Road & Rail

Five of Hawaii’s top road trips

Are great road trips really possible on a collection of islands in the middle of the Pacific Ocean with just under 10,931 square miles of total terra firma among them? You better believe it!

Road trippers sampling Hawaii’s uber-scenic island roadways simply have to adjust their definition of the Great American Road Trip a bit. Rather than hundreds of miles of driving, think dozens. Instead of multiple days to finish, think multiple hours.

Best of all? Hawaii’s road trips are as varied as they are unique. From stunning sea-level and sea-cliff coastal drives to cool inland countryside and mountain journeys, road trips in Hawaii boast nature, scenery and experiences that can’t be found anywhere else in the world.

Are your clients ready to put some miles on that rental car? Here are five of Hawaii’s top road trips, complete with must-see scenery, activities, towns to check out and groovy stops along the way.

Hamakua Coast via Modern and Old Mamalahoa Highway (Island of Hawaii)

Rainbow Falls, Hilo

The modern sections of Mamalahoa Highway showcase the northeast Hamakua Coast’s rugged sea cliffs, lush stream-cut valleys, waterfalls and multiple profiles of Hawaii’s tallest mountain, Maunakea, with lots of scenic spots and small towns along the way.

Travellers can take some time to pull off onto remnants of Old Mamalahoa Highway, and they’ll see everything roll by a bit slower and more up close and personal.

Start here: Hilo. Your clients can head to Waianuenue Falls early to experience firsthand how morning sunlight lent the cascade the nickname Rainbow Falls. Then, they can grab a bento from a local lunch shop or fresh island-grown fruit from the Hilo Farmers Market before heading up the coast.

On the road: it’s worth visiting Hawaii Plantation Museum, Onomea Scenic Route, Akaka Falls State Park, Honomu town, Laupahoehoe Point, and Kalopa State Recreation Area.

Brake here: Honokaa. Your clients can explore the main street of the coast’s largest and most vibrant former sugar plantation town, and then make a short detour onto Route 240 to the scenic wonder of Waipio Valley Lookout.

Finish here: Waimea. Travellers can out the paniolo (Hawaiian cowboy) town’s heritage centre and handful of visitor-welcoming working ranches, which share the island of Hawaii’s longtime place in US ranching history.

Roads taken: Route 19 and sections of Old Mamalahoa Highway

Total distance: 55 miles (72 if taking the Route 240 side trip to Honokaa and Waipio Valley Lookout)

Windward Coast and North Shore (Oahu)

Road in Hoomaluhia Botanical Garden

Honolulu’s super-cool and all, but for a respite from all things city, travellers can spend a day on this country-ish two-lane road trip winding alongside the foot of the sumptuous Koolau mountain range and quietly lapping shoreline waters of Oahu’s Windward Coast.

Along the way are beaches, bays, offshore islands, parks, world-famous surf spots and great eats, from Hawaiian food and garlic shrimp plate lunches to fresh-made poke bowls, local fruit smoothies and shave ice.

Start here: Hoomaluhia Botanical Garden. Your clients can steal a pre-road trip moment (or hour) of zen at this 400-acre tropical rainforest garden and lake at the foot of the majestic Koolau range.

On the road: it’s worth visiting Byodo-In Temple Hawaii, Kualoa Regional Park and Mokolii Island, Kahana Bay Beach Park, Ahupuaa o Kahana State Park, Malaekahana State Recreation Area, North Shore beaches and surf breaks.

Finish here: Haleiwa. Travellers should make this relaxed North Shore surf town and its main street lined with shave ice stands, funky boutiques, assorted eateries and surf shops, their end-of-road-trip reward.

Brake here: Shrimp shacks and shrimp trucks. Your clients can follow the intoxicating aroma of sizzling garlic and butter to the multitude of shrimp plate lunch purveyors between the towns of Haleiwa and Kahuku. They can find the best of them by looking for the lengthy queues of hungry customers.

Roads taken: Route 83

Total distance: 41 miles

East Molokai via Kamehameha V Highway (Molokai)

Road sign in Hawaii

One of the loveliest sea-level coastal drives in the islands takes road trippers from Molokai’s main town Kaunakakai past several centuries-old loko ia (Hawaiian fishponds), and at times right beside tranquil or tempestuous shoreline on its way to breathtaking end-of-the-road Halawa Valley and Beach.

