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

Should you visit Toledo or Windsor?

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

If you're trying to decide where to visit between Toledo or Windsor, this travel comparison, which includes costs, can help. The overall cost of travel is usually a consideration when deciding where to go next, and the cost comparison down below can help you decide based on the average prices from other travelers along with your own travel budget.

Toledo

Toledo is a fascinating, beautiful, and ancient city. It's a beautiful place to visit, too. And you can't forget about the shopping, museums, and nightlife.

Windsor

Windsor is a royal, traditional, and touristy town. Since it offers so much small town charm with a variety of activities, it attracts plenty of visitors, too. It's considered by many to be an absolutely beautiful destination, too. Other reasons to visit include nightlife, food, and museums.

Toledo and Windsor: Pros and Cons

Is there more to do in Toledo or Windsor?

Travelers will usually find more to do in Toledo. Although Toledo and Windsor are popular destinations, Toledo has more sights and attractions for tourists. Toledo is very popular for its food, historical sights, and shopping, while Windsor attracts visitors for its small town charm and impressive beauty. Toledo is more touristy than Windsor and is popular for its medieval buildings, ancient landmarks, and fascinating history. It is also well known for the Catedral de Toledo. Windsor is famous for being home to the largest and oldest operating castle in the world.

How is Toledo different from Windsor?

Which is Better for a Holiday?

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

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

Spend time exploring the very good sights and museums in either Toledo or Windsor.

With a variety of museums, monuments, and historical sights, a trip to Toledo can be an interesting and educational experience. This medieval city is filled with ancient landmarks including the iconic Catedral de Toledo. In the old town you'll find many many historic buildings and a fascinating Jewish Quarter. Other notable sights include the Monasterio de San Juan de los Reyes, the Alcázar de Toledo, and the Museo de Santa Cruz.

You'll find a good number of museums and monuments packed into Windsor. 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.

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

Toledo 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 Toledo. The city offers a great cuisine at a reasonable price. The dishes are influenced by the city's diverse past. You'll find many meat dishes due to the area's long running tradition of hunting. There are also classic dishes like carcamusas, which is pork covered in a tomato sauce. Dishes in general tend to be heavy and saucy with filling and delicious flavors.

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 Toledo or Windsor Better for Nightlife?

The nice nightlife scene is relatively similar in Toledo and Windsor.

With a handful of venues, visitors can find a fairly lively vibe in Toledo. Most tourists visit the town as a day trip, so things can quiet down somewhat at night. There is a large student population that frequents the bars around town and help keep things lively.

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.

Is Toledo or Windsor Better for its Old Town?

Toledo 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 Toledo is revered around the world. Perched on a hill and spilling out around the cathedral, this Spanish old town is filled with historic landmarks.

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 Toledo or Windsor?

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

Toledo offers some nice shopping areas. Calle Comercio is the main shopping street in town and there are two major shopping malls in the new part of town.

Windsor is not a noteworthy shopping destination.

Is Toledo or Windsor Better for Families?

Toledo and Windsor are both nice destinations for the whole family.

Toledo is a family-friendly city. The ancient streets are fun to explore. There are city gates, ancient Arab walls, and older kids will be fascinated by a visit to the Toledo Torture Museum. The city is known for its swords, and there are shops that you can visit to learn about this craft.

You'll find plenty of kid-friendly things to do in Windsor. 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.

Is Toledo or Windsor Better for Couples?

Windsor is a very popular place for romance. Also, Toledo is not quite as popular, but is fairly good for its romantic activities.

Windsor makes for a fun place to visit for 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.

Toledo makes for a fun place to visit for a couple. It's an ancient city that is filled with fascinating history and impressive historic sights. Couples will enjoy wandering the medieval streets and visiting the ancient gates.

Is Toledo or Windsor Better for Backpackers and Budget Travelers?

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

Plenty of budget travelers visit Toledo. Many travelers visit Toledo as a day trip from Madrid, but for backpackers who want to spend more time, there are a handful of hostels in town.

Windsor is not a backpacker-friendly destination.

Is Toledo or Windsor Better for Students?

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

Toledo is a very popular city for students and younger travelers. The city is popular with students, and you'll find many activities and a lively atmosphere both during the day and at night.

Windsor is not popular with students.

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

Visitors will find nice public transit in both Toledo and Windsor.

Toledo has some public transit options. There is a good bus system through town.

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.

Is Toledo or Windsor a more walkable city?

Toledo and Windsor are very good when it comes to walkability.

Toledo is very walkable. It's a compact and easily walkable city, particularly within the old town. The bus and train stations are also about a 15 or 20 minute walk from the city center.

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

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

Should I spend more time in Windsor or Toledo?

How long in Toledo or Windsor?

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

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

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

Backpackers and budget travelers should spend more time in Toledo 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 Toledo.

One day in Toledo or Windsor?

In Toledo, 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.

Windsor might be a small town, but there's plenty to do in the area. One day is often enough time to do most activities.

A weekend in Toledo or Windsor?

In Toledo, 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 Toledo has to offer.

Windsor is a great place to explore. It is common to spend a weekend here. With all of its activities, you can easily fill a weekend here. Your budget might influence how long you stay.

Five days in Toledo or Windsor?

Toledo 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.

It's hard to know how much time to spend in Windsor. Five days may feel like too much time unless you plan to do a lot of relaxing. It has many unique tourist attractions and fascinating things to do.

A week in Toledo or Windsor?

It's hard to know how much time to spend in Toledo. Many people enjoy the museums and nightlife when visiting Toledo. 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.

Windsor is a small town, so it's a great destination if you're short on time. This town offers a variety of activities to choose from. Most people find that one week is more than enough time to see everything.

For some great organized tour ideas, see The Best Adventure Tours to Spain, The Best Sightseeing Tours in Spain, The Best Historical Tours in United Kingdom, and The Best One Week (7-Day) Tours in United Kingdom.

When we compare the travel costs of actual travelers between Toledo and Windsor, we can see that Windsor is more expensive. And not only is Toledo much less expensive, but it is actually a significantly cheaper destination. So, traveling to Toledo would let you spend less money overall. Or, you could decide to spend more money in Toledo 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 Toledo.

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

Which is Bigger, Toledo or Windsor?

Toledo has a larger population, and is about 3 times larger than the population of Windsor. When comparing the sizes of Toledo and Windsor, 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.