The Molokai channel can either be challenging or brutal depending on how strong the trades are blowing. If the recent winds hold, the trip would be tending to the brutal. Keep an eye on the weather
. If small craft warnings are happening, you'll find every leak you didn't know you had in your boat and better have a strong stomach. You'll be looking at very steep seas, 10' or more and gusty 25-30 mph winds on the nose. If the trades settle down, it will still not be comfortable but any boat and crew shouldn't have a problem. You'll still be beating into 15mph plus winds but the seas will be lower than 5' and not as steep. With the flukey winds we have had, you might find southerly winds and the trip could be a sleighride but I wouldn't count on that. Winds are almost always north easterly even when the trades aren't happening. There is a significant lee off Molokai. If you want to sail all the way, stay close to Lanai. If you are heading to Kaunakakai or Hale'o Lono on Molokai, you'll probably end up doing a bit of motoring unless you really like to sail in flukey ghosting conditions. Kaunakakai is the 'Big' City on Molokai. It's a small laid back town worth visiting. Hale'o Lono is on the west end of Molokai and basicall just a commercial
harbor without commerce. Otherwise, there isn't anything there except when the Molokai Channel Canoe races are getting ready to leave.
You can anchor
off most of the lee shore of Maui except where you are exposed to the winds coming through the saddle. Lahaina Harbor is tiny and doubtful that you'd find a space. Maalea is a windy, surgy semi commerial harbor that has little to reccomend it other than it's a place to hide from the winds in that area.
Later on in the year, when the surf and trades settle down, you can anchor
on the windward side of the islands. I plan on trying out the windward sides when I got my boat over here this summer. From the air, there are some really inviting looking bays and valleys to explore.
Manele Bay on Lanai is a nice anchorage, winds permitting, but the harbor is tiny and space very limited. The other harbor on Lanai is a commercial
harbor and not very interesting. There are probably a lot of places to anchor around Lanai, once again, if the winds and waves cooperate.
So bring a dinghy
as you'll be anchored out much of the time. I used to love to hang out in Kaunakakai but haven't be boat challenged and haven't been back in a number of years. It's a great sail back to Oahu, that is if you like surfing at 10 plus knots.