12 Best Day Trips from Florence, Italy + Helpful Tips

I may have traveled around the world, but to this day, some of my most treasured travel memories have been on day trips from Florence, Italy.

From zipping through the countryside on a vintage Vespa and exploring medieval hilltop towns, to devouring delicious farm-to-table feasts in Chianti, there’s no place like Tuscany. 

If you’re visiting Florence soon, you’re in the right place! In this post, I’m sharing the 12 best day trips from Florence – exploring the region of Tuscany, and beyond.

Whenever I visit Florence, I always stay for at least a week so I can schedule a few day trips. I have personally done each of these day trips at least once, so know that you can trust these recommendations!

Some of these Florence day trips are organized guided tours. Because, sometimes, you just want a local travel expert to handle the logistics for you!

But if you’re feeling extra adventurous, you’ll also find my top recommendations for self-guided day trips from Florence (via trains and rental cars). 

No matter which one(s) you choose, it’s impossible to go wrong. Here are the 12 best day trips from Florence, Italy!

12 Best Day Trips from Florence, Italy

1. Tuscany in One Day: Siena, Chianti, San Gimignano & Pisa

If this is your first time in Tuscany, then this classic Tuscany in One Day Tour is a non-negotiable must-do!

On this Tuscany in One Day Tour from Florence, you’ll visit three of Tuscany’s most endearing destinations: Siena, San Gimignano, and Pisa. Plus, you’ll enjoy a long and leisurely farm-to-table lunch and wine tasting at a family-owned vineyard in the Chianti Hills.

I have done this tour twice, so I can confidently say that this is the most comprehensive day trip from Florence. (And thousands of other 5-star reviews back me up.)

Here are some of the highlights of the Tuscany in One Day Tour:

Siena (1st Stop)

First up on the Tuscany in One Day Tour is Siena. Despite its proximity to Florence, this UNESCO World Heritage Site features its own unique culture, heritage, and traditions. You’re going to love it!

You’ll kick off your day with a guided historical tour of the city center, and learn all about Palio; this biannual festival (first held in 1482!) includes a horse race in the main Piazza del Campo, as well as a parade, horse-blessing ceremonies, flag throwing, and historical costumes. If your day trip falls in July or August, then you may be lucky enough to witness this hallmark of Sienese culture – or at least feel the buzz in the atmosphere!

Next up, the best part. You’ll see the dazzling Duomo di Siena, featuring Renaissance art by the likes of Michelangelo, Donatello, and Pisano. This Romanesque-Gothic cathedral is a true stunner!

And finally, you’ll have free time to roam the charming medieval streets and sip an espresso in one of the coffee bars. Siena is also famous for its panforte di Siena (fruitcake), spiced with cinnamon and black pepper; make sure to try it! 

The views atop the bell tower, Torre del Mangia (in the Piazza del Campo), are also worth the climb!

Lunch in the Chianti Region (2nd Stop)

Ready for my favorite part of the Tuscany in One Day Tour? Lunch at a Chianti vineyard!

Before a long, leisurely farm-to-table lunch, you’ll walk the vineyards, learn about the farm’s olive oil and wine-making processes, and savor incredible views of the Tuscan countryside.

The garden salad, fresh pasta, local cheeses, cured salami and prosciutto, homemade bread, artisanal olive oil and balsamic vinegar, and many bottles of wine go down easily here…

San Gimignano (3rd Stop)

Next on the Tuscany in One Day Tour, you’ll visit San Gimignano. This medieval hilltop town was originally founded by the Etruscans in the third century B.C.! 

Known as “the Manhattan of the Middle Ages,” San Gimignano features 14 stone towers (but there were 72 originally!), narrow cobblestone streets, and the most incredible views of green rolling hills, Cypress trees, and terracotta roofs.

There, you’ll see the bustling Piazza della Cisterna, cute enoteche (wine shops) offering wine tastings, a plethora of quaint restaurants, and a few craft leather shops, in case you’re looking for a stylish souvenir.

But the town’s real claim to fame? Gelateria Dondoli. This small gelato shop has won the gold at the Ice Cream World Championships multiple times!

With creative flavors like Pink Grapefruit & Sparkling Wine and Gorgonzola & Walnuts, it’s near-impossible to choose! But me? I love their pistacchio; classic and so good. The long line moves very fast, so don’t let it deter you!

Pisa (4th Stop)

And finally, the last stop on the Tuscany in One Day Tour is Pisa. 

