I am considering the following idea for Feb '14. Weather dependant of course, would speak to Ranger at Ohe'o Gulch before proceeding.
Rent a jeep for first 3 days from local company that allows vehicle on backside Hana rd.
After 2 nts in Hana (Nahiku actually - booked - check out by 11am) drive to Upcountry via rd past Kaupo. Visit Lavender farm and/or winery and/or gardens. Drive to Haleakala to take in the sunset. Then drive to Kihei to check into condo (would arrange late check in) and swap jeep for car the following morning.
Not too concerned about the roads, I have experience on unpaved active logging rds with one lane bridges on blind corners!
I am curious about the timing/logistics - how long between Nahiku and Tedeschi winery via this rte? from there to Crater Rd? how long is drive on Crater Rd to summit?
How is the parking situated at the summit? Can you hang out & sit in/on vehicle to watch sunset?
I ask because we will have our luggage with us in an unsecure vehicle.
Do I have to be paranoid about my stuff when in parking areas for winery, lavender farm or gardens too? Would any of these places have somewhere more secure to stash bags while visiting?
I am aware that a jeep isn't necessary for Hana, not getting it because it's 'cool' either. Do like that I'm not breaking any rules taking the 'forbidden' route and the idea of this itinerary.