Hawaiian Islands Guide: Oahu, Kauai and the Big Island

Sugarloaf pineapple at Hole in the Mountain Farm

More than just surfing, shave ice, pineapples and leis, Hawaii is an archipelago of endless possibilities. Here’s our guide to determining which island is best for you and getting the most out of your next trip to the Aloha State.

For Maui tips, look here.


Honolulu is the easiest city in Hawaii to get to from the mainland and most tourists end up along Waikiki. It’s a fun, vibrant neighborhood and for a small area does a great job of delivering memorable experiences with rich, authentic culture, like the oceanfront lu’au at The Royal Hawaiian Resort. Along the beachfront, Halekulani is one of the grand dame hotels and provides thoughtful service in a classically elegant setting. A little bit south of the crowds on Waikiki is another luxurious option, The Kahala Hotel & Resort, where you can get the best lomi lomi massage on the island at the all-suite spa.

Don’t fall into the trap of thinking that Oahu is all about Waikiki though. There is so much untouched nature within a short drive, so make sure to get out to see the beaches and legendary surfing of the North Shore, and find a nice hike too. The Kaniakapupu Ruins are spectacular and just an easy eight-minute hike from Nu’uanu Pali Drive. Look for a “restricted watershed” sign to mark the trail entrance and follow the bamboo-shaded trail to find what’s left of King Kamehameha III and Queen Kalama’s summer palace. An estimated 10,000 guests attended a luau here in 1847 to celebrate Hawaiian Restoration Day.

Oahu —Kaniakapupu
Kaniakapupu (Photo by Peter Tsai.)

Hawaii’s the only state in the country that can grow cacao beans, and there are quite a few bean-to-bar chocolate makers on the island. You can get in on the action too, making your own bar at Madre Chocolate, Oahu’s first bean-to-bar chocolatier. Sign up for classes and farm tours here and learn about the complex chocolate-making process before pouring your own bar and filling it with inclusions like hibiscus, coconut, rosemary, sea salt and ground espresso, much of it grown in the garden out back.

After your chocolate fix, head to dinner at any of Chef Ed Kenney’s restaurants. Mud Hen Water is serving the most interesting contemporary Hawaiian food on Oahu in a super casual, shared small plates setting. Chinese sausage madeleines are a fun snack to start and impossibly tender grilled octopus comes in a lu’au and fresh coconut milk sauce — Hawaii’s version of creamed spinach. Kenney’s newest restaurant, Mahina & Sun’s, just opened inside the newly renovated the Surfjack Hotel & Swim Club and it’s the most coveted reservation in town.

Oahu — Mud Hen Water
Mud Hen Water’s Grilled Octopus and Lu’au (Photo by Amber Gibson.)

For a sweet gift to take home, stop by Royal Hawaiian Cookie on Waikiki. Their macadamia honey and sesame seed Florentines with a Hawaiian spin are more sophisticated and elegant than the shortbread you’ll find at the ubiquitous Honolulu Cookie Company stores. Or visit Hawaiian Shochu Company in Haleiwa for a rare bottle of Namihana shochu. Husband-and-wife team Ken and Yumiko Hirata make just 6,000 bottles of shochu from Hawaiian sweet potato each year, and the only place to taste and purchase a bottle is at their unassuming distillery. They are extremely gracious hosts, but be sure to call ahead to make an appointment because the distillery is not open to the public. 

Oahu — Hawaiian Shochu Company
Hawaiian Shochu Company (Photo by Peter Tsai.)


While Oahu is a balance of cosmopolitan with nature, in Kauai it’s truly a jungle out there. Here are the lush, majestic landscapes that have been backdrops for “The Descendants,” “Pirates of the Caribbean” and “Jurassic Park.” You can’t entirely circumnavigate the island by car, so a helicopter ride will give you the best overview. Two or three days are enough to cover the rest of the island by ground and your biggest decision with accommodations will be whether you want to stay on the north or south shore.

If you opt for the sunnier south side, stay at Ko’a Kea Hotel & Resort at Poipu Beach. The 121-room boutique resort has a more intimate vibe than the neighboring Marriott and Sheraton properties. Service is outstanding and the waves are fantastic for learning to surf. I could practically dive into the ocean from the terrace of my third floor oceanfront room. You’re that close to the beach.

On the more secluded north shore are a couple of Starwood properties, including the St. Regis Princeville, which manage to incorporate St. Regis brand standards (nightly champagne sabering, butler service) into a laidback Hawaiian environment. There’s an excellent Jean-Georges restaurant, Kauai Grill, along with what is hands down the best spa on the island where vegan, organic OSEA and Hawaiian-made Malie Organics products will nourish your skin after a long day in the sun.

