Crossdressing friendly vacations

May 25, 2008 1:20 PM

Anyone have any good vacation recommendations for crossdressers?

My husband enjoys crossdressing. I’m cool with it, in fact, we have been having a lot of fun lingerie shopping. Neither of us is gay, and we both enjoy our new hobby. We are looking for vacation destinations that are accepting of crossdressers. Does the hive-mind have any suggestions for such vacation destinations?

posted by anonymous to travel & transportation (10 answers total)

The Village/Lower East Side in NYC. I don't know if it's a crossdressing vacation destination per se, but he'll be in good company and have many shopping options.
posted by whoaali at 1:33 PM on May 25, 2008

I think most any big city - I mean, in San Francisco people would certainly be accepting.
posted by crinklebat at 1:35 PM on May 25, 2008

How about Provincetown, MA? It's on the tip of Cape Cod and is really a fun and relaxing place to go for a vacation in the summer. It's noted in Wikipedia as a "gay resort" and is also very artsy and would probably be really hospitable to you and your husband.
posted by belau at 2:10 PM on May 25, 2008 [1 favorite]

You just missed this year's, but for next year: Esprit in Port Angeles, Washington.
posted by The corpse in the library at 2:34 PM on May 25, 2008 [1 favorite]

How about Key West?
posted by Maxwell_Smart at 3:14 PM on May 25, 2008

Cross dressing is fairly well accepted in many parts of Thailand for the locals, I don't imagine it'd be very different for foreigners.
posted by NormandyJack at 3:51 PM on May 25, 2008

i was going to suggest nyc, san francisco, austin, key west, and provincetown (esp. provincetown). also, new orleans! around the french quarter, no one will give you a second glance. abroad, you might have a lot of fun in amsterdam. in the caribbean, you might look into st. john. in mexico, try puerto vallarta. definitely check out the lgbt travel sites first, though. anywhere that welcomes gays will welcome your husband, and probably be plenty of fun for you too.
posted by thinkingwoman at 4:44 PM on May 25, 2008

Provincetown is an excellent choice -- maybe the top gay vacation destination in the world. At this point, you are probably not going to find accommodations there this summer for love or money, so maybe start planning now for next year. There is no chance you will feel even slightly awkward or out of place. Keep in mind, your husband will probably get hit on by lots of gay guys, so if that is a problem...
posted by Rock Steady at 6:27 PM on May 25, 2008

I knew people who would vacation in Miami Beach for this specific reason. I can't imagine anyone would bat an eye if he were to go out dressed at night on Lincoln Road.
posted by the_bone at 7:27 PM on May 26, 2008

I know of one specifically for crossdressers in November 2009 called Alluring Affair. It is being held at a resort in Canada so travel is easy and they are advertising workshops, a dance, pyjama party and a Broadway style show. Could be an interesting weekend for anyone who likes to crossdress and their significant other
posted by nrobinson at 12:05 PM on December 10, 2008