Maui is one of my favorite places to road cycle. I’ve done the West Maui Loop a bunch of times, Haleakala three times, and a variety of other rides. I have a few general pointers and then some specifics below.
Ride early. Traffic always picks up as the day goes on, and so do the winds. West Maui Loop and Road To Hana are in particular best early. The downside is Julia’s Banana Bread shop won’t be open yet, but it’s so much nicer to have less traffic.
Put a rear light or Garmin Varia on your bike. The more visible you are, the better. There are a lot of distracted tourists. Personally I wouldn’t ride without a Varia.
Be considerate to the locals. Nothing infuriates the locals more than having someone block the road as they are making their commute to work or back home. The Varia helps a lot here. I always pull to the side and give a wave to the locals. Nine times out of ten they wave back. I’ve seen other riders refuse to move to the side and it just creates a really bad situation.
Roads can be slippery, especially the West Maui Loop, when wet. There is a lot of red clay on the west side of the Island, so if the roads are damp be careful because the clay is very slippery. Intermittent short showers can hit too, so disc brakes are nice to have too.
28s are awesome on the Maui roads. Haleakala is generally smooth, but the 28s are great for the descent. The West Maui Loop and Road to Hana can have some chopped up pavement in parts and the 28s really help smooth this out.
West Maui Cycles is a great bike shop and has some detailed information on their website for some of the Maui rides including Haleakala. They are located in Lahaina. I usually pick up some CO2’s there when I arrive since you can’t fly with them. They will then give you store credit back if you don’t use them and bring them back.
Maui Cyclery is in Paia and do some a number of guided/supported rides on the island. They have a supported Haleakala ride that usually runs once a week. If it is your first time doing Haleakala I would recommend this option. They will have someone riding along with your group, but allow you to ride at your own pace. There will be a vehicle they bring with supplies, food, and water. They can go up about two thirds of the ways, but they are not allowed in past the park gate, so after that point you are on your own. You call the shop to schedule the rides and they will let you know what days things are happening. They also rent bikes and will try and set up the bikes similar to your own bike if you send measurements. I always bring my own but their rental bikes looked good and the people I rode with had no complaints.
I’ve done Haleakala three times, the first two as a supported ride with Maui Cyclery, the third on my own, but my wife was driving up that day and did hand me some bottles on the way up. There are places to get water, per the guide. Depending on your pace you will need to carry two or three bottles at a time. Bring money and a credit card. You have to pay to get through the gate to the park 2/3s of the way up. Weather is the big variable. It can get very stormy up top, so best to pick a day with a good forecast. Carry a rain jacket, arm and leg warmers and gloves. That will get your through most things.
I’ve ridden two different bikes up Haleakala. This first was a SRAM 10 speed set up with a standard crank up front and a wide range rear cassette (I believe 11-36) with WiFli rear derailleur. It worked fine. I then switched to my current road bike with has a compact set up in the front and a 11-28t in the rear. It’s a great set up for the entire island.
The Haleakala climb is a long grind, but not super steep. You will hit much steeper stuff on the West Maui Loop, but Haleakala is 36 miles of almost all uphill. You just have to settle in and grind it out. If you don’t like long tempo or zone 2 work, you will not like this climb. Wind can be a factor and slow you down is places, but you just have to grind through it.
I love the descent, lots of big sweeping switchbacks that you can carry a fair bit of speed through. The road is generally in very good shape with wide shoulders. The problem I found is that I will descend faster than the cars, so if the cars don’t let you by it can be a drag having to follow them. I ride 28’s with a disc brake equipped Emonda, so a great climbing and descending bike. Discs let you dive into the corners a little more aggressively and will also help a lot if there is some rain.
West Maui Loop:
I agree with riding clockwise. This keeps you on the inside of the road. I start in Kaanapali which sets up the ride perfectly. You get some flats and a slow steady climb to warm up and then you hit the awesome rolling hills along to coast past Kapalua as the road narrows. Tons of amazing photo ops. As mentioned, I go early so the traffic is super light. Julia’s is closed at this time but the Art Gallery just past it may be open and have water. Awesome photo spot there too. After the climbs are over, you will work your way across the island, usually with tailwinds, and then circle back along the coast. Multiple places to stop for food and water here. I do the loop on three bottles and don’t have to stop, but depending on your pace there are lots of spots to stop, enjoy the view, and get food and water.
It was mentioned on TR podcast that this ride may be “overrated”, but I disagree. It’s my favorite road ride hands down and I always look forward to going back. I’ve seen a few pro’s out over the years too. Rob Britton used to ride there every Christmas and once flew past me up Haleakala. Emily Batty just returned from a Maui training camp and posted multiple pics on her Instagram from the West Maui Loop.
Road to Hana
This is another iconic ride. I’ve only ridden it in one direction though, from Paia to Hana. I park in Paia and leave shortly after sunrise. The result is an amazing ride up and down the coast with spectacular scenery and little traffic. It is so much fun. I’ve met up with family in Hana after and ended up driving back later in the day after doing some hiking. I think it would also be ok to turn around in Hana and head back, as most of the traffic would be coming the other way. The road is similar to West Maui along the west shoreline, rolling, sometimes a bit wet, and some chopped up pavement, but the views…
Please feel free to message me if you have any other specific questions, or just post here. Happy to share any knowledge I have that might help.