I have been to Maui four times but never attempted the ride down Haleakala because I feared it would be too dangerous. I (almost) never feared for my life while biking down the volcano because not only do you have one guide on the bikes with you, but another guide is following in a van, blocking traffic and making sure everything is going smoothly. The guides were also funny, welcoming (they gave us doughnuts on our way up in the van), and knowledgeable, and I enjoyed spending time talking with them. We did the 9 am ride and it was somewhat cloudy, but that did not detract from the experience. I would do this again and again.
Tip: Make sure you bring a fleece or coat as it is very chilly up at the top, especially when you have windchill while riding. Some people even wore gloves, but those were provided by Easy Riders.
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