How to Island-Hop Your Way Through Hawaii

Two thrill-seeking travellers hike, swim, dive and paddle their way through paradise.

Adventure travellers Dan Moore and Mitch Oates spent two weeks chasing thrills while soaking up the distinctive beauty of four Hawaiian islands.

“Hawaii was much more diverse and adventure-filled than we had expected,” Moore says. “Every island has its own style, different from the next – including the landscapes. We don’t think you have truly experienced Hawaii until you have visited at least three islands to get fully immersed in what it has to offer.”

From home bases at Four Seasons Resort O‘ahu at Ko Olina, Four Seasons Resort Maui at Wailea, Four Seasons Resort Lanai and Four Seasons Resort Hualalai, the pair paddled, swam, dived and hiked their way through paradise – taking time out to unwind and savour the delights of their temporary island homes.

In the slideshows below, each photo is labelled with one of three adventure ratings: “Easy does it” for low-key activities, “On the move” for moderate-energy experiences, and “Off the charts” for adventures boasting the highest adrenaline rush.

Paddling low, climbing high on Oahu

Moore and Oates’ first stop was Oahu, where they relieved jet lag with a little pool time. Refreshed and ready for island life, they dialled up the action with canoeing, hiking through secluded areas of Kualoa Ranch and pursuing the ultimate underwater ocean adventure.

Adventure rating: Easy does it
Relaxing by the pool at Four Seasons Resort Oahu at Ko Olina was the perfect way for adventure travellers Dan Moore and Mitch Oates to recover from jet lag. Photography courtesy Dan Moore
Adventure rating: On the move
Moore and Oates enjoyed a private, guided hike – a hike “you can’t do without knowing the right people,” Oates says – through Kualoa Ranch on Oahu, made famous by the film “Jurassic Park.” Photography courtesy Dan Moore
Adventure rating: Easy does it
“We hiked to the top of the valley – which very few people ever get to see – and looked down through the Kualoa,” Moore says. “It was mesmerizing; we watched the sunrise and a mist flow through the valley.” Photography courtesy Mitch Oates
Adventure rating: On the move
Moore and Oates embarked on three canoe trips during their stay on Oahu, each with a unique mission. “One was a cultural and educational experience, one was surfing on a canoe in Waikiki, and the third was a more relaxing paddle,” Oates says. “We saw wild turtles, sea urchins and a variety of fish.” Photography courtesy Dan Moore
Adventure rating: Off the charts
The most thrilling experience on Oahu for the adventurers was a private trip arranged by the Resort to swim alongside Galapagos sharks—without a cage. “It’s a bucket-list item, something we’ll never forget,” Moore says. Photography courtesy Mitch Oates

Four Seasons Oahu at Ko Olina

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From poolside to countryside on Maui

With only 24 hours on Maui, Moore and Oates wanted to experience as much of the island as possible. With a guide, they took a 12-hour photographic journey to some of Maui’s most scenic locations. “The drive through the island was just as picturesque as the waterfalls and taro farms we visited,” Oates says. “Simply breathtaking.”

Adventure rating: On the move
Moore and Oates spent some time in the water before touring the island, paddling a traditional Hawaiian outrigger canoe from Four Seasons Resort Maui at Wailea. Photography courtesy Dan Moore
Adventure rating: On the move
They visited a taro field, which was next to one of the oldest churches on the island. Here the natives grow the starchy tubers used in making poi. “It was really eye-opening to see how the ancient Hawaiians farmed,” Moore says. Photography courtesy Mitch Oates
Adventure rating: On the move
During the tour, the pair marvelled at the many pools and waterfalls of Ohe‘o Gulch. Photography courtesy Dan Moore
Adventure rating: Easy does it
After their whirlwind excursion on Maui, Moore and Oates spent several hours lounging at the Resort. “You know they actually play music underwater in the pool?” Oates says admiringly. Photography courtesy Mitch Oates

Four Seasons Resort Maui at Wailea

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Exploring Lanai on foot, by horseback and with wheels

“Lanai is the adventure island, with anything you want to do,” Moore says. During their stay, the pair tackled horseback riding, freediving, hiking, and mud-running in an ATV and a jeep. “Even the golf course offers motorized skateboards that you can put your clubs on instead of a golf cart,” he says. “Everything about this island is amazing, from the brand-new, tech-savvy Four Seasons Resort Lanai to remote areas that almost look like you are in an episode of Survivor.”

