Crossdressing on Holiday


by Simon

With British Summer Time now upon us, and the weather slowly improving, many of us will be turning our attention to booking a holiday. After all, going on vacation is always a wonderful break from daily life.

Having the opportunity to kick back and relax away from the grind of usual work and daily life is something we all treasure, no matter how short the break is. Getting away from it all is also a chance to spend time indulging our pleasures and dressing up.

But there is one key point for us to consider, and that is deciding on whether to make it a crossdressing holiday - which is a very big decision! With this in mind, it’s important to consider a number of factors before booking your en femme escape.

Let’s have a look at some of the basics to consider when deciding about crossdressing on holiday

Before You Travel

Before jetting off into the sun, there are a few things to think about. First and foremost is choosing the right destination, and we will look at some of the top places to choose later in this article.

Next we need to think about what we want from our vacation, particularly when considering life as a crossdresser back in our home environment. What activities do you enjoy when crossdressing? Think about whether you will be able to indulge in similar pursuits whilst on holiday. Or perhaps you are looking to try out something new? Whatever the choice, make sure you take these into consideration when booking your holiday.


Next it’s very important to look at local customs and laws of your chosen destination. Whilst many countries are more open and accommodating to crossdressing than previously, there are still many who have very strict rules about how people are required to behave in public. With this in mind, it is essential to check if your chosen location is crossdressing-friendly.

Finally, whilst the travelling restrictions of COVID have now eased, it’s worth remembering that some countries have changed their rules about crossing international borders. Make sure to check the entry requirements of your chosen country before completing your booking, and ensure you meet their conditions.

Choosing the Right Place

As with all holidays, you need to give some thought to the type of destination that is likely to ensure you get the most out of your time off. Are you going for a city break with plenty of places to have a good time, or would a cruise suit you better. If you’re looking for a more relaxing getaway, then perhaps a countryside retreat would work best.

Having decided on the best type of holiday to suit your needs, and having thought about what you want to do whilst away, it’s now time to think about where you want to head off to, and spend your well-earned money. Here are some of the best crossdressing-friendly havens from around the world.

If you are thinking of heading east, then Thailand and Japan offer the best choice. Thailand is of course the number one destination that most people think of, particularly when thinking about wild and crazy cultures. But it also has some of the most amazing beaches in the world, as well as some of the most incredible people. When it comes to freely enjoying your feminine side, then Japan is a must. They have probably the most respectful population, so you will feel free and safe whilst walking down the streets.

In the USA, crossdressing is acceptable in most places, however the best places to go for an open-minded holiday are New York and San Francisco. Heading down into South America, you can indulge your alter-ego in Brazil, Argentina, Colombia or Chile, all of which have plenty to offer. And remember, Brazil hosts one of the biggest pride parades in the world, making it the ideal place for a vacation!

For destinations that are a little closer to home, there are plenty of places to choose from across europe. Spain is well known for its wild nightlife, and is therefore a common place to go. However, Portugal also offers a perfect getaway for those who are thinking of somewhere to go that’s not just the usual suspects!

Spending Time on the Beach

Going to the beach is a very daring choice, even for the most experienced crossdresser. Having the confidence to crossdress on the beach definitely deserves respect and admiration. The challenge here is whether you can pull off the right type of look, such as a bikini or swimsuit.

The idea of being a female at the beach is very thrilling, so choosing a beach holiday and spending time en femme is a super idea - if you’re brave enough. A lovely sundress and sandals are the classic outfit, and will complement the perfect sunset on the sand. 

What to Pack

Whatever your holiday plans are, the final thing to think about is making sure you have a good idea of what items you need to take with you. Also, don’t worry about airport security staff - they’ve seen it all before, so they won’t be fazed by what’s in your luggage, trust me!

But do bear in mind that anything silicone will usually cause someone to take a look in your luggage. Breast forms, girdles and hip pads often appear suspicious in scanners, so be prepared to have to explain your contents.

Make sure to make a list of all the things you are going to need, from clothes to make-up and accessories. Of course, most destinations are bound to have a good array of shops for any odd items you forget.

Finally, you may decide to fly en femme, but remember you will have your ID checked. So, if this is your plan, then you will need to make sure to carry some other form of documentation with you, to confirm who you say you are - be prepared.

Whatever your plans for a holiday, wherever you go, whether you crossdress or not, just remember one thing - have a great time and enjoy yourself!

Crossdressing Closet

Bring Out The Woman In You


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