How to Spend 3 Days in Florence - A Guide for First-Time Visitors
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Considering Florence is one of the World’s most famous cities, you might be surprised that I recommend “only” 3 days here. But although it’s Tuscany’s capital, the birthplace of the Renaissance, and genuinely packed with an absurd wealth of artistic masterpieces and glorious architecture, the city is still relatively small (only about 300,000 residents) and extremely compact.
This means that for casual visitors who have a passing interest in art, architecture, and the city’s history, but who don’t want to spend 8 hours a day visiting museums and churches, Florence really can be comfortably explored in 3 days.
You could even pack everything into just 2 very busy days, but I don’t think that would be an especially pleasant trip, as you’d basically be rushing straight from one sight to the next, checking off boxes on your to-do list.
And while there are some things that you absolutely must see when here, for me a lot of the pleasure of being in Florence lies in going for aimless wanders, often outside of the very center of the city, and enjoying the little gems that you unexpectedly stumble on.
To have time for “getting lost”, you need to have some open space in your itinerary, and I think 3 days is just right for that.
It’s the perfect amount of time in that you can spread out your visits to the city’s marquee sites and attractions, visiting a couple of them each day, while still leaving ample time for leisurely meals, pleasant wanders, and some “aimless” lounging around.
Check out my detailed itinerary below for a step-by-step guide on what I recommend for 3 days in Florence.
For more help planning, have a look at some of our other guides:
Table of Contents
Florence planning cheatsheet
Plan your itinerary with expert advice
- Book an Italy travel consultation with a local expert
My favorite hotels in Florence
- Palazzo Guadagni - fabulous Renaissance style in Oltrarno. $300-450 USD
- Hotel Calimala - gorgeous boutique hotel in the absolute city center. $250-450 USD
- La Maison du Sage - with a whole lot of style, this is my favorite hotel in Santa Croce. $250 USD
- Hotel Silla - lovely hotel in a great Oltrarno location for a good price. $150-225 USD
- Locanda de Ciomp - warm and inviting guesthouse in Santa Croce. $150-200 USD
- Casa Leopardi - pleasant B&B near Mercato di Sant'Ambrogio. $175 USD
- Residenza San Gallo 79 - cheerful little B&B near the Accademia. $100-200 USD
Guided tours and activities
How to get around
- Car rentals with DiscoverCars
- Train tickets from Trenitalia and Italo
- Urban tram routes at GEST
Discover authentic Tuscany with Stefano
If you could use some help planning your trip to Florence and Tuscany, then reach out to Stefano, our Local Expert!
Originally from a little town in the Tuscan countryside, Stefano has been a guide and trip planner based in Florence for 20 years now. He offers Tuscany travel consultations and private day trips.
Where to stay
Before looking at the itinerary, a quick note on choosing where to base yourself. For an in-depth look, check out our Florence neighborhood guide which discusses our recommended neighborhoods and the pros and cons.
But if you just want some quick options, the map below includes a selection of good hotels across the various neighborhoods that we recommend.
Day 1: The main sights
Florence
Morning - Admire some of Italy's finest art at the Uffizi Gallery and Duomo Complex
On your first morning in Florence, I recommend visiting the city's most iconic sights and a few museums. Not only will you see some of the most beautiful art the Western World has produced, but you'll also get a better understanding for how unbelievably important of a place Florence held during the Renaissance.
So, I've dedicated a few hours for the Uffizi Gallery and then given you some options for which sights to see in the Duomo complex.
Uffizi Gallery
Begin your first day at the Galleria degli Uffizi, the erstwhile headquarters of the Medici banking empire and now a museum stuffed to the rafters with the masterpieces of the Renaissance.
In gallery after gallery you’ll encounter Botticelli, Michelangelo, Leonardo… this is one of the world’s great museums, so take your time and spend the entire morning here.
When you want to take a break from all the saints and swirling angels, head up to the view-filled rooftop café.
A statue and painted ceiling in the Uffizi
Pro tip: I recommend arriving early to try and beat the worst of the crowds (you can never beat them altogether). The gallery opens at 8:15 am and, if you can manage an early start, that's when I'd recommend booking your entrance. Tickets do sell out, so I highly recommend getting them well in advance of your desired date.
Getting tickets: For tickets, always purchase on the museum's official website. You'll notice quite a few different options as well as some packages that also include entrance to the Pitti Palace, Boboli Gardens, Vasari Corridor, etc. To be honest, there's not much difference in pricing whether you buy separate tickets or a combined one, so don't stress too much.
