12 Best Day Trips from Florence, Italy + Helpful Tips

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

Between zipping through the Tuscan countryside on vintage Vespas, exploring medieval hilltop towns, wine-tasting in Chianti, and hiking to colorful seaside villages, countless adventures await outside Florence’s ancient city walls!

Whenever I visit Florence, I stay for at least a week so I have time to schedule a few day trips.

In this guide, I’m sharing my favorite day trips from Florence, featuring unforgettable experiences across Tuscany, Emilia-Romagna, Liguria, and beyond.

I have personally done each of these Florence day trips at least once, so you know you can trust these recommendations!

Whether you’re looking for a guided tour or want to go on your own (via train or rental car!), I’ve got you covered. Here are the 12 best day trips from Florence, Italy!

Best Guided Day Trips from Florence

Let’s start with the best organized, guided Florence day trips.

Because, sometimes, you just want a local travel expert to handle the logistics so you can relax and enjoy.

1. Tuscany in a 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 and olive grove in the Chianti wine region.

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!)

Click here to book your Tuscany in One Day Tour!

Highlights of the Tuscany in One Day Tour

During this Tuscany in One Day Tour, you will…

• Go on a guided historical walking tour of Siena (a UNESCO World Heritage Site) to learn about the city’s rich history and unique cultural heritage – including Palio, a biannual horse-racing festival (first held in 1482!) in Siena’s Piazza del Campo. 
• Visit the magnificent Duomo di Siena, featuring Renaissance art by Michelangelo, Donatello, and Pisano. This Romanesque-Gothic cathedral is a stunner!

• Enjoy free time in Siena to climb the Torre del Mangia for incredible views, stroll the charming streets, sip an espresso, and try Siena’s famous panforte di Siena (fruitcake), spiced with cinnamon and black pepper.
• Visit a family-owned vineyard in Chianti for lunch. Walk the vineyards, learn about olive oil and wine production, and savor incredible countryside views. For your farm-to-table lunch, you’ll enjoy garden salad, fresh pasta, local cheeses, cured salami and prosciutto, homemade bread, artisanal olive oil, and plenty of wine. This is my favorite part!

• Explore the medieval hilltop town of San Gimignano on your own. Known as “the Manhattan of the Middle Ages,” San Gimignano features 14 stone towers, narrow cobblestone streets, cute wine shops offering tastings, craft leather shops, and incredible views of Tuscany’s green rolling hills, Cypress trees, and terracotta roofs.
• Taste some of the world’s best gelato; the gelateria in San Gimignano’s Piazza della Cisterna has won gold at the Ice Cream World Championships multiple times!
• See (and climb up!) the iconic Leaning Tower of Pisa and go for a peaceful stroll along the Arno.

Click here to book your Tuscany in One Day Tour from Florence. This tour sells out almost every day, so don’t wait to book it.

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

PREFER A PRIVATE OPTION? Book this Private Day Trip to Siena, San Gimignano, and Chianti instead. It accommodates a group of up to seven people, so this can be a very cost-effective option! Click here to book it.

2. Cinque Terre Day Trip from Florence

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 Italian 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 – Riomaggiore, Manarola, Corniglia, Vernazza, and Monterosso al Mare – in one day, via a combination of hiking trails (optional), quick regional trains, and even a scenic boat ride!

As you explore the five towns, you’ll discover jaw-dropping views, stunning swimming spots, gelato shops, beachfront wine bars, fresh seafood, and pesto-topped everything… (Fun fact: pesto was invented here, in the Liguria region!)

This full-day trip is about 14 hours long, so you’ll be exhausted when you return to Florence. But I promise, it’s worth it. You simply have to see this UNESCO World Heritage Site – and 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.

Note: Even though it’s possible, 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 (particularly from May through September) will be overwhelming.

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

PREFER A PRIVATE OPTION? This Private Tour to Cinque Terre from Florence is the perfect option. Click here to book it.

3. Wine Tasting on a Chianti Wine & Cheese Safari

It’s SO hard to choose, but I think this is my favorite day tour 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 husband and I recently went on this wine tour and we had the best time. 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 tour guide taught us a lot about wine-making – 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.

