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The original was posted on /r/sailing by /u/Mehfisto666 on 2025-07-30 20:16:36+00:00.
I know this sounds like a really dumb question but cope with me for a second.
I've worked at sea a few years but only had my first sailboat for 1, a lovely 29ft fin keel cruiser that is great in light wind. I've been living aboard in summer and a few weeks in the winter and love living aboard so much. I solo sail 99% of the time and I've probably been out for around a couple thousand miles so far. But as a self-taught sailor i'd be lying if i'd say i've been through all kind of situations. I shy away and try to be in the harbor if i know it's gonna blow around 20kn although i've been caught in 24kn winds a couple times and I could manage reefing, heaving-to etc with little problems, other than my auto pilot becomes quite useless with over 1m waves and strong winds but that's ok.
I quite like my little boat but I'm considering switching to something in the 34-37ft range for a few reasons. One is that I do have friends visiting sometimes to go skiing and climbing, and having a slightly bigger boat to be more comfortable and fit a more decent dinghy would be great. Then it's a very light boat and kinda needs reefing in 8m/s winds and gets overpowered so easily although i can manage, but i'm wondering if a bigger boats handles heavy winds better. The other one is that my little boat gets bullied and gets thrown around quite a lot as soon as there's a bit of a swell and some wind. Which brings me to the last point which is I don't have an anchor locker let alone a windlass, and anchoring is a pain. I am really concerned about anchoring in anything but fair weather because for one thing it'd be hella uncomfortable but mostly it's just a pain in general.
Oh and lastly a little extra hull speed wouldn't hurt as while it's true the boat stays still for long periods of time (i liveaboard while i work) I also don't really care for sailing around the place for the sake of it, and when i do set sails is to go explore and I go fairly long distances on multi day trips. Starting next spring i will have extra time available and i plan to cruise more.
Now in all of this suddenly a question came to mind: what is actually the difference between a 29ft and a 35ft? I have only ever been on my little sailboat and I have zero clue how different it would feel. I understand every boat is different but taking two similar fin keels, how differently do they handle the wind? how different is the feel at anchor? Does a bigger boat feel safer in bad weather conditions?
Would be curious to hear your more experienced thoughts, especially from those of you that moved from a smaller boat to a bigger one and if you think it was worth it