1) October can be hot. The rainy season usually starts a bit later, but some parts of the island (Hana, Waihee) are much rainier than others (Kihei, Lahaina) in any case. 2) Probably OGG-Kahului, definitely OGG if you re on a jet. A few small planes go to Kapalua or Hana. Most of them are 9-seaters on island hops. You ll get the safety speech directly from the pilot, who will ask you to take your aloha bag with you when you get off the plane if you use it. Those flights are great for taking pictures, not so great for digestion. Wait until you arrive to eat.3) Plenty of condos near the beach in Kihei and north of Lahaina. There are plenty of agencies who connect owners with renters. I like to use VRBO.com when I go on vacation to other places.4) As a general rule, you ll get the best deals about three weeks before you leave, and you ll have fewer changes to the flight plan. Cheap Tickets and Pleasant Holidays are two websites people from Hawaii often use. Hawaiian airlines often has some good deals on their own website, and they are celebrating their 80th anniversary this year.5) Let s see: surfing, windsurfing, kiteboarding, stand up paddling, snorkeling, scuba diving, snuba diving, Maui Ocean Center, ululena, local music performances, attend a luau, drive up a dormant volcano, go hiking, shopping, swimming, hanging out on the beach, golfing, tennis, driving to Hana, people watching on Front Street in Lahaina, taking a ferry to Molokai or Lanai, eating fantastic food inspired globally and grown locally, and the usual drinking or going to the movies.6) You should rent a car. Maui is much more spread out than Oahu. There is a bus system with several routes, but some of them only run every 90 minutes. You don t want to spend your vacation waiting on a bus. Plus, Maui is very drivable. Compare it to Oahu, a slightly smaller island with 7 times more people trying to get to work, school, the mall, little league games, and the supermarket. Maui does occasionally have traffic jams, but we are surprised when they happen.
there are quite a few sites that you can search that will likely give you the best prices available. check out the website BookMe and you will be able to compare prices on all the reputable travel sites in just a couple minutes. it s very convenient and will save you a bunch of time and money. Also, make sure you buy them online... otherwise they charge much higher fees for phone orders. good luck.