Tours: If you're interested in a guided tour of the museum, here are a couple of options:
Private Uffizi tour - This is a very good almost 2-hour tour that covers the museum's major treasures. I recommend it because it's always the same guide (Irina), not just a random person assigned on the day of the tour.
Small-group Uffizi tour - For a group tour, I recommend this one because the max size is 9 people (some tours will have 12 or 15 participants, which is too many) and you have the option of either a 1.5 or 2.5-hour tour. The 2.5 hour tour provides a much better experience.
Uffizi & Accademia combined tour - I personally think you should visit these two museums on separate days, but if you'd prefer to "do” them together, then this is a good option. The tour lasts around 3 hours, includes skip-the-line tickets, and caps group sizes at 9.
Florence Duomo complex
Next stop is Florence's cathedral, known as the Duomo (as with every cathedral in Italian cities), which is actually a complex of buildings. Like with the Uffizi, there are 3 different levels of tickets for it.
The Duomo itself is free to enter, but if you want to climb the Brunelleschi dome, visit the OPA museum, enter the Baptistry, or go up the Campanile bell tower, you'll need to purchase entrance tickets.
If you get to the Uffizi for 8 or 9 am, consider that you'll probably be at the Duomo complex around 11:00 am. This means that it will be be busy. So, make sure to buy your entrance tickets well in advance. If you try to get tickets on arrival, you will be stuck in line for ever.
Florence's Duomo
The complex is large and you don't really have time to do everything, so I'd recommend choosing only one of the 4 options below:
Duomo/Cathedral
One of the city's greatest Renaissance achievements, the Duomo was the largest church in the world when it was completed around 1436 and topped with Filippo Brunelleschi’s dome (which was also the largest in the world in its time). The Duomo itself is free to enter, but while incredibly impressive from the outside, it's actually surprisingly plain inside.
Brunelleschi Dome
The enormous cupola that dominates Florence's skyline is called the Brunelleschi Dome. Climbing up its narrow staircases wedged between the inner and outer shells is a not-to-be missed experience and the views from the top top are fabulous and iconic.
Battistero/Baptistry
Next door is the octagonal Battistero (Baptistry), where the East Doors, executed in gilded bronze by Lorenzo Ghiberti, depict 10 scenes from the Old Testament with such grace that Michelangelo said “They are so beautiful they would grace the entrance to Paradise.” They’ve been known ever since as The Gates of Paradise. The doors now in place are copies, and the originals are in the Museo dell’Opera del Duomo, which is often called the “Opa Museum".
Campanile (Giotto's Bell Tower)
The Campanile, also known as Giotto's Bell Tower, is exactly what it sounds like; the Duomo's bell tower. A climb of 400 steps brings you to another amazing city view, all the better here because you’ll get a close-up look at Brunelleschi’s dome. The bell tower is generally less crowded than the Duomo, so a good choice if the thought of even more crowds and lines has you stressed.
Getting tickets: To look at your options and buy tickets, the Opera del Duomo website is the official site and has some helpful explanations of the different sights and ticket options.
Tours: A guide is nice for the Duomo, but if you're only going to book 1 or 2 art-focused tours, I would save it for either the Uffizi or Accademia. Even so, if you want to go with a guide, this 2-hour small group tour is quite good and includes entrance tickets.
Afternoon - More masterpieces in the Centro Storico
The better part of your afternoon will be spent still in Florence's centro storico (historic center), but now you'll have a bit more time for wandering and exploring in addition to stopping inside one of my favorite palaces/museums.
If you'd like to explore the center with a guide, my recommendation is always local guide Sam Socci. He's been running tours of Florence for over 2 decades and is incredibly knowledgeable and just loads of fun. His Florence highlights walking tour is one of the best experiences in the city.
Lunch in Piazza della Signoria
Now, enjoy a late lunch and some of the best people watching in Florence from the terrace of Rivoire or one of the other cafes on the airy Piazza della Signoria, one of Florence's main squares. Yes, the cafes are touristy and your meal will be overpriced, but there are few better locations in the city to enjoy a good lunch.
Piazza della Signoria
Tour the Palazzo Vecchio
Right on Piazza della Signoria is Palazzo Vecchio which was built in the 1200s. Once Florence's city hall, it was later a Medici family residence and stronghold. Today, it is a sort of palace-museum that I find particularly wonderful because it perfectly shows how power, art, and politics were such a major component of Renaissance life in Florence.
