FOR PLANNING A SIMILAR EXPERIENCE:
RULE 1 Book a hotel you know the family will love even when you’re not there. We went for the Andaz Maui at Wailea Resort, knowing the family would be happy enjoying the mahalo beach vibes.
RULE 2 Do a lot of research. Gentry offered to take us on a guided tour of the island, but usually he’ll simply tell you where to go and how long it will take. The internet is your pal and kept us away from the torturously slow Road to Hana. For the right wheels, book early. The prices on Turo and DriveShare vary, but expect to pay a few hundred dollars per day for a whip like the Lotus and up to a thousand-plus for an exotic, insurance included.
RULE 3 When all else fails, ask the hotel concierge, as they can set up almost anything and everything for you, including guided tours. That’s what we did at the Four Seasons Resort Lanai; an hour later and a few hundred dollars lighter, we were bombing red-dirt back roads in a Polaris RZR side-by-side.