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Island Discovery - Hawaiian Islands: Road Trippin' USA

Dreaming of setting off on an island-hopping adventure through Hawaii, the land of idyllic beaches, waterfalls, emerald rainforests, and vibrant culture? Well, we have good news! This epic road trippin' journey, visiting six islands, can make those dreams come true.

Dreaming of setting off on an island-hopping adventure through Hawaii, the land of idyllic beaches, waterfalls, emerald rainforests, and vibrant culture? Well, we have good news! This epic road trippin’ journey, visiting six islands, can make those dreams come true.

Grab your grass skirt and coconut bra and hire yourself an open-top Jeep because the tropical paradise of Hawaii is calling.

This “Island Discovery – Hawaiian Islands” itinerary is a lush journey that will have you embracing the unique personalities of the islands of Oahu, Kauai, Hawaii (the Big Island), Maui, Lanai and Molokai.

You do, of course, need to fly between the islands to connect this epic itinerary’s dots. Once there, however, you can best honour the aloha spirit and incredibly lush scenery by opting for the freedom and convenience of a rental car.

These six major islands speak to the state’s aloha spirit and showcase its lush landscape as well as its fascinating history, and travelling by road is, hands down, the best way to get a real feel for each island.

So, are you ready to experience delicious food and a laid-back lifestyle that will leave you longing for more?

Explore all of Brand USA’s 31 Amazing Self Drive Road Trip itineraries here.

Island Discovery – Hawaiian Islands: Route Highlights

1. Oahu, Hawaii (Day 1 to 3)

Battleship Missouri Memorial, Honolulu
Battleship Missouri Memorial, Honolulu

Aloha Hawaii. Start your journey in the state’s capital on the island of Oahu, where there is plenty to see and do.

Begin your island-hopping adventure at Diamond Head State Monument, a 300,000-year-old crater, where you can hike less than a kilometre to the rim for incredible views of the Pacific Ocean and the city.

“December 7, 1941, a date which will live in infamy”. Learn why these words, spoken by U.S. President Franklin D. Roosevelt hold such weight for Americans and the world alike. Immerse yourself in that infamous day as you pay your respects and view the historical exhibit at the USS Arizona Memorial, which stretches over the sunken ship and commemorates the lives lost in the attack.

Merpeople can then choose to dive and snorkel to see wrecks, reefs and marine life in magical Hanauma Bay, and more Earth-loving individuals can watch a lava pour and examine 24 million cultural artefacts at Bishop Museum.

Surfs up at Oahu’s North Shore, which is known as the “surfing capital of the world”. This spot is home to many of the top surf tournaments, with over eleven kilometres of beaches and waves regularly reaching nine metres or more.

If the thought of big wave surf terrifies you, no worries! Head to the world-famous Waikiki Beach where smaller waves are the go, and perfect for beginners.

Culture buffs can’t leave Honolulu without visiting Iolani Palace, the restored 19th century home of Hawaii’s monarchy, or the Polynesian Cultural Center to experience a true taste of the ethnic and cultural diversity of the region.

2. Oahu > Kauai (Day 4 to 6)

Lumahai Beach, Kauai
Lumahai Beach, Kauai

Just 30 minutes by plane from Honolulu, discover this 6-million-year-old “Garden Island” made popular in blockbusters such as Jurassic Park, Hook, Pirates of the Caribbean, The Descendants and Avatar.

This lush oasis provides mind-blowing hikes in Waimea Canyon State Park and Koke’e State Park, featuring Waipoo Falls and sweeping views of the Kalalau Valley.

Reconnect with nature as you meander through the rainforest, fish for trout or explore the natural history museum. Why not Kayak through Na Pali Coast State Wilderness Park for dramatic views of the “pali” or cliffs while you’re there too?

Intrepid types can take a 17 kilometre coastal hike along Kalalau Trail, one of the world’s most scenic hikes and sun-worshippers can sunbathe on the popular Poipu Beach on the southern coast, a paradise for surfers, swimmers and snorkellers.

  • FLIGHT TIME: 152kms: 30 mins flight time

3. Kauai > Hawaii (The Big Island) (Day 7 to 9)

Hawaii Volcanoes National Park
Hawaii Volcanoes National Park

Synonymous with Hawaii, The Big Island is the archipelago’s largest island.

Jump in the car and get acquainted by diving right into its turquoise waters bounded by striking beaches. Want to tick something amazing off your bucketlist? Go snorkelling with sea turtles, which are called “honu,” in Kailua-Kona’s shallow lagoons.

Then get your boots on as you head to Waimea, which is cowboy country, to trek over lush nature areas and ranches via horseback or ATV. Hike through a forest in Waipi’o Valley to journey past black sand shores, waterfalls and mystical-looking craters with steaming vents.

Next up, channel your inner Moana and check out even more volcanic activity as you explore Hawaii Volcanoes National Park.

Marvel at two active volcanoes here; one of them, Mauna Loa, is the biggest in the world. Drive over lava on Chain of Craters Road before visiting the park’s Jaggar Museum and Volcano Art Center.

