Lanzarote isn't that bad Snape, I've been there and have a very discerning friend who travels extensively and goes to Lanzarote once a year. I would say it's better to go in Winter as it's quite near but hot.
I have been on lots of holidays, last few years have been to the Arab countries. I got badly bitten in Greece and this year I just fancy Spain so Spain it is. I am in a way pleased you are paying for yourself, as I've said before, it's strikes better balance. Let him treat you though, IME if a man really likes you he will want to be able to treat you, it's not about the money. It's more about wanting you to be happy.
Unexpected, I wouldn't ask him outright. Nothing wrong with dropping hints e.g say you haven't had a great night out for a while. If he asks you out then great, if not he isn't interested, sorry. However, you need to know that he is definitely single. I've had men who I am sure have flirted then never followed through and it turned out they were in a relationship.
Velvet, if it's any consolation, me and the guy I'm seeing now, had a now and again arrangement for 2 whole years. He would never forget a birthday as it was an excuse to arrange a date. The only reason I was happy to keep it going was because I wasn't in a place for a relationship, I knew he wasn't and in between I got on with my own life, I didn't give him as second thought except to smile about the date. Saw other people, etc as I didn't think of him as relationship material, too much of a player. Of course, this all changed and he stepped up eventually, although as everyone knows, it's still undefined. I'm OK with it for now, at least. Some people do take their time, but I would have expected a birthday acknowledgement, maybe not if he is abroad and out of touch. See what happens when he is back.