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The ultimate 5-day Oahu road trip

Consider this the ultimate road tripper’s guide to the best of Oahu– from the glitzy shops of Waikiki to the laid back beaches of the North Shore.

Many tourists who visit Oahu end up getting stuck in Waikiki. Don’t get me wrong; this iconic beach and surrounding neighbourhood in Honolulu has its virtues– shopping and an excellent surf break in the summer being top of the list. But in my opinion, it’s a tragedy to leave the rest of the island undiscovered.

Waikiki Oahu Hawaii
There is more to Oahu than just Waikiki. (Image: Hawaii Tourism Authority/Vincent Lim)

To best do that, you’ll need a vehicle. Those travelling on a budget can rent a sprinter van and stop at beachside campsites for an immersive and adventurous experience. Alternatively, you could rent a car and stay at luxury hotels for the ultimate blend of relaxation and exploration.

Whichever type of vehicle you choose, road tripping around the entire island is the best way to broaden your horizons on your next Oahu trip.

Day 1: Waikiki

Some people love Waikiki’s family-friendly beaches, shopping and great surf in the summer; others hate the crowds and touristy feel. Either way, Waikiki is an iconic neighbourhood and certainly worth scoping out for at least a day or two. After flying into Honolulu, spend your first day wandering around the many shops and restaurants. The International Market Place is a great place to start.

Shaved Ice in Waikiki
You won’t be short on food and shopping options in Waikiki. (Image: Hawaii Tourism Authority/Ben Ono)

Eat Poke

Baptise your first day with a lunch or dinner of poke– one of Hawaii’s most quintessential and delicious dishes. This Hawaiian favourite of cubed, raw fish over rice has evolved to include the option of several toppings– seaweed salad, cucumbers, pineapple or avocado just to name a few. Try the ceviche poke bowl at Maguro Brothers–the bright acidic flavour is balanced by creamy avocado and salty soy sauce.

Poke Bowl in Hawaii
Make your first meal in Hawaii a poke bowl. (Image: Hawaii Tourism Authority/ Blake Bronstad)

Surf at Waikiki

I can’t let you leave Waikiki Beach without a surf session. Whether you are an experienced shredder or a surf novice, there’s a break for you here. There are plenty of options for boards to rent on the beach.

Surfing in Waikiki
Don’t miss the chance to go surfing in Waikiki. (Image: Hawaii Tourism Authority)

Road Trip Tips

  • Be prepared to drive on the opposite side of the street in the American state of Hawaii! The Hawaii Tourism Board advises that Australian drivers licences are accepted in Hawaii but that drivers may be required to be at least 25 years old and in possession of a major credit card to hire a vehicle.
  • Oahu has a surprisingly limited number of campsites to reserve for your trip– if possible, be sure to book your campsites as far in advance as possible. Hipcamp is an app where you can search for campsites and overnight parking spots.
  • Even an island paradise isn’t immune to crime– be cognizant of your surroundings and don’t leave valuables unattended at the beach.
  • It’s important to note that Hawaii often is harmed by over tourism and careless visitation. During your visit, be respectful of the locals, keep your distance from wildlife, and leave each beach cleaner than you found it.

Day 2: Waikiki

Boat tour and swim with dolphins

Many island tours and guided experiences leave from the Waikiki area, so take your last morning in Waikiki as an opportunity to embark on an epic adventure at sea. There’s something for everyone: a Pearl Harbour tour may appeal to history buffs or a shark cage dive to thrill seekers. A sailboat trip and snorkel session with spinner dolphins as your companions is sure to suit just about everyone.

Snorkel with spinner dolphins in Hawaii
A snorkel session with spinner dolphins is an unforgettable experience. (Image: Hawaii Tourism Authority/ Heather Goodman)
Spinner Dolphin Hawaii
Get up close to the curious spinner dolphin. (Image: Hawaii Tourism Authority/ Heather Goodman

Sunset at Spitting Cave

Finish the day at Spitting Cliffs for prime sunset viewing. A dramatic cliffside drops into the sea where a shallow cave spews out sea mist– the phenomenon from which the spot gets its name. Wear closed-toe shoes and watch your step– there are no rail guards in place. You may even witness some humpback whales, as they are known to be especially visible here from December to April.

