Your ultimate Hawaii island-by-island travel guide

written by Chadwick Kieser April 19, 2017

Hawaii is one of those destinations where you get out what you put in. If all you’d like to put in is the effort required to sink into the nearest beach chair, no problems, Waikiki Beach is right this way… But if you’re after something a little more adventurous, Hawaii will reward you in spades. Get off the main resort drag in Honolulu and the islands are an adventure playground: helicopter rides over the Na Pali cliffs on Kauai, trekking lava fields in the Volcano National Park on Big Island,  snorkelling the Olowalu peninsula on Maui – these are the things you won’t find in the average resort brochure.

We sat down with Intrepid leader, Chadwick, to get the low down on the real Hawaii. The islands and jungles beyond the airport lei-overs (sorry not sorry). Here are his top tips.


Honolulu is definitely a shopper’s paradise, but there’s more to the island than the Alana Moana Shopping Centre (no matter how big it is). I’d definitely recommend a sunset catamaran sail on Honolulu Bay. There’s no better way to say farewell to the sun than sipping mai tais while watching the rainbows and sunset colours dance over the city skyline.

The other must-do while staying in Honolulu is to hike up Diamond Head, the volcanic tuff cone that looms over the east end of Waikiki Beach. This will require sturdy walking shoes and a bit of cardio, but the views of downtown, the mountains, and surrounding sea are well worth the effort. Diamond Head is easily accessible by public bus from Waikiki, and if you still have some energy after the climb, walking back down to the beach can be an enjoyable experience.

One of my favourite places to grab a cocktail and share some appetisers in Honolulu is Rumfire. You’ll find it on the beach at the Sheraton Waikiki. This location has the feel of a tropical Vegas lounge – there’s even booths with fire pits to gather round after dark.


Honolulu is a great place to spend a couple of days, but the real magic of Hawaii happens away from the big resorts. The best place to get in touch with the local wilderness? Kauai. This jungle island paradise is one of the wettest places on earth. It’s so lush and green it almost glows in the dark.

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Adventure-seekers flock to Kauai all year round, and there are plenty of on-ground activities to keep you busy, but one of the best ways to experience the island is from the air. Try to make time for a helicopter tour and experience Waimea Canyon, also called the ‘Grand Canyon of the Pacific’, and the dramatic sea cliffs of the Na Pali Coast. There are also unbeatable opportunities here to hike through the jungle, swim under hidden waterfalls, and kayak tropical rivers – your Intrepid guide can arrange all these for you. For food? Caffe Coco is a hidden gem of a restaurant with a very mellow, homey vibe and offers fantastic vegetarian and vegan options while dining under the stars. It’s in the Kapaa area tucked off the main highway.

Big Island

Let’s clear up some confusion: Big Island and ‘Hawaii’ are the same thing. We spend four nights here on the Intrepid’s Hawaii Discovery tour. Big Island is often overlooked by tourists, which is strange. It actually offers a bigger range of activities than any other island in the chain. Here you can find great snorkel spots, hiking opportunities, jungle trails, and even live volcanic activity!

We split our time on the Big Island between two locations because, well, it’s a big island. We spend the first couple of nights on the west (or ‘Kona’) side of the island. This side is drier and gets the bulk of Big Island tourists. But there’s a reason for that: some of the best snorkelling in all of the islands can be found in Kealakekua Bay where schools of bright yellow tang practically pose for photos. Kona also has one of the most unique dives on the planet: a rare manta ray night dive where swimmers lie with a mask and snorkel along a bright light in the dark water. This attracts plankton, the favourite food of giant manta rays, which then glide up from the depths. It’s absolutely crazy.

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After that, we head to the eastern side of the island, via the southern coast. If you’re taking this route, be sure to stop at Punaluu Bake Shop for some delicious Portuguese malasadas. They’re a great road snack and come in tropical flavours like mango dough (or my personal favourite – lilikoi passion fruit icing). Set up camp in the small town of Volcano, just outside of Hawaii Volcanoes National Park. This is where you can walk over a hardened lava lake bed, through lava tubes, and watch the glow and spatter from an active volcanic crater. If you’re lucky, you may even have the chance to see red hot lava flowing across the ground and falling into the ocean! Not your typical holiday experience.

Hiking in the national park is a must-do on any trip to the Big Island. We use the Volcano Inn as our base to explore the national park and it’s a delight. It has the feel of a small bed-and-breakfast (in fact waking up to their fresh papaya with yogurt, fruit and homemade banana bread will have you blowing kisses to the cook as you head out the door).  If you’re ever staying there, make sure to check out their jungle hot tub; set in the middle of a tropical fern forest and bright anthuriums.


For the following days we set off to Maui and spend the remaining nights of our trip at Lahaina. Along the drive from the airport there is a small peninsula called Olowalu that’s got one of my favourite restaurants on the Islands. It’s called Leoda’s Kitchen and Pie Shop and has some of the best homemade pies I’ve ever tasted (think weird tropical combos like banana cream, pineapple cobbler, taro, and purple sweet potato).  I like to get to-go meals and desserts from the shop and drive further along to one of the many beautiful beach and picnic areas lining the highway. If you time it right, you can carry your picnic dinner to Puamana Beach Park, a local surf spot, and watch the sun set while surfers catch waves and you eat pie. That’s a good Hawaiian night right there.

On Maui, all of the guide books suggest driving the Road to Hana, and I agree. It’s beautiful and offers a chance to swim in waterfall pools and chill on the black sand beaches of Waianapana State Park. If you make the drive, I advise stopping in at Hana Fresh food stand for lunch; you can buy organic picnics and carry them to a nearby beach. Another bonus of this route: you’ll pass through the cute, hippie town of Paia on the way there and back. It’s got boutique shops, good/strong coffee (try Honolulu Coffee Company on the main street), and a fantastic beach just west of town. My last recommendation for Maui is Ululani’s Hawaiian Shave Ice. With a couple locations on Maui, one of them in downtown Lahaina, this shop offers tropical flavours such as guava, mango, coconut, passion fruit. A good treat on a hot day.

A few general notes about travel in Hawaii

Getting around. The best way to get around all the islands, except for Oahu (Honolulu), is car rental – or a group tour. Book early for lower prices. In Honolulu, public transport is plentiful and reliable so you can get away with not renting anything.

Transport between islands. We use Hawaiian Airlines for inter-island travel, which has proven easy and reliable. There are multiple flights per day and they’re not too expensive. You can save money by becoming a HawaiianMiles member for free and save $10 off baggage fees on inter-island trips.

If you’re traveling on your own, I suggest using the commuter airline, Mokulele. They operate very small planes between the islands, and their check-in counters are often separate from the main airport terminals. This means they can check you in for your flight and have you ready to board in just a few minutes. No standing in long security lines and taking off your shoes, emptying pockets, etc. Ferries only operate between the islands of Maui to Molokai and Lanai. The crossings are not super cheap and can sometimes be quite rough. Most people prefer to simply fly since the price isn’t much different.

Local Etiquette. My advice? Embrace the island attitude. People who live on the islands are usually very friendly and chill, and rarely in a hurry. Learn the shaka hand signal and use it freely for everything from hello, goodbye, thank you, what’s up, and hang loose. If you want to sound like a local, ditch the hello, how are you or g’day greeting and instead say aloha, howzit?

Want to see the real Hawaii? The islands beyond the big chain hotels? Check out our Hawaii Discovery group tour. 

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