I actually find this to be one of the most interesting museums in town and its design, layout, and the type of art on display make it more "tolerable” for people who otherwise find museums boring. It feels more like wandering around a stunning palace than admiring art in a museum.
Palazzo Vecchio. Photo: Francesco Bini, CC BY-SA 4.0, via Wikimedia Commons
Here are a few of my favorite areas:
Salone dei Cinquecento: a huge hall with massive frescoes and a seriously impressive ceiling.
Medici rooms and apartments: these are the preserved living quarters of the Medici family and the rooms are decorated with frescoes, painted ceilines, and lots of art.
Studiolo di Francesco I: a small, hidden study packed with paintings and secret cabinets.
Torre di Arnolfo: a tower that you can climb for one of the best views of Florence.
Underground ruins: remains of a Roman theater that are hidden under the palace.
Getting tickets: The Palazzo is open every day from 9:00 am to 5:00 pm, with reduced hours on Thursdays when it closes at 2:00 pm. Tickets cost 10 euros and should be purchased in advance to ensure availability at the time that fits your itinerary. Buy them on the official website.
Orsanmichele Church
Just beyond Piazza della Signoria is what might be the most charming church in Florence, unusually occupying a converted grain warehouse. The doors are usually locked, but the show is on the exterior, where the Renaissance trade guilds filled the niches with statues of their patron saints.
Evening
A night out in Oltrarno
A walk at dusk takes you across the shop-lined Ponte Vecchio bridge and then over it into the Oltrarno, or “other side of the Arno” (across the river from the city center).
You’ll come out in the neighborhood of Santo Spirito. Once a working class area that was popular with craftspeople and artists, it’s changed significantly in the last twenty years and is quite gentrified these days.
The narrow streets are still filled with artists’ studios, workshops, and antiques shops, but they’re now competing for space with boutique stores, trendy restaurants, and hip bars frequented by fashionable people from all over Florence. It’s a fun place to go for an aperitivo and dinner.
Ponte Vecchio bridge
Day 2: Markets and gardens
Santa Maria Novella church and square. Photo: Diego Delso, CC BY-SA 4.0, via Wikimedia Commons
Morning - A walk in Santa Maria Novella and a quick visit to the Accademia
I know that yesterday was an art and museum-heavy day, so most of today is dedicated to more leisurely and less “academic” wandering. However, although you may be feeling a bit "museum’ed out” I do think you should also at least quickly visit the Accademia, if for nothing else than to the Michelangelo's masterpiece, the David. So, I would do that first thing after breakfast.
Then, you can spend the day wandering and enjoying the city all around you, first in the busy Santa Maria Novella neighborhood and then the Oltrarno neighborhood in the afternoon. Finish the day with sunset at two of Florence's best viewpoints.
Accademia Gallery
The original of the city’s most famous sculpture (the David) is in the Accademia Gallery, so a visit here is sort of a must. While you could easily spend hours browsing the incredible works here, you can also visit pretty quickly, especially if you opt for a guided tour which are almost always run by art history experts and do a good job of quickly moving you through the collection.
Michelangelo's David sculpture in the Accademia Gallery
Getting tickets: To purchase tickets, use the official museum website. As with all the major museums in Florence, reserving your time in advance is absolutely necessary.
Tours: The museum is, of course, entirely visitable on your own. However, it's quite large so having a guide helps because not only will they give you context for what you observe, but they'll also help you efficiently navigate the must-sees, cutting down the amount of time needed for your visit. If you'd like a tour, here are two options:
Private Accademia tour - I really like this tour offered by local guide Francesca Zambini because, in addition to the Accademia, you also get a guided tour of the city center. And Francesca herself is a delight!
Small group tour - Only 1-hour in length, this is a good tour if you've already been to the Uffizi, are feeling a little "museumed-out”, or just want a quick overview of the art here (and the David!).
Church of Santa Maria Novella
Another treasure trove at this end of the Centro Storico is the church of Santa Maria Novella, covered with frescoes by Massaccio and Ghirlandaio. When the resident Dominican monks weren’t busy surrounding themselves with great art they were growing herbs with which they concocted similarly transcendent scents and soaps for their wealthy patrons.
Church of Santa Maria Novella
Officina Profumo-Farmaceutica
The monks at Santa Maria Novella put their knowledge of herbs and plants to good use in creating recipes for perfumes and other toiletries that have been for sale for centuries around the corner from the church at the atmospheric Officina Profumo-Farmaceutica di Santa Maria Novella, said to be the world’s oldest pharmacy.
