I am looking to take a vacation. Is there a place you like? I would like a place where I can crossdress and feel I could go to lunch or shop or meet another crossdresser?
Hi, unless I am traveling for work, I rarely leave the two block radius where I live, so I am afraid I can’t recommend a specific destination.
As for other crossdressers, it’s not like we have our own city or anything. Crossdressers live EVERYWHERE. There is also no such thing as a place such as a city or a store where you are guaranteed to be welcomed and accepted by everyone you interact with.
I have two suggestions:
- Make a friend first, and then go meet them in their city. Of course, you need to be smart and you need to be safe. PLEASE don’t meet a stranger at a hotel room or at their home. Meet in public. Get to know them over a few months before you invest your time and money in traveling. There are websites that connect people like us, such as crossdressers.com and urnotalone.com
- Go to a transgender conference such as Fantasia Fair, Espirit or Keystone.
Love, Hannah
Have a question for me? Oh yes you do. Ask me here!
Hannah McKnight 
Go to Las Vegas and visit Stephanie Danderson at N2 The Looking Glass for information, makeovers, clothes and supplies. Here is a link for details. https://n2thelookingglass.co/
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Know anybody in Columbus, Ohio? I’m told it a safer place for us. Have fun, stay safe. Go before Jan 20th.
I hope to see you in March at Keystone.
Mike
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I know of a few people from Columbus, such as NV Gay who is an amazing photographer and trans activist.
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i agree with Hannah that nowhere is 100% safe, but Saugatuck Michigan is a nice town that is very open. There is an LGBTQ hotel called the Dunes or you can stay in a B&B there. My wife and I spent a weekend there, I was Camille 100% of the time, and had zero issues other than the fact that someone from my town was the other guest at the B&B which was totally 6 degrees of separation. My daughter worked it the lady. Not sure if she put it together but nothing was ever said. We shopped the surrounding towns, swam at the pool at the Dunes, and went out to eat at various restaurants.
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I agree Vegas is defiantly one place girls like us can be who we are.
But even where I live in a very conservative state I’ve never felt I could not be out an about as myself, but yes be smart and safe
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The City of San Diego and the community of Hillcrest is very welcoming of the Pride Community.
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Places to visit cross dressed:
1. New York City.
(I live nearby, and I am usually in Female mode when I visit alone.)
2. Chicago.
(I did a full week there with 3 Cis-Females and had a great time)
3. San Francisco.
(I’ll likely never wear trousers there again!)
4. Los Angeles.
(Reasonably safe. Just be careful not to go in the “hood”.)
5. Washington, DC.
(The city has LGBT rights, even though #47 would erase them.)
6. Eastern Canada coastal cities.
(I’ve cruised there en-femme and will do so again.)
7. Bermuda.
(I double checked with port agents beforehand – no trouble.)
Places to avoid:
DO NOT VISIT FLORIDA! Going to the loo cross dressed is a CRIMINAL OFFENSE there.
Many Caribbean islands consider cross dressers and others in the LGBT spectrum as criminals. Don’t get off at these islands unless you have checked with their tourist and immigration bureaus beforehand.
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Every fall the tri ess group plans a cruise and you can dress 24/7 and tour the stops and shop with no problems. we usually have anywhere from 12-24 girls and wives on each cruise Get ack with me if you and your wife are interested. This years plans haven’t been set yet but soon. RicciMarie
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Go to a place that looks interesting to you dear. A place someone else likes may not hold any interest to you. No place is 100% safe, but people go out and about cross dressed everywhere.
That said, I have been out and about all over New England and never had an issue.
We can be elusive unicorns out in the wild, so going somewhere and hoping to bump into another cross dresser is not likely, but Provincetown, MA, on Cape Cod is the home of Fantasia Fair/Trans Week and is a popular tourist spot and known to be LGBTQ friendly all times of the year. Attending an actual cross dressing event would be your best chance to meet others though.
Norah
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A couple of suggestions. If you live near Omaha, NE Van Maur is a wonderful place to shop. My wife found a personal shopper there who was thrilled to help her build her wardrobe. This woman shared with us that it is corporate policy to accept all shoppers.
When we vacation we go to Excellence Playa Mujeres in Cancun. We rent a private car (who works with the resort) so we go from airport to the resort without problem. We have been to the resort a number of times. The only issue has been an occasional misgendering but only from the perspective of confusion as to her gender not to be rude. Once we correct someone they usually remember. They also allow my wife to sign in with her preferred name and put that on their guest list.
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I’m going to a girl’s weekend event called Paint the Town Chicago next month. I’m excited for it!
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