Generally speaking I think it could be said that any of the dinner cruises you will find listed on our site are going to prove to be a fun experience but I personally believe that your departure point is an important point to consider. For me, I believe that the West Maui departures at either Lahaina or Kaanapali provide the best conditions and views. This is of course a subjective decision but my reasons are born upon years of traveling on dinner cruises that depart from the West Side and also out of Maalaea Harbor in Central Maui.
Every day is different, so these are generalities, but as a rule of thumb, on most trade wind weather days (our most prevalent weather condition in Hawaii) the giant 5000′ West Maui Mountains provide a wind shadow behind them which creates the calm area referred to as the ‘Lahaina Road Stead’. This area of typically calm water is experienced from the harbor of Lahaina and also the coastline of Kaanapali. Departing from these areas on most days will allow for calm sailing and as a bonus from either location you will be able to see the surrounding islands of Molokai, Lanai, Kahoolawe and also look back upon the beautiful West Maui Mountains with their typical halo of clouds fully lit in color behind them.
The beauty of a dinner cruise from Maalaea Harbor should not be relegated to a second place finish however because the views of Haleakala behind you and the Makena Coastline are a spectacular site as well and also for many people the distance driving to Maalaea from their hotel or condo will make much more sense. Just keep in mind that quite often there may still be a bit of a blustery breeze or wind still working its way through the central valley.