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I've never been on anything more than dayhikes solo. All overnighters have been with 1-6 other people.
I feel safer going with friends, plus we can share stuff like stoves, water filters, canoes, gas for car, drugs. Can split tasks to accomplish more. Can cover more ground because we push eachother and compete.
I've been caught out in the canoe with some crazy rain storms that I probably wouldn't have survived if I was solo. Usually only go with people I trust. Have known some of them for my whole life. Have brought a few people who had to be carried over the years, but they were out for the first time so I'd rather show them how awesome it can be, as people showed me.
I will probably go on a solo portage trip this year, maybe 2 nights. I'm fairly new to the outdoors and am only now becoming confident in my gear and abilities. I do want to see what it's all about, but I honestly don't see it becoming a huge thing for me that I do often.