Siena, a medieval town in Tuscany, Italy is definitely worth visiting. The town boasts of rich history and culture that can be seen in its art and architecture. Its proximity to renowned Italian wine regions also makes it a great destination for wine lovers. Siena also offers various activities including Tuscan wine tastings and cooking classes. With so many things to do and see, it’s no wonder why Siena is a popular tourist destination.

When we tell others we are full-time travelers, one of the most popular questions people ask is: “Where should I go?” The honest answer is: “It depends.” The best destination depends on what you want to do on your trip.

Every city is different and has its pros and cons. We can’t say which city is best or our favorite because we like them all (or, at least, most of them) for very different reasons.

When we start thinking about where we’re going to go next, we consider several factors. Some are given more weight than others, but we want to ensure the destination has what we’re looking for and that there are no disqualifying issues (like weather or crowds).

To help you decide if Siena is a good choice, we’ve analyzed a list of factors we consider when choosing a destination and answered the frequently asked questions.

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We spent two weeks in April in Siena and felt like we knew the city well. Based on our experience, we assigned each factor a score from 1 to 5, with one being the worst and five being the best. If the attribute is unavailable or does not apply, we give it a 0.

If you’re asking yourself, “Is Siena worth visiting?” hopefully, this information will help you make a more informed decision.

Some factors may sway you in one direction or another, depending on your circumstances and interests—for example, the weather. If you like to go to the beach, you may be looking for hot weather in the summer. If you like winter sports, you may be looking for cold weather in the winter. On the other hand, if you want to explore the old town (like us), you may be looking for milder weather in the summer and winter. For this reason, you may need to take your situation into account.

While there are some exceptions, we assume the weather will be good in the Spring and Fall everywhere we consider visiting. So, we focus primarily on the Summer and Winter weather.

Hot in the Summer – 2

We were not in Siena during the summer months, but the average highs for June, July, and August are 80℉, 87℉, and 86℉, respectively.

Cold in the Winter – 3

We spent the first two weeks of April in Siena, and the weather was cold but not too cold to keep us from going out during the day. We wore jackets, hats, gloves, and scarves. Our French Bulldog, Gus, loved the weather since he quickly overheats. It did rain often, so pack waterproof shoes, a raincoat, and an umbrella. Also, make sure your waterproof shoes have a grip sole. The stone gets very slick when wet. I didn’t have a pair and have since purchased a pair of Gore-tex hiking shoes for the smooth stone often found in old towns.

The average highs for December, January, and February are 49℉, 49℉, and 51℉, respectively.

Few Tourists in Large Groups – 2

There were lots of tourists in large groups. In addition to large groups of tourists, there were many large groups of students.

Few Cruise Ship Passengers – 5

Siena is not a cruise ship port and has no cruise ship, passengers.

Few Tourists in Couples or Small Families – 2

There were lots of tourists as couples and small families. We were there in early April, which I thought would be off-season, and there were many tourists.

Pedestrian Only Areas – 4

Vehicles are limited in Siena, but they are still around, and you need to watch out for them. It is a pedestrian-dominated area with some taxis and small city buses trying to get through.

Lines at Attractions – 5

We did not wait in lines at the sites even though many tourists roamed the streets.

Beaches with Calm Water (Kid-Friendly) – 0

Siena is landlocked and there’s not a lake or river in sight, so beaches are not an option.

Beaches with Rough Water – 0

Boating Activities/Kayaking – 0

Rocky Swim Spots – 0

Sunbathing – 2

Some hotels near Siena have pools that would allow you to sunbathe in the Tuscan sun but sunbathing on the beach is not an option.

Wine – 5

Siena is in the Tuscany wine region, which produces fantastic red wines including the popular Chianti. These wines pair perfectly with the steak and prosciutto of the area.

Insider Tip: If you want to buy excellent table wine like a local, go to a bulk wine shop (vini sfusi).  For more information, read our article titled “How to buy bulk wine like a local in Siena.” We went to all the bulk wine shops in Siena, developed a relationship with one shop, and went there regularly (perhaps, too regularly, according to our waistlines).

Beer – 1

Siena is not in a beer-production region and is not known for beer.

Specialty Liquor – 2

Siena is in the Tuscany wine region, not one of Italy’s regions producing Grappa or Limoncello.

Specialty Food – 3

The specialty food that Siena is known for is its cured meats and cheeses.

Seafood – 1

Siena is landlocked and is not known for its seafood.

Meat – 5

Siena is a meat-eating destination. All your carnivore desires will be sated with regional steaks and cured pork products.

Street Food – 2

Siena is not a street food destination. There are sandwich shops, but I wouldn’t say it offers fantastic street food.

