by Lisa  |  5 October 2022

white marble female statue looking up in ponder

‘So which city do you prefer more, Siena or Florence?’ asked Ginevra, my Italian roommate at the Siena Hostel. Not to offend anyone, I replied quite diplomatically ‘I like all cities I explore’. She shook her head and said ‘Here in Italy, you’re either a Siena person or a Florence person’.  

This intrigued me, that you had to be only one type of person. Perhaps it stemmed from the long history of rivalry between these two Tuscan cities. For centuries they’ve had many political and war battles. 

I had visited Florence many years earlier on a Contiki tour. But as those whirlwind tours means you only spend one night at each place, I didn’t really get a chance to properly explore the city and get a sense of its vibe. So, I told my new friend, ‘After Siena I shall go and explore Florence and then I will let you know if I’m a Siena or Florence girl’. 

We exchanged Facebook names and off I went. I made a mental note of the differences and strangely enough, I realised that I did have a preference. But before I let you know whether I’m a Siena or Florence person, below are my notes of what I noticed, experienced and felt between the two cities. And I share some of my handy tips, as well as on the dedicated Italy travel tips page.

Also, you’ll find the following information useful if you’re limited on time and you are trying to decide whether you should stay in Siena or Florence. 

 
The historical centre 

As with most cities in Europe, there is always the charming historical centre. The birthplace of the original town. Then as the population grew and architecture styles changed, the ‘new’ town grew around it. I’ve mainly focused on the historical town centre. 

Siena 

Siena’s historical centre is smaller in size. But it makes up for it with its distinctive Italian gothic architecture, very large town square and winding streets.  The town does sit on a hill and most of the buildings are from the 12th to 17th centuries. 

As you stroll around the cobble streets of Siena, it may feel like you are getting horribly lost. But remember this, all roads lead to Piazza del Campo. It’s a huge piazza, which gradually slopes downwards towards the tower and Civic Centre. Just like a natural amphitheatre. All the way around its lined with restaurants. 

view of piazza del campo in Siena central

Piazza del Campo, Siena  [photo by author]

You can either marvel in this massive square from the ground by sitting at one of the many cafes sipping on a cool aperol spritz. Or from above, after you’ve climbed the tower of Torre del Manjia. It's worth the 400 steps for the views of the old town below. And is the best vantage point to see the surrounding countryside with its rolling hills dotted with vineyards. 

HOTEL RECOMMENDATIONS...
table and chairs under an umbrella overlooking the tuscan hills

By staying just outside the historical city gates, you can save money and get dreamy views over the stunning Tuscany hills. Only a 15 minute walk to the centre.

grand hotel foyer with chandeliers and fresco paintings on the walls

Feel like you are staying with the 17th century Tuscany elite. This luxury 5 star hotel, located in the historical centre, features frescoed ceilings and period furnishings to match. Treat yourself.

Florence 

The historical centre of Florence boomed during the 15th and 16th centuries, under the influence of renaissance period and the Medici family. In later centuries, the modern part of Florence then sprawled widely outside the 14th century walls. Hence the reason why you can't see the surrounding countryside from any tower in the historical centre.  

View overlooking florence city from piazzale michelangelo

View overlooking Florence from Piazzale Michelangelo  [photo by author]

Due to its social and urban achievements, the town centre was built with wide main thoroughfares, as well as smaller cobblestone streets. Many churches, beautiful ornate buildings and museums were also built in a style that became known as renaissance style architecture. It was the powerhouse of Italy, politics and the arts. That makes sense as it seems a lot busier than Siena, with more activity and people. 

Although it's still a medieval town in essence, it somehow feels modern too. Therefore, Florence has a more cosmopolitan feel about it. 

HOTEL RECOMMENDATIONS...
table and chairs on a rooftop terrace with florence cathedral in the background

Stay right in the heart of Florence within steps of all the major attractions. Then relax at the rooftop terrace overlooking Florence Cathedral. The hotel is beautiful blend of modern and renaissance furnishings. 

bathroom setting with black and white chequered floor and an open window overlooking Florence cathedral

This hotel is so central its located right next door to Florence Cathedral. They have elegant rooms, with some boasting views of the cathedral. 