Obviously, the famous Leaning Tower of Pisa is the main attraction here. 

But beyond the tower, Pisa is unexpectedly charming (albeit, touristy). You’ll have time to stroll along the Arno River, pop into some shops, or stop by a wine bar before the journey back to Florence.

This day trip sounds pretty epic, doesn’t it? Click here to book your Tuscany in One Day Tour from Florence. This tour sells out every single day, so don’t wait.

READ MORE: Tuscany in One Day Itinerary: Siena, Chianti, San Gimignano, Pisa

Self-Driving Tours of Tuscany

Feeling adventurous? If you’d rather ditch the guided Tuscany in One Day Tour and drive yourself, it’s totally doable.

Renting a car gives you the most flexibility of any other Florence day trip option – and leaves room for spontaneity! Plus, many of Tuscany’s hidden gems are inaccessible by train.

There are endless combinations for a self-driving day trip from Florence. But here are my top three recommended self-driving routes, by region!

2. Self-Drive to Eastern Tuscany: Lucca, Pisa

My top pick for a day trip to Eastern Tuscany is the beautiful medieval walled city of Lucca. I love Lucca. It’s peaceful, quiet, super green, and so underrated.

While in Lucca, explore the city streets, climb up Torre Guinigi, and have lunch at Sottosotto.

Then, hop in your car to reach this winery experience, 15 minutes from the city. I learned SO MUCH about wine on this tour; it’s a very intimate experience! The wine was delicious too. Click here to book it!

Next time, I want to check out a certified organic and biodynamic vineyard called Fabbrica di San Martino. Go, and let me know how it is!

And finally, before driving back to Florence, savor a fantastic multi-course dinner and some more wine (if you’re not the driver!) at the local farm/vineyard Fattoria Sardi. Further afield, Antica Locanda di Sesto is another super tasty dinner option. Either way, you must make a reservation. 

Talk about a perfect day trip from Florence!

Note: The sights in/around Lucca can easily occupy a whole day, so I don’t think Pisa is worth going out of your way for. But if you really want to see the Leaning Tower, you can visit both cities in one day.

3. Self-Drive to Southern Tuscany: Cortona, Montepulciano, Montalcino

Want to visit some of the lesser-visited gems of Tuscany? Then head south instead!

On a day trip from Florence, you’ll have time to visit two or three of the destinations listed below:

• Consider visiting the charming town of Cortona (featured in one of my favorite movies ever, Under the Tuscan Sun). Make sure to dine at Osteria del Teatro – oh my goodness, the food here is amazing.
• Then check out the famous wine-making town of Montepulciano. The streets and shops are lovely, but you must explore underground, too! This Montepulciano Cellar Tour includes a guided walk through a vast, ancient cellar, followed by tastings of six different wines, including Rosso di Montepulciano and Nobile. Also, make sure to stop into La Vineria di Montepulciano for a seriously fantastic and well-priced tagliere misto (meat and cheese board) and a glass of local Montepulciano wine!
• The nearby hilltop town of Montalcino, known for its premium wine – Brunello di Montalcino – is the treasure of Tuscany. This wine tasting tour at Castello Tricerchi is fabulous, but Sanlorenzo and Camigliano also offer tastings worth considering!
• As you drive, you’ll be awestruck by the views of the Val d’Orcia. It’s one of the most beautiful landscapes in all of Italy!
• If you have even more time (which is highly unlikely), then you can explore the stunning medieval city of Arezzo and have dinner at Trattoria Cavour 42 before you drive back to Florence. Or, better yet, split this day trip up into two days; stay the night in Arezzo (at La Corte Del Re!).

Hot tip: If you’d rather go on a guided tour to this region, check out this Siena, Cortona, Montepulciano & Val D’Orcia Semi-Private Tour from Florence. (Note: I have not been on this one before.)

4. Self-Drive to Central Tuscany: San Gimignano, Vineyards, Siena

For a classic Tuscany day trip, rent a car and drive yourself to the medieval hilltop town of San Gimignano, a vineyard in the surrounding countryside, and the beautiful city of Siena. 

Kick off your day of explorations in San Gimignano. Then, outside of the town walls, visit this organic family-run winery and have a typical lunch; it includes tastings of eight organic wines paired with the local olive oil, cheeses, cold cuts, and other artisanal products. Click here to book it!

