Inspiration Destinations USA Maui to Molokaʻi: The Hawaii Island Guide 

Maui to Molokaʻi: The Hawaii Island Guide 

July 28, 2023

You’re ready to say aloha to Hawaii – but where to begin? Whether you seek smouldering volcanic landscapes or legendary surf, find your perfect island here.

Hawaii conjures images of quintessential paradise: surfers riding white-tipped waves, coral reefs in rainbow shades and high-end resorts in beachfront locations. Here you can find a taste of the good life, but with so many islands to choose from (137 in total), it’s not easy deciding where to indulge. We’ve narrowed down our top six islands – all you need to do is choose your favourite and forge ahead with the Hawaii escape of your dreams.   

Ready to book? Discover our Hawaii offers here.

The Big Island: legendary volcanoes and pristine beaches 

The legendary volcanic landscapes of the Big Island.

Nature has a way of humbling us, and on the Big Island, there’s no landscape more awe-inspiring than at Hawaiʻi Volcanoes National Park, home to Kilauea and Mauna Loa. They’re two of the world’s most active volcanos and you’re almost guaranteed a glimpse of action in the form of long plumes of steam and vivid red lava between cracks of blackened earth. When you’re ready to cool off, head to Makalawena Beach. Just one of the plethora of stunning white stretches of coast, Makalawena in particular is great for snorkelling in the shallow reef and lazing on sugary sand. 

Where to stay: At the oceanfront Mauna Kea Beach Hotel, Autograph Collection.

Oʻahu: Waikiki Beach and top surf 

Waikiki Beach is famed the world over for its surfing.

A great island for first-timers, Oʻahu offers something for every type of traveller. If you’re an enthusiastic surfer (or eager to learn), pick up a longboard at the world-famous Waikiki Beach. Here you can find waves suitable for all skill levels, as well as several surf schools if you’re just starting out. Not only is this beach renowned for its white sand and turquoise waves, it also hosts a handful of high-end restaurants, including the open-air La Mer at Halekulani Hotel. 

Where to stay: In the heart of it all, at Outrigger Waikiki Beachcomber Hotel

Maui: whale-watching and windsurfing 

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Catch a glimpse of a humpback whale in Maui.

Maui sets the stage for tens of thousands of humpback whales who migrate here from the chilly waters of Antarctica to breed, calve and nurse their young. If you want to catch the show, plan to go between November and May (January is peak season, so this will be your best bet). Head out on a whale-watching tour, or make your way to McGregor Point and Lighthouse lookout. If you’re a practised windsurfer or a novice keen to give it a go, Kanaha Beach is considered one of the best on the island for the sport.  

Where to stay: At Montage Kapalua Bay, home to a world-class spa and championship golf course.

Kauai: pristine natural beauty

Nature lovers will find Eden at Kauai.

Smaller and more rural than its sister islands, Kauai is a sidestep from the crowds and boasts pristine natural landscapes that remain largely undisturbed. Often coined the ‘Garden Island,’ Kauai is covered in tropical rainforests, sloping green valleys and craggy sea cliffs. Witness vibrant, almost technicolour scenery, as though the saturation dial here has been cranked to the max. Best ways to fully appreciate Mother Nature’s work? Hike to Waimea Canyon's lookout and admire the ‘Grand Canyon of the Pacific’, saddle up for a horseback ride through sugarcane fields and secluded beaches, or kayak along Wailua River.  

Where to stay: At Royal Sonesta Kauai Resort Lihue, home to Hawaii’s largest single-level pool. 

Lanai: pineapples and private luxury

Venture off the beaten track to serene Lanai.

If you seek tranquility and quietude, Hawaii’s most secluded island beckons. You won’t find any high-rises here. Instead discover the historic town, Lanai City, with its charming handful of shops, restaurants and even a restored cinema. Lanai was once home to the USA’s largest pineapple plantation company in the early 1900s, and you can partake in pineapple appreciation at the annual Pineapple Festival held in summer, featuring crafts, ono (‘delicious’) food, cultural performances and – you guessed it – pineapples.  

Where to stay: In signature luxury at Four Seasons Resort Lanai

Moloka‘i: untouched landscapes and soaring cliffs

Head to Moloka‘i for Indigenous culture and nature in full bloom.

The sleepy yet seductive landscapes of Moloka‘i are a far cry from the buzzing shorelines of Waikiki and Wailea. Here, protecting the natural environment and Indigenous culture is of utmost importance. This means accommodation is limited, but with easy 25-minute flights from Honolulu International Airport (HNL), you can explore Moloka‘i on a day trip. The landscapes are jaw-dropping: picture valleys blanketed in green, the world’s tallest sea cliffs and beaches so stunning you won’t want to leave. Pack snorkelling gear and explore Hawaii’s longest coral reef (measuring 45 kilometres), swimming among sea turtles, gentle manta rays and tropical fish. 

Ready to explore the islands of Hawaii? Check out our range of handpicked escapes

Looking for more inspiration? Top Hawaii Resorts for Wellness Enthusiasts.

About Felicia Arhontissas
A keen traveller and a margarita enthusiast, Felicia is all about getting to the nitty gritty of each destination she visits and discovering its hidden gems (and then running home to write about it).

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