Yeah I like how @Asian Sensation put it. Wife said, "do whatever you want" when I asked sooo that sounds like a green light to me.
Couple of things i forgot to mention. Take your drink/smoke of choice and a flashlight with you to Little beach. Also when you go to Haleakala, keep your receipt bc you can use it to get into the Pipiwai Trail which is usually the last stop on road to hana (the pass is good for 3 days). Last, be careful at the pink beach, current is strong....literally saw someone pulled under and drown in front of me there...was crazy. Have fun!
I second the Maui Revealed book, by the way. One warning about convertibles: it is very easy to hit a 10 minute pop up rain shower, so watch the clouds around the mountains. It'll be sunny one minute, then you're getting wet the next. We had a convertible Mustang, which was fun, but we had to stop a couple of times to put the roof up. We stayed at a "residence" style room at the Ritz in Kapalua, so we got groceries and that was a good thing to have. We also enjoyed eating sushi at Sansei in Kapalua. I believe that have Karaoke too, but not sure if every night.
Maui Mama's Fish House - make reservations well in advance Fleetwood's on Front street. Mick may be there playing with the band
Bump. Came back from Maui and damn it was gorgeous. Stayed at the Westin Ocean Villas at Kaanapali. I decided to rent a mustang convertible and I was pretty amazed by the car. It was the ecoboost so we barely spent any gas despite doing the road to Hana and going around the island. Figured with the winding roads Id want something with a sporty feel and the mustang delivered. Halaekela was awesome for the sunrise tour/bike ride down. Road to Hana got me a little dizzy even, though I was driving, but worth the trip. Food wise Mama's Fish House was a highlight as well as Tin Roof Maui. Cool Cats at Lahaina was pretty good also. Edit: couple pics from my phone
