My big trip bucket-item project to do is travel around the world partly by kayak and partly by bicycle, but I’d put a sail on my kayak.
There is a guy who did successfully kayak from CA to HI.
Paddling from California to Hawaii
by Ed Gillette
http://www.legendinc.com/Pages/MarbleheadNet/MM/Articles/EdGillette.html
There have been a few of people who have paddled across the Atlantic, too.
Looking like a castaway Polish man finally reaches land after paddling across the Atlantic on a six-month 6,000 mile journey in a kayak
23APR2014
http://www.dailymail.co.uk/news/article-2611294/Polish-Kayaker-paddles-Atlantic.html
http://en.wikipedia.org/wiki/Peter_Bray
Peter Bray was in 2001, the third person known to cross the Atlantic Ocean alone in a kayak (Franz Romer in 1928 and Hannes Lindemann in 1956 preceded him) but the first one to paddle west to east (i.e.: not riding favorable currents) and also the first one not using sails to help his paddling.
This is a mention from Expeditionkayak.com
On June 25, 1987, Ed Gillet (3) departed alone from Monterey, California in a production Necky Tofino double laden with 600 pounds of food and gear with the intention of mostly sailing his way to Hawaii. However, it was an El Nino year and the anticipated trade winds and currents failed him. Gillet spent less time using his parafoil sail than actually paddling the ‘Bananafish’.
He carried desalinization equipment to ensure a fresh water supply. But when he lost his radio on week two, with it went all contact with the outside world for the remaining eight weeks. When Gillet failed to appear by his predicted arrival window his family flew into a frenzy. They unsuccessfully lobbied the Coast Guard to search for him. Sixty-three days after his departure and four days after he ran out of food, suffering from 40 hours of sleep deprivation and subject to winds and currents driving him north, past the islands, Gillet steered in a hallucinatory dawn into Kahului Harbor and landed on Maui Beach.
“…a life raft experience. It amazes me, when I think back on it, that I didn’t die,” he says. “It doesn’t amaze me that I paddled to Hawaii—that’s more or less a straightforward thing to do. You make the mileage, you paddle your boat, you get there. It’s benign at that time of year: You don’t have hurricanes at the latitudes I was traveling at. But physically, I’m still amazed I was able to withstand that kind of punishment.”
Despite advances in technology, Gillet’s 2,200-mile Pacific journey remains so epic none have ever tried to match it. A few kayakers have achieved greater mileage, but not on an open-water crossing of the Pacific.