A room in the pharmacy. Photo: Moon rabbit 365, CC BY-SA 4.0, via Wikimedia Commons
Mercato San Lorenzo (and maybe the Capelle Medici)
You can’t come to Florence without shopping, so plunge into the Mercato San Lorenzo. While there is an actual covered market here (called the Mercato Centrale - recently renovated and home to a huge selection of restaurants), most of the goods being sold are at stalls/stands lining the streets outside the physical market.
You'll find lots of different items, but the focus is really on leather. Many of the goods are low quality and made in China, so don't expect high-end pieces, but it’s hard to walk away without at least a change purse, for which you should bargain relentlessly.
If you want a quick and easy lunch, head inside the covered market and pick a restaurant. It's not a local market and the restaurants cater to tourists, but you can still find lots of good food.
Also nearby are the Capelle Medici in the church of San Lorenzo, housing the sumptuous sarcophagi that Michelangelo created for Florence’s ruling family.


Afternoon - A wander in the Oltrarno
This afternoon, take things easy and enjoy a break from museums and art in the Oltrarno neighborhood. Enjoy an aimless wander, browse the pleasant boutique and artisan workshops, and relax in some lovely gardens.
Cross into the Oltrarno via Ponte Santa Trinita brdige
Yesterday you crossed into it via Ponte Vecchio, so today make the crossing via Ponte Santa Trinita, a bridge noted not only for its elegant beauty but also for the fact that what you see is a complete reconstruction.
Retreating German troops blew up the original 16th century bridge in 1944, and in the 1950s workers painstaking reconstructed the span with the original stonework dredged from the river bottom.
Santa Maria del Carmine Church
Your first stop in the neighborhood is the church of Santa Maria del Carmine, where Massaccio painted the “Expulsion from Eden” and other frescoes in the Cappella Brancacci that are said to have set the stage for the Renaissance masters who followed him (quite a legacy for a young man who died at age 26). Pop inside for a quick look.
One of many gorgeous frescoes in the capella/church. Photo: Masolino da Panicale, Public domain, via Wikimedia Commons
Palazzo Pitti & Boboli Garden
A ten-minute walk through the streets of the Oltrarno brings you to the monumental Palazzo Pitti, a fitting residence for the Medici dynasty. In the days before Louis XIV built Versailles this was the largest and most opulent palace in the world, and today the grand salons are yet another Florentine repository of works by Raphael, Titian, Rubens, and other European masters, along with the furnishings that Medici dukes left behind.
As with Palazzo Vecchio, I think that Palazzo Pitti feels more like touring a palace than visiting a museum.
Behind the massive palace stretches the Boboli Gardens, a lovely green space that is the perfect place to close out two busy days of sightseeing among ponds, fountains, and grottoes.
For tickets, if you didn't already buy the package that includes Uffizi, Pitti, and Boboli, you can look on the official website. If visiting the Palace and Garden, buy the combined ticket which will save you a few euros.
The Pitti Palace and Boboli Gardens
Evening
Sunset views from Piazzale Michelangelo (or San Miniato al Monte church!)
While you’re still in Oltrarno, plan on catching an incredible sunset over the city. You have two main viewpoints, one very popular and one much lesser-known, but equally impressive.
For the shortest walk, climb the elegant staircase up to Piazzale Michelangelo, the city’s favorite spot for watching the sunset - and with the Duomo gleaming in the slanting rays, what a sight it is.
For a less-known viewpoint (i.e. less crowded), consider heading deeper into Oltrarno and making your way to the church of San Miniato al Monte. This viewpoint is higher up, so offers an even more expansive panorama over the city.
The view of Florence from San Miniato al Monte. Photo: Ввласенко, CC BY-SA 3.0, via Wikimedia Commons
Dinner in the San Frediano neighborhood
For dinner, walk into San Frediano, a neighborhood within the larger Oltrarno area just slightly west of Santo Spirito.
While gentrifying, this area has changed less than Santo Spirito and is still home to lots of actual Florentines. It has a very local feel and is a nice place to have dinner without the tourist crowds.
A meal at Al Tranvai is always a good bet.
Afterwards, you could go back to Santo Spirito for a bit of relaxed bar hopping or head over to the buzzing Santa Croce neighborhood if you want more exuberant nightlife.