Accommodation Tips

  • Surfjack: A cute, retro-style hotel within easy walking distance of all Waikiki has to offer.
  • The Royal Hawaiian: This historic, pink hotel enjoys a coveted position directly on Waikiki beach.
Royal Hawaiian Hotel Waikiki
The pink Royal Hawaiian Hotel has a prime position on the beachfront in Waikiki.

Day 3: Kailua

A thirty-minute drive from Waikiki, Kailua is known as the ritzier residential side of the island with stunning beaches.

Pair standup paddleboard in Kailua Bay Hawaii
Kailua is known for its stunning beaches. (Image: Hawaii Tourism Authority/ Heather Goodman)

Lanikai Pillbox Hike

Often cited as one of the best hikes in Oahu, the Lanikai Pillbox Hike shows off Kailua’s beauty in all of its glory. It’s a relatively easy 2.7 kilometre, out-and-back trail with sweeping ocean views. If you make the extra effort to wake up early and watch the sunrise at the top of the hike, your efforts will be rewarded with some pretty spectacular views.

Views from the Lanikai Pillbox Hike
The spectacular views from the top of Lanikai Pillbox Hike.

Windsurf at Kailua Beach

Kailua Beach is a gorgeous three-mile stretch of crescent-shaped shoreline. The protective reef makes the warm, salty waters here perfect for a swim or– for the more adventurous of spirit– some windsurfing.

Day 4: North Shore

The North Shore is the laid back antithesis to Waikiki’s bustling shores and my personal favourite part of the island.

Cliff jump at Waimea Bay

This beach is one of the North Shore’s most beautiful and jumping off the 25-foot cliff is perfect for beginners. Otherwise, it’s a lovely spot to spend a beach day.

Cliff jumping in Waimea Bay
Jump off the 25-foot cliff at Waimea Bay.

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Eat garlic shrimp

One of the beauties of the North Shore: you’ll never go hungry. There are several little food villages made up of a conglomeration of humble food trucks and huts serving authentic dishes packed with local flavour. Be sure to stop by and get a steaming plate of buttery, garlic shrimp with rice– a North Shore favourite. Giovanni’s Shrimp Truck in particular is well-renowned for this dish.

Surf at Turtle Bay

Turtle Bay is the largest (and debatably the best) resort on the island of Oahu. Find a spot in the resort parking lot to access the public beach. From there, you can either head to sandy Turtle Beach to swim and look out for turtles or the rockier Turtle Bay side for an excellent surf spot. The resort often hosts surf lessons at this spot overlooked by the property pool. After catching some waves, head in for a Lava Flow cocktail at the pool bar and enjoy the stunning view.

Turtle in Turtle Bay Hawaii
Be on the lookout for turtles on the rocky side of Turtle Bay.

Accommodation Tips

  • Malaekahana Beach Campground: Perfect for sprinter vans, those who fancy pitching a tent right by the ocean, and budget-conscious travellers.
  • Turtle Bay: A luxurious resort stay on a secluded and scenic stretch of Oahu.
Turtle Bay resort Oahu
Stay at the luxurious Turtle Bay resort. (Image: Turtle Bay)

Day 5: North Shore

Sunrise Shack coffee

Start your morning with a bulletproof coffee and an acai bowl with added macadamia butter at this highly-Instagrammable, bright-yellow health foods hut.

Sunrise Surf Shack
Get your caffeine and breakfast fix at Sunrise Surf Shack. (Image: Sunrise Surf Shack)

Snorkel at Sharks Cove

Don’t be frightened by the name– you are very unlikely to see sharks at this family-friendly snorkelling spot. On the other hand, you are likely to see schools of colourful fish gliding just below your feet and even sea turtles. It’s best to arrive in the morning to beat the crowds.

Snorkel at Shark Cove Hawaii
Snorkel at the family-friendly Shark Cove.

Ted’s Bakery pie

Soothe your sweet tooth with a slice of Ted’s Bakery’s famous chocolate haupia pie or pineapple macadamia nut cheesecake.

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12 grand journeys throughout North America

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    Discover North America’s epic adventures — from Route 66 and Alaska cruises to Hawai‘i road trips, NYC culture, Mexico trails and more.

