@bdiederich24 Unquestionably, you should do Haleakala!. And based on your description of your fitness, you can do it!
Pending decent weather (check the forecast for the mountain), you will be treated to some phenomenal views. They are particularly great to enjoy on the descent. You can stop at the switchbacks. Living where you do, you probably don’t have a lot of descending experience, but the Haleakala descent is rated as the 3rd best in the world - wide, smooth turns, excellent pavement. Even without the skills to take them at speed, you will enjoy it.
Now, for the climb. It’s obviously long, but the gradient averages about 5%. Even as a non-climber, you will have no trouble. There’s no “steep stuff” other than a short 10% section near the top. A couple of suggestions, some a repeat of @thesupermarket comments:
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Pace yourself/take your time early on (conserve your energy). Above 6500ft, the air starts thinning out and you want to have what you will need at 8k and 9kft to the finish (it will take 10-20% more energy to climb the same distance).
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Stop at Kula Market on your way up. It is after Kimo Drive and just before you get to Crater Road. It’s a great place to refill your water bottles, get some food and take a 20min break at the picnic tables. There’s some bathrooms there as well (backside of the market). Here’s my ride if you want to zoom in on its location:
https://www.strava.com/activities/450392293/segments/10827424414 -
Of course, when you get to the top (ride through the parking lot up the path to the observatory) you need to get the obligatory photo of holding your bike over your head with the 10,023ft sign behind you. It’s a special memory!
If you are staying on West Maui, West Maui Cycles is a great place to rent a bike. They are a great shop, very friendly and very knowledgeable. While you can reserve online, I would strongly suggest calling them (ASAP). They will ear mark your exact bike and have it set up for you. The bikes they have include the Specialized Roubaix. It is a perfect bike for enjoying Haleakala. They may have pedals, but I’d recommend bringing your own. I also brought my own helmet.
If you are staying elsewhere, Maui Cyclery in Hana is a great place to rent bikes. I know the owner, Donnie Arnoult (former pro racer with Team Saturn), very well (I have ridden with him several times; he manages the annual “Race to the Sun” Haleakala race in August). They offer guided rides around Maui (for avid cyclists) and used to offer a ride up Haleakala (I did it twice with Donnie). However, Maui pulled all commercial licenses up the mountain inside the park due to a couple of deaths from those downhill bomber tours (extremely untrained riders in snow suits with motorcycle type helmets).
Parking: It’s pretty hard to find parking on the street near the entrance to Baldwin Ave unless you get there early. However, there’s public parking about 1/4 mile back on the inland side next to the Shell station. This time of year should be no problem getting a spot.
After the ride, you should stop in at Paia Fish Market at the corner of Hana Highway and Baldwin ave. Fantastic fish sandwiches and great beer in a lively atmosphere with bench seating (i.e. no problem being on your own). It’s a fantastic treat after a great accomplishment!
As for West Maui, I might suggest that you and your wife take a drive there. It is very windy, but if you take it slowly you can stop for some amazing views. It does get narrow as you go further so you can stop and turn around if she gets uncomfortable.
Let me know if you have other questions.