Single-handing in really small boats

[ScooterGuy]

While I'm land-locked now, and do my back-roads 'cruising' on a maxi-scooter, I still hark back to some small boats I owned or built.

Regretfully, this one wasn't available at the time (1960 thru 1985): Paradox a micro-sailboat coastal cruiser

Anyone else out there sail pretty small boats, for overnight or longer cruises, just to be 'messing around with boats,' in 'thin' water or just to 'gunkhole?'

[sailor]

There is four of us (2 adults and 2 small kids) and we daysail and overnight in a 17ft "pocket cruiser" sailboat.
When I was younger, 4 or 5 of us (me & my buddies) would do 2 weeks at a time in a 22ft.
Nowadays when we go longer/further we bareboat charter a bigger boat, but also "pretty tight packing" for its size - for example we had 5 adults and 3 kids on a 32 footer in Greece last summer.

[lazygood4nothinbum]

i'm considering a retired liveaboard life on a relatively small sailboat (maybe 40 ft--ya, i know, relatively large compared to a microsail) so single-handling takes on a whole new meaning. it is a little intimidating but i think after i acquire a new skill set & with enough experience i'd be ok. to complicate it more i really like pilothouses which are more difficult to set up for single-handling.

i was raised in motor boating family so my sail experience is very limited. the ol'man had a dinghy set up for sail which i'd use to escape the mother ship. also i had a sunfish which i'd sail every day after work while employed at a weekly newspaper many years ago. i lived across the street from a good sized lake and turned a golf bag caddy into a mini boat trailer to get the sunfish over to the lake by myself. that little boat was a lot of fun. in a good wind i'd be using the gunwale as a keel with the mast almost parallel to the water. i had that boat dancing.

my only other experience in small sail was a friend's 23 footer which he kept moored off coconut grove in miami. also fun but nothing was as much fun as that sunfish so i'd imagine microsails very fun as well. love the pics on your link. i guess you can't be as crazy on those as i was on the sunfish. but then, i was young and as bulletproof as that boat.