Day 3: Santa Croce & Sant’Ambrogio and an afternoon walk in Fiesole
A view over Florence from a viewpoint in Fiesole
Morning - Explore Santa Croce
After two busy days, treat yourself to a leisurely start and a light morning. All I specifically recommend doing is taking a walk in the Santa Croce neighborhood and having a great meal in the Sant’Ambrogio market. Other than that, I've left the morning free in case you missed some things yesterday or want to sleep in!
Take a walk in Santa Croce
Santa Croce is one of Florence's most picturesque neighborhoods and it's adjacent to the historic center. It's a well-heeled area that's also very popular in the evenings, with lots of fun bars open relatively late. You'll be visiting in the morning when it's quieter and a bit more serene!
The main sight on your radar should be the Basilica di Santa Croce (you should go inside - tickets cost 10 euros and can be purchased here) which is, in my opinion, Florence's second most beautiful church on the outside and by far most beautiful on the inside. Aside from great frescoes, paintings, and stained glass windows, you also have the tombs of famous historical figures like Michelangelo, Galileo, and Machiavelli.
Aside from the church, there are no major sights in the neighborhood, but it's just a gorgeous area to walk around, especially close to the river.
The Basilica di Santa Croce. Photo: Rhododendrites, CC BY-SA 4.0, via Wikimedia Commons
Lunch at the Sant’Ambrogio Market
After your wander in Santa Croce, walk up into the area that surrounds the Sant’Ambrogio market. This section of town feels quite local and has a nice mix of shops, restaurants, and cafes that are markedly less touristy than the historic center.
The wonderful Sant’Ambrogio market, where you should have lunch, is a market entirely dedicated to the sale of local Florentine and Tuscan products - locals do their shopping here - and there are a number of good restaurants.
I won't tell you a specific restaurant to go to because the best thing to do is grab a few things from various restaurants/kiosks so that you can try lots of typical Florentine cuisine.
Fruit vendors at the outdoor area of Mercato Sant’Ambrogio. Photo: Sailko, CC BY-SA 3.0, via Wikimedia Commons


Afternoon & Evening - A visit to Fiesole
Head out to the hills in nearby Fiesole
Enjoy a well-deserved leisurely lunch then take an outing to airy Fiesole, an ancient town that despite the proximity to the Tuscan capital feels like another hilltop village.
The pleasant bus ride up green hillsides takes less than half an hour and at the end of the road are sweeping vistas over the valley below, cooling breezes, and even some Roman ruins.
If you're felling active, you can also walk up into Fiesole along a pedestrian path. From central Florence it'll take you 1-2 hours depending on your level of fitness. While it's uphill, it's not strenous. Even so, you could also take the bus up and then walk back down if you want an easier experience.
Fiesole's town center
Sunset cocktail in Fiesole, dinner back in Florence
Return to Florence for you final dinner, but don’t rush away from Fiesole. Enjoy a cocktail on a breezy café terrace and watch the sun set over the city below.
In fact, many Florentines make the trip up here at the end of a work day for the lovely end-of-day experience.
You could linger for dinner in Fiesole, but I think it's a bit more atmospheric to end your stay here with a dinner in Florence proper.
Looking out from the Fiesole hills


Day 4 bonus - a day trip
Montefioralle, in Greve in Chianti
If you have a fourth day or if you pack the itinerary I've listed into just 2 days, then I think taking a day trip into the countryside is a great idea.
Florence is in an excellent location for day trips, with a whole host of wonderful places within an hour's drive or train ride.
Below, I've listed a few places that I think make for the best day trip choices. You'll note that I have not included Montepulciano or the Val d’Orcia, which is because they're simply too far away and not a good use of time.
Chianti & Siena
Beginning right on the outskirts of Florence (to the southwest and northwest) is the wonerful Chianti wine region, one of the most beautiful areas in Tuscany. It's a hilly landscape of vineyards, olive groves, dense forests, and pretty stone villages.
The main road that cuts through the region is the SR222, also called the Chiantigiana, and all along it are dozens of wineries where you can stop to taste the Chiantis and Super Tuscans that put the region on the wine map.
The city of Siena is at the far southwestern edge of Chianti, and is easy to include in a full day of touring. You could spend an entire day in just Chianti or just Siena, but if you won't otherwise be visiting, I really think getting to see both is ideal. Read more about it in my guide to Siena.
