is the crowds.

Everyone comes to the piazza and this means you have tons of cheap souvenir vendors, food trucks and relative litter everywhere. So usually, the best way to see it is to come very early in the morning, before the crowds descend on it, or at the end of the day – especially if you don’t want to climb the tower, getting here out of hours is really special!

You can also easily combine a trip here with Lucca.

To make the most of your day in Pisa, I recommend you read our guide to one day in Pisa with our recommended itinerary.

If you prefer a guided experience, have a look at this half-day excursion to Pisa from Florence.

Siena

Siena is one of the most beautiful towns in Tuscany: the center and famous Piazza del Campo, one of the most beautiful piazzas in Italy, is jaw-dropping but the whole city is full of churches, pretty roads and palazzi that echo its medieval past.

Siena also has lovely shops and restaurants, which make it perfect also if you want a relaxing day getting your fix of Italian food and style!

Despite all these riches, Siena is easy to visit in one day and requires very little planning: the town is compact and you can easily explore just by strolling. For a lovely meal, you will be able to choose from an infinity of places or, if you prefer to have a plan, you may enjoy Taverna di San Giuseppe, La Finestra or Le Logge

Tip for families with kids: Siena is not very stroller friendly but has some nice areas for kids and a wonderful park. You can find our guide to Siena with kids here.

Siena is easiest to reach by car, although train and bus from Florence are also available. If you prefer a guided tour, good tours to and of Siena worth checking out are:

• Siena tour from Florence which also includes San Gimignano
• Or a more luxury options, Livtours offer this stunnning and super comfy tour to Siena and San Gimignano. I know the price is steep but there is a reason why the cost is as such: the care is excellent too!

Val D’Orcia

A longer yet stunning day trip from Florence is also that to Val D’Orcia, maybe the most iconic of all areas in Tuscany.

Val d’Orcia is where the rolling hills, cypress trees and olive groves that many associate with Tuscany actually are.

The area is ideal for a road trip as some of the most beautiful views in Val D’Orcia are from the scenic drive between Chianciano, San Quirico d’Orcia and Pienza; however, several bus tours offer tours of the area that can be a valid alternative.

You can find our not to be missed places in Val d’Orcia here and you can check good day tours from Florence to Val d’Orcia following the links below:

Cheese and wine tasting Val D’Orcia tour from Florence (Pienza is famous for its cacio cheese)
From Florence, wine tasting day tour of Val D’Orcia

Florence beaches and Tuscan Riviera

Florence is surprisingly close to the sea.

The motorway connects the city to the coast in less than 2 hours and here, you can easily choose between several localities offering sandy beaches, rocky coves, trendy settings or secluded experiences. Basically, whatever beach experience you are after, the beaches of Tuscany will deliver!

You can find my guide to the best beaches near Florence here

Cinque Terre

Cinque Terre is an area of outstanding natural beauty in Liguria (the region to the North West of Tuscany) which needs little introduction.

This is the area of Italy where you find the colorful villages that seem to hang off a cliff overlooking the sea and where some of the most iconic images of Italy are taken.

Visiting Cinque Terre from Florence is possible and while I recommend to spend more than just a day here, if you have no alternative to visit this beautiful area than to come here on a day trip, I have all the info you may need!

You can read here >> exactly how to take a day trip from Florence to Cinque Terre, with exact schedule and itinerary.

It you prefer an organized tour that will take care of transport arrangements, this is also an option: have a look at this good day tour from Florence to Cinque Terre by bus to see what the day includes and the exact schedule.

Tip for families: If traveling with children, make sure you check our guide to Cinque Terre with kids: this area of Italy is not child friendly (for the terrain, not the people) and extra tips are useful.

Day trip to Rome from Florence

I do not particularly recommend taking a day trip to Rome as the city truly needs a minimum of three days to be visited even at the most superficial level (I am from Rome and sorry to be blunt but those who say Rome can be ‘done’ in a couple of days or even three days just do not know Rome at all).

However, sometimes this may be the only chance to see the city and in that case, I want to help you!

Getting to Rome from Florence is easy as you can catch the fast train which will bring you there in less than 2 hours. Once in the city, I recommend one of two approaches: 1) take a golf cart tour of the city, so you cover a lot of ground without getting exhausted (this by LivTour collects you from near the station and is excellent);

2) exploring in your own time, focusing on the city center; in this case, I have a Rome city center walking itinerary you can follow also with restaurant and food tips!

I hope you enjoyed this overview of our favorite side trips from Florence. Safe travels!