All of this.Congrats on crossing that hurdle. I personally have not. I cannot leave my furkids behind and enjoy a vacation. Cap'n Jack is especially attached to me and I'm also the only one he trusts fully at home. I feel like he would be feeling abandoned if I went off.
As for the Op, as you can see, I'm sorry, I have no tips for you. I haven't gone on any vacations since I got the cats. Perhaps you can tell your minder to be extra attentive to Gordon and send you frequent updates as mentioned.
So far whenever my SO and I head out on a trip we make it to pet friendly places that allow pets.
To be perfectly honest and I know this isn't fair.... I would be willing to board Shepherd Book. He's sociable and enjoys activity and company and would be bored at home and it would be HECK taking him with us so...
MowMow however is a true mama's boy and when I tried to board him I had to come home early because he refused to eat and after 3 days they called me. He wound up with a UTI as well and she told us he hadn't peed either. Now (years later) we just always take him with us. He's been to the mountains @ ski lodges and to the coast in beach side condos and to the high dessert in hotel rooms.
We've been kicking around the idea of a two or three week RV trip this coming summer or fall. Again, I doubt that would be conducive to my spaz monster but I think Mow Mow would enjoy travelling with us like that and SO has been hunting up ideas of a screened 'porch' around the RV door so MowMOw can get out of the vehicle and into fresh air without escaping.