Large Food Market with Restaurants – 2

Siena does not have a large food market. It does have large specialty stores that offer cheese and salumi, which are fun to shop at.

Experiences

Want to learn about the local food and wine of Siena? Book a highly-rated food and wine experience in Siena!

History – 5

Siena is one of the best places to dive deep and get lost in Italian history. The best way to start is with a tour of Siena. Our travel guide includes a suggested itinerary for a walking tour of the city. Alternatively, there are many organized small group tours that will introduce you to the rich history of Siena.

Architecture – 5

Siena has amazing architecture and the entire town will transport you back in time. The historic center has been designated as a UNESCO World Heritage Site, which attests to its status as one of the best-preserved medieval cities in Italy. The must-see architectural sites are the Duomo di Siena and the buildings in the Piazza del Campo and the Piazza del Duomo.

The Piazza del Duomo is home to some of the most magnificent treasures of Siena, including the Cathedral, the Crypt and the Piccolomini Library. The exterior of the Gothic-style Siena Cathedral has a beautiful white marble facade designed by Giovanni Pisano whose work was inspired by his father Nicola Pisano. The cathedral houses works by famous artists like Donatello, Nicola Pisano, Michelangelo, and Pinturicchio.

Art – 4

Siena is definitely worth visiting for art lovers. The city is known for its impressive collection of Renaissance and medieval art.

The interior of the Siena Cathedral features stunning artwork by famous artists such as Pisano, Donatello, Bernini, and Michelangelo. Additionally, the Piccolomini Library in the cathedral showcases well-preserved frescoes by Pinturicchio, a renowned painter from the Renaissance era.

The Museo Civico, located in the Palazzo Pubblico, houses some of the most iconic artwork from Siena’s rich cultural heritage. Significantly, it features the fresco cycle of Good and Bad Government by Ambrogio Lorenzetti that covers three walls.

Museums – 4

We got the city pass and went to all the museums. They were excellent.

A couple of combination ticket passes in Siena help you save money on museums. One is the Opa Si Pass which gives you access to the Siena Cathedral, the Baptistery, the Piccolomini Library, the Crypt, and the Cathedral Museum.

The other is a Municipality of Siena combo ticket. We purchased ours at the Civic Museum ticket office. There are different combos that you can do. We did the full combo, which included the Civic Museum, Santa Maria della Scala, climbing to the top of the Torre del Mangia, and the National Art Gallery of Siena.

Castles – 0

Siena does not have any medieval castles.

Walled-City – 4

Siena is a great walled city. Ryan loves city gates, so we walked to every gate.

Palaces – 4

Siena has some lovely palaces.

Hiking – 2

Siena is not a hiking destination, and there are few hiking trails around the city.

For more information on Siena hiking, check out AllTrails.

Insider Tip: Take the train down the Ligurian coast to Cinque Terre for some incredible hiking.

Running – 2

You can run in Siena, and we saw people running and even a small race. But the hilltop location makes for a hilly run with hard cobblestones.

For more information on Siena’s running routes, check out Map My Run.

High – Fashion Stores/Shopping – 2

Siena is not a high-fashion shopping destination. It is a red wine, cheese, and prosciutto destination…. so, bring forgiving clothes.

Nightlife – 3

Siena has many busy bars and restaurants that seem to close early. We stayed in the heart of Siena, a stone’s throw from Piazza del Campo, and the area was tranquil when we went out for Gus’s evening walks. In our experience, it’s not a late-night party city.

Dog Friendly – 3

Siena is dog friendly. Dogs are welcome inside shops but are not allowed in restaurants and grocery stores. The locals are very dog friendly.

Kid Friendly – 2

We don’t have kids, but we saw some kids in Siena. They seemed to enjoy climbing the Torre del Mangia and the Facciatone, but other than that, there didn’t seem to be a lot of kid-friendly activities.

Experiences

Want to learn about Siena’s history with a guide? Book a highly-rated Siena city tour!

Great Grocery Stores – 3

The grocery stores in Siena were medium-sized and had a good selection.

English Widely Spoken – 4

English is widely spoken in Siena.

Outwardly Friendly Locals – 4

We found the locals to be very friendly. We did have our Frenchie, Gus, and they are very friendly toward dogs – so that helped.

American Tourists – 5

If you like to see and talk to Americans, this is the place for you. There are lots of Americans in Siena.

Accessible by Train – 5

Siena has a train station ready to take you pretty much anywhere else in Europe you want to go.

Day Trips by Train – 5

There are lots of day-tripping options available from the train station, but Siena is a popular base for exploring Tuscan towns not on the train line by car. The popular towns are San Gimignano, Montepulciano, and Montalcino. You can explore these towns by taxi, private transfer, or renting a car and driving. For taxis and private transfers, we recommend GetTransfer. For rental cars and price comparisons of national and local brands, we recommend Discover Cars.

