The Plan

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Karin and the kids are going to visit friends and family for a couple of months while I do the ungentlemanly thing and bash my way upwind to Hawaii.

Itinerary

Fiji [670 nm]
This first hop is pretty obvious. The great circle mileage will stretch out to 1000nm if we assume winds on the nose so about 6 days. Average winds are E or SE at about 16 knots.

Basic weather strategy is to jump on an east bound cold front or at least avoid huge high preassure and the associated reinforced trade winds.

Tonga (Neiafu) [435 nm]
A possible stop if the winds do not suit for a direct passage from Fiji to Samoa or we want a couple of shorter hops.

American Samoa [670 nm]
Same assumptions and weather concerns as for the first hop, about a 6 day trip.

Cook Islands - Penhyrn [815 nm]
A longer hop than the first two, but as it includes about 300 miles of northing, we can hope for a slightly more direct course. Probably 6 or 7 days of sailing.

A stop at the Suvarov Islands is possible.

If, as several people have warned, we encounter light winds and contrary current, on this leg, we'll head south to Rarotonga

Kiribati - Christmas Island [660 nm]
Should be mostly beam winds so 4 days is doable.

Hawaii [1160 nm]
By the guides and pilot charts this passage is mostly on the wind but we shouldn't need to get too far off the great circle - 8 or 9 days should do the trick.

All told, a total of about 28 days of sailing in the course of about 2 months.