Battle of the cathedrals 

You need to see both cathedrals for different reasons. One is impressive on the inside and the other for the outside decorations. 

Siena 

Inside the lavish siena duomo, made of marble and fresco paintings

Inside Duomo di Siena (Siena Cathedral)  [photo by author]

The façade of the duomo di Siena does have intricate carvings on the outside. Not so much shiny gold bits but it's still pleasant to see. But, it’s the inside that wow’s you. 

We spent an hour walking through this impressive church. It’s almost like a museum with paintings by Donatelli and Bernini. Plus, a sculpture by Michelangelo. There’s a cool library with the most amazing frescos on the walls and the biggest sized books you’ve ever seen. No expense was spared for this lavish cathedral.  

The highlight for me was the 30-minute Gates of Heaven tour, which involves walking around the top of the cathedral. The commanding views from above looking down into the impressive cathedral gave another perspective. Even got to see the original gargoyles that now live under cover to preserve them (copies are on the façade now).  

view of front facade of Siena duomo

Check out Viator's selection of 'skip the line' tickets. Includes options to combine it with a Siena walking tour.

Florence 

So can you guess what is impressive about the Florence Cathedral? Yep, it’s the exterior of the building.  

View of Florence duomo, front view

Florence Duomo (cathedral)  [photo by author]

I think it’s the most beautiful cathedral in all Europe because it isn’t decorated in the typical colours and designs you see in other European cathedrals. The exterior is a beautiful mix of white, jade green and pink coloured stone, adorned with so many ornate carvings. It’s so striking to look at because it is so different.  

The inside however was disappointing. There was no extravagance like at duomo di Siena. The cupola (dome section) does have beautiful frescos but is too high up to truly appreciate it. And the walls have lovely stained glassed windows, but that’s it. So to make it a more enjoyable and fuller experience, I would recommend paying extra for the Brunelleschi Pass. It includes a walk around the side of the cupola to view the frescos from close range and the bell tower climb. 

TG Tip:  Females are not allowed to wear shorts inside. Which seemed unfair as men could wear shorts and they allowed females in wearing short dresses. I quickly fixed the problem by wrapping my sarong around my legs! 

view of Florence cathedral dome from above

Check out Viator's selection of 'skip the line' tickets. Includes options to climb the bell tower and close up view of the dome interior. You can also pre-buy tickets to multiple museums.

Cultural differences 

Siena 

It felt like that Siena is deeply rooted in and proud of their medieval cultural traditions. In fact, it's probably one of few Italian cities where you can feel the atmosphere of the Middle Ages. Travellers can be sure to witness an interesting medieval celebration of some sort. 

horses racing around a dirt track around spectators in the middle, in a town square

Siena's Piazza del Campo converted into a racetrack for the Palio.

  • The Palio (Corsa del Palio) is a horse race that occurs every year on 2 July and 16 August. This medieval festival began in 1482 and features an exciting 1-minute horse race. The day starts with a colourful street parade, representing the 17 ward organisations of the city. In medieval times they were rivalry military companies. Only ten wards are selected to race. The jockeys dress in typical 15th century costume and race bare back frantically around the Piazza del Campo three times. Its quite a spectacle. 
  • The Feast of St Joseph is celebrated on March 19 every year with street banquets. Long tables are set up in the streets with food and treats. The city also hosts colourful shops and fairs, selling dolls and toys. Again, this festival stems from medieval times where drought was near to causing starvation. A prayer was made to St Joseph which miraculously brought in the rains thereby saving the crops. 
a row of traditional costumes housed in a glass case

If you will miss the spectacle or couldn't get a ticket, the next best thing to do is learn all about the traditions and get insight into a Contrada's daily life. 

