Island-Hop to These Hawaiian Hotspots for an Extraordinary Adventure
From O’ahu and the Big Island to tiny Lāna'i, this is the best of Hawaii.
If the Hawaiian vacation of your dreams involves lounging on Waikiki Beach and going to a lūʻau, we’ve got news for you: that Hawaii is a thing of the past. Now, it’s all about mālama, or giving back and taking care of the islands. It’s about sinking into the true fabric of Hawaii, ruminating in its flavors, more deeply appreciating its landscapes, and getting to know its people.
It’s also about fully exploring one or more of the Hawaiian islands—and giving the mainstream, overcrowded areas of each a well-needed break from tourism. From mouthwatering local restaurants to sunny surf spots you'll never forget, here’s an island-by-island itinerary that'll get you far from the well-trodden path—and closer to mālama.
Note: As of spring 2022, Hawaii’s pandemic mandates are just starting to lift. More and more businesses and locations are starting to open back up—check local orgs and business pages for current updates.
Head to Hawaii’s Gathering Place to surf, shop, and stroll
Home to about 1 million people, O’ahu—also known as the “Gathering Place,” since the majority of Hawaiians live here—is known for its bustling city life, excellent culture, and grade A restaurants…plus the traffic that comes with all of the above. Plan accordingly. If you can, spend a few days here before moving on to other islands.
Since Hawaii—and specifically O’ahu—is the “Surfing Capital of the World,” why not learn to hang ten in iconic Waikiki or the North Shore? The Hans Hedemann Surf School offers lessons on both shores, so no matter where you post up, you’ll get to see why surfing is one of the first things President Obama does when he comes home to visit.
If you’re more of a land animal, stroll through the trendy, incredibly walkable Kaka’ako District. Spend the day discovering locally-owned boutiques and restaurants and grab a few selfies in front of your favorite art piece; part of Pow! Wow! Hawaii, the vibrant murals here are created by renowned local and international artists and usually get a refresh every year. (For the record, as with many other things, the current murals haven’t changed since 2020.)
When you’re finished feasting your eyes, feast on authentic Hawaiian fare at Highway Inn, a favorite with locals since 1947. If you’re feeling nostalgic, walk over to Hawaii’s oldest record store, Hungry Ear Records, for some retro vinyl and cassette tapes spinning with the sounds of local musicians, and if you’re into coffee and chocolate, don’t miss the Waialua Coffee Tour.
Want the same vibe away from the hustle and bustle of the city? The surf town of Kailua is worth a visit. If nothing else, stop for surf gear and shave ice at Island Snow (another Obama favorite). If you’re meal-hungry, grab a more substantial bite at Moke’s Bread and Breakfast—be sure to get the lilikoi pancakes, made from a family recipe, and keep an eye out for Moke himself if and when he happens to emerge from the kitchen. Kailua is a lot more spread out than Kaka’ako, so rent a bike to cover more ground and discover more fun.
Eat mouthwatering farm-to-table food on the Valley Isle
The second-largest Hawaiian island, Maui has a rich agricultural history that co-exists with modern commerce. It’s a favorite for both island-hopping visitors and locals as it offers almost as many urban, cultural, and outdoor activities as extra-busy O’ahu. Many dining experiences on this island aren’t just farm-to-table—some chefs have been farmers or fishermen for decades, which results in hyper-local ingredients in kitchens and hyper-local knowledge pushing the culinary envelope.
To enjoy a little dining and imbibing, visit both Surfing Goat Dairy and Ocean Vodka, two local farms on the slopes of Haleakalā, each with their own unique offerings; take a tour, taste their wares (goat cheese, truffles, spirits!), and take in the scenic views. At Surfing Goat, in fact, you not only can meet their friendly goats—you can even milk them and tuck them in for the night.
A little-known fact for fans of Top Chef: Maui is home to three notable contenders. Sheldon Simeon’s (Season 10) Tin Roof Maui in Kahului is a hotspot for lunch (go early to beat the crowds); Lee Anne Wong (Season 1), executive chef and partner of Koko Head Café in Honolulu, is also executive chef and partner of Pioneer Inn’s signature restaurant Papa’aina Maui in Lahaina; and Pichet Ong (Top Chef: Just Desserts) is the executive pastry chef at the Hotel Wailea.
