Think of Hawaii and your first thoughts are likely to be of surf breaks, grass skirts, and pineapples. And if you are planning a trip to Hawaii chances are it’s not with cycling front of mind. But with such a variety of rides within close proximity and a landscape that was surely formed with cyclists in mind, it’s time to add Maui to your list of cycling holiday destinations.

Making the connecting flight to Maui from Honolulu it is impossible not to notice the two looming (and reassuringly extinct) volcanos which form the east and west sections of the island. What becomes immediately apparent is that the entire island is simply two volcanos shunted together.

Skirting the edge of east Maui at height feels like a surfer picking lines in the break — a spiderweb of twisting, curving roads snake their way across, over, and through the island. Head away from the coast and everything is up.

While not as lush as the Jurassic Park-esque Kauai, Maui clearly is incredibly beautiful. The barren upper reaches of Haleakala poking through the cloud look like a moonscape, whereas the densely forested lower reaches seem inviting and cool.

Heading out from the airport nestled in the valley you could be forgiven for thinking you are in any suburban centre (save for the imposing 3,000m peaks extending into the cloud above your head), but within a couple of minutes drive this is quickly replaced by the tropical surrounds you might expect from a Hawaiian island.

After setting ourselves up and getting the bikes into gear it was time to get out and explore the island by bike. Our group was picked up by Donnie and the team at Go Cycling Maui and driven to the lower reaches of Haleakala.

With an uninterrupted view down the long slopes into the saddle between east and west Maui, it was easy to forget we were sitting higher than the majority of peaks in Australia. We applied sunscreen – which needs to be a second skin there — and headed east in the direction of Hana.

After a dozen winding, weaving and downright fun kilometres through the forest we were spat out above the long legs of the lower slopes of Haleakala as we slowly circumnavigated the island. Imagine collecting up a large sheet in the middle — we were traversing the furrowed ridges, slowly scrubbing off altitude, but constantly rolling, climbing, and descending to the next undulation.


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Andre Cheuk takes in the view.

As we continued to round the island we noticed the landscape starting to change. Replacing the thick forest were the windswept crinkles of the lava fields. We could now see the road dipping and weaving far ahead of us, stretching around toward Hana. In the distance we could see the magnificent wind turbines humming against a foreground of green scrub and deep blue water. Feint alarm bells started to sound. Surely where there are wind turbines … and then smack we were hit in the face with a block headwind.

“Our goal when taking cyclists out on the island is to use the altitude gain to our advantage” explained Maui Cyclery’s Donnie Arnoult. “We want to always try to descend into the wind, and climb protected”. With the predictable daily Moa’e tradewind it becomes easy to plan ahead.

Despite getting knocked around with each slight change of direction, we were dumping altitude at a constant rate, and the headwind’s only effect seemed to be raising the required conversation level to a dull roar. The road was beautiful, the surface smooth (something we were to encounter constantly on this trip), and the ‘winter’ weather a stunning 27 degrees Celsius.

Turning around and heading back we were faced with a tailwind-assisted 1,000m of climbing. With virtually no resistance from the baby-smooth tarmac and a stomping tradewind in our sails it felt like an unfair (but welcome) advantage.

Just above our fresh sandwich lunch stop at the infamous “Grandma’s” we took a small detour along a narrow handbuilt rockwall-lined laneway. With incredible views and white picket gates it was unsurprising to hear of the high property prices and famous neighbours. After a quick natural break at the entrance to Oprah’s Hawaiian getaway we were back on the road, homeward bound.

Due to the earlier climb we were owed another 2,000m of descending so once again we took off into the wind. In a tight pack the descent was fast, taking us down the mountain and deep into the sickly-sweet-smelling sugarcane plantations.

Back on the main road the highway junk kays should have been less enjoyable but a wide bike path, tailwind, and a quick group meant that the time passed quickly. There are only a handful of freeways on the island, and all either feature wide shoulders or specific bike paths. They are a somewhat necessary evil, with limited linkage roads joining the fun stuff. We came to know this particular stretch well.


The road outside Oprah Winfrey's Hawaiian getaway.

The road outside Oprah Winfrey’s Hawaiian getaway.

For a bunch of climbers, the Haleakala climb and descent provided the biggest drawcard during this trip, its taunting 3,000m peak in view almost the entire time when on the island.

Speaking with a few of the local riders they were surprised by the interest. The majority of cycling visitors head straight to the Road to Hana a 60-mile (100km) stretch of road that hugs the north-east coastline and features a staggering 617 corners. With a large group we opted out of this, as it is best tackled early in the morning, and with a small crew. The road’s tight blind corners and small shoulder are no mix with the tourist traffic.

In fact such is the road’s reputation that hire cars are not insured beyond a certain point. Somehow that just makes it all the more appealing, and combined with many firsthand recommendations it is on the list for another visit.

At a shade under 100km and 300m of climbing, the West Maui loop is a weekender’s favourite with a regular crew leaving from West Maui Cycles. Rides midweek tend to be solo unless you specifically hook up with one of the bike shops.

Many of the tours sold on the island tend to focus on the Haleakala descent, but do your homework before booking anything, as many of these are with full-face helmets and coaster-braked cruisers.

Rides on the island are best started early, before the heat of the day sets in. If you are taking in Haleakala pack for all conditions. We departed Paia in 30 degree heat and were faced with sleet at 2,500m. An ascent three days later by one of the riders saw him rolling from left-handed switchbacks in the sun, to belting rain on the right-handed switchbacks during an hour of climbing. Water stops are available, but scarce, so ask around before heading off.

It seemed that wherever we rode on the island – from the jumbled lava fields and black sand beaches, to the deeply cambered switched climbs, or rollercoaster traverses — the roads were smooth and well maintained. One road is a happy coincidence, but after a week of riding constant hotmix it tends to spoil you for anything less.

Click here to see Andy’s Strava file from the ride. Click here to read Andy’s article about test riding Shimano’s new Ultegra groupset (including disc brakes) on Maui.

Disclosure statement: Andy’s trip to Hawaii, including flights, meals and accommodation, was provided by Shimano, whom we would like to thank for this opportunity. No payment was made for this article. Shimano advertises separately on CyclingTips.