Going on a Crossdressing Vacation: A Risk or an Escape?

Going on vacation is always a wonderful break from daily life.  Opportunities to kick back and relax away from the grind of usual work and daily life are something I treasure, no matter how short a break it is.

Getting away from it all is also a chance to spend some more time indulging my femme side and dress up.  Deciding to take a crossdressing holiday is a big decision, and it’s important to consider a number of factors before booking your en femme escape.  Let’s discuss a crossdressing holiday and some of my ideas about it.  When we’re done, you should be ready to make a decision about where to go or what to do.

1. Tips to know before you travel

Choosing the best place for your escape is obviously the number one thing to consider.  There’s so much to choose from, and given where your home base is and what you enjoy doing, you might have different ideas. I’ll try to outline a few general choices and some thoughts about each of them.

Obviously, travelling during the era of COVID has made going across international borders more difficult; thankfully a lot of these rules are slowly becoming less onerous, however crossing international borders still requires some research beforehand.

2. Choosing the best place

● A city break

I think a city break is quite a safe choice for a girly vacation.  If I were you, I would choose a big city that’s known for a liberal cultural attitude.  Cities like New York, London, Amsterdam, Tokyo, and Berlin are all good examples.  They are huge cities with a number of different LGBT friendly venues.  I would also take comfort in the fact that there is a certain anonymity amongst the huge crowds of people; all of whom have more important things to get on with than gawking at you out and about.  Cities like these also embrace eccentricities and a crossdresser isn’t something anyone hasn’t seen before.  Not to mention that there are always scores of things to do in big cities, all of which you can do while dressed up.

My advice for crossdressing city break would be this; make sure you get a hotel with a sizeable room.  Most hotels in these places will have smallish rooms, and this won’t allow you space to lay out your wardrobe and get ready.  Also, be sure to let some of the hotel staff know that you’ll be crossdressing during your stay.  Finally, be mindful of where and how you go places in the evenings.  Women are always quite aware of their surroundings during nights out, and you should be too.

● The beach

Going to the beach is a very daring choice; any crossdresser with the confidence to take this on has my respect and admiration.  The challenge of a beach holiday as a woman isn’t something I would try, just cause I don’t think I’m confident enough to pull off a bikini or one piece swimsuit in public.  Being without my feminine hips and breast forms isn’t something I would want to do.  If you’re worried about this, but still crave your beach trip, Roanyer’s Body Suits are an excellent solution.  Roanyer has video instructions about how to wear it and pair it with a tasteful bikini.

The idea of being a girl at the beach does thrill me though; going on a beach holiday and spending some time dressed up as a girl is also an idea.  A lovely sundress and sandals are a classic outfit for going out to watch the sunset and meandering around the sand in the evenings.

I have spoken to some other crossdressers who have done a beach holiday and they had a few pointers.  I think the best tidbit of advice was this; they always tried to stay at an all-inclusive resort.  There were a few reasons for this.  Firstly, it’s a controlled environment and safe; the room is always close by and well equipped.  Also, staff at these resorts are very accommodating; you can email in advance of booking to see if they are CD-friendly and to let them know your plans.  If you’re lucky, they’ll even refer to you with your female name when chatting with them.

● A countryside holiday

If you like open spaces and nature, this might be the choice for you.  Venturing out into the countryside can be a lovely refreshing experience.  There are going to be a lot of differences from the city or the beach, but a change of pace can be nice.  I think the big differences are going to be the type of place you can stay and how to get around.  A trip to the countryside might also involve a bit more planning than the previous two.

Big hotels are likely not going to be an option here, but there will be loads of charming bed and breakfasts to choose from.  Once again, it’s important to contact anywhere you’re planning on staying beforehand to notify them of your crossdressing plans.  Airbnbs in small artistic communities will likely have no problems with you.  I’m thinking of places like Vermont in the USA, or Cornwall in the UK.

One thing to keep in mind when planning this type of crossdressing holiday is how to get around.  You’re probably going to be needing a car to get around unless you’re looking to enjoy village life; this will mean driving, being separated from your home base and your supplies.  If you suffer a wardrobe malfunction while out, it’s going to be more than a slight annoyance.  Also, if you’re moving from place to place while on vacation, you’re obviously going to have to pack up and move all your things more often.

● A cruise

Cruising might give you the best of all worlds; the activity of a city, the relaxed atmosphere of the beach, and the change of scenery of a countryside trip.  The single reason why I would consider a cruise though, is this; it is possible to go on a crossdressers cruise, where all of the other participants are crossdressers, all of the staff are used to crossdressing, and all of the details have been arranged by someone else.  I recommend Cross Dress Travel, which has a cruise at least once a year.

The acceptance and peer support on offer with this option is something that I think makes this a really good option for any crossdresser, and it could even be a great opportunity to upgrade your skills and connections through all the new friends you’ll make.

3. What to bring along and how to get there

I’d imagine that whatever your plans are, you’ve got a pretty good idea about what items to bring along with you.  As a seasoned traveler and a former airline employee, I’d like to give you a few bits of advice.

● Packing your stuff

Airport personnel have seen everything, so don’t be fazed by a security guard opening your luggage and seeing it full of lingerie and heels.  You might be a topic of break room gossip for five minutes, but not much more.  However, bringing along nearly anything silicone will cause someone to look into your luggage.  Breast forms, girdles and hip pads will appear as suspicious items when they get scanned, and you will be asked to explain what it is.  If you’re going to bring them and you don’t want to be outed in front of other travelers, put them in your checked luggage.

● Flying en femme

This is generally less of a problem than you’d think, although I would advise against it.  Anytime you’re going to have to have your ID checked, you might have to have a follow up conversation.  I know transwomen that fly with letters from their doctors explaining the difference in their appearance, and explaining your identity to a random person isn’t the easiest thing to do.  If you’re prepared for this, you should be allowed to fly.  As long as the details in your passport match your ticket, and the shape of features on your face match your ID, you’ll be fine.

● Returning home

Just like when you travel to your destination, be mindful of what you pack and where you pack it.  Make sure you’ve cleaned and put baby powder on any breast forms or girdles you’ve worn.  You’ll want them in the best condition for continued use.  And don’t forget to back up all your photos so your treasured memories stay safe; cloud drives or sd cards work fine.

Going on holiday as a woman can be a wonderfully fulfilling experience.  Spending some extended time as your female self will be rewarding and exhilarating.  Whether or not you plan on spending all or just some of your time on vacation dressed up as a woman, I’m sure the experience will be one you won’t forget.

Plan carefully ahead of time to try and nip any small problems in the bud before you depart.  Have a plan to deal with any issues once you arrive, and then you’ll likely be prepared for every eventuality.  I hope you’ve found some of my ideas helpful, and I’d like to with you the best with your womanly travels!

Ciao!