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I prefer to book hostels online (own website/goibibo/booking.com)
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As a guy I didn't ever think too much about it just didn't carry expensive stuff, jwellery etc.
(never got robbed yet, neither any physical harm)
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ease to reach, weather, crowd probability.
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I've found genuine info from cleaning staff/watchmen/other guests who've already spent few days.
(Somehow I don't trust the cab drivers, shop keepers)
I'll share my first solo trip story, I started finding destination which is minimum hops from my home and not full peak season.
Decided Bir in Himachal as I could take a morning flight to Delhi and a overnight bus that drops there itself.
For stay booked hostel for 10 days ( the hosteller own website they had post covid workation offers)
Had nothing else planned except wanted to experience paragliding.
My first day went uneventful, i just slept and had food.
The next day met a guy who was also alone, our agenda aligned so we went to do stuff together for couple of days, then he left.
As luck would have it, while having pizza I saw someone seculded from his group went to talk to him, turns out he wanted to visit some waterfall which required mild hiking, we went together.
Rest of days flew by, eventually did paragliding.
In numerous other trips, from getting lost on the way reaching different village, to just lazing around for a week straight, nothing was planned and predictable.
Being sceptical aside, people at non touristy places are generally good and won't fleece you.
At popular destinations higher chances one can have bad experience also as one of my friend was sold a dhupbatti for ₹2000 in kasol (iykyk scam) so need to be careful.
Instead of setting up perfect itinerary i just fix a destination and book stay, travel, now I've stopped even booking return journey also as had to cancel flights twice because extended the trip on the last day.
One thing is don't book budget hotel at places where hostels are not available (less likely to find solo travelling people) instead try to find homestays.
Knowing driving a 2 wheeler would be plus, as rentals be cheaper than cabs.
yolo it, have fun, you're not likely to get killed.