Adventure rating: Easy does it
“Sweetheart Rock is roughly a 20-minute stroll from your hotel room,” Oates says, “and watching the sun rise over the red landscape is definitely worth the early rise.” Photography courtesy Mitch Oates
Adventure rating: On the move
Moore and Oates enjoyed a horseback ride through the wooded valleys and trails of the hills surrounding Koele, once the center of ranching operations on the island. Photography courtesy Dan Moore
Adventure rating: Off the charts
During what they called the most epic road trip, Moore and Oates explored Lanai behind the wheels of an ATV and a Jeep. “There are four-wheel-drive paths, secluded beaches and a shipwreck – and you barely see another person,” Moore says. Photography courtesy Dan Moore

Four Seasons Resort Lanai

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Water sports and wildlife on Hualalai

On Hualalai, their last stop, Moore and Oates enjoyed a mix of thrills and relaxation. “We actually didn’t leave Four Seasons Resort Hualalai,” Oates says. “It literally has everything you could possibly think of, including turtles scattered along the beach and dolphins just off the beach.”

Adventure rating: On the move
The beaches of Hualalai are the gateway to water sports (think underwater scooter snorkelling and stand-up paddle boarding) and wildlife. “The whole place has an epic vibe about it,” Moore says. Photography courtesy Dan Moore
Adventure rating: Easy does it
When you come in from those epic adventures, you relax here, with friends. Photography courtesy Mitch Oates
Adventure rating: Easy does it
The two men say Four Seasons takes its pools very seriously. “The beach is a matter of metres in front of us, the air temperature is always warm enough to dry you out, and the views are stunning,” Oates says. Photography courtesy MItch Oates
Adventure rating: Off the charts
“We were heading out to do some paddle-boarding and sea-scootering, and we actually came across a pod of 50 or so dolphins,” Moore says. “This was one of the most amazing experiences we’ve ever had.” Photography courtesy Dan Moore

Four Seasons Resort Hualalai

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See more of Moore and Oates‘ adventures in Hawaii

An aerial view of the approach to Lanai. Photography courtesy Dan Moore
Aerial view of Four Seasons Resort Maui at Wailea. Photography courtesy Dan Moore
The view from the top of the valley looking down on Kualoa Ranch on Oahu was “one of the most beautiful locations we have ever seen,” Moore says. Photography courtesy Mitch Oates
“I could have spent days relaxing by the pool, but there are so many experiences to have,” Oates says of their adventure on Oahu. Photography courtesy Mitch Oates
Even the view from an upper floor inside Four Seasons Resort Oahu at Ko Olina is photo-worthy. Photography courtesy Dan Moore
“The shipwreck was amazing,” Oates says of the unusual sight on Lanai. “We walked as close as we could and even though we were a few hundred metres away, it was massive. It’s not every day you explore a shipwreck.” Photography courtesy Mitch Oates
Relaxation and dessert at Four Seasons Resort Maui at Wailea was a perfect ending to an active day. Photography courtesy Dan Moore
The wedding chapel at Four Seasons Oahu at Ko Olina. Photography courtesy Mitch Oates
“Today was all about adventure, and it was an epic experience,” Moore says of the pair’s activities on Lanai. Photography courtesy Mitch Oates
“I could call this home! Moore says of the sunset from Four Seasons Oahu at Ko Olina. Photography courtesy Dan Moore
Mists rise above the Kualoa Ranch valley on Oahu. Photography courtesy Mitch Oates
One of the many vantage points along the beach at Four Seasons Resort Hualalai. Photography courtesy Mitch Oates
The beach is just a few metres away from Four Seasons Resort Hualalai. Photography courtesy Mitch Oates
The rugged shore of Lanai greets adventurers. Photography courtesy Mitch Oates
“The jeep ride was really fun,” Oates says of their Lanai adventure. “We went out with one mission, to cover it in mud.” Photography courtesy Dan Moore
The pair enjoyed lounging – and refreshments – at the pool at Four Seasons Resort Maui at Wailea. Photography courtesy Mitch Oates
“Welcome to paradise – I’ve found my private slice of heaven!” Moore says. Photography courtesy Dan Moore