Would you pay upfront for a vacation trip?

[+ mds1]

I have done this once before, and it was a similar amount as you. I paid 25% when we agreed on the vacation, 25% the day we left for vacation, another 25% in the middle of the vacation, and the final 25% after the vacation. It was all done electronically with Zelle. This was someone I had seen before and trusted with my name, so Zelle wasn’t an issue. 
Also, one of the reasons I broke it up this way was to stay within the daily limits on Zelle with my financial institution.

[aiseeya]

I only hire long time trusted provider for a multiple days session. That said for big amount, for safety reasons, I prefer transfer over cash.

[+ SirBillybob]

No.