The World’s 11 Most Crossdresser/Transgender-Friendly Cities

Indeed, we live in a world that’s plagued with discrimination or prejudice against people who fall outside the “norm.” Some people judge and ostracize others when they don’t meet their subjectively normalcy thresholds; unfortunately, we crossdressers more than often fall under the excluded group. And so my question is, do you feel judged? Are you afraid to transform into your feminine self because of the locals’ perceptions? Did you ever travel somewhere and felt unwelcome or out of place?

If you answered yes, don’t worry, I got you covered. Below is a list of 11 crossdresser friendly cities in the world where you can escape and have all the fun in the world. Apart from the well-known London, Sao Paulo, and Amsterdam, I have included other hotspots for your choosing.

My goal is to help you travel with ease. And find a little paradise even if it’s only during the Summer holiday. So, read on and start selecting!

1. São Paulo, Brazil

If you ask anybody what their favorite Pride event is, they will almost certainly choose São Paulo’s Pride. Why? It is the best crossdresser destination in South America. My partner would certainly say so.

Yes, I know I am oversimplifying a little, but the fact is that São Paulo likely has the highest number of transgender travelers because it holds the world’s largest pride march.

Its pride parade attracts over four million people camping on Paulista Avenue’s main promenade and neighboring streets.

Nightclubs offer a diverse range of entertainment, including drag and male striptease. There, you can put on your favorite leggings or skirt and rock the night.

2. San Francisco, USA

San Francisco is most likely America’s drag queen capital. Its transgender community is among the world’s most prominent and most visible.

The metropolis by the Bay has long been a global hub for crossdresser nightlife, art, and politics. It has Castro, one of the country’s earliest communities.

Castro is what they famously call “a drag queen Disneyland.” Here, you can dress in whichever crazy outfit you want. You can put on your makeup and wig, wear your heels and rock the streets; no one will be eyeballing you!

San Francisco also has more partying than you can think of. Both day and night events rock! It should definitely be on your travel list.

3. Tel Aviv, Israel

Tel Aviv, located along the beautiful Mediterranean Sea and nicknamed the “City that Never Sleeps,” is recognized for its seashores, nightlife, and crossdresser community: It is the ideal tourist hotspot for our kind!

The city is expansive, liberal, and inviting, in stark contrast to some of Israel’s and the neighboring region’s more conservative and restricted cities.

It ranks among the most crossdresser-friendly cities on the planet. It welcomes tourists with open arms while also providing a haven by offering tour packages, hotels, and Pride Week celebrations.

Did you know, 25% of the city’s population falls under the LGBT+ category? That means total freedom and tolerance for us crossdressers.

4. Amsterdam, Netherlands

Being the first country in the world to make significant strides towards acceptance and tolerance, the Netherlands has a solid link to members of the crossdressers.

Its capital, Amsterdam, often called the gateway to Europe, has a dynamic crossdresser culture and serves all fetishes and appetites.

It’s worth noting that the crossdressing scene goes far beyond Amsterdam, including saunas, bars, and cinemas in numerous Dutch metropolises, including Amersfoort, Rotterdam, Groningen, and The Hague.

Still, Amsterdam tops them all with vibrant pride events that have full participation from the locals, including politicians. So far, the largest canal parade is the Pride Amsterdam which allegedly attracts more than 350,000 every year during the summer holidays.

5. Madrid, Spain

Imagine yourself sipping cava with your significant other on a patio in Madrid!

Despite the growth of anti-LGBT+ political groups, Spain is among the most culturally open countries for crossdressers.

Crossdressing themes are frequently explored in Spanish literature, music, and film. The country provides a broad and hospitable scene for all drag queens, especially Madrid.

Nevertheless, while doing my research, I was pretty taken aback after finding that Madrid is predominantly Catholic. We’ve got to give the city and the country, in general, some props for being quite tolerant as a profoundly religious region—based on the latest Pew Research poll, I found out that 90% of people are tolerant.

Each year, the city attracts close to 2 million people for its gay pride, known as Orgullo.