Some other options for a farm-fresh lunch and wine tasting include Fattoria Poggio Alloro or Azienda Agricola San Quirico. Wherever you visit, you must book in advance!

However, if want to dine in San Gimignano, then don’t miss Le Vecchie Mura. The views, food, and service are *chef’s kiss!*

Then, make your way to Siena. Make sure to go on this Siena guided walking tour, which includes a skip-the-line ticket to the magnificent Duomo! I recently went on this tour and it was fantastic.

Oh, and grab a sandwich at Il Bocconcino!

Hot tip: Have more time? Break up your grand tour of Tuscany into two days and spend the night at a romantic agriturismo (farm stay). I recommend either Agriturismo Mormoraia or Tenuta Sovestro!

Important Tips for Self-Driving Day Trips from Florence

• This is the website I recommend for finding great deals on rental cars in Italy. 
• Select a compact car! Roads around Tuscany can be tight.
• Rental car shops at the Florence airport open earlier and close later than the ones in the city center do. Ideally, you’d pick up your car from the airport no later than 8 AM and return it as late as 11 PM (but this depends on the company you book with). This strategy maximizes your time for having fun!
• Arrive at the car rental shop as early as possible (i.e. 10 mins before it opens) to avoid waiting in a queue to get your car.
• Generally, you can’t drive into/park inside medieval city centers (they are “ZTL” zones). Find free or paid parking outside the historic center, and then walk in. 
• To that point, never drive down a street signposted with “ZTL attiva” or “ZTL closed”. You’ll get a big ticket!
• Before you leave your home country, get an international driver’s license! We were recently pulled over in a traffic stop in the Dolomites and my fiancé was fined €282 for not having one.

5. Cinque Terre Day Trip from Florence with Optional Hiking

I’ve embarked on this Cinque Terre Day Trip from Florence twice, so I can say with certainty… Visiting the colorful seaside towns of Cinque Terre will be a highlight of your Italy vacation!

If you didn’t already know, the Italian word cinque means five. On this Cinque Terre Day Trip, you’ll explore all five wondrous villages of Cinque Terre – Riomaggiore, Manarola, Corniglia, Vernazza, and Monterosso – in one day.

How’s that possible? Via a combination of hiking trails (optional), very quick regional trains, and even a scenic boat ride!

This Cinque Terre tour is jam-packed with incredible vistas, stunning swimming spots, gelato shops, beachfront wine bars, and delicious food…

After all, pesto was invented here, in the Liguria region! Plus the seafood is amazing. 

This day trip is about 14 hours, so you’ll be exhausted when you get back to Florence. I certainly was!

But you simply have to see this UNESCO World Heritage Site – its sparkling azure waters, rocky cliffs, lush terraced farms, and rainbow-colored houses – with your own eyes.

Click here to book your Cinque Terre Day Trip from Florence.

P.S. Because Cinque Terre is so beautiful, it’s very crowded. Especially between May and September. (Thanks, Instagram…) But I promise, you’re going to love it anyway.

Note: I do NOT recommend going on a self-guided day trip to Cinque Terre. Between trains, ferries, hiking trails, and national park tickets, there are a lot of details to coordinate. It’ll probably be more stressful than fun. Plus, dealing with the crowds will be overwhelming. However, in my guide, How to Take the Perfect Day Trip from Florence to Cinque Terre, I explain how to go on a self-guided day trip.

READ MORE: How to Take the Perfect Day Trip from Florence to Cinque Terre

6. Wine Tasting on a Chianti Wine & Cheese Safari

It’s SO hard to choose, but I think this is my favorite day trip from Florence!

Wine lovers, you can’t visit Florence and not embark on this epic wine tour, known as the Chianti Wine & Cheese Safari!

On this amazing Florence day trip, you’ll go off-roading in a 4X4 through Chianti’s rolling hills – past olive groves, rustic farms, and ancient monasteries – to visit some of Tuscany’s most luxurious and historic Renaissance-era villas and wine estates.

You’ll feel like royalty as you stroll through the estates’ vineyards, drink Chianti Classico in their cellars, and taste all kinds of traditional Tuscan food. 

My fiancé and I recently went on this wine tour, and it exceeded our expectations. Throughout the day, we tried so many incredible local wines – from Chianti Classico to Super Tuscan to sparkling rosé – that I lost count of how many we tasted… at least thirteen! 

Along the way, our expert wine guide taught us a lot about the wine-making process – and what sets Chianti wine apart from the rest. 