  • FLIGHT TIME: Into Kona 448kms: 55 mins flight time / Into Hilo: 536kms: 2 hours flight time

4. Hawaii (The Big Island) > Maui (Day 10 to 12)

Wai'anapanapa State Park
Wai’anapanapa State Park

The second-largest Hawaiian island, Maui, is synonymous with whale-watching and pristine sand beaches, and not only white sand, but black and red, too. Pretty cool, huh?

Yup, you’ve guessed it – there is an array of water activities to enjoy here too, from snorkelling to diving, surfing to windsurfing and kayaking to paddle boarding.

The whales visit in the cooler months (whale watching season in Maui is November-May with peak season typically running between mid-January and March), with the sheltered waters the perfect place for loving mothers to tend to their newborn calves.

Roadtrippers get excited because the Road to Hana is a spectacular drive; you can swim at many secluded waterfalls such as Twin Falls, bathe on a black-sand beach at Wai’anapanapa State Park and explore the ocean caves.

Haleakala State Park offers waterfalls in the Kipahulu district, swimming in the Seven Sacred Pools and hiking among ancient Hawaiian ruins.

Rest and rejuvenate in Hana and if you’re an early bird, sunrise at Haleakala is a must-see experience.

You must be hungry by now too, and luckily dining in Maui is of the highest levels with farm-to-table cuisine and fresh seafood being menu staples. Do not miss the chance to experience a luau, where you can taste native Hawaiian dishes, listen to local music and watch the famous hula dancers with a spectacular sunset as your backdrop. *Drool*.

  • FLIGHT TIME: From Kona 122kms: 40 mins flight time / From Hilo: 177Kms: 55 mins flight time

5. Maui > Lanai (Day 13 to 15)

Sunrise over Menele Bay on the island of Lanai
Sunrise over Menele Bay on the island of Lanai

Just fourteen kilometres from Maui, Lanai is the smallest inhabited island in Hawaii.

Find a cornucopia of experiences, from luxury accommodations and world-class golf to horseback riding, backcountry off-road adventures, stunning beaches, lush rain forests and spectacular nature preserves.

Don’t be fooled by Lanai’s size. It’s small, but beautifully mighty.

  • FLIGHT TIME: 62kms: 35 mins flight time

6. Lanai > Molokai (Day 16 to 18)

Sea cliffs of Molokai
Sea cliffs of Molokai

Say “Aloha” to Hawaii in its truest form. From the 600 metre cliffs to the white-sand beaches, Molokai is still true to its Hawaiian roots. The island is a haven for outdoors enthusiasts who are looking to escape into a piece of the earth unspoiled by civilisation. 

Hey, you might even want to stay! After this trip, returning to reality might be a little bit of a struggle!

  • FLIGHT TIME: 70kms: 35 mins flight time

Download the complete Island Discovery – Hawaiian Islands‘ itinerary here!

Get the Road Trip Playlist

Prepare yourself for some seriously idyllic vibes and be instantly transported to Polynesia with this sweet playlist.

Get your ukulele and singalong with Israel Kamakawiwo’ole, Jack Johnson, The Ventures, Elvis, Ziggy Marley and more.

With songs dedicated to this other-worldly destination, you’ll be ready and waiting to set off and explore as soon as you possibly can.

Agents: Download, Escape and Explore GoUSA TV

GoUSA TV is a free premier travel entertainment channel. Watch full episodes, documentaries and films, told from the diverse perspectives of real people across America. 

Discover the Queens area of New York City through the diversity of the Latinx diaspora in the series, Americanos, available on GoUSA TV. Explore how Latinx culture brings American cities to life through the stories of those who embrace their roots and shape the future.

With more than 400 authentic and short format videos featuring destinations from all 50 states, 5 territories, and the District of Columbia, there’s never been a better time to get online and enjoy some incredible travel entertainment!

Available for download in the App or Play store and on Apple TV.

More info here.

Agents: Join the USA Discovery Program

Rainbow Falls, Big Island
Rainbow Falls, The Big Island

The USA Discovery Program is Brand USA’s official trade training platform for the USA.

Earn specialist badges as well as bespoke partner badges as well. Get clicking and complete badges and skill up in a fun and interactive way.

Click here to register and get all the knowledge for the USA.

PLUS! Design your own Road Trip with the USA TRIP PLANNER

The Visit USA Trip Planner is an amazing (and free!) tool that matches your personal travel preferences and style.

With over 230 million data points including the best places & times to visit, reviews and hidden gems, this is one smart piece of travel tech.

This little travel genius optimises your itinerary to minimise travel time, checks when attractions are open and even recommends how much time to spend at each stop off. Brilliant!

Finally, it lets you share & collaborate with your fellow road trippers and is easy to add or revise points of interest as you go.

Find out more: Trip-Planner.VisitTheUSA.com

Get all the tools on Brand USA’s TRAVEL TRADE SITE


From Trip Planners to itineraries and the USA Discovery Program and destination information, Brand USA’s Travel Trade Site for agents has you covered.

Hero image – Kauai, Hawaii

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