The Best Hawaiian Island Guide: Find Your Perfect Match

Hawaii’s tropical paradise is bursting with adventure, natural beauty and a unique cultural heritage – but choosing the best Hawaiian island to visit depends on what kind of experience you’re after.

From the dramatic volcanic landscapes of the Big Island to the peaceful tranquillity of Kauai’s Garden Isle, each island offers something uniquely different.

This guide is designed to help you choose the best island to visit in Hawaii based on your personal travel style – whether you're planning a romantic escape, a family adventure or a golfing getaway. For each island, we’ve handpicked our favourite luxury stays, including some utterly luxurious escapes at Four Seasons Resorts.

From sunrise hikes to snorkelling spots, quiet retreats to buzzing beach towns, we’ll help you find the Hawaiian isle that suits your itinerary and interests best, so you can focus on what matters most: experiencing the magic of Hawaii. 

Or, if you're intrigued by all that Hawaii has to offer, island-hopping is the perfect way to explore, as our Product Manager David shares in his expert guide. 

1. Oahu

Best for:

• Big city attractions

• Surfing

• Waikiki Beach

Home to the state capital, Honolulu, Oahu is the most developed and popular of all the Hawaiian Islands. Honolulu itself is a vibrant hub of culture and entertainment on the south shore, with museums, parks, galleries and live performances throughout the year.

With options to explore the historic Pearl Harbor, hike up Diamond Head, wander through the Koko Crater Botanical Gardens and more, you’ll never be short of things to do here.

Visit Waikiki Beach for exquisite dining, chic boutiques, vibrant nightlife and some of the best beginner and intermediate surfing in Hawaii.

“Oahu is considered the birthplace of modern surfing, so if you’re serious about surf, venture north to Waimea Bay and Sunset beach for towering swells and big wave action.” – David Pointer, Senior Product Manager

Where to Stay?

The Four Seasons Resort Oahu at Ko Olina is undoubtedly one of the Hawaiian Islands most exclusive hotels and is a tropical-luxe haven that looks out over beautiful beaches.

Another exclusive pick, Halekulani Hotel is a foodie’s delight with the only Forbes Travel Guide 5-Star restaurant in Hawaii, perfect for a luxury couples’ break or honeymoon.

2. Big Island

Best for:

• Hawaiian culture

• Adventure at Volcanoes National Park

• Scenic golf

Commonly known as “Big Island”, The island of Hawaii is the largest and most geologically diverse in the Hawaiian Islands. Here you’ll see immense contrasts in landscapes as bubbling volcanoes and lush rainforests fade into gentle beaches, some of which boast volcanic black sand.

If you love exploring, Big Island is perfect for you. Hire a car for picturesque drives past sacred valleys, botanical gardens and lava deserts, and get a glimpse into local life in the charming towns of Hilo and Waimea.

“Whilst Big Island is most famous for the Hawaii Volcanoes National Park, the coffee estates are a must-visit and are often set in verdant valleys with nearby waterfalls to explore.” – David Pointer, Senior Product Manager

Where to Stay?

The Four Seasons Hualalai offers a luxurious stay on Big Island with an exceptional 18-hole Jack Niklaus signature championship golf course to enjoy. 

Kona Village, A Rosewood Resort

Set along the dramatic shores of Kahuwai Bay on Hawaii’s Big Island, Kona Village, A Rosewood Resort places you in 81 acres of pristine volcanic landscape. Here, you’ll stay in one of 150 standalone hales – inspired by traditional Polynesian structures – so you’ll feel totally immersed in the spirit of Hawaii.

Don’t miss: The impressive local art collection – or, for kids, the Explorers Keki Club.

3. Kauai

Best for:

• Dramatic scenery

• Farm-to-table dining

• Kauai coffee

Nicknamed the Garden Isle, Kauai has some of the most dramatic scenery in all of Hawaii. Life moves at a gentle pace here, so it’s the perfect place to come if you’re looking to unplug from the busy world and revel in the island's rainforest serenity.

The Waimea Canyon and the Na Pali Coast are both stunning to see first-hand. Both provided the iconic backdrop to the Jurassic Park movies in the 1990s, although no dinosaurs are likely to ruin your peace nowadays.

“For the full Jurassic Park experience, charter a private yacht or take a scenic helicopter tour around the pristine and remote Na Pali Coast for romantic views of Hawaii’s most beautiful coastline on the Garden Island.” – David Pointer, Senior Product Manager

Where to stay?

1 Hotel Hanalei Bay

Boasting one of Kaui’s most spectacular settings, the stylish 1 Hotel Hanalei Bay is perfectly placed for admiring the tranquil shores of Hanalei Bay and the dramatic Nāpali Coast. From here, you can easily head out to explore rainforest trails or tee off to stunning views on the Robert Trent Jones Jr-designed golf course.

Don’t miss: Upgrade to the Retreat Collection for exclusive benefits, including spa treatments and beach cabanas.

