And I have been on plenty of trips with gents I'd never met until we began our trip. The key is communication. A lady has to know herself and her limits, and how to read between the lines of a prospective friend's emails.
I am fortunate in that I am a very laid back and accommodating person in general- extremely easy to get along with. Nothing type-A about me in my companionship style. Lol! That has allowed me to enjoy many different personalities. I've traveled with both gents who have insisted on spending 24-7 with me, and with gents who have had to do their own thing on trips. I'm fine either way. But again, communication is key!
It is important for either party to feel free to bring up anything that is annoying them without feeling like it will make a scene or bad energy between them. There are always diplomatic ways of doing this. No need to lash out at someone or be nasty. And the best trips are those where we checked in with each other to make sure things are going as expected for both parties.
The flight thing is an interesting dance. I usually book my own travel unless it is a friend I've known for many years (which I have a few). Obviously, keeping track of tickets, etc., is important in preserving one's identity, but being able to have boarding bar codes on phones now helps (at least with domestic travel).
Hotel keys is another thing- make sure you get a key for each of you and pray it works and that she doesn't lose hers or get locked out of the room because hers doesn't work (don't put your key next to a mobile phone!). Or have a back-up plan should a key issue occur. I have never had a hotel ask my ID on check-in when I have been checking in with a gentleman. I do get "Mrs. [insert last name of gent I'm traveling with]" from time-to-time, but this always makes us giggle, and we just go with it.
And do have a bottle of the linked product below on-hand.

Keep it handy where either of you can use it. Speaking of which, the lobby is your friend.
I had a girlfriend have the unthinkable happen while on a multi-day engagement with a guy- they were in an accident (his fault, and he was driving) resulting in her having to spend time in the hospital. It was a nightmare for her because he was a real jerk about it. So sad. So I would caution everyone to be careful and not drink and drive or not get into a vehicle driven by someone who has been drinking.
Finally- remember to check the safe before you check out! Don't leave anything there- it can cause very embarrassing situations.
Have fun!! Traveling with a fun friend can be such a wonderful experience. I'm fortunate that my worst experience was merely boring or annoying- nothing terrible like my girlfriend experienced.
I'm sure you will have fun!
-- Modified on 7/7/2015 1:07:06 AM