Other medieval festivals in surrounding areas include: 

  • Monteriggioni di Torri si Corona takes place at the beginning of July at Monteriggioni fortress. Musical performances by folk groups and local dish tastings. 
  • The La Disfida della Valdelsa is held early June at the open-air museum of Parco Archeologico di Poggibonsi. It includes nightly tournaments and buhurts, reconstruction of a battle, craft fairs, tasting dishes and falconry. 
  • Medioevo In Rocca festival is hosted by the town of San Gimignano. A colourful procession meanders along the main street, with participants parading in medieval clothing of real noble men of the time. You can also expect craft fairs, exhibitions, musical and theatrical performances. 

Florence 

Florence on the other hand is steeped in art history. After all, the Medici family could be held responsible for single-handedly giving birth to the renaissance period. They heavily invested in the best artists to attract them to Florence and as a result the city has the most amazing museums to showcase all this work.

Frescos and sculptures displayed in a grand room

Inside the great town hall of Palazzo Vecchio (Old Palace) [photo by author]

  • Museo di Palazzo Vecchio was a pleasant surprise. The Town Hall rooms were all grandly decorated with frescos on ceilings and walls. Some rooms were lined with sculptures, including one by Michelangelo. The ticket includes a climb up the tower where there is a special platform to take a selfie with the Florence Cathedral dome and tower in the background.  
  • Uffizi Museum requires 3 hours of your time if you want to see and read about every artwork in this huge building. Lots of busts, sculptures and paintings. The most famous being the Bottecelli’s ‘Birth of Venus and Spring’. 
  • Accademia Gallery is most famous for housing the incredible Statue of David. Much better seeing the real thing than cheap copies. The whole statue shone brilliantly in the centre. 

TG Tip:  Note that government run museums all over Italy close every Monday. But privately owned museums stay open

TG Tip:  To avoid long queues or see two museums in one day, I would recommend purchasing a ‘reserved’ ticket online. They cost about an extra EUR4 per ticket, advertised as ‘skip the line’. In actual fact, you queue in a separate line to other tourists, but it moves much faster as they have priority.  

female white sculpture looking up to the ornate ceiling

Uffizi Gallery tickets

Check out Viator's selection of 'skip the line' tickets. You can opt to have a guided tour or breakfast included. Perhaps combine your purchase with multiple museums.

statue of david - white marble male figure with tourists below

Accademia Gallery tickets

Check out Viator's selection of 'skip the line' tickets to visit the Statue of David. With options to include a guided tour.

TG Tip:

I highly recommend reading Paul Strathern’s ‘The Medici, Godfathers of the Renaissance’.  It gives a thorough historical account of the family, how Florence grew and their contribution to the arts. Even better is to read it while you’re in Florence, as majority of the buildings mentioned in the book are still standing today. You’ll gain a greater appreciation of Florence’s architecture

 

The shopping 

Siena 

Shopping in Siena is a mix of the old and modern world. As you walk around the narrow old town streets, you are flanked with the high medieval buildings made of stone. But as you peer into the shop windows or walk through the doors, you step inside into the modern world. It looks like any other shop at your local shopping centre. After you make your purchase and you step outside, you’re back into the old world again. 

The main shopping street is Via Banchi di Sopra. It is lined with boutique shops selling the usual Italian ware of clothes, bags and shoes. However, be daring enough to veer off the main track to explore the smaller streets. Via Pantaneto or Via di Citta for local is great for handicrafts, ceramics and Italian souvenirs.   

Shopping in Siena is a quiet and relaxing experience. And if nothing takes your fancy, then head back into the main plaza, sit down at a café, order an Aperol spritz and watch the people and world go by. 

Florence 

There’s lots of shopping opportunities in Florence which I roughly categorise them as follows: 

  • Upmarket shops, like Prada and Gucci, can be found mainly along Via De’ Tornabouni, and Via Delgi Strozzi that leads to Piazza Della Republica. 
  • High end medium-priced shops are located along and in-between Via Roma and Via De Calzaioli 
  • Lower end shops are typically found along on the roads that radiate from the Florence Cathedral and Basilica di San Lorenzo 

Or you can browse at one of the city markets: 

  • Mercato Nuovo, located along Via Calimala, is known for its leather goods and scarfs. It’s only a block away from Piazza della Signoria. 
  • Mercato Centrale (Central Markets), located along Via dell’ Ariento west of San Lorenzo, is a covered market selling fresh produce. Treat yourself to lunch at the gourmet food court. 
  • San Lorenzo outdoor market consists of small stalls set up in the streets of San Lorenzo neighbourhood, around the Mercato Centrale. Browse the leather goods, clothing and Florentine souvenirs.  
two woven gold bracelets laying on a green table

Guided Shopping Tour in Florence

Have your own personal guide to shop for jewellery on Ponte Vecchio and a reputable showroom. And then visit the leather district.