We also tasted many artisanal foodie specialties, from local cheeses, cured meats, and olive oils, to bruschetta, black truffle ravioli, and cinghiale (wild boar) pappardelle… Complete with wine pairings, of course!

Not to mention, the scenery the entire time was so gorgeous. My eyes kept tearing up as I stared out the window of the 4X4. (Yes, even before having any wine…)

This wine, cheese, and lunch tour is the most magical day trip from Florence. It’s an experience you’ll never forget!

Click here to book your Chianti Wine & Cheese Safari.

7. Eat Your Way Through Bologna: Italy’s Food Capital

Foodies, listen up! Bologna is the undisputed food capital of Italy. And lucky for you, this delicious (young, lively, and cool) city is just a 40-minute, high-speed train ride away from Florence.

On a day trip from Florence to beautiful Bologna, your main objective should be to try as many Bolognese dishes as possible! Including:

• Tagliatelle al ragù alla Bolognese;
• meat-filled tortellini with ragù alla Bolognese;
• tortellini in brodo (in broth);
• ricotta-spinach-stuffed tortelloni in sage butter;
• lasagna verde alla ragù Bolognese (green lasagna, thanks to spinach in the pasta sheets!);
• mortadella (a delicious pork cold cut);
• premium, aged balsamic vinegar from nearby Modena; and of course,
• Prosciutto di Parma and Parmigiano Reggiano from nearby Parma.

I highly recommend booking this Bologna Walking Food Tour to taste as many of Bologna’s top dishes as possible in one day. All while learning about the city’s history and food culture!

I was completely stuffed (and so very happy!) after this food tour.

Before/after your Bologna Walking Food Tour, there are a few more activities you shouldn’t miss in this beautiful city! My favorites include strolling under the Portico di San Luca up to the Sanctuary of San Luca; seeing the leaning Two Towers; exploring the magnificent Santo Stefano complex; browsing the many artisanal food shops; and having a cocktail in lively Piazza Santo Stefano.

No matter what you do, you’ll love strolling along the city’s beautiful portico-covered terrazzo sidewalks! 

Oh, and in addition to this food tour, make a reservation at Vicolo Colombina. Order the “roasted rabbit with its side dishes.” It’s incredible.

They don’t call Bologna “La Grassa” (“The Fat One”) for nothing. It’s time to eat!

8. Florence Vespa Tour: Tuscan Hills and Italian Cuisine

What could be more quintessentially Italian than cruising through the Tuscan countryside on a vintage Vespa to a farmhouse lunch?

This Vespa Tour of Tuscany is bucket list material – and one of the most unique things I’ve experienced in Italy!

On this amazing Vespa tour of Tuscany, you’ll stop by a beautiful 11th-century church and cemetery, offering the best secret viewpoint of Florence. Then, you’ll ride by centuries-old castles, medieval towers, and other historic monuments, little villages, endless rolling hills, olive groves, and wildflowers.

All under the Tuscan sun.

The entire experience is wildly beautiful and so freeing!

The experience peaks with a luscious farmhouse lunch including a beautiful antipasto platter of local cheeses, bruschetta, cured meats, artichokes, and olives, pasta, bread, and more. And of course, local red wine! (Not too much, though!)

And then, you drive back to Florence.

After many trips to Italy, to all different regions, I can honestly say that this Florence day trip is one of the best things I’ve ever done in Italy! You’re going to love it.

Click here to book your Florence Vespa Tour of the Tuscan Hills.

9. Self-Drive Vintage Fiat 500 Tour from Florence

If driving a Vespa isn’t your thing, no worries. You can embark on the exact same guided tour I mentioned above… But in a vintage Fiat 500 car instead of a Vespa!

You can’t trust me to drive anything (successfully) on two wheels. If I hadn’t been the passenger on our Vespa, I would’ve booked this tour Fiat 500 Tour of Tuscany instead.

Click here to book your Self-Drive Vintage Fiat 500 Tour from Florence.

10. Cooking Class in the Tuscan Countryside

If you’re a foodie like me, then you’ll jump at the chance to take a cooking class, led by an expert Italian chef, at a farm in the Tuscan hills!

And yes, sipping on Chianti wine over amazing views is a key part of the experience. Obviously.

I have two amazing class options for you to choose from; it just depends on what you want to learn to make!

