I thought I'd post an update on how things went in Boston.
After my AirB&B mates left for the airport I did have a few hours on Sunday night to spend by myself and as myself. So after getting dressed I went out to grab some dinner in the area where I was staying. I found a little Asian soup place of which I had heard that they have great Ramen and was very nervous when approaching it. However, one of the staffers immediately invited me in and was very friendly with me which put me at ease. And the fact that nobody raised an eyebrow about that 6'6" trans lady was further affirming. Here is a picture of my outfit, I topped it off with a denim jacket:

The Ramen soup really was delicious, btw. Of course my lipstick didn't hold up to it, however my worst fears of looking like a clown with lipstick all over the lower face didn't materialize either, so it could be fixed easily.
Since the night was still young I jumped on the T and visited a recently opened lesbian / queer bar in the Back Bay area of which I had read about. I expected low volume on a Sunday night, but it was packed with women watching the WNBA finals and I had a great time enjoying all their enthusiasm for the game. After the game was over I took the T back home. I really enjoyed being out in public as myself and I had a great time.
I have to mention that I am generally a very insecure person and this was the first time I was out alone while presenting as a woman. That by itself is somewhat out of character for me and would usually make me extremely nervous, but it didn't and I was really calm, at peace with myself and truly enjoyed the night. I guess that tells me something...
Since everything went really great I decided to go out in daylight the next morning to get some breakfast. On the way I passed a school and one of the volunteers stopping traffic for the kids greeted me and told me that she liked my purse. I didn't expect that and it was a highly affirming moment. Again, no eyebrows raised and very friendly service at the restaurant. I did notice that one woman on the street looked me up and down twice, but didn't say anything. Not sure what she thought, it could have been anything from: 'Wow, what a gorgeous tall woman! Isn't she beautiful?' to: 'What is this weird trans person doing here in our neighborhood?'. I like to think it was the former.
That's it on my adventures being out as myself and by myself. It was an extremely positive experience, which I am still somewhat processing since I haven't come down entirely yet from my emotional high. I certainly would like to do it again very soon!
Thanks for listening,
Heidemarie