Work off all that glorious food with a hike. Most people make a visit to Haleakalā National Park to watch the sunrise, and then they promptly leave. Instead, make the most of your morning with one of the many hikes of varying distances and skill levels. As it turns out, everywhere in this national park is beautiful at dawn. (And dusk, and every time in between.)
Also worth looking out for: Ocean blowholes. The key is to look for tiny parking lots that jut off to one side followed by a small path to hike closer to it. Their power and beauty are entrancing but keep an extra-safe distance, lest you get blown straight out to sea. If you’re in Maui, check out Nakalele Point Blowhole off Highway 30, and keep your eyes peeled for the heart-shaped rock nearby.
Active volcanoes and colorful beaches await on the Big Island
Aptly nicknamed the “Big Island,” Hawai'i Island is about twice as large as the other seven islands combined, and it’s still growing. Home to two of the world’s most active volcanoes, Kīlauea and Mauna Loa, there’s a good chance you’ll something erupting from afar at any given time. Due to the high elevations of the massive Maunakea and Mauna Loa, locals often joke that you can go skiing in the morning and surfing in the afternoon. (The snow isn’t good quality, so you theoretically could do it, but you’d ruin your equipment.)
The island is basically divided into two sides, Kona and Hilo, each with very different climates and offerings. Kona coffee, grown on Hawaii’s west side, is considered to be the best in the world for cuppa aficionados. Several farms, like Ueshima Coffee Company, Greenwell Farms, and Buddha’s Cup, have tours—many for free.
The drive from Kona to Hilo takes about 90 minutes if you take the direct route. To go off the beaten path, drive from Kona to Ka Lae, the southernmost point in the state. This is believed to be where the ancient Polynesians first landed; you can land here, picnic in the area, and take in the panoramic views at your own pace.
From there, stop at Papakōlea, a green sand beach, or Punalu’u Bake Shop, whose long, rectangular loaves of flavored sweetbreads are known and beloved throughout the state. As you make your way up the coast, you’ll encounter Punalu’u, a black sand beach, as well.
If you have time and would enjoy even more coffee, it’s worth visiting Ka’u Coffee Mill for a free tour. Whereas Kona coffee has been around for 200 years and is recognized throughout the world, Ka’u has only been producing coffee since 1996—yet it’s already known to coffee enthusiasts as “Kona’s sexier younger sister.”
Make time for a hike in the Kahuku Unit of Hawai’i Volcanoes National Park to get to know the terrain and the science behind the volcanoes. The trails are anywhere between one-half to seven miles, and many offer views of lower Ka’u.
When you get to Hilo, be sure to explore downtown and stop for a poke bowl at Poke Market, a tiny hole-in-the-wall that’s a favorite with locals. For dessert, go across the street to Makani’s Magic Pineapple Shack for the most Instagrammable soft-serve cones on the island (they’re delicious, too!). For dinner, one of the best hidden gems is Moon and Turtle, a neighborhood restaurant featuring locally sourced seafood on a creative, ever-changing menu.
The to-do list goes on: Get over to Ponoholo Ranch on Kohala Mountain in Waimea for a panoramic horseback ride that stretches through three climate zones; they even have sunset ride options. Dahana Ranch in Kamuela doesn’t do rides at dusk but is your go-to for free-range riding, including a cattle drive for groups of four or more. (You might even want to make horseback riding a regular occurrence as you island-hop since it’s a great way to see a lot more landscape than highway traffic will afford you.)
A guided snorkel is your best way to swim safely while respecting wildlife and still see some incredible, out-of-the-way formations. Go with the pros at Big Island Divers, who will help you experience the vibrant life of the ocean the right way. Highly recommended: their night snorkel program, where you'll get to observe manta rays and dolphins from a safe distance. And hey, it comes with hot chocolate!
Since you’re already on the beach at night: Hawaii's absence of light pollution will change your entire life. Seriously. You’re on an island in the middle of the Pacific, you won’t find clear views and beauty like this anywhere else. Mauna Kea on the Big Island is where you’ll want to be; if you can, sign up early for their stargazing program on Tuesdays, Wednesdays, and Saturdays.
