Hawaiʻi: Where to Eat, Stay & Play

Image courtesy of 1 Hotel Hanalei Bay

Hawaiʻi doesn’t seem like it should be in the United States. The tropical archipelago in the South Pacific is a veritable paradise, a geological marvel brimming with greenery and wildlife. 

Hawaiʻi consists of six major islands — Kauaʻi, Oʻahu, Molokai, Lānaʻi, Maui and the The Island of Hawaiʻi (also called The Big Island) — plus several smaller islands and atolls. The islands themselves are the result of volcanic activity in the middle of one of Earth’s tectonic plates. In fact, the Big Island is still technically being formed, in a way, by its active volcanoes, Mauna Loa and Kīlauea. A little over 20 miles southeast of the archipelago is the Kamaʻehuakanaloa Seamount, an active underwater volcano that may one day become Hawaiʻi’s newest island.

Here is where to go for a mix of everything: lounge the day away on the beach, embark on satisfyingly grueling hikes, explore laid-back towns, golf, snorkel, eat outstanding food, connect with the local culture…Hawaiʻi offers something for everyone. 

Below is a collection of recommendations for where to stay, what to do and where to eat on Hawaiʻi’s five habitable islands — the Big Island, Oʻahu, Lānaʻi, Kauaʻi and Maui. This is just a sampling, of course — a little travel inspiration — as Hawaiʻi’s options abound. You won’t be at a loss for things to enjoy. 

When you connect with me, I’ll design a dream itinerary tailored to you and your travel style. I’ll get an understanding of your vibe and preferences, and then craft your perfect vacation. Tap into the aloha spirit: Hawaiʻi is calling. 

The quick and dirty:

Currency: $, US dollar (USD)

Languages: ʻŌlelo Hawaiʻi & English

Airports: Daniel K. Inouye International Airport, Oʻahu (HNL); Kahului Airport, Maui (OGG); Kona International Airport, Big Island (KOA); Hilo International Airport, Big Island (ITO); Lihue Airport, Kauaʻi (LIH) (most travelers will likely fly into HNL, and then board another flight to reach their final destination)

Transportation: If you want to explore beyond your resort (highly recommend), then renting a car is a great idea, especially if several hiking routes have caught your eye. Taxi services, as well as ride-sharing services (Uber, Lyft) are also available.

Best time to visit: There’s no bad time to visit; it really depends on what you’re after. January through March is best for whale watching, while the winter months are best for big-wave surfing. September will see fewer crowds, with June, July, August and December being the busiest months to visit. (Unsurprisingly, the summer months tend to have the best weather, with the least rainfall.)

Ideal length of stay: Again, the best vacation length will depend entirely on what you’d like to do (or not do). On balance, five to 10 days is ideal, although shorter and longer trips can be just as doable — and enjoyable.

Signature dishes: shave ice, poke, saimin (noodle soup), laulau (taro-leaf-wrapped pork cooked in an underground oven), malasadas (Portuguese doughnuts)

Key phrases: aloha (hello/goodbye), mahalo (thank you), e kala mai (excuse me), e ʻoluʻolu ʻoe (please, eh oh-loo-oh-loo oh-eh), ʻohana (family), moana (ocean)

Dress code: your favorite swimsuit paired with comfy shorts, flowy pants or a dress — and don’t forget a hat and sunnies. For breezy nights, especially in the cooler nights, it doesn’t hurt to pack a sweater. 

The Island of Hawai’i (The Big Island)

The Island of Hawaiʻi (also known as The Big Island) is one of the best Hawaiʻian islands for families (especially the Kona side, with its calm waters, coffee farms and wide selection of restaurants and cultural landmarks). There’s a lot to do here, including hiking, snorkeling, exploring active volcanoes in Hawaiʻi Volcanoes National Park (a must), scenic helicopter rides, stargazing on Mauna Kea and so much more. Hawaiʻi is very spiritual as well, and the island’s properties preserve its heritage with strong programming intended to keep its culture alive.

