It all sounded so simple - connect with a local sailor from the Yacht Club and do an overnight passage to Nawiliwili Harbor some ~95 nm's to the Northwest. You know, sail 271 degrees for 16 miles to clear Barber Point, then reset the autopilot to 301 degrees for 12 hours of idyllic beam reaching under gentle seas and amazing stars and you're there.
I had met my new watch captain and some of her crew earlier in the week, then sailed with them as a team off Waikiki in a dying breeze the evening prior to our departure. The crew was a bunch of friendly thirty-something's - personable, interesting and immediately likable. Most were imports from the mainland, here for the positive culture and awesome weather. The watch captain was a retired nursing professor from the local university, and owner of a 35' sloop. On departure day the crew began arriving about 4 pm under overcast skies. The weather forecast models highlighted the absence of the usually dependable trade winds as a series of big low pressure systems approached from the NE. Since low pressure systems are nasty things that typically roam the oceans at will, our night passage conditions were uncertain at best. Time would tell. After casting off from Ali Wai, we motored West an hour to Keehi Boat Harbor for diesel, as Nawiliwili has no fuel dock and our last resupply was last October in Bora Bora. However, in typical tropical style, the fuel dock had been damaged the prior weeks or so, so we were out of luck! Not a show stopper as we had plenty aboard to make Kauai, I just didn't want to haul diesel to the boat in Jerry cans. Don't even start with the Jerry can and Jerry rigged jokes please : - )
As we motored NW in the fading evening light, cartons of Thai take-out surfaced -transforming our cockpit table into a huge buffet of white rice, spring rolls, fish, and every curry sauce you've ever heard of! In hindsight, that may not have been the best food choice for this passage. Oh, did I mention the crew and their skipper numbered eight? Normally, this would be an easy sail, and I'm sure most crew envisioned sitting in the cockpit all night telling jokes. The actual passage was quite different however!
With dinner complete, we raised sails in the darkness off the Ko Olina in 3-5 knots apparent wind. For non-sailors, apparent wind is what the boat "feels" which is always different than "true" wind on a moving boat. For example, if the wind is blowing 10 knots, and the boat is moving 7 knots into it, the boat feels 17 knots. Conversely, if the wind is blowing 10 kts from behind, you only feel 3 knots. This night, the wind blew from every direction at 3 to 22 knots apparent, with lighting and rain squalls skirting by. Combined with a fairly agitated sea, this passage was not an easy one. The result was seven seasick crew (including me and my other watch captain) of the nine. The other two reportedly slept through the ordeal, and were quite chipper at our dawn arrival.

The other thing that happened was the "Bravo" watch, tired of hearing the mainsail slat in the light winds and bumpy seas, tightened the mainsail sheet firmly - unfortunately, the sail ripped in two under the huge loads generated by 15 tons of boat rolling in the sloppy seas. Coming onto watch, the first thing I do is to check the sails for trim and condition. My heart sank when I looked up to see my relatively new sail was in two pieces. Interestingly, I was the only person to even notice! I quickly dropped the sail and we motored onward to Kauai. In the middle of the ocean, this would have been a disastrous situation, but we had the luxury of simply motoring to our destination. A small stack of Ben Franklins' and few trips to the Airport to get the sail repaired in Honolulu is the remedy this time. Live and learn!
Cheers from Nawiliwili.