6. London, UK

If I could, I would place London on top of my list since it has one of the best crossdresser scenes in the world, having a variety of gay villages in different parts.

However, it might not be an excellent choice for a short-term traveler looking to sunbathe and party during the long summer nights. Still, if you’re looking to find a supportive community, it is the best place to go.

The city hosts London Pride in July, which has consistently attracted over 1.5 million people over the years.

In 2012, the Pride event coincided with the Olympic Games and the WorldPride. The event was a blast.

7. New York City, USA

New York City – home to the very first Pride march, Stonewall, and the inspiration for the modern progressive movement — is recognized as a sanctuary and cultural center years after the Stonewall Inn protests of 1969 began the activist group.

It has a vibrant and lively crossdresser community with many distinct facets. There are a plethora of pubs and clubs to select from, ranging from muscle mary clubs to theatrical piano bars, tiny private bars to contemporary lounges.

The origins of the Pride event are in Greenwich Village, where the Stonewall protests on Christopher Street sparked our freedom. Hell’s Kitchen is the new crossdresser hotspot, with stylish pubs, restaurants, and clubs.

8. Toronto, Canada

Toronto is the world’s most crossdresser friendly city in the world. Unlike any other country I’ve visited, it goes above and beyond to welcome us, in my opinion.

Where else can you see a country’s leader leading a pride march, hoisting an LGBT+ flag, and shouting “Happy Pride”? The world saw Justin Trudeau do this when he attended the Fierte Pride March.

It boasts a vibrant transgender scene, equipped with a slew of events year-round. The prominent one is Toronto’s Church & Wellesley Village.

Toronto also hosts one of the world’s largest Pride celebrations, attracting about 1.5 million people each year.

I don’t know what it is about Toronto, but each time I visit, the atmosphere seems warmer—more welcoming. It’s a place where I can comfortably say you’ve got to stay!

9. Miami, USA

Miami receives over one million LGBTQ+ guests each year, and Miami Beach now has its own LGBTQ+ Visitor Center. And, while our cultural heritage continues to evolve, one thing remains constant: Miami adores members of our community.

Transgender clubs in Miami have been around since the 1930s and are known for having an active nightlife culture that is open 24 hours a day, seven days a week. However, it was not until the late 1960s that the locals began to take the main stage.

During the “golden period,” pubs sprouted up all over town, and the first Pride week was held on Lincoln Road.

The crossdresser community in Miami is louder than ever.

The city also hosts some of the hottest drag queen-friendly events globally, including Aqua Girls and Sizzle South Beach.

10. Berlin, Germany

Berlin is a place so close to my heart. Unlike other cities in Europe, which often have a pretty restricted range for our spaces, this city has a diverse and expansive scene where members of our community can seek refuge.

I met my current partner in Berlin shortly after its former Mayor came out by saying – “Ich bin schwul – und das ist auch gut so!” which means “I am gay – and that’s a good thing!”

During the Cologne Carnival in February, we clicked straight away. We were particularly enchanted by the vibrant and highly dynamic gay nightlife.

Berlin also hosts the largest Pride march, which attracts more than 1 million people every year.

We visited the last event in 2019—before the coronavirus pandemic—, and I must admit, it was mind-blowing. People from all walks of life, races, and ethnic groups expressed themselves freely and just being in their element. I was particularly mind blown by the different types of outfits.

11. Barcelona, Spain

Barcelona has quickly become one of Europe’s most popular locations for crossdressers. As an open-minded and multicultural metropolitan area, the city provides its tourists with a plethora of attractions connected with diversity, freedom, and accessibility to all.

It has an abundance of cross-dresser-friendly pubs, shops, and restaurants. A walk through the alleys to see all the rainbow flags hoisted with pride from rooftops and in retail and bar openings is ideal for absorbing the mood of Barcelona’s gay culture.

And with that, I end the list. These are the safest, friendliest, and most welcoming crossdresser cities in the world. Should you feel threatened, unsafe, or need to expand your horizon, start crossing them off your travel list. Do you know others that we can add? Feel free to share with members of our community below.

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