Waimea Canyon on Kauai’s west side is known as the Grand Canyon of the Pacific. The dramatic gorges are great to explore by helicopter, or the adventurous can hike down the Kukui Trail. Going down is easy, but you’ll want to stock up on chilled coconut water to propel you back up the 2,000-foot elevation drop along the 2.5-mile trail.

Kauai — Waimea Canyon
Waimea Canyon (Photo by Peter Tsai.)

There are so many hidden gems on this small island including many small farmers and artisanal food producers. Learn about herbal medicine at Kauai Farmacy, where herbs, spices and artisanal teas are lovingly grown. Farm tours are available Wednesday and Friday mornings and you’ll meet Doug and Genna Wolkon and their three cherubic kids.

Kauai Farmacy
Kauai Farmacy (Photo by Peter Tsai.)

Stop by Monkeypod Jam’s café in Lawai for lunch or a snack. Former schoolteacher Aletha Thomas creates more than 50 seasonal jams and preserves using exclusively Kauai fruit and at her newly opened café she also serves baked goods, quiche and Sugarloaf pineapple soft serve (the sweetest pineapple you’ll ever taste). With so much tropical fruit readily available, juice and smoothie bars are around every corner too. Aloha ‘Aina makes the best acai bowls and smoothies while Kauai Juice Co. specializes in cold-pressed juices. Farmers markets can be found nearly every day of the week, and these are the best places to get an appreciation of the local food scene.

Kauai — Sugarloaf Pineapple
Sugarloaf pineapple at Hole in the Mountain Farm (Photo by Peter Tsai.)

Hawaii Island

Most often referred to as the Big Island, Hawaii is home to the most diverse climates and the only active volcanoes in the state. Kilauea and Maunaloa are both located in Hawaii Volcanoes National Park, with the former erupting continuously since 1983 and the latter due for an eruption soon.

Explore the volcanoes, rainforests, mountains and waterfalls with Hawaii Forest & Trail, Hawaii’s premier small group eco-adventure tour operator. They have some great all day tours that take you deep into volcano country, but I opted for a half-day Hilo Tropical Waterfalls Tour. We saw several waterfalls and even had time to swim, kayak and paddleboard under privately owned Kulaniapia Falls before lunch. Along the way, we drove through OK Farms and sampled macadamia nuts and tropical fruit, including lychee I plucked straight from the tree. When I mentioned that I hadn’t had coconut water from a coconut yet, Harrison (our guide who also happens to be an organic farmer) took us on a small detour by his house to get me a fresh one. This is just one example of the profound aloha spirit I felt on this island and a reminder to enjoy life’s small pleasures.

Hawaii — Hilo Tropical Waterfalls Tour
Hilo Tropical Waterfalls Tour with Harrison (Photo by Peter Tsai.)

Hotel options in Hilo are slim, but Hilo Hawaiian Hotel is your best bet. While the lobby admittedly smells overwhelmingly like car freshener, the ocean-view rooms have a private balcony and nice view of Hilo Bay. All of the true luxury properties, however, are on the drier Kohala Coast.

Mauna Kea Beach Hotel is the most iconic of these resorts, nestled along Kauna’oa Bay and the prettiest white sand beach on the island. When Mauna Kea first opened its doors in 1965, it was the Big Island’s first world-class resort. Today, more than 50 years later, guest rooms and public spaces are clean and contemporary while still preserving the mana of the past. The bathroom in my oceanfront room was so spacious, with a rain shower, oversize bathtub and even its own lanai. When the resort underwent a $150 million renovation in 2007, the hotel decreased its room inventory to expand all of the rooms by 50 percent. Between the Rees Jones-designed golf course, water activities, pool, spa, shopping, beach and great food, there’s no reason to leave the property.

Sunday brunch here is an institution for locals and visitors alike, including a sushi station, dim sum, chilled seafood, a colorful salad and fruit bar and dessert table.

In the evening, relax with friends and family at newly redesigned Copper Bar. Cocktails, wine and beer are all on tap, including the signature Mauna Kea Mule with fresh ginger beer. Chef Rio Miceli serves Asian-influenced tapas like Szechuan green beans, sushi rolls and kung pao ahi tuna.

If a helicopter adventure is in the plans, Paradise Helicopters is the premier tour operator, with tours that leave from both Hilo and Kona. There’s no better way to appreciate the Big Island’s dramatic valleys, volcanoes, waterfalls and shoreline and access areas that you simply can’t see by car.

Hawaii — Lava as seen from Paradise Helicopters
Big Island lava from Paradise Helicopters (Photo by Peter Tsai.)