I would say you dont need a trip sitter IF you're taking a reasonable dose and most importantly a place thats's physically, socially and mentally safe.

Things that make a place more shroom-friendly (non-exhaustive):

Plants, fresh air, low-effort food, animals, ready-to-go playlists (you will not want to deal with the nauseus sguiggly rune screen once a trip is underway), ready water supply, art, silence, ambient music, pretty lighting, non-dangerous hobbies like painting

Things that make a place less shroom-friendly (non-exhaustive):

Strangers, behavioral expectations, loud noise, traffic (foot or motor, bikes are fine) bad smells (this is a big one), conflict, crowds, too many screens, really just generally negative or overwhelming stimuli. However, if you're good at playing it cool, tripping in a liminal public space like a mall or museum is a very interesting time- def not for beginners though lol

Oh, and you might experience a thing where your mouth opens and you don't know if you need to yawn, burp or vomit. Don't worry, it's never vomit. You kind of just end up croaking like the grudge for a second, it's fine.

Last last edit: if you get a few hours into a heavy trip and you feel like a rusty old robot, drink something sugary