    1. Route 66, the Main Street of America

    Travelling with: Ricky French

    Sunset on Route 66 in the California Mojave Desert.
    Hit the open road and trace America’s legendary highway. (Image: Getty/Der_Thomasa)

    Dubbed the Main Street of America, Route 66 radiates serious main character energy, cemented into popular culture through everything from John Steinbeck’s novel The Grapes of Wrath to the Disney Pixar film Cars. Spanning nearly 4000 kilometres from Chicago to Los Angeles, the historic highway celebrates its centenary next year, a timely invitation to take the mother of all road trips along the Mother Road. Allow two to three weeks to tackle the full length, or bite off a smaller chunk at either end, cruising the dramatic deserts of California or the more pastoral landscapes of Illinois, lined with neon-lit diners, retro gas stations and quirky roadside attractions.

    2. Mexico’s Día de los Muertos

    Travelling with: Carla Grossetti

    emblematic catrina of mexico with flowers and necklace with sempasuchil flowers
    Celebrate life and honour loved ones in vibrant style. (Image: Getty/Fabian Pacheco)

    You might know Oaxaca as the birthplace of mole and mezcal. But the state in southern Mexico is also where the Día de los Muertos (Day of the Dead) began. Time your visit to coincide with the colourful holiday, on 1–2 November, which honours and celebrates loved ones who have passed away. Oaxaca is also Mexico’s Michelin-starred culinary capital, with 18 restaurants and a humble taco stand listed in the 2025 guide.

    3. Museum-hop in New York City

    Travelling with: Carla Grossetti

    The Guggenheim Museum’s iconic spiralling exterior, a highlight of North America Epic Adventures.
    Step inside and marvel at bold, world-class art. (Image: Damiano Fiore)

    Your map app will look like it’s been scattered with confetti after you’ve dropped pins on all the museums you want to visit in New York City. Must-sees are the Solomon R. Guggenheim Museum, the Metropolitan Museum of Art aka the Met, and the Museum of Modern Art. The American Museum of Natural History is also a draw. It’s also worth venturing into the boroughs to browse institutions such as the Brooklyn Museum, which has a huge permanent collection categorised by culture.

    4. The USA’s music scene

    Travelling with: Elizabeth Whitehead

    The Seattle skyline at night, aglow with city lights on North America Epic Adventures.
    Soak up skyline views and dive into the city’s coffee culture. (Image: Abigail Boone)

    If you’re a muso, chances are you’ve wanted to make a pilgrimage to the United States, the epicentre of so many beloved genres. Whether you’re head-banging your way around the Grunge Circuit in Seattle, chasing the twang of the pedal steel through Tennessee or bouncing between blues bars in the Mississippi Delta, the USA’s rich music culture has something that’ll strike a chord.

    5. Road-tripping Hawai‘i

    Travelling with: Carla Grossetti

    A woman surfing in Hawaii, gliding across turquoise waves on North America Epic Adventures.
    Catch the waves and ride Hawaii’s iconic swells. (Image: Ben Ono)

    Hawai‘i is one of the most diverse US states to road trip around. Of the six major islands to visit, the Island of Hawai‘i packs in everything from the snowy summits of Mauna Kea and Mauna Loa to black-sand beaches and lava fields frozen in the act of flowing forward. Change down a few gears on the island of O‘ahu, too, where you can find your own patch of sand on Waimanalo Beach. Visit poi and pineapple plantations. And hang ten on beginner-friendly waves on the North Shore.

    6. Cruising Alaska

    Travelling with: Carla Grossetti

    Explora Journeys ship cruising in Alaska.
    Sail past glaciers and spot whales in pristine waters.

    Seeing Alaska from the sea allows you to cover a lot of distance quickly. This immersive frontier now beckons more than ever before with Explora Journeys adding the American state to its global destination portfolio. Best of all are the pre-and post-journey immersions that connect the luxury of a cruise onboard Explora III with the rugged grandeur of the Alaskan interior. UnCruise Adventures also weaves in access to remote national parks, legendary wildlife corridors and authentic cultural experiences on its Alaskan itineraries.

    7. The Wixárika Route in Mexico

    Travelling with: Elizabeth Whitehead

    People journeying through the Wixarika Route.
    Journey deep into sacred Huichol traditions and art.

    For generations, the Indigenous Wixárika People of Mexico have walked a sacred path known as Tatehuarí Huajuyé, or ‘The Path of Our Grandfather Fire’. The annual pilgrimage route spans 500 kilometres, taking in significant sites in Wixárika spirituality and cosmology. The route passes through the deserts, mountains and forests of northern Mexico before reaching Wirikuta, believed to be the place the sun first emerged. The route is a living cultural landscape of Indigenous culture pre-Columbian influence and, in July this year, was formally inscribed into UNESCO’s World Heritage List.