Image courtesy of Mauna Lani

Where to stay on the Island of Hawai’i (The Big Island)

Mauna Lani, Auberge Resorts Collection: A luxurious (and very family-friendly) oasis that honors the land’s historical roots.

Kona Village, A Rosewood Resort: Perfect for multi-generational travel, with free-standing hale and elegant suites adorned with locally made art.

Images courtesy of Four Seasons Resort Hualalai

Four Seasons Resort Hualalai: A sophisticated and serene stay deeply connected to the local heritage.

Fairmont Orchid, Hawaiʻi: Located on a private bay, with an open-air spa and several oceanfront dining options.

Mauna Kea Beach Hotel, Autograph Collection: The white-sand Kauna’oa Bay is home to this resort, complete with a championship golf course and other top-tier amenities. Please note that as of February 2024, the property is currently undergoing a renovation.

What to do on the Island of Hawai’i (The Big Island)

The Island of Hawaiʻi is a nature-lover’s paradise. Hike to a solidified lava bed in the Kīlauea Iki Crater, located in Hawai‘i Volcanoes National Park, or explore the biodiverse Kona Cloud Forest Sanctuary on Mt. Hualālai. View the island’s several volcanoes from above, via helicopter, including Kīlauea, the most active. Snorkel with majestic manta rays at night, and during the day, don’t miss Papakōlea Beach and its distinctive green sand.

Where to eat on the Island of Hawai’i (The Big Island)

CanoeHouse, at Mauna Lani, is arguably one of the island’s best restaurants, serving a Japanese-inflected menu highlighting the finest local ingredients. The Four Season’s Ulu Ocean Grill, too, is perfect for an oceanfront fine-dining moment. Also a must is Kona Brewing Company, where locally brewed (and consciously made) beer is paired with good vibes and hearty fare (pizza, burgers, tacos, pupu). 

For the best shave ice, the legendary Hawaiʻian dessert, head to Anuenue Ice Cream & Shave Ice, or to Kula Shave Ice, which makes their own syrups using organic, locally sourced fruit. For more sweetness, you can’t go wrong with Punalu’u Bake Shop, where the malasadas, yeasted doughnuts dusted with sugar and often filled with various flavors (Punalu’u’s flavors include guava, lilikoi, taro-mango and several others), are mandatory. 

The Island of Hawaiʻi’s poke game is strong, too. Two favorites are Da Poke Shack, a lively hole in the wall with the freshest seafood, plus vegetarian options, and Suisan, a fish market that happens to serve some of the best poke bowls around.

Oʻahu & Lānaʻi

Oʻahu is Hawaiʻi’s most commercialized island (it’s home to the state’s capital, Honolulu), but it’s still very much worth visiting. It’s the best island for surfing: the North Shore is legendary for its big-wave surfing, and is home to the famous Banzai Pipeline, which attracts the world’s best (and bravest) surfers. 

It’s also amazing for first-time visitors, families and those with limited time. You can visit two spots on Oʻahu and feel like you’ve hit two islands: stay a couple of nights in Waikiki and then jet up to the North Shore; you’ll get a taste of everything the island has to offer. 

Lānaʻi is quiet, small and blissfully free from crowds. It houses a couple luxury resorts, and is mostly owned by Larry Ellison, the co-founder of Oracle.

Image courtesy of Turtle Bay Resort

Where to stay on Oʻahu & Lana’i

Turtle Bay Resort: A supremely located (especially for surfers) and secluded five-star stay on Oʻahu’s North Shore. Turtle Bay Resort also just went through a multi-million dollar renovation. It is famous for being featured in Forgetting Sarah Marshall.

Four Seasons Resort Oʻahu At Ko Olina: A western Oʻahu retreat perfect for families, golfers, wellness enthusiasts and adventurers alike.

Aulani, A Disney Resort & Spa: Disney’s signature magic in the South Pacific, catering to guests of all ages. 

‘Alohilani Resort Waikiki Beach: A brand new, lively resort complete with a massive oceanarium and two restaurants helmed by Chef Masaharu Morimoto.

