Best Hawaiian Road Trips

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Whether you have one day or five—no matter which island you’re exploring—Hawaii delivers incredible views. Besides, a few hours can feel like a lifetime if you’re on the Road to Hana.
We have selected the five most incredible drives in the Aloha State to share with you. Our selections are located in Kauai, Maui, and the Big Island.
You’ll have to get there first, of course, but it’s well worth the effort. To make your experience extra special, consider renting a Jeep or a convertible!
Before you hop on a plane to try one of the best road trips in Hawaii, be sure you’re happy with your car insurance situation and check out Jerry’s roadside assistance membership. It could come in handy if a tropical storm or a stray chicken decides to interrupt your adventure.
Ready to discover the best Hawaiian road trips?

North Shore of Kauai

Sometimes, the most beautiful destination is not where the tourists are flocking. If that idea appeals to you, then head here. This route is a 45-minute drive one-way on HI-56 N and HI-560 W if you go nonstop.
It’s off the beaten path—and a fairly short drive—but that makes it the perfect route to enjoy a quiet, slow exploration of Kauai’s North Shore.

Why you should go

On Kauai’s North Shore, there are plenty of places to stop and enjoy the island’s many beaches (with far less foot traffic than on Maui or the Big Island). Discover quiet surfer towns surrounded by waterfall-studded mountains. Encounter gorgeous native birds and learn about taro and its importance to native Hawaiians—all within a stunning 45-minute drive.

What to do

Start at Kilauea Point Lighthouse on a wildlife refuge. Gates open at 10 AM, and it’s the perfect time for peaceful birdwatching. Then, head west and follow the shoreline.
Along the way, take a dip at any of these incredible beaches: Kauapea, Kalihiwai, Lumahai, Wainiha, Hanalei, and Anini.
If you’re interested in a hike, stop after 20 minutes at Okolehao Trail just before you reach Hanalei. You’ll be rewarded with mountain views of the town and bay below. Five minutes west in Hanalei, the taro fields are a must-see.
Check out Kilauea Fish Market or Tahiti Nui Restaurant & Lounge for a good meal.
End your journey 20 minutes west at Haena State Park and the famous Ke’e Beach. This is where the sacred Nā Pali coast begins. The clear blue waters at Ke’e are perfect for a relaxing snorkel after a long day on the road, although parking may be tricky if you visit during peak hours.
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Kilauea Point Lighthouse from a distance overlooking the Pacific Ocean
Kilauea Point Lighthouse, Kauai, Hawaii

Upper Loop Maui

This route takes just one hour if you drive it nonstop, but we guarantee you’ll be pulling over every 10 minutes. Choose this route if you want the most diverse variety of picturesque landscapes in the shortest amount of time.
HI-37 serves up agricultural lowlands, cloud-adorned forests, and volcano views.

Why you should go

If you have a sweet tooth—or you have someone back home who does—this route is for you. You can sample pineapples, lavender, strawberries, and goat milk cheesecake at the various farms along your path.
Plus, this trip culminates with a vista of the resorts lining Maui’s southeast coast as well as Molokini islet, the island’s prime snorkel spot.

What to do

Your journey begins at the Hali’imaile Pineapple Company, home of the Maui Gold pineapple. In addition to pineapples and pineapple products (like vodka and wine), this neighborhood is interesting because it’s committed to traditional farming and thoughtful urban design.
Now, head south 20 minutes to Kula Country Farms to sample the best strawberries in Hawai’i. Six minutes east on Waipoli Road is Ali’i Kula Lavender Farm, where you can enjoy scones and lemonade with a view.
Get back on HI-37 for the last leg. If you need caffeine, stop at Grandma’s Coffee House where the homemade coffee cake will blow your mind.
Another 15 minutes south and you’ll arrive at Ulupalakua Settlement and Ranch, where you can explore pastureland and jacarandas on the protected slopes of Haleakala. It’s here that you’ll enjoy views of the coast and Molokini.
Turn around and head back north to Makawao for a triumphant finish in a historic cowboy town. Komoda Store & Bakery serves up cream puffs and doughnuts on a stick to mark the occasion.
Key Takeaway Spend an hour on Maui’s Upper Loop to satisfy your sweet tooth.
Sunny countryside and green grasses of Haleakala National Park in Makawao
Haleakala National Park, Makawao, Hawaii

Kealakekua Bay to Kilauea, Big Island

The southern coast of the Big Island has a lot to offer: volcanos, marine reserves, black sand beaches, and historic intrigue. This route will take you two hours to complete one way on the Hawaii Belt Road (aka HI-11). It passes through national parks and fishing villages before a grand finale at the lava fields.