Typically, I recommend spending the morning visiting a few vineyards, a couple of the pretty medieval villages (Greve and Castellina make for a nice mix), and driving around Chianti's gorgeous scenery. Then, in the late afternoon you can visit Siena, making sure to enter the Duomo and go for an evening walk in the center when it becomes its most atmospheric.
While you can reach Siena by bus, you'll need a car to see any of Chianti. If you won't have one, here are some tour options:
Private Chianti day trip with Stefano - Sommelier and outdoors guide Stefano Mazzantini runs great day trips to Chianti, including visits to vineyards you'd never be able to visit on your own. He has all different tour options, ranging from walking winery tours (my favorite), to e-bike tours, and then more standard ones by car. You always have the option to add on a visit to Siena.
Small group Chianti wine tour - This tour visits 3 wineries, stops in the town of Greve, and includes lunch. It's a bit more expensive than some group tours, but it caps group sizes at 15 instead of the 25-50 people that many allow.
San Gimignano
San Gimignano is a lovely little town about 1 hour from Florence. It's famous for its many towers which were built in the Middle Ages by noble families who were each trying to one-up each other in a show of wealth and power.
Because the town itself is very small, most tours here also stop at a few other places, usually Siena and Monteriggioni, both of which are close by.
You can read more about Siena in my guide to Siena.
Public transport to San Gimignano is quite poor, so you'll need a car or to book a tour. Here are some options:
San Gimignano, Siena, and Pisa - This is an absolutely packed day, with a duration of almost 12 hours. You first visit Siena, then have lunch in the countryside, before heading to San Gimignano. In the late afternoon, you visit Pisa and then return to Florence. I personally think it's too much for a single day, but if you have limited time in Tuscany, it lets you see many of the highlights. Group size is capped at 15.
San Gimignano and Siena - Also a small group tour, this cuts out Pisa, allowing you to have a more relaxed experience and better enjoy these two gorgeous towns. Lunch at a winery is included in the cost.
Lucca
The wonderful walled city of Lucca is just 1.5 hours from Florence by direct train. It has a lovely pedestrianized city center, Renaissance architecture, and some pretty churches. The city's walls have also been turned into a park, so you can stroll atop them.
Because it's right on the train line, this is one of the easiest places to visit from Florence, and you could realistically even visit in a half-day. I don't recommend taking a tour to visit as there's just no need.
Cinque Terre
The Cinque Terre is a national park on the coast of the region of Liguria, which borders Tuscany to the northwest. There are 5 colorful fishing villages within it that have become world famous, as have the stunning hikes overlooking the sea that connect them all.
To visit the Cinque Terre, you really should spend a minimum of 2 days there, staying overnight. Even that is short and 3-4 days would be much better. However, it is doable as a (very long) day trip from Florence.
To get there, you'll want to take the train to the city of La Spezia (you'll need to make a change in Lucca) and then switch to the local "Cinque Terre Express” train that will bring you into the national park. You can then walk between the towns, take the train between them, or, if the weather permits, use ferries to get around.
If you don't want to go on your own, lots of tours leave from Florence. All day trips from Florence last, at the minimum, 12 hours. Here are a few to consider:
Private Cinque Terre day trip - Run by local guide Stefano (the same guide I recommend for Chianti day trips) this is an expensive, but very exclusive way to visit the region. Stefano is a licensed hiking guide, so can suggest good walks and routes to do together, and you can customize the day to your preferences.
Small group day trip - This is a good option at a reasonable price. You get a guide on the bus and for a section of [optional] light hiking, some free time in a couple of towns, and a train/boat ride in the national park.
Small group day trip with Pisa - This is almost identical to the above tour, but also includes a stop at the Leaning Tower of Pisa on your route.
Arezzo or Cortona
These two cities lie to the south of Florence, both reachable by direct train. Arezzo is less than an hour away, while Cortona is 1.5.
Of the two, Cortona is undoubtedly the prettier city, but it's also much more touristy. It's located on the top of a hill overlooking the agricultural Valdichiana valley and shimmering Lake Trasimeno. It's a really pretty place to walk around.
Arezzo is not as impressive as Cortona, but is still lovely. It's a medieval city with stone walls and a lovely center. Although tourists have started to visit, it receives a fraction of the attention of other cities, so it's a nice place to visit if you want to see somewhere a bit more local.
Like with Lucca, there is no reason to book a guided tour to visit either place.
More Tuscany travel info
For more advice on planning your trip to Florence, Tuscany, and Italy, have a look at some of our other guides and itineraries!
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