Clean Streets – 4

The streets of Siena are clean.

Noise – 4

Siena was not very noisy. This could be because the restaurants and bars closed relatively early. As mentioned above, it was very quiet when we took Gus out for his evening walk.

Food Cost – 3

Siena is an expensive city, and food is not cheap, but there are many budget-friendly options.

Accommodation Cost – 2

Siena accommodation is very expensive. It was one of our most expensive Airbnb stays.

Activities Cost – 4

The tickets to the local sites are not expensive since they offer combined tickets, and you can spend most of your time walking through the beautiful streets for free, which makes the activity cost low.

Transportation Cost – 4

The local train station makes transportation costs low.

If taking the train is not your thing, you can use a taxi, private transfer, or rent a car and drive. For taxis and private transfers, we recommend GetTransfer. For rental cars and price comparisons of national and local brands, we recommend Discover Cars.

Siena is a charming city in the heart of Tuscany that boasts many unique attractions and experiences. One of its most famous landmarks is the Piazza del Campo, which features the beautiful Gaia Fountain (Fonte Gaia) and doubles as a race track for the Palio di Siena horse race twice a year. The Siena Cathedral, perched atop a hill overlooking the piazza, is also well worth a visit for its stunning architecture and historical significance.

Yes, Siena has historic buildings, hilltop location, beautiful Tuscan countryside views, grand main square, and unique fountains.

If you are planning a trip to Siena, we recommend spending at least two busy days exploring the hilltop town. This will give you enough time to soak in the Tuscan views, marvel at the Piazza del Campo, and visit some of its famous sites, such as the Siena Cathedral. For a list of the top things to see and a suggested walking tour, check out our article “19 Best Things to See in Siena, Italy.”

Yes, Siena is very expensive. It is a popular tourist destination in the heart of Tuscany but small in size and located on the top of a hill. So, there is not an abundance of hotel and dining options, resulting in high prices for everything.

Yes, Siena is very safe.

There are many great places to stay in Siena. For the best experience, we recommend staying near the Piazza del Campo (the castle marker on the map below).  It is centrally located, near the most popular sites, and is where the best restaurants and bars are located.

Here’s an interactive map with hotel and apartment options that can be filtered to meet your needs. Select your travel dates to get specific availability and prices.

Book your stay now!

The time of the year with good weather and fewer crowds is often referred to as the shoulder season. The shoulder season in Siena is March, April, October, and November. For many, this is the best time of the year to visit.

We spent the first two weeks of April in Siena. The first week was cold, but it warmed up the second week. There were tourists, but it was manageable and didn’t impact our enjoyment of the city.

If you fly into Florence Airport, you can get to Siena by train (with a short tram ride on one end and a short taxi or bus ride on the other).

First, you travel to Florence’s main train station, Firenze Santa Maria Novella (SMN), by tram. The tram will drop you off in front of the train station. From the Florence train station, you can take a regional train to the Siena Train Station. It is a 1 hr 30 min train ride. The Siena Train Station is at the bottom of the hilltop town. To get to the top, you can take either a taxi or the bus. We have heavy luggage and a French Bulldog so we took a taxi from Siena train station to the top of the hill and it cost 12 euro.

If all that is not your thing, you can get to Siena by taxi, private transfer, or renting a car and driving. It is a 1hr 15min drive. For taxis and private transfers, we recommend GetTransfer. For rental cars and price comparisons of national and local brands, we recommend Discover Cars.

It is not necessary to speak Italian to visit and enjoy Siena. A large percentage of the locals speak English.

Your Siena packing list should include very comfortable walking shoes for the hard cobblestones.

Do you need wifi during your trip and don’t want to pay for roaming? We use eSIMs from Airalo during our travel and highly recommend them. They are cheap, easy to set up, and allow you to leave your primary sim card in your phone (so you don’t loose it). Click below for more info.

Siena is located in the Tuscany region of Italy. Tuscany is in central Italy and is famous for its red wine, cured pork, and hilly countryside.

Siena is a hilltop city in central Italy. It is a 1hr 30min train ride south of Florence, a 2hr 30min ride south of Bologna, a 3hr ride north of Rome, and a 4hr 15min ride south of Venice.

Both Florence and Siena are beautiful Tuscan cities with their own unique charm and attractions. Florence is known for its Renaissance art and architecture, while Siena is famous for its medieval town center and the Palio horse race. Each city has its own culture, history, and atmosphere that make them worth visiting. Ultimately, which of these Italian cities is nicer would depend on the traveler’s interests and preferences.