Stroll through charming old towns on the Garden Isle
The northernmost Hawaiian island, Kaua'i is all lush greenery thanks to massive amounts of rainfall. In fact, the island’s Mt. Waialeale is one of the wettest places on Earth, with an average of about 373 inches of rain per year. (For reference, Seattle gets 37.)
First things first: get your first meal at a food truck, whether you pick Kalua pork, poke, Huli-Huli chicken, or fried Spam. Not only is the food delicious, but chefs are often well placed to hear about island happenings that are still news at the street level. What’s more, the trucks tend to offer views that sit-down restaurants would charge a mint for.
Nature-loving locals and visitors alike fly to Kauai specifically to hike or camp in spots like Waimea Canyon or Kokee State Park. And if camping isn’t your thing, maybe history is: Two revamped historical towns, Koloa and Hanapepe, are absolutely worth checking out. Koloa is on the south shore, where the commercial sugar industry first started in the state of Hawaii. You’ll be going there anyway since you’ll certainly want to drive through Kaua'i’s famous Tree Tunnel.
Just west of Koloa, you’ll find a real hidden gem in Taro Ko Factory, just before you enter Hanapepe. The run-down plantation building looks a little sketchy, but insiders know to go there for the best taro and potato chips of your life. No insider can tell you, however, when the owner will decide to be open or closed, so it’s basically luck of the draw if you get there and it’s open. Try to get there as early as possible, because once they sell out for the day, they’re out.
With taro chips hopefully in hand, you’ll then drive directly into the charm of Hanapepe, “Kaua'i’s biggest little town.” It’s hard to believe that this was one of Kaua'i’s busiest communities from World War I to the early 1950s since its exteriors haven’t changed much over the years. The colorful plantation-style buildings now house homestyle restaurants, local boutiques, and several art galleries, with an art walk every Friday from 5 to 9 pm.
Reach new heights on the Friendly Isle
What it lacks in land area—measuring just 38 miles by 10 miles—Moloka’i makes up for in verticality: the island is home to the highest sea cliffs in the world. It’s also worth mentioning that few tourists visit Moloka’i, period. Turn off your phone (it’s essentially useless since most service providers don’t work very well here, anyway) and take in the slow pace of the island.
A Moloka'i Hot Bread run is THE thing to do on Molokaʻi. If you’re down to stay up late, seek out Kanemitsu Bakery’s back door between the hours of 7:30 to 10 pm from Tuesdays to Thursdays and Sundays and 7:30 to 11 pm on Fridays and Saturdays. You’ll need to walk down a mysterious, dark alley with a light at the end.
The staff is already baking fresh bread for the next day, so if you order quickly like a pro and provide the exact change, you can enjoy their famous bread, steaming hot out of the oven, slathered with butter or cream cheese and your choice of topping. You can also order other fresh pastries if they’re available.
Be sure to visit the post office while you’re on Molokaʻi, too. No one sends snail mail anymore, right? You can impress your friends with your thoughtfulness by sending them a coconut from Hawaii to anywhere in the world. The coconuts themselves are free; postage to the mainland United States can run between $12 and $20, depending on the size of the coconut.
See stellar sunsets and shipwrecks on the Pineapple Island
Lāna'i is the smallest of the visitable islands, with a very small-but-friendly local community. The island—yes, the whole island—is owned by multi-billionaire Larry Ellison and has pivoted from its focus on agriculture to hospitality.
There are no traffic lights on Lāna'i and only three paved roads, but there are still plenty of things to do. Like most visitors, you’ll probably want to rent a jeep and visit Kaiolohia (also known as Shipwreck Beach) and the otherworldly Keahiakawelo (Garden of the Gods) rock garden.
For our feline fanatics, a visit to the Lāna'i Cat Sanctuary is in order. The rescue ranch houses about 600 cats, as well as a bird sanctuary as well (yes, birds and cats really can coexist!), so can play with the cats while learning about the island’s endangered avian population.
To get moving, take an easy hike from Hulapoe Bay to see Pu’u Pehe, a landmark best observed from the top of the cliffs at sunset. Otherwise, Lāna'i is arguably the best island for unplugging and unwinding. Don’t worry about an itinerary; let the itinerary find you.