    8. Drive the Iceberg Coast in Canada

    Travelling with: Carla Grossetti

    Iceberg off the east coast of Canada
    Chase icebergs along Expedition 51 on Canada’s east coast. (Image: Canadian Tourism Commission/ Chris Hendrickson)

    Download the icebergfinder.com map to better plan your road trip along Canada’s Iceberg Coast. The new highway, which has been nearly 25 years and CAD$1.1 billion in the making, threads through the country’s pleated coastlines around Quebec, Newfoundland, Labrador, Nova Scotia and New Brunswick before looping in the French islands of St Pierre and Miquelon. As well as chasing icebergs along Expedition 51, travellers will have the opportunity to engage with cultures that have thrived in the pristine provinces for thousands of years.

    9. A foodie tour of Nova Scotia

    Travelling with: Katie Carlin

    Lunenberg Nova Scotia
    Try lobster rolls in Lunenburg on the east coast of Canada in Nova Scotia. (Image: Natalia Kvitovska/ Unsplash)

    World-famous for its lobster, Nova Scotia is a Canadian province best savoured through its culinary clout shaped by sea and terroir. Bite into lobster rolls at historic Lunenburg’s Salt Shaker Deli & Inn and sip maple rum at Ironworks Distillery. Winery-hop around Wolfville’s rising vineyards (don’t miss Lightfoot & Wolfville). Take a maple syrup tour at Sugar Moon Farm near Earltown. And pull up a seat at waterfront Bar Sofia in Halifax, where Nova Scotia oysters aguachile arrive bright with cucumber, lime and pickled onion.

    10. Soak up the sun in the Caribbean

    Travelling with: Carla Grossetti

    Overwater bungalows off a beach in the Caribbean
    Experience the white-sand beaches and cerulean seas of the Caribbean on board a cruise.

    The Caribbean is on the radar for seasoned cruisers. And it’s easy to see why, with white-sand beaches, cerulean seas and swaying palms so picture-perfect they look AI-generated. Cruise with Windstar, Royal Caribbean, and Celebrity on its inaugural Xcel season to the Caribbean to enjoy action-packed excursions such as snorkelling coral reefs and shopping for local trinkets. And those sea days? Spectacular.

    11. Red Chair Hikes of Canada

    Travelling with: Kassia Byrnes

    Red Adirondack chairs overlooking Lake Minnewanka in Canada
    Take a seat at Lake Minnewanka, one of more than 400 red Adirondack chairs scattered across Canada’s hiking routes. (Image: Getty Images/ Autumn Sky Photography)

    No one appreciates the great outdoors more than Canadians, emerging from snow-covered winters to tread glacial rivers and snowshoe through forests, or to hike mighty mountains and wildflower-strewn valleys come spring. Along popular hikes around the country, more than 400 red Adirondack chairs have been placed in peaceful, breathtaking locations. What started as a social media contest now sees hikers soaking in classic Canadian lake and mountain vistas, overlooking historic sites or gazing down on the mountainous path they just travelled.

    12. Ride the Rocky Mountaineer from Denver to Moab, USA

    Travelling with: Carla Grossetti

    Sweeping views from the Rocky Mountaineer.
    The Rocky Mountaineer will continue as the Canyon Spirit in 2026, seen here carving through Ruby Canyon.

    Sighting wild animals is one of many incredible thrills along the two-day luxury Rockies to the Red Rocks route onboard the Rocky Mountaineer across America’s Southwest between mid-April and mid-October. In addition to the lone bear, we spot bighorn sheep, elk, beavers, pronghorn antelope, bald eagles and ospreys. Riding the rails onboard the luxury train, which was founded in Canada in 1990 and has been awarded the prestigious World’s Leading Travel Experience by Train several times, has never been about just getting from A to B. Ride the train from Denver to Moab and you will see the scenery change from snow-capped peaks to meadows, red-rock canyons and soaring cliffs that resemble ornate Gaudí-esque cathedrals. But it’s not until you get off the train that you can produce the ultimate Venn diagram, with nature and adventure in the intersecting spheres.