4. Florence Vespa Tour: Tuscan Hills & Italian Cuisine

What could be more quintessentially Italian than cruising through the Tuscan countryside on a vintage Vespa to a lovely farmhouse for 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 an 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.

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

5. 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 one instead.

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

6. Cooking Class at a Tuscan Farm

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.

Best Cooking Day Trips from Florence

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

• 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.
• Or, 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, 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. 

Best High-Speed Train Day Trips from Florence

From Pisa and Bologna to Pistoia, let’s talk about the best day trips from Florence by train, departing from Florence’s central train station: Santa Maria Novella.

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 may be fined if you don’t.

7. Bologna: Welcome to 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 Bologna, your main objective should be to try as many Bolognese dishes as possible… including tagliatelle al ragù alla Bolognese, tortellini in brodo (in broth), lasagna verde alla ragù Bolognese (green lasagna, thanks to spinach pasta sheets!), aged balsamic vinegar from Modena, and of course, Prosciutto di Parma and Parmigiano Reggiano from 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. Click here to book it!

After your Bologna Walking Food Tour, there’s more to discover. While in Bologna, make sure to also:

• Stroll under the Portico di San Luca, from the city center up to the Sanctuary of San Luca
• See the leaning Two Towers
• Explore the magnificent Santo Stefano complex
• Browse the artisanal food shops and markets
• Have a cocktail in lively Piazza Santo Stefano
• Make a dinner reservation at Vicolo Colombina (order the “roasted rabbit with its side dishes” – it’s incredible!)

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

READ MORE:
Bologna Food Factory Tour: The Best Foodie Experience in Italy!
19 Best Things to Do in Bologna (Italy’s Food Capital!)

8. Other Day Trips from Florence via Train

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

• Pistoia (33 minutes)
• Pisa (1 hour)
• Arezzo (1 hour)
• Lucca (1.5 hours)
• Verona (1.5 hours)
• Florence to Siena day trip (1.5 hours via regional train; it’s faster to bus or self-drive)

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

More options: It’s also possible to spend one day in Milan (2-hour train), Rome (1.5-hour train), or Venice (2.25-hour train). But, hopefully, you’ll visit these major Italian cities independently – they deserve more than just a day trip.

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

Best Self-Driving Day Trips from Florence by Rental Car

Feeling adventurous? Renting a car is my favorite way to explore Tuscany – it gives you the most flexibility, allows for spontaneity, and enables you to visit hidden gems (like wineries and small towns!) that are inaccessible by train.

That said, renting a car comes with some hassle (i.e. picking up the car, dropping it off, getting gas, etc.). It’s worth it though.

There are endless combinations for a self-driving day trip from Florence. But here are my three favorite self-driving routes for one day in Tuscany, by region!

HOT TIP: This is my favorite website for finding amazing deals on rental cars in Italy and beyond!

9. 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 (so delicious!).

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. It’s amazing. 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.

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

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

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.

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

• Montalcino: The nearby hilltop town of Montalcino, known for its premium wine – Brunello di Montalcino – is the treasure of Tuscany. This wine tour at Castello Tricerchi is fabulous, but Sanlorenzo and Camigliano also offer tastings worth considering!
• Cortona: 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.

• Montepulciano: 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.

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.)

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

For a classic Tuscany day trip (similar to #1), 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!

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

Then, continue on your day trip 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!

12. Truffle-Hunting & Charming Tuscan Towns

And finally, the most unique day trip from Florence: a Truffle Hunting Experience in the Tuscan Countryside, followed by a visit to one or two charming small towns.

First up, truffle hunting! In your rental car, drive 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 an expert truffle dog named Ciocco, you’ll search the forest for black summer truffles. To my surprise, we found at least 20 truffles in about 30 minutes – some of them were massive!

Then, you’ll return to the villa for a traditional, truffle-focused three-course meal. Everything is covered in fresh truffle shavings! You can even up the ante with truffle olive oil, truffle salt, and even truffle balsamic vinegar. Plus, you’ll taste the delicious wine Francesca’s family produces.

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

After your 3-hour Truffle Hunting Experience, hop in your rental car and visit one or two lovely towns nearby: 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 use public transportation and taxis to reach San Miniato if you don’t want to rent a car!

Best Florence Day Trips: FAQs