Siena in Italy: Is It Worth Visiting?

Siena is a beautiful city in the Tuscany region of Italy, with many great aspects. It has historic sites, easy connections to other Tuscan towns, and fantastic food and drink options. We visited Siena for two weeks, staying in a hotel and self-catering accommodation.

Our visit was in August, during the summer, with Henry, which added a new layer to it. I found it quieter than the nearby cities of Florence and Venice during peak times. I loved walking through the narrow medieval streets, seeing the epic attractions, and taking some day trips to local villages.

We also had two celebrations on our trip: my wife’s birthday and our wedding anniversary. Both were great days in beautiful surroundings complemented by good local food.

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About Siena in Italy

Siena is located in central Tuscany and is surrounded by hilly countryside; the city is rather hilly, and it was a good workout getting around daily. It is famous for its history, art, and pretty countryside, which draw visitors, including us. The historic centre is a UNESCO World Heritage Site for its well-preserved medieval architecture.

During the 12th century, the city lay on important medieval trade routes to Rome, bringing prosperity. It is also on a famous pilgrimage route, the Francigena, which runs from Canterbury in England to Rome, the capital of Italy.

Why Is Siena Worth Visiting?

As the city centre is a UNESCO World Heritage Site, there are well-preserved medieval buildings to see or visit inside. The main square, Piazza del Campo, is epic and is a big draw. Duomo di Siena, the city’s cathedral, is also a popular site that sits atop a hill, making it the highest point. Between these, there are other things to do in Siena that can keep you engaged for days.

There are also various museums, cathedrals, churches and one fortress. It was a pleasure to wander around at all times of the day, including some special sunrise dog walks. There are also activities and guided tours on the GetYourGuide website.

Day Trips In Tuscany

There are day-trip options by bus or train, and since we were staying for two weeks, we enjoyed a few for a change of scenery. You can also visit other cities in Tuscany for the day, including Florence, Pisa or Livorno. We have earmarked these for future stays, so we decided to enjoy some unique villages in the Tuscan hills.

We enjoyed visiting Colle di Val d’Elsa, a medieval hilltop town with many historic and beautiful features. Also in Colle di Val d’Elsa, we walked the Sentierelsa Trail and swam in the river near its beautiful waterfalls.

Another day out was a visit to the fortified hilltop village of Monteriggioni, a beautiful place to explore. This was a popular place with cyclists, hikers, and pilgrims walking the Francigena pilgrimage route.

Food and Drink Out

We found it to be an excellent place to dine out for lunch or for dinner. There is a good range of restaurants, and they are quite laid-back, with outdoor seating. Everywhere seemed pet-friendly, so Henry enjoyed some lovely places. Some of the standout places for food were Ristorante La Finestra, Compagnia dei Vinattieri and Osteria La Chiacchera.

As it was summer, lots of refreshment stops were made for coffee, water and beers to stay cool and relax. We found places to sit and chill, including bars, cafes and bakeries. I found many mainstream beers and also some regional craft beer options on my visit. My favourites were outside the popular areas, and as a bonus, they were a bit cheaper. For those interested in cuisine, there are various food tour options.

Shopping For Food

As 10 days of our time here were self-catering, I enjoyed cooking and making breakfasts at our apartment. For food shopping, there are supermarkets, street markets, and small artisan shops. We enjoyed local ingredients, especially the cured meats and pecorino cheeses. I also purchased fresh Pico, the local pasta, and various meats from local butchers to make ragu.

Where To Stay?

We stayed in two places, one in a quiet suburb to the west of the city and one in the centre near the main sites. I enjoyed the hotel in the centre much more, as there was less hassle doing things and the dog walks were more scenic. If on a short stay, I would recommend central accommodation to save time. There are lots of options available on the Booking.com website, including hotels, dog-friendly options and self-catering apartments.

The first of our stays was 10 nights at The Nest Apartment, a 25-minute walk from the historic centre. This was in a quiet neighbourhood and on a handy bus route to the centre. The apartment was OK and had all the facilities we wanted; however, it could have been cleaner.

For the last four nights we stayed at Hotel NH Siena, which was in a lovely building with views of the Medici fortress and the local football stadium. The room was nice and dog-friendly, and everything worked. They also had a breakfast buffet, including cooked breakfast and a few healthier options. This was our favourite, as it was easy to enjoy the historic centre with minimal walking in the heat.

Getting Around The City & Nearby Villages

Public transport is great and easy to use; you have local buses in the city, for starters, where you just tap a bank card when getting on. For pets, there were no charges. For buses to the nearby towns and villages, you can buy tickets on the AT app, which is very straightforward to use. I found the buses mostly ran on time; however, there were some frustrations with 131/130 buses not stopping when heading into the city from our accommodation.

Siena also has a mainline station, which is how we left and arrived. This took us via Empoli, then onwards. You can plan train travel from the city using the Trenitalia app, which is simple to use.

Is the City Dog Friendly?

The city is very dog-friendly, as is most of Italy, and I love visiting with Henry. First up, pet-friendly accommodation was easy to find, and many options had no extra fees for dogs. Food and drinks out were very easy, and we didn’t find anywhere Henry couldn’t visit. Trains and buses were straightforward with Henry, too, and the local buses were free, a nice bonus.

So, is Siena in Italy Worth Visiting?

We had a great time in Siena and enjoyed all aspects of the trip. The historical sites and attractions were all interesting, and we’re glad we visited them. The city was also great for sightseeing walks with nooks and crannies to explore off the main tourist trail. Food and drinks out were a highlight of the trip; the city has a very relaxed, informal vibe. We didn’t find it as overcrowded as other cities we visited in the summer, but there were bottlenecks at times. We loved the early and late hours, when the crowds were gone.