4. Maui

Best for:

• Sunrise hikes

• Honeymoons 

• Foodies

• The scenic Hana Highway

Maui is locally known as the “Valley Isle”. Two dormant volcanoes bookend its fertile valley in Haleakala National Park: to the east, the Haleakala summit is famed for sunrise vistas, perfect for early morning hikes; to the west, the West Maui Mountains overlook lush rainforests and waterfalls. Between them runs the island’s spine and the famous road to Hana, with dozens of waterfalls to explore and a black-sand beach at Waianapanapa.

Maui also has vibrant seaside towns, Lahaina is best for art galleries and whalers’ history, whilst Paia boasts a roaring windsurfing culture. The agricultural upcountry of Makawao is especially charming, and its farms produce Maui’s famous sweet onions, goat cheese and lavender. You can even do insider farm tours here including pizza at a lava-stone oven, tours of lavender fields, and wine-tasting at local vineyards to taste it all.

Where to Stay?

With direct access to Wailea Beach, Four Seasons Resort Maui at Wailea combines sophistication and the serenity of an exotic hideaway with the family fun of a relaxed beach retreat.

5. Lanai

Best for:

• Secluded stays

• Desert views

Lanai offers refined seclusion far from the well-trodden paths of the other islands. Once a pineapple plantation, it’s now largely privately owned, with just one small town and a handful of ultra-luxury resorts. Yet beneath its understated profile lies immense appeal: rugged cliffs, hidden beaches, and forested highlands with scenic hiking trails.

Manele Bay offers the chance to tick off your bucket list experience of swimming with spinner dolphins in crystal-clear waters, whilst the windswept plateau of “Garden of the Gods”, Keahiakawelo, is best visited at sunset to see its red-hued boulders and ancient lava canyons glow in the waning sunlight.

Shipwreck Beach on Lanai's north shore is also worth the trip to see the skeletal remains of a World War II concrete barge resting on the shore reef.

Where to Stay?

The Four Seasons Resort Lanai is the perfect spot for a couple’s holiday full of special moments or a relaxing honeymoon. With a romantic setting, sumptuous spa and plenty of things to do, this is a truly luxurious Hawaiian island paradise.

Ask the Expert

How easy is it to hop between Hawaii’s islands?

It’s so easy to island-hop in Hawaii, and it adds so much to the experience. There are several flight connections between the islands, plus a ferry between Maui and Lanai. Our Travel Specialists arrange all of this for you, so you can relax and soak it all in.

Which islands do you recommend – and how many should you include in one trip?

It depends on your interests and how long you’d like to be away. Each island offers a different side of Hawaii, from golden beaches to cool surf spots, volcanic craters and nature-inspired wellness. You can linger as long as you like, though I recommend around four nights on each island to give yourself enough time to relax and explore. 

What is your personal favourite island?

I have two favourites – Maui and Kauai.

Maui offers beautiful, upscale hotels, some of the best golden beaches, and a range of activities, from volcano hikes and sunset experiences to snorkelling and iconic coastal drives. Kauai, meanwhile, is home to my favourite hotel, 1 Hotel Hanalei Bay, and the stunning Nāpali Coast.

What type of experiences do you suggest to make the most of Hawaii?

Where to start! To see Kaui’s Nāpali Coast in all its glory, I recommend spending a day cruising the coast. Snorkelling is best in Maui, known for some of the clearest waters in Hawaii – with highlights including Molokini Crater and Turtle Town – and on the Big Island, where you can snorkel or dive at night with manta rays.

Of course, nothing is more iconic than surfing in Hawaii, and we can arrange expert-led sessions for all levels. Don’t underestimate the food, either – stop by the tasty food trucks across any island, or visit the likes of O’Farm Maui for fantastically fresh farm-to-fork dining.

What are your ultimate ‘must-dos’ in Hawaii?

A helicopter tour would be top of my list; it’s the best way to appreciate the drama of Hawaii’s landscape, from the ridges of Waimea Canyon to the mist-shrouded Mount Wai‘ale‘ale. A drive down the famed Hana Highway in Maui is just as impressive, and you can stop along the way to visit Laulima Organic Farms winery, and to take a dip in nearby waterfall pools. Of course, Pearl Harbor is a must-do. Stargazing from atop
Mauna Kea and watching the sunrise at Haleakalā volcano are personal favourite memories of mine, too.

Top tip: Visit between May and October for the best weather, or January to March for whale watching.

Hawaii Island-Hopping Escape

Start dreaming up your island-hopping escape with this itinerary suggestion. Or speak to a Travel Specialist to tailor your own, with every hotel and experience created exclusively for you.

Oahu

Day 1-4

Take a tour of the island, visiting the volcanic cone of Diamond Head and Oahu's prime snorkelling spot, Hanauma Bay. Spend your second day exploring Pearl Harbour or relaxing on Waikiki Beach.

Kauai

Day 5-7

A real treat awaits on Kauai – visit the breathtaking Waimea Canyon, or soar over it with a helicopter ride.

Maui

Day 8-10

Embark on a scenic drive along the bridges and sweeping roads of the Hana Highway, stopping at the surf town of Pa’ia and to explore the waterfalls of Kaumahina State Park.

Big Island

Day 11-13

Tour the island and explore Volcanoes National Park. The following evening, scale Mauna Kea for a stargazing session with a world-class telescope.