A number of West Maui hotels rent Hobies. Mostly Waves. STAY AWAY FROM THE HYATT!! Their boats are very poorly maintained.
West Maui Sailing Center in front of the Castaways restaurant north of Black Rock has a 16 and a Getaway. Chuck, the owner, is a long time Hobie guy.
The sailing here can be interesting. If the trade winds are up, you'll be in a consistent 20 + wind. It's 5 PM HST and the wind is at 17 mph gusting to 29. If you hang to the west of the wind line, you won't have any problems.
The old locals say sharks won’t bother you if you don't go in the water early in the morning, late in the afternoon, if it's cloudy, and after a rainstorm when the water is murky from run off. Most of the latest shark bites have been in the South Maui area.
There is absolutely no way you can get from Hana to Kaanapali in one hour. Between traffic and road conditions, you'll be lucky to make it from Hana to the airport in 1.5 hours. The summer visitors are here so you do not want to be on the roads in West Maui between 3 and 6 PM. It may take a half hour to get from Kaanapali to Lahaina.
Don't worry too much about saying any of the names correctly. The locals have already got you classed as a visitor because of your either pale or red skin.
Use lots of sunscreen and wear your Cool Dude Sunglasses.
If you're looking for food try the Plantation Course clubhouse in Kapalua for breakfast. Prices are reasonable and you get a 100-mile view. Dinner at Pacific'o, 505 Front St. Extremely fresh fish. Make a reservation for 6:30 and ask for a seat on the hedge. You'll get a great sunset. The owners are long time sailors.
If you're In Lahaina Friday (June 21), stop by the Lahaina Yacht Club. I'm teaching junior sailing and should be there unless the senior instructor decides we're taking the kids out on the club's Olson 30.