A Travel Price Comparison for Families, Couples, and Backpackers Windsor vs. Siena for Old Town, Couples, Attractions, and Food

Should you visit Windsor or Siena?

Which is cheaper to visit? Which is more expensive for vacation?

Should I visit Windsor or Siena? This is a common question asked by many travelers. By figuring out which city has activities that align with your interests along with knowing which is more affordable, you'll understand where you can get more bang for your buck. So, let's dive into the details and the data, which all comes from actual travelers.

Windsor

Windsor is a beautiful, royal, and traditional town. This is also a fantastic small town with plenty of charm and local activities. You'll find world class beauty here as well. It's also known for nightlife, food, and museums.

Siena

Siena is a beautiful, romantic, and charming city. The famous beauty of this place is one of the main draws. And you can't forget about the shopping, museums, and nightlife.

Windsor and Siena: Pros and Cons

Is there more to do in Windsor or Siena?

Travelers will usually find more to do in Siena. Although Windsor and Siena are popular destinations, Siena has more sights and attractions for tourists. Siena is very popular for its food, historical sights, and shopping, while Windsor attracts visitors for its small town charm. Windsor is famous for being home to the largest and oldest operating castle in the world. Siena is famous for its beautiful medieval architecture, its delicious local restaurants, and the twice yearly Palio horserace. It is also well known for Piazza del Campo.

How is Windsor different from Siena?

Which is Better for a Holiday?

Let's take a look at the differences and similarities between Siena and Windsor. Then, you can decide for yourself which place is better for your next trip.

Are the Museums and Historical Sights Better in Windsor or Siena?

Plenty of people visit the great sights and museums in both Windsor and Siena.

Windsor offers many unique museums, sights, and landmarks that will make for a memorable trip. The main draw is the Windsor Castle, which many people explore in a few hours. Then you can pass some time wandering around the town.

Many visitors head to Siena specifically to visit some of its top-rated museums and other sights. At the heart of the city is Cathedral of Santa Maria Assunta and Piazza del Campo. Other world famous sights include Palazzo Pubblico and Museo Civico, Torre del Mangia, and Pinacoteca Nazionale.

Is the Food Better in Windsor or Siena? Which Destination has the Best Restaurants?

Siena is well known for its restaurant scene. Also, Windsor is still popular, but not quite as popular for its local flavors and cuisine.

Eating is part of the travel experience when you visit Siena. The town is all about local flavors and many restaurants use local ingredients in their dishes. Pecorino of Pienza is the local cheese, and you'll also find many cured meats. Local pasta dishes include wild boar ragu and a local spaghetti. You'll also find local meats such as lamb, rabbit, chicken and pork.

Windsor is becoming an appealing option for foodies. There are cafes, pubs, and local restaurants that let you sample regional dishes. There are also chain restaurants and international options including Japanese and Thai food.

Is Windsor or Siena Better for Nightlife?

Party-goers will find similar levels of energy in Windsor and Siena.

Windsor has an active nightlife scene for those who seek it out. There's a low key nightlife scene with local pubs and a theater. Dinner cruises are also a fun activity.

If you're looking for night time activities Siena has a few options to choose from. The nightlife is laid back and relaxed. Most visitors enjoy socializing in the evening and meeting friends at Piazza del Campo. There are often live performances which you can enjoy as well as many cafes and wine bars around town.

Is Windsor or Siena Better for its Old Town?

Siena is a world-class destination for its old town. Also, Windsor is still popular, but not quite as popular for its historic old town charm.

The historic old town of Siena is revered around the world. The beautiful old town is filled with medieval brick buildings. At the heart of the city is Piazza del Campo, which is a lively square with many neighborhoods spreading out from there.

Windsor has an old town worth visiting. The old town is opposite the castle and caters specifically to tourists with its restaurants, pubs, and a few shops.

Is the Shopping Better in Windsor or Siena?

Siena is a popular place for its shopping opportunities. However, Windsor is not a noteworthy shopping destination.

Siena offers some nice shopping areas. The main shopping street in town is Via Banchi di Sopra, which has many boutiques that sell clothing, bags, and other items. The town also has many leather goods, ceramics, and other local items available.

Windsor is not a noteworthy shopping destination.

Is Windsor or Siena Better for Families?

Windsor is very good for its family-friendly activities. However, Siena is a mediocre city for its kid-friendly activities.

Windsor is a family-friendly place to visit. Kids will enjoy seeing a working castle when they visit Windsor Castle. While a visit to Windsor Castle is the obvious draw to the town, there are also river cruises, parks, and even the Royal Windsor Maze at the Goswells Park that the whole family will enjoy. There is also a Legoland in the area for those who have more time.

