Heading to Maui today for the week and packed the bike. Any group rides you all know of?
Maui Cycling may know more. The owner, Donnie, is a good guy. My wife and I did a couple of guided rides with him and his crew.
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Maui has some really great road cycling and you can do a lot of really good rides in a week.
Some rides are fairly easy to do unsupported and others are good to do supported, especially if you have never done them before.
As mentioned, Maui Cyclery, owned by Donnie, in Paia is the go to for guided rides. Note, these are not free group rides but rather you pay for the support. They do rides on all sections of the island but I would really recommend them for the Haleakala climb. They start with the shop and usually have one or two riders go with the group, depending on the size. They also have a truck that goes up with supplies and stops along the way. They are able to go with you to just before the park gate, a little below 7000 feet, and then you do the last 3000 on your own before turning around and riding back to the shop (you regroup at the shop and pay after the ride usually). They include food and water/mix, etc. I have done the guided ride up Haleakala twice with them and then once on my own. They tend to do Haleakala only once a week, so you may want to phone ahead to find out what day the ride will be.
There are a few places to rent road bikes bikes in Maui. Donnie’s shop and also West Maui Cyclery in Lahaina.
I usually go to Maui for two weeks in the winter, so bring my own bike. With American Airlines no longer charging for bikes its become even more economical to bring my own.
One of the best rides is the West Maui Loop around the western half of Maui. We stay in Ka’anapali, so riding clockwise gets you to the rolling hills up and down the coast, then you cut across the island (usually with a tailwind) and then loop back on the flats along the coast. It can be done with 3 bottles at a reasonable pace. You will always see a lot of riders out doing this. My preference is to do it early in the morning, but the banana bread stops might not be open yet…
The road to Hana is also an iconic ride. The key here is heading out early and beating the traffic. I start this ride in Paia and met up with my wife in Hana who drove the road. You can go further but the road does start to deteriorate. Canadian Pro Rob Britton have often done winter training camps out there and rides the full “East Maui Loop” but you should have support for that and definitely not do alone. There is long stretch where you can’t get water and the roads can be bad so high risk of flats.
If you have other questions, please let me know. You are going to have a blast.
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