I have to admit that I have needed a break for quite a while.  Things have been extremely stressful and to get away for a while will be great.  So I have booked two weeks in early November in Southern Italy.  I'm not a sun worshipper and I plan to do quite a bit of walking on the Amalphi coast with my camera as companion.  I also want to see Pompeii and Herculeaneum again.

My passport is still in my male name and I will have to at least travel in male mode.  I had to get some holiday/travel clothes and it is becoming increasingly apparent that I no longer pass as a man.   Putting on male clothes not only feels weird but to me looks incongruous.  I no longer have a male shape.  Boobage is apparent and most of all my face shape is becoming increasingly feminine.   I planned to go full time in the Spring but I now think I will have to bring things forward a bit

One quick question.  I will have to register with my passport at the hotel reception (this is European law).  Has anyone done this and then gone on to enjoy the holiday in female mode?  Important to note that I will be travelling on my own, to an area that is not only strongly catholic but which is also fairly reserved.

I flew on a passport with a male gender marker to Boston from Canada, looking anything but male and nobody bothered me at all other than a couple of double-takes. I couldn't have passed as a guy at that point without drastic measures. I can't vouch for the hotel, but generally people who want your money try to be polite. You could call/email the places you will be staying in advance to make sure you won't have problems.

Italy is a lovely place for a holiday. Though I've tended to go further north - Umbria and Tuscany. The last trip was 7 years ago and I spent a lot of time wandering around inside churches looking somewhere between a femme gay guy and an androgynous girl and I neither burst into flames nor was tossed out. Most people seemed pretty relaxed.

Even though I haven't been to Italy myself, I heard it is a very accepting place when it comes to this sort of thing. And Italy aside, those people want your money, which makes their acceptance even higher of things they might not otherwise be accepting of.

If you really want to make sure, the best is to just call them and ask. It likely won't be a problem.