6 Recommended Cities/Towns For Your Next Crossdressing Holiday

Something I’ve always dreamt about is taking a vacation en femme. Going on holiday for a few days with my partner as my feminine self; the thought of it just makes me so excited.

Travelling as a crossdresser is not the easiest thing to do.  If planning outfits and packing wasn’t stressful enough, we’ve also got to think about the best environment to spend time in. A crossdressing vacation entails being dressed up and acting feminine nearly all day, quite a lot of the time, out in public.  Choosing the right city, town or hamlet is crucial to having a fun and safe holiday.

I’d like to share a few places I’ve been to or had recommended to me for my dream en femme holiday.

North America

Provincetown, Cape Cod (Massachusetts, USA)

This isn’t the easiest place to get to, but it is certainly a must visit for anyone looking for an LGBTQ+ holiday destination.  Provincetown is one of the first gay & lesbian tourist destinations in the USA.  As a result, it has become a very open and accepting place for any crossdresser looking for a welcoming destination.

Commercial Street is home to most of the town’s businesses, which include the Atlantic House, which many travel guide’s call the premier LGBTQ Bar in the United States.  It’s also home to the Fantasia Fair, a long running conference focusing on gender diversity and related issues.  Nearby beaches offer some excellent locations for some amazing beach selfies in your bikini, and the secluded cottages for rent are great locations to rest and sunbathe en femme.

East Stroudsburg, PA (Rainbow Mountain Resort)

This might seem like an odd suggestion; a town nestled in the Pocono Mountains of Pennsylvania.  However, for those of you who aren’t into the beach, the Rainbow Mountain Resort is a lovely LGBTQ+ hotel offering beautiful grounds with hiking trails and amazingly well equipped rooms.

In the winter, a number of nearby mountains are outfitted for skiers.  During the summer months, the resort has a number of special events, including a TG/CD Weekend and a Drag Queen Festival.  You’ll be sure to find a supportive group of fellow travelers here.

Las Vegas, NV

I couldn’t leave Sin City off of a list of places to go as your girly self.  Anyone who has ever been to Vegas can attest to its open mindedness and live and let live attitude towards those individuals who are a bit different.  24-hour entertainment, amazingly well equipped hotels, ample shopping, floor shows, and concerts all ensure that you won’t suffer from a lack of things to do.

I’m adding Las Vegas because if you’re lacking confidence in your own transformation skills, there are any number of freelance make-up services to help you transform into the most feminine beauty you can be.  N2, The Looking Glass and Be You, Just You are two professional male to female makeover services available in the city.  Both offer packages to get you all dolled up for a legendary night out you’ll never forget!

San Francisco, CA

The spiritual home of the American LGBTQ+ movement is an obvious choice for an en femme holiday.  The Castro neighborhood has a huge number of bars, shops and other businesses that cater to the trans community and will be CD friendly.

You can get in touch with the local community by joining the SF TG and CD Meetup Group and going to one of their events.  Or spend an afternoon getting waxed and a facial at Luxa Skin, a TG/CD friendly beauty salon.  What girl doesn’t dream of having her nails done and a facial during a luxury spa day?

Europe

Amsterdam, Netherlands

The tolerant Dutch attitude towards sexuality and gender makes the capital of the Netherlands a top choice for any crossdresser travelling in Europe.  Famous for its Red-light District, full of peep shows, sex shops, and BDSM clubs, it is certainly not lacking for kinky venues or activities.

Amsterdam is host to one of the largest Pride events in Europe every summer at the end of July.  Amsterdam Pride is the home of the Drag Queen Olympics, where you’ll see some of the best female impersonators anywhere in the world.  TransAmsterdam sponsors other Trans inclusionary and Crossdressing friendly activities year-round.

Sitges, Spain

Most everyone will know Barcelona, but not many will know of Sitges; a small beach town about an hour away.  It’s the 2^nd most popular gay and trans friendly tourist destinations in Europe, after Mykonos.

This whole beach town is orientated towards LGBTQ+ tourism; the lion’s share of the businesses in the town center cater to tourists.  In addition to not having to worry about being judged by passers-by, the town itself is stunning.  Get lost in the narrow, cobbled streets, but be sure to choose your footwear carefully.  Cobble stones and heels don’t always go together.

Tahiti!

You read that correctly; if you want to splash out on your once in a lifetime girly adventure, consider French Polynesia.  Imagine laying back on an unspoilt white sand beach in your favorite bikini and drinking a cocktail with one of those little umbrellas.

Aside from the unforgettable scenery, weather and accommodation, I’d like to make you aware of the gender blurring traditions of Polynesia.  Like many destinations in South Asia and Pacific, third gender individuals, Rae Rae or Mahu in Tahitian, are a part of local society.  Modern, western conceptions of crossdressing might not be very prevalent, but you can be sure that you won’t look or feel out of place in this tolerant and accepting culture.

Going on holiday is something we all look forward to every year.  I’m just waiting until the day I can take my female self on holiday with my partner, and be girlfriends for an extended time period.  I hope that my list of crossdressing or trans friendly destinations has given you some ideas if you ever decide to take a vacation en femme.  OR perhaps you have taken a trip as your female self, where did you go, tell us about it below in the comments!