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Eat like a local 

All Italian food is delicious. However, you can find dishes that are unique to the area, as below. 

Siena 

When I visit new lands, I like to eat the local fare. I want to eat what the locals eat. In Siena, the local cuisine is basic but flavoursome. You must try at least one of the following: 

shop front of a cold meats deli, with a pink wooden pig in front

A typical salumeria.  [photo by author]

  • Local cured meats such as Capocollo and Finocchiona. In the backs streets you will find salumeria’s, a small shop selling cured meats, cheeses and wine. Find one with a sit-down area and order all three. 
  • Go for local pasta called Pici. The rustic made pasta is a long and thicker spaghetti to what we are normally accustomed to. It always comes with a nice rich sauce. 
  • Another pasta dish is Paglia e fieno. It’s a combination of yellow and green (made of spinach) tagliatelle pasta, combined with onions, prosciutto, peas, olive oil and cream.  
  • For meat lovers, look for dishes containing chianina beef (raised in local pastures) or Cinta Senese (local breed of pigs that produces delicious meat). 
  • As for typical desserts, it consists mainly in the form of biscotti (biscuits). The most popular ones are cantucci, panforte, cavallucci and ricciarelli. Try them all! 
group of females standing around the cooking bench in a kitchen

Siena cooking classes

Check out Viator's selection of Italian cooking classes in and around Siena. Bring home with you the skills to create traditional Italian meals when you get home.

Florence 

The typical food in Florence also contains pasta and meats, just like in Siena but with their own style. 

  • Bistecca alla Fiorentina, or Florentine steak is the most famous dish in Florence. It’s a dish to share as it consists of a very large t-bone steak, also from the ancient breed of cattle called Chianina.  
  • If visiting in the winter, you must warm yourself up with a hearty Ribolitta. It’s a tomato based soup loaded with beans and green vegetables. It’s like a reheated vegetable soup. 
  • A traditional Florentine meal is Pappardelle al Cinghiale, which translates to ribbon pasta with wild boar. Firstly, they dry the meat and then marinated in a wine sauce overnight. The delicious flavour goes so well with al dente pappardelle pasta! 
  • And for dessert the Florentine have Schiacciata al Uva, which means smashed bread with grapes. It looks like focaccia bread with a grape sauce smeared over the top. Delicioso! 
aerial view of a plate of pasta

Florence Foodie tours

Check out Viator's range of foodie tours. Have an expert show you the best food options for sampling Florence delights. You'll get to learn the locals favourite haunts and where to get fresh food.

The nightlife 

Siena 

I find the historical centre of Siena quiet and relaxed in the evenings too. The locals and tourists alike enjoy the traditional evening stroll along the streets, mainly through Banchi di Sopra. A bit of window shopping or chatting with friends.  

People milling around Sienas central square in the evening, lit up by soft lights.

Siena's Piazza del Campo, in the evening.  [photo by author]

We strolled from café to café or bar to bar, which are all small and intimate. My favourite pastime though was to lounge around at one of the bars in Piazza del Campo. Sometimes you are treated to live music or performances by improvisational entertainers such as fire eaters or clowns.  

For those who like a bit more action, don’t worry. Siena is a university town, so you can still find in the old town a couple of lively bars with loud music that stay open until 2 or 3am. 

Florence 

Florence has a livelier nightlife and more options than Siena. This is the city for people who like to go out in the evenings. 