Best Cooking day trips from florence

• On this 7-hour day trip, you’ll visit a historic, local market in Florence to collect fresh ingredients to make your 4-course Italian feast! Then, out at the farmhouse, you’ll learn to make pasta from scratch, along with porchetta (this is a pretty impressive thing to know how to make at home!), bruschetta, and tiramisù. Click here to book your Tuscan Farmhouse Cooking Class and Market Tour.
• On this shorter, half-day trip, you’ll skip the market and head straight for the hills. There, you’ll learn to make pizza and gelato from scratch! I opted for this class, and it was so much fun! As a group, we made 14 different gelato flavors! Then we crafted our pizzas; we kneaded out our dough, added our favorite toppings, and watched the expert pizzaiolo fire them in the wood-burning oven. And finally, we savored the flavors and views over unlimited Chianti wine. Heavenly! Click here to book your  Pizza and Gelato Farmhouse Cooking Class. 

Both of the cooking classes above include a digital recipe booklet so you can recreate an amazing Tuscan feast at home!

HOT TIP: If you plan to book this Vespa tour or this Fiat tour, then I recommend NOT booking one of these cooking classes! Simply because they’re held at the same farmhouse. The experiences are totally different, but you may not want to go to the same place twice.

Instead, consider this Florence Cooking Class & Market Tour, held in the city center. I have done this cooking class too (I still use the recipes to this day!), and it is 100% awesome.

11. Hunt for Truffles in the Tuscan Countryside

And finally, the most unique day trip from Florence: a Truffle Hunting Experience in the Tuscan Countryside! 

In our rental car, we drove out to San Miniato (50 minutes east of Florence) to Francesca’s beautiful hilltop villa. There, her family has been truffle hunting and growing grapes and olives for four generations!

Alongside her expert truffle dog, Ciocco, we roamed the forest in search of black summer truffles. And to my surprise, we found at least 20 truffles in about 30 minutes. Some of them were massive!

Just, wow. That’s all I have to say. (Oh, and now I want to become a truffle farmer!)

Then, we returned to Francesca’s for a traditional, truffle-focused three-course meal. As you’d expect, everything was covered in fresh truffle shavings! Plus, truffle olive oil, truffle salt, and even truffle balsamic vinegar were on the table to up the ante.

And of course, we drank plenty of the delicious wine Francesca’s family produces too! 

If you love food, wine, dogs, and nature, you will love this Truffle Hunting Experience… Click here to book it! 

Hot tip: This Truffle Hunting Experience is only about 3 hours long, so if you go via rental car, I recommend combining it with a visit to one or two of these nearby destinations: San Gimignano, Volterra (Twilight fans, New Moon was filmed here!), and/or Siena.

Looking for quieter, less touristy spots? Check out Monteriggione and Colle di Val d’Elsa.

Note: You can also take a combination of public transportation and taxis to reach San Miniato if you don’t want to rent a car!

12. Day Trip from Florence via High-Speed Train

As mentioned in #7, Bologna is my top pick for a day trip from Florence via high-speed train. However, there are other destinations in Northern Italy and beyond within day-tripping distance:

• Pistoia (33 minutes)
• Pisa (1 hour)
• Arezzo (1 hour)
• Lucca (1.5 hours)
• Siena (1.5 hours; this is a regional train, so it’s faster to drive/take the bus)
• Verona (1.5 hours)
• Roma (1.5 hours)
• Milan (2 hours)
• Venice (2.25 hours)

Note: I’ve only included destinations with direct train routes (no changes). Book high-speed trains where possible!

HOT TIP: The easiest way to purchase train tickets is via the Trenitalia website or app. Remember to check-in/validate your tickets in the smartphone app before you board (you can be fined if you don’t!).

12 Incredible, Can’t-Miss Day Trips from Florence, Italy

From strolling along the Arno River at sunset and savoring Bistecca alla Fiorentina over full glasses of wine, to admiring the breathtaking medieval architecture and Renaissance art, Florence itself is incredible.

But if your Florence itinerary doesn’t include time to explore the Tuscan countryside (and beyond!), then you’ll miss out on this region’s unparalleled beauty and charm. On truly magical experiences.

So please, when you visit Florence: Take. It. Slow. Leave plenty of time to leave the city and take a few day trips. If I were you, I’d stay a week in Florence, and take a couple of day trips.

Whether you’re into food, wine tasting, medieval history, art, cooking, hiking, architecture, or vintage Vespas, there’s a Florence day trip for you. Andiamo!

Best Florence Day Trips: FAQs