Siena is not always a place people visit with their families. The beauty and history may be lost to the little ones but there is a great atmosphere that even the young ones will appreciate. Kids will enjoy climbing to the top of Torre del Mangia or visiting one of the many playgrounds around town.

Is Windsor or Siena Better for Couples?

Siena is a world-class destination for its romantic activities. Also, Windsor is still popular, but not quite as popular for couples.

Siena makes for a terrific place to visit as a couple. With its impressive beauty and long running history, this is a truly romantic city. The atmosphere is relaxed and there are plazas and neighborhoods that are great for exploring. There are also many great restaurants, superb wine, and world class sights that are not to be missed.

Windsor is a great town if you're traveling as a couple. Exploring the Windsor Castle, taking a river cruise, and wandering the parks and gardens hand in hand make this a great place for a couples retreat.

Is Windsor or Siena Better for Backpackers and Budget Travelers?

Siena is a popular place for backpackers. However, Windsor is not a backpacker-friendly destination.

Plenty of budget travelers visit Siena. Many backpackers visit Siena as a daytrip from nearby Florence. While there are some affordable places to stay here, the atmosphere isn't as backpacker friendly as nearby Florence.

Windsor is not a backpacker-friendly destination.

Is Windsor or Siena Better for Students?

Siena is well known for students. However, Windsor is not popular with students.

Siena is a very popular city for students and younger travelers. It's home to one of the oldest universities in Italy, and it's a wonderful study abroad destination for any student who wants to spend some time in Italy.

Windsor is not popular with students.

Is Windsor or Siena Better for Public Transit? Which Is Easier to Get Around Without a Car?

You'll find somewhat comparable public transit options in both Windsor and Siena.

You'll find some public transit in Windsor, but it may not be enough to take you everywhere. There is a bus system around town.

While Siena offers some public transit options, it might not be your first choice. TIEMME is the bus service that runs in and around town. Many lines pass through the train station and provide service from there.

Is Windsor or Siena a more walkable city?

Windsor and Siena both are great when exploring on foot.

Windsor is a very walkable town. The town is compact and relatively easy to walk around. There are also several walking routes in the area.

Siena is a very walkable destination. The compact town center is best explored on foot.

For even more information, also check out Is Windsor Worth Visiting? and Is Siena Worth Visiting?.

Should I spend more time in Siena or Windsor?

How long in Windsor or Siena?

You'll be able to find lots of things to do in Windsor or Siena to fill your time. In our opinion, Siena has more to see and do, so we recommend spending more time in Siena than Windsor. However, 1-2 days is a good amount of time to spend in either destination.

Families should spend more time in Windsor than Siena. Because of the many family-friendly attractions and fun things to do for kids in Windsor, it's a great place to visit with the whole family.

Couples should spend more time in Siena than Windsor. You'll find plenty of romantic sights and fun activities in Siena that are perfect for a weekend getaway or a longer couple's trip.

Backpackers and budget travelers should spend more time in Siena than Windsor if your budget allows for it. With a larger number of budget-friendly sights, good nightlife, and active things to do, anyone traveling on a budget would have a good time in Siena.

One day in Windsor or Siena?

Even though Windsor is a small town, it has plenty of activities to choose from. This town offers a variety of activities to choose from. Because of this, one day is usually enough time for a trip here.

In Siena, you'll find nightlife and food. Most visitors spend time around the old town while in the area. This city offers something for everyone. This would be the perfect place to spend one day, as it has just the right amount of activities.

A weekend in Windsor or Siena?

It's hard to know how much time to spend in Windsor. For many, it makes a great getaway for a weekend. This would be the perfect place to spend a weekend, as it has just the right amount of activities. The length of your ideal trip is an individual decision.

In Siena, you'll find food and shopping. The length of your trip often depends on your style of travel. A weekend here is typical. Visiting the old town is also a must. A weekend is a great amount of time to relax and see the many things that Siena has to offer.

Five days in Windsor or Siena?

Windsor is a fun place to experience. Windsor is a small town, so it's a great destination if you're short on time. Most people find that five days is more than enough time to see everything.

Siena is a great place to explore. The old town is one of the main draws for visitors. Five days is more than enough time to enjoy everything. Take some day trips to nearby places to fill the extra days. Anyone can find something fun to do here.

A week in Windsor or Siena?

Windsor is a small town, so you can explore the area with less time. Take your pick from the many activities offered here. One week is plenty of time to see everything, even with extra days to spare.