Florence skyline view at night with lights on buildings and along the riverfront

Florence by night. Santa Croce area is around the church to the right of this photo.

The Santa Croce area is considered the heart of the nightlife in the historical centre. It extends from the Arno river to Piazza di Santa Croce, along Via dei Benci and some of the smaller adjacent streets.  It’s full of bars, restaurants, wine bars and pubs.  

If visiting during the summer, ask the locals where’s the best rooftop bar. Nothing better than to sit high on a roof terrace, sipping on Aperol spritz while the sun glistens over Florence. 

Of course, you can still find bars scattered around in other parts of the old town but its more concentrated in Santa Croce area. Alternatively, you can head over the river Arno to explore the Santo Spirito district. It's known for its Florence born drink Negroni, made of red vermouth, gin and Campari. Or the neighbouring San Frediano district for cocktails and more modern fusion foods. 

a group of people saluting with their beer glasses

Explore Florence by night

Check out Viator's selection of nightlife tours. Discover typical Tuscan drinks and the best bars, while at the same time making new friends. One tour incorporates the sunset too!

The wines 

I am a wine lover, so I had to add this section in. I sampled as many wines as I could from the Tuscan region. The whole wine growing area of Tuscany is divided into sub regions. And each region is known for their own type of wine. Influenced either by grape variety used or it’s fermenting process. Therefore, what you like depends upon your own palate. But I will let you know my favourite... it was the Brunello wines from the Montalcino region. 

Group of people sitting at a table sampling red wine

Sampling Brunello di Montalcino wine at Abbadia Ardenga winery  [photo by author]

Around Siena: 

  • Visit Pienza and Montalcino for Chianti and Brunello wines. Be sure you know how to read labels before you buy Chianti wines.
  • I don’t know what came first, but you will find the dark red Montepulciano wines in the town of Montepulciano! 
old medieval town sitting on a top of a green hill

Siena wine tours

Check out Viator's selection wine tours from Siena. Visit famous Tuscan towns such San Gimignano, Monteriggioni, Montalcino, Montepulciano and Pienza. Not only do you sample great wine, but also marvel at the beautiful Tuscan hills.

Around Florence: 

  • The Carmignano is a dry red wine from Prato region. About 20km west of Florence, they were the first to blend Sangiovese with Cabernet Sauvignon grapes. In 1716, the grand duke Cosimo III de’ Medici granted the region special legal protections due to its superior wine making skills.  
  • I don’t know what came first, but you will find the dark red Montepulciano wines in the town You’ll also find here the Chianti Classico wines and Florence is at the northern end of the Chianti region.of Montepulciano! 
glasses of wine and grapes sitting on a barrel overlooking the  vineyard

Florence wine tours

Check out Viator's selection of wine tours from Florence. Visit a variety of vineyards in Tuscany's beautiful chianti region. A nice break from visiting museums!

Exploring the surrounding countryside 

Siena 

There are a myriad of smaller towns to visit outside of Siena, making it a great base to visit the following towns. Below are some of the best day trips from Siena. 

  • Monteriggioni is a small town 30 minutes away, with an old fortress perched on a hill. Only a few tourists walking around the old fortress walls, the few artisan shops and two cafes.  
  • San Gimignano is a picturesque medieval Tuscan town about an hour way by bus. The main drag from the gate to the Piazza Cisterna is the busy tourist thoroughfare lined with all sorts of tourist shops. This is one of the places to go if you like ceramics. A definite must is to climb up the tower of Torre Grossa in Piazza del duomo. More stunning views of the chequered rolling Tuscan hills from above. Then finish the day with a glass of vino at fortress Rocca. They conduct free 3D wine tours too. 
  • Pienza, located further afield, is a tiny, cute town perched on a hilltop, as they all are! It was also the most unusual town I saw, in terms of building design. Construction of the buildings were at different angles to each other.   
  • Montepulciano will certainly give your legs a workout. It’s quite a hilly medieval town but plenty of cafes and wine shops for a drink or two. It's also worth going up the very narrow staircase of the tower in the main piazza for the majestic views of rolling green hills.  

