Built my first boat in 1985 a 17' skiff to fish from with my 7 year old son, enjoyed the process so much I immediately started on the next, a 12 foot Phil Bolger designed catboat (in which I learned to sail) and then a larger boat, a 25' skipjack sloop, launched in Lake Champlain in 1989.
Spent the month of January 1992 sailing an 18' yawl in Florida Bay and the Keys and on my return to Vermont started work on a 36' schooner. Launched on the lake in 1998, i sailed it south and cruised the Caribbean for the next 8 years, single-handed. Based mainly in Trinidad whee steel band practice was a near daily ritual.
Forced to leave Trinidad by a hostile, angry immigration officer, despite the need to haul the boat to make some necessary repairs, I set sail for an overnight passage to Grenada, during which I collided with a submerged shipping container, which broke the prop and opened a leak in the hull, 20 miles from land.
Stayed with the boat all day, trying to make landfall, bailing water till the damaged jib blew out. Eventually left the disabled boat to try to make it to land in the dinghy, and was being carried out to sea when a lone fisherman appeared "out of nowhere" and picked me up 12 miles from land, and so ended my 8 year sailing adventure.