Why you should go

This route has it all, and it’s one of the best ways to get up close and personal with a steaming volcano crater. You can also see petroglyphs, explore a marine reserve by kayak, marvel at black (and green!) sand beaches, and enjoy a truly intimate experience with the most remote part of the Big Island.

What to do

Most people fly into Kona, and your starting point for this Hawaiian road trip is only 40 minutes away. Embark at Kealakekua Bay, where you can rent a kayak and paddle across to a small beach. Here, an obelisk marks the spot where Captain James Cook was killed in a skirmish with the native Hawaiians in 1779.
Pull off at Papakolea after an hour and a half to explore a green sand beach (and the most southern point of the island). Just around the bend at Punalu’u is a black sand beach.
Continue for 20 minutes on HI-11 to Hawaii Volcanoes National Park and Kilauea. The 19-mile Chain of Craters road takes you through a Mordor-like landscape of lava fields—and it’s best experienced at sunrise.
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Steam coming out of the volcano Kilauea at Hawaii Volcanoes National Park
Hawaii Volcanoes National Park, Big Island of Hawaii

Waimea to Kona, Big Island

You may not think of rolling hills when you think of Hawaii, but this route will prove you wrong. Coffee and cowboys dominate the northern part of the island if you know where to look. This route takes two hours nonstop via Kohala Mountain Road.

Why you should go

Hawaii’s paniolo are the native cowboys, and this route gives you the opportunity to explore a real ranching community. Plus, you go right past the north face of Mauna Kea where you can try Kona coffee cultivated on the slopes of the volcano.

What to do

Start in Waimea at Village Burger to fuel up with Big Island-sourced ingredients before your adventure.
Then head north to Kahua Ranch to meet the paniolos, lei-wearing descendants of Mexican vaqueros. Take a tour or a trail ride and be astonished. Then head north 30 minutes to Pololu Valley for black beaches.
Now hug the west shore on HI-270 and head to Hapuna Beach State Recreation Area. Enjoy the picture-perfect white sand and small-wave surfing, then continue south 40 minutes to your final stop in Kona. This is said by some to be the best coffee in the world.
Key Takeaway Did you know Hawaii has cowboys? The Waimea to Kona route can make an introduction.
Two people walking on the dark colored sands along the shores of Pololu Vallley
Pololu Valley, Kona, Hawaii

The Road to Hana (Hana Highway), Maui

One of the most famous roads in Hawaii, the Road to Hana is 64 miles of beautiful (and dangerous) highway along Maui’s east coast. It takes two and a half hours nonstop. You could do it in one day, but we recommend stretching it out across two days.

Why you should go

This route has beaches of every color (white, black, and red sand), waterfalls, plus incredible views around every single turn—and there’s 620 of them. If you want a straightforward and brag-worthy route, this is it.

What to do

Start in Paia for hippie surfer vibes, then head east on HI-36. Stop after 20 minutes at Twin Falls and get fresh banana bread from the famous Aunty Sandy’s Keanae before continuing 30 minutes to Waikani Falls for a swim.
Pull off at Nahiku Road for a 10-minute detour to explore a village with extensive views of the coast. Now hop back on HI-360 to round the eastern point and head for Haleakala National Park Kipahulu Area. Finish your trip with a swim at the famed river pools of ‘Ohe’o Gulch (but check with the rangers first).
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A front yard fence made of surfboards in the beach town of Paia
Paia, Maui, Hawaii

Roadside assistance

In a place like Hawaii, you never know what adventures will cross your path.
A good adventure is a quiet beach all to yourself—but a bad adventure is a flat tire on the slope of an active volcano. Stay safe with Jerry’s roadside assistance. For $6.99, it covers flat tires, fuel delivery, lockout assistance, winching, and more.

How to find cheap car insurance

Jerry is the easiest and most effective way to find a car insurance policy that is customized for you.
After providing you with a comprehensive cross-analysis of the best policies across providers, Jerry will handle the phone calls, paperwork, and renewals for your top pick so that you don’t have to. They even help cancel your old policy! So why do all that extra work when Jerry can do it better?
“Fantastic, seamless process. Thank you Jerry for saving me half my bill!” —Tina M.

FAQs

Are there any special rules for renting cars in Hawaii?

Yes! Some rental agencies do not allow you to take their vehicles on unsealed roads (that is, gravel or unpaved roads). Some sections of famous Hawaiian roads are unsealed, so check your rental agreement carefully before choosing your route.

Is Hawaii more expensive?

Yes. You can expect to pay more for food and gas while visiting Hawaii, since many products have to be imported. Budget accordingly!

Should I expect seasonal road closures in Hawaii?

Yes. Small back roads in Hawaii can get washed out in heavy rain, and occasional landslides or traffic work can sometimes result in road closures. Check this website before you head out to avoid disappointment!
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