If you don’t have time to stay in all these towns separately, then seeing them on a one-day bus tour will give you a quick overview and some tastings! 

Florence

Florence is another great base to visit small towns in the northern Tuscan region. 

  • Greve-in-chianti is only an hour away by local bus. A cute one piazza town. The only town centre that I’ve seen in a triangle shape rather than a rectangle. If you don’t have a car to explore the Tuscan countryside yourself, you do have three options for wine tasting. There’s the Enoteca Falorni on the main street. An underground wine store with a unique wine tasting system using a bar card and pressing a button on any wine you want to taste.  An 8-minute walk down the street is Castello di Uzzano, a small tasting cantina as their winery is a further 2km away. And for the more energetic, there is the Viticcio winery about 1km away.  
  • I stopped in the town of Tavarnalle for two nights, just to experience a quiet Tuscan town, away from the tourist hoards. It can quite easily visit here as a day trip as it's only a 50-minute bus ride from Florence. I loved walking around the hills and into local wineries for tastings.  
  • Lucca is the other tourist Tuscan mecca. The still standing fortified walls enclose the historical centre. It's very impressive and reminded me a little of Siena. Only 1.5 hours away by bus or you could join a bus tour. 

If you dont have a car, there are bus tours from Florence to Montepulciano and Pienza. However, if you’re already planning to stopover in Siena, then there is less bus travel time if you take the tour from Siena rather than Florence.   

Summary 

There is a lot of reading above. So, I have condensed all the differences for you in the handy table below, to help you decide if you should stay in Siena or Florence. 


Siena

Florence

HISTORICAL CENTRE 

Gothic architecture. 

Narrow cobblestone roads. 

Super large central piazza. 

Renaissance architecture. 

Wide roads/avenues intermingled with narrow cobblestone streets. 

Several piazzas. 

CATHEDRALS 

Impressive interior 

Impressive exterior 

CULTURE 

Deep roots in medieval traditions. 

Host traditional festivals. 

Rich in renaissance art – buildings, frescos, paintings and sculptures. 

Many museums & galleries. 

SURROUNDING COUNTRYSIDE 

Use as a base to visit: Monteriggioni 
San Gimignano 
Montalcino 
Pienza 

Montepulciano.  

Use as a base to visit :
Greve in Chianti 
Tavarnelle 
Lucca. 

SHOPPING

Small shops located along the main thoroughfare. 

Shopping mecca with all types of shops to suite all budgets, from high end to markets. 

FOOD

Focus on the simpler meals and desserts. 

The dishes like to be big and fancy. 

NEARBY WINE REGIONS 

Chianti Classico 

Brunello di Montalcino Montepulciano wines. 

Chianti Classico 

Carmignano wines. 

NIGHTLIFE

Relaxed atmosphere. 

Small bars and cafes scattered around. 

Livelier atmosphere. 

Santa Croce – concentrated nightlife area. 

THE VIBE 

Gentler and more relaxed atmosphere. 

More upmarket and cosmopolitan atmosphere. 

TG Tip:   If travelling by train from Florence to Siena or vv, I would recommend taking the Regionale train option. Firstly, it's cheaper which saves you enough money for a glass of wine! Secondly, the train travels at a slower pace. It allowed me lots of photo taking opportunities of the chequered rolling hills of farmlands and vineyards. Choose a seat that has a working window that can lower if you want clearer photos.

Are you a Siena or Florence person? 

I thoroughly enjoyed visiting both cities. As you just read, each one provides a unique experience.  

But surprisingly, I did find myself liking one more than the other. I guess Ginevra was right, you’re either a Siena or Florence person. So, which one am I?  Drum roll................ I'm a Siena girl! The Sienese atmosphere is gentler and more laid back, which is more my style. 

So, what about you, which city suits your style? Are you a Siena person or Florence person? Let me know in the comments below. 

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Book your own holiday online using the most trusted travel websites.
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About the author

Lisa is a travel gypsy by heart, having already been to over 70 countries and still counting. Founder of Travel Groove, to share travel tips, tricks and knowledge with other travellers.

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