8 Cycling Tours in Hawaii Worth Booking

1.Haleakala Sunrise Best Self-Guided Bike Tour

★★★★★★★★★★4.5 · 745 reviews · 7 hours (approx.) · from $272Our pick

Leave Haiku before dawn for Haleakala’s summit, watch sunrise above the clouds, then ride a custom mountain bike downhill from 6,500 feet. Guides such as Eddie Buddy, Corey, and Russell provide safety tips, history, and humor. A shuttle covers part of the route before a second ride toward Makawao and Haiku.

“We left our condo an 2 am to arrive at 3. It sounds like a sacrifice but it was well worth it. Beautiful sunrise, focus on safety, great tour guide. But the extras made it special. First, Don gave us history and sense of place with a large dollop of humor. You need that early in the morning. Second, a surprise side trip gave us what will be one of my 5 all-time favorite photos. Well worth the investment of time, energy and money!”

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2.Waimea Canyon Downhill Bike Ride

★★★★★★★★★★5.0 · 650 reviews · 4 hours (approx.) · from $154Top rated

Join guides such as Ernesto, Tom, Michael, or Jared for a four-hour Kauaʻi outing that combines a scenic van ride, canyon viewpoints, and an 11.7-mile downhill bike ride. You’ll stop in three state parks, learn about local nature and culture, and finish near Kekaha Beach. The ride uses paved public roads and requires confidence on winding descents.

“Wonderful guides took us on a fabulous and safe coast down Waimea Canyon. It’s a great way to see the canyon as there are stops along the way up to see the sights. Our guides offered wonderful stories and shared knowledge throughout the tour. The coast down was super fun! There wasn’t much traffic going up due to the time of day, so it felt like we had the road to ourselves. Guides were very safety conscious”

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3.Fat Tire E-Bike Tour through Volcanoes National Park

★★★★★★★★★★5.0 · 546 reviews · 3 hours (approx.) · from $199

Meet Nicole, Derek, Tyler, Scott, or Bill at Kilauea Lodge for a safety briefing and guided ride into Hawaii Volcanoes National Park. Fat-tire e-bikes make the hills manageable as you visit forest paths, a lava tube, crater viewpoints, and possibly seaside overlooks. Expect about 3 hours, 12 to 15 miles, a small group, and cool, changeable weather.

“My husband and I took this bike tour and it was one of the highlights of our trip! Bill & Scott were excellent guides and very knowledgeable about the National Park. We would 100% recommend this tour!”

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4.Best Haleakala Downhill Self-Guided Bike Tour with Maui Sunriders

★★★★★★★★★★5.0 · 496 reviews · 4 to 5 hours (approx.) · from $139

Start at 6,500 feet on Haleakalā, coast through Maui’s uplands, pause in Makawao, and finish in Paia. Maui Sunriders supplies a front-suspension bike, helmet, gloves, weather gear, route map, and roadside help. Guides such as Remy, Dane, Matthias, and Roy handle the drive and safety briefing while you ride the route at your own pace.

“Amazing time biking down this mountain. The views were insane and ending in Paia was wonderful! Highly recommended”

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5.Water Bike Tour in South Maui

★★★★★★★★★★5.0 · 372 reviews · 1 hour 45 minutes (approx.) · from $124Best value

Start at Makena Bay in South Maui for a 1-hour-45-minute water bike outing with up to 10 people. Your guide, including staff such as Aukai and Kahili, teaches bike handling, Hawaiian words, local history, and marine life as you pedal toward reef areas and a rare black sand beach.

“Very cool experience. Much easier than kayaking and our guide was outstanding. Bikes were very steady and never felt uncomfortable. Highly recommend.”

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6.Haleakala Express Self-Guided Bike Tour with Bike Maui

★★★★★★★★★★4.5 · 271 reviews · 5 hours (approx.) · from $146

Start at 6,500 feet outside Haleakala National Park, coast downhill on a Kona mountain bike, and continue through Upcountry Maui toward Makawao and Haiku. Guides such as Kimo, Dan, Tim, and Nico add local stories during the drive. The ride is self-guided, with some sections handled by shuttle because of local road restrictions.

“This excursion came highly recommended by friends and we’re so happy we did it! Kimo was a great tour guide up and down the mountain - very knowledgeable, personable, and had lots of stories to tell :) Amazing views and cool activity to partake in. Definitely check out the local towns - so much to see and do ❤️”

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7.Haleakala Sunrise Best Guided Bike Tour with Bike Maui

★★★★★★★★★★4.5 · 271 reviews · 8 hours (approx.) · from $317

Start before dawn at Bike Maui’s Haiku base, ride by shuttle to Haleakala’s summit for sunrise, then bike from 6,500 feet through the famous 29 switchbacks, Upcountry Maui, and Makawao. Guides such as Dan, Drew, Russell, and Steve lead the ride, with warm gear, bikes, helmets, photo stops, and a breakfast stop included.

“Guides were awesome. Biking was safe and amazing. Schedule was perfect. Wind and low temps at top of mountain were rougher and colder than expected. Bring at least three layers and gloves!”

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8.Maui Haleakala Sunrise Downhill Bike Tour with Mountain Riders Rated #1

★★★★★★★★★★4.5 · 262 reviews · 7 hours (approx.) · from $279

Start at 2:45 am for a Haleakala sunrise, then ride a chrome cruiser bike down 29 switchbacks from 6,500 feet. Mountain Riders provides transfers, helmets, snacks, water, and guides such as Joe, Nani, Abe, and Everett. The morning ends in historic Makawao Town before returning to Paia.

“The early wakeup is worth witnessing the sunrise at Haleakala. Beautiful and majestic. The bike ride with Mountain Bikers was a thrill unlike any other. Highly recommend doing both - together or individually. Our tour guides Abe, Nadia, Char and Joe were awesome. Joe did a great job awakening our inner child for the thrill of going downhill on the bike ride.”

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