It's hard to know how much time to spend in Siena. Many people enjoy the museums and nightlife when visiting Siena. Exploring the old town is a popular activity. One week may feel like too much time unless you plan to do a lot of relaxing.

For some great organized tour ideas, see The Best Historical Tours in United Kingdom, The Best One Week (7-Day) Tours in United Kingdom, The Best Family-Friendly Tours to Italy, and The Best Hiking & Trekking Tours in Italy.

When we compare the travel costs of actual travelers between Windsor and Siena, we can see that Windsor is more expensive. And not only is Siena much less expensive, but it is actually a significantly cheaper destination. So, traveling to Siena would let you spend less money overall. Or, you could decide to spend more money in Siena and be able to afford a more luxurious travel style by staying in nicer hotels, eating at more expensive restaurants, taking tours, and experiencing more activities. The same level of travel in Windsor would naturally cost you much more money, so you would probably want to keep your budget a little tighter in Windsor than you might in Siena.

If you're trying to decide if either of these two destinations are within your price range, also see Is Windsor Expensive? and Is Siena Expensive?.

Which is Bigger, Windsor or Siena?

Siena has a larger population, and is about 86% larger than the population of Windsor. When comparing the sizes of Windsor and Siena, keep in mind that a larger population does not always imply the destination has more attractions or better activities. So, always research the type of place that you want to visit along with the activities and attractions that interest you.

When is the best time to visit Windsor or Siena?

Both destinations experience a temperate climate with four distinct seasons. And since both cities are in the northern hemisphere, summer is in July and winter is in January.

Should I visit Windsor or Siena in the Summer?

The summer attracts plenty of travelers to both Windsor and Siena. The small town charm and the family-friendly experiences are the main draw to Windsor this time of year. Also, many travelers come to Siena for the family-friendly experiences.

In July, Windsor is generally cooler than Siena. Daily temperatures in Windsor average around 18°C (64°F), and Siena fluctuates around 23°C (73°F).

People are often attracted to the plentiful sunshine in Siena this time of the year. Windsor usually receives less sunshine than Siena during summer. Windsor gets 195 hours of sunny skies, while Siena receives 316 hours of full sun in the summer.

In July, Windsor usually receives around the same amount of rain as Siena. Windsor gets 46 mm (1.8 in) of rain, while Siena receives 45 mm (1.8 in) of rain each month for the summer.

Should I visit Windsor or Siena in the Autumn?

The autumn brings many poeple to Windsor as well as Siena. Many travelers come to Windsor for the small town atmosphere and the natural beauty of the area. Also, many visitors come to Siena in the autumn for the shopping scene and the natural beauty of the area.

Windsor is cooler than Siena in the autumn. The daily temperature in Windsor averages around 12°C (53°F) in October, and Siena fluctuates around 16°C (61°F).

In the autumn, Windsor often gets less sunshine than Siena. Windsor gets 107 hours of sunny skies this time of year, while Siena receives 177 hours of full sun.

Windsor usually gets less rain in October than Siena. Windsor gets 58 mm (2.3 in) of rain, while Siena receives 87 mm (3.4 in) of rain this time of the year.

Should I visit Windsor or Siena in the Winter?

Both Siena and Windsor are popular destinations to visit in the winter with plenty of activities. Many visitors come to Windsor in the winter for the museums and the cuisine. Also, most visitors come to Siena for the museums, the shopping scene, and the cuisine during these months.

Windsor can get quite cold in the winter. In the winter, Windsor is much colder than Siena. Typically, the winter temperatures in Windsor in January average around 4°C (40°F), and Siena averages at about 7°C (45°F).

Windsor usually receives less sunshine than Siena during winter. Windsor gets 52 hours of sunny skies, while Siena receives 105 hours of full sun in the winter.

In January, Windsor usually receives less rain than Siena. Windsor gets 52 mm (2 in) of rain, while Siena receives 64 mm (2.5 in) of rain each month for the winter.

Should I visit Windsor or Siena in the Spring?

Both Siena and Windsor during the spring are popular places to visit. Most visitors come to Windsor for the small town charm and the natural beauty during these months. Furthermore, the spring months attract visitors to Siena because of the natural beauty.

In April, Windsor is generally cooler than Siena. Daily temperatures in Windsor average around 9°C (48°F), and Siena fluctuates around 12°C (54°F).

In the spring, Windsor often gets less sunshine than Siena. Windsor gets 147 hours of sunny skies this time of year, while Siena receives 192 hours of full sun.

Windsor usually gets less rain in April than Siena. Windsor gets 45 mm (1.8 in) of rain, while Siena receives 70 mm (2.8 in) of rain this time of the year.

Typical Weather for Siena and Windsor