Start here: Kaunakakai. Molokai’s only true town is a little-changing, authentically rustic main street of small retailers, eateries and food trucks dedicated to serving island residents, making visiting Kaunakakai all the more wonderful. Travellers can fortify here before hitting the road east.

On the road: An East Molokai road trip is actually less about specific places to stop than the view along the way, especially as Kamehameha V Highway narrows and holds tight against the island’s rugged southeast shoreline, at times sending crashing surf across the road. Travellers can pull over for views, but only where they’re not blocking the passage of other drivers.

Finish here: Halawa Beach. Halawa Valley, as lush and enticing as it is, should only be hiked with a guide, as its acreage is privately owned. Your clients can, however, take in amazing views from the valley’s rugged, remote beach. There’s no swimming here. But the sea-level tranquility at road’s end is enough of a reward.

Roads taken: Route 450 

Total distance: 28 miles

Waimea Canyon and Kokee State Parks (Kauai)

Waimea Canyon

Road trippers should give themselves a day to truly explore winding Waimea Canyon Drive and Kokee Road from sea-level Waimea town all the way up into the chill, misty mountain forests of Kokee State Park.

This isn’t a long road trip, but it’ll seem lengthier as your clients make stops to trek a trail or two. Travellers should check out the road-ending Kalalau Valley lookouts, and take in all of the breathtaking wonder that is Waimea Canyon.

Start here: Waimea. Yep, like the island of Hawaii, Kauai also has a Waimea town; this one also rich with Hawaiian cowboy history, but with the added coolness of being an historic seaport. We recommend travellers stop at the West Kauai Technology and Visitor Center for an illuminating look at the town’s present and past.

On the way: it’s worth visiting Kekaha Lookout, Waimea Canyon State Park and Lookout, Waimea Canyon Trail/Cliff Trail Lookout, Kokee State Park, Kalalau Lookout and, if your clients have time and stamina for a great hike, the Iliau Nature Loop, Kukui Trail or Awaawapuhi Trail.

Finish here: Puu O Kila Lookout. Situated at the literal end of the road (Kokee Road, that is), this overlook boasts stunning views of the Napali Coast’s massive amphitheatre-shaped Kalalau Valley – even better than the Kalalau Lookout a mile before it.

Brake here: Kokee Natural History Museum. The best place to get a sense and appreciation of the flora, fauna, hiking trails, valleys and history of the vast Kokee area forest reserves before getting out an experiencing it all.

Roads taken: Route 550

Total distance: 19 miles

Northeast Coast and East Maui via Hana Highway (Maui)

Driving in Maui

What do you get when you combine 59 or so mostly single-lane, century-old bridges, hundreds of asphalt curves, and 54 miles of roadside waterfalls, verdant rainforests and stunning sea-level and thousand-foot elevation East Maui coastal views? One of Hawaii’s best (and most famous) road trips – period.

Start here: Paia. The gateway to Maui’s renowned north shore surf spots, this trendy little surf town and its restored sugar plantation-era storefronts are home to a modern mix of casually hip retailers, groovy eateries and – no surprise – lots of surf shops.

On the way: it’s worth visiting Hookipa Beach Park and Lookout, Kaumahina State Wayside, Keanae Peninsula and Lookout, Wailua Valley State Wayside, Puaa Kaa State Wayside, roadside waterfalls (lots of them), Kahanu Garden, Waianapanapa State Park, Hana town Hana Bay Beach Park, and Hamoa Beach.

Finish here: Haleakala National Park Kipahulu Visitor Center. Way downslope (we’re talking sea-level downslope) of Haleakala volcano’s 10,023-foot elevation summit, travellers can take the three-mile hike from the coastline freshwater Pools of Oheo through a lush bamboo and rainforest valley to the 400-foot Waimoku Falls.

Brake here: Banana bread stands. Your clients see more than a few of them alongside Hana Highway as growing conditions on East Maui are – pardon the pun – ripe for bananas. If travellers visit early in the day, there’s a good chance they’ll receive their fresh-baked banana goodness still warm from the oven.

Roads taken: Route 36 and Route 360

Total distance: 54 miles

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