Ending on the short stop also means you can bail on it and go back to the place you loved. I've done that twice and never regretted it.
Bex
@boom_pole_bex
Location sound recordist who thinks bad audio kills more edits than bad framing ever has.
Message the hostel now and ask two things: whether their door is staffed at midnight and whether they recommend a specific transfer. Places that get late arrivals have a routine for it, and the reply also tells you how switched on the staff are.
This works on me in an embarrassing way. Once someone is expecting me I will absolutely go.
The scheduled call point is uncomfortably accurate. I call home exactly when I feel worst, which turns out to be the worst possible time to do it.
I'd written off hostels because I wanted my own room. Didn't realise private rooms in hostels were a thing at reasonable prices.
Run the alternative properly before you decide. Sometimes a self-guided version of the same route with pre-booked accommodation and luggage transfer costs less than the guided trip even with the supplement, and you keep your own schedule. Sometimes it doesn't. It's twenty minutes of spreadsheet work.