Image courtesy of Sensei Lanai, A Four Seasons Resort

Four Seasons Resort Lānaʻi: Ultra-private and tranquil, with five-star dining, golf, wellness treatments and more.

Sensei Lānaʻi, A Four Seasons Resort: A luxurious wellness retreat, with a Japanese-inspired spa and dining courtesy of Nobu.

What to do on Oʻahu & Lānaʻi

Hike up to Maunawili Falls, a beautiful reward following a medium-grade trek through lush rainforest. Explore the 400 acres of the Ho’omaluhia Botanical Garden, where a diverse array of flora is organized based on geography. 

On Lānaʻi, the tiny Lānaʻi City is particularly charming. Browse the local shops, peruse the local art displayed at the Lānaʻi Art Center and play with rescued cats at the Lāna‘i Cat Sanctuary. 

Where to eat on Oʻahu & Lānaʻi

Sunrise Shack is the place to go on Oʻahu for açai bowls and smoothies (there are multiple locations). The Pig and the Lady is a hip Vietnamese spot in Honolulu’s Chinatown, while ARVO, also in Honolulu, is a vibrant, chic café serving nourishing cuisine with a hint of California vibes. 

On Lānaʻi, the Four Seasons Resort Lanai knocks it out of the park, with expertly crafted Japanese fare at Nobu Lanai, as well as locally sourced deliciousness at the poolside Malibu Farm.

Kauaʻi

Kauaʻi is aptly referred to as the Garden Isle; indeed, most of the island is covered by rainforest (Kauaʻi is also Hawaiʻi’s geographically oldest island). Consequently, there is not as much infrastructure here, resulting in a more laid-back, down-to-earth vibe compared to some of the more populated islands. Nature lovers will rejoice at Kauaʻi’s rugged cliffs, white-sand beaches, challenging hiking trails, stunning waterfalls and overall natural splendor. Mount Waialeale, in the island’s center, is nearly a mile high, and is one of the wettest places on Earth.

Images courtesy of 1 Hotel Hanalei Bay

Where to stay on Kauaʻi

1 Hotel Hanalei Bay: A gorgeous, relatively new contender to the hotel scene (it opened in 2023), 1 Hotel Hanalei Bay is an eco-chic property with farm-to-table food, sustainable practices and a focus on wellness.

Grand Hyatt Kauaʻi Resort & Spa: A sprawling, plant-filled resort on Poipu Beach.

Ko’a Kea Resort on Poipu Beach: Contemporary, romantic and intimate, perfect for couples.

What to do on Kauaʻi

Kauaʻi is primed for outdoor adventures. Waimea Canyon State Park is a natural wonderland filled with challenging hiking trails and breathtaking views. Mahaulepu Coastal Trail, replete with sand dunes, rock formations, diverse flora and fauna and more of nature’s richness, extends from Shipwreck Beach to the remote Mahaulepu Beach, the perfect spot for whale watching. If you want to get closer to the whales (and see an epic view of the Nāpali coast), make sure to book a tour with the Native-owned Makana Charters. 

Makauwahi Cave, Hawaiʻi’s largest limestone cave, is a unique attraction filled with fossils, and the breathtaking cliffs of Nāpali Coast State Wilderness Park are a sight to behold from various vantage points. If you want to get an intimate view of the Nāpali Coast State Wilderness Park, make sure to take a hike. Plan to spend at least a day for the hike; reservations should be made in advance and book up quickly. 

Where to eat on Kauaʻi

Head to the breezy Kauaʻi Juice Co. for locally sourced smoothie bowls, soups, salads, juices and house-made nut milks. Additional locally sourced, nourishing fare (ahi poke, multi-hued salads) can be savored at Living Foods, as well as at 1 Kitchen, 1 Hotel Hanalei Bay’s signature restaurant, whose wine list champions organic and biodynamic producers. 

You can’t go wrong with any of the food trucks at the chic Warehouse 3540, where local artisans display their wares, or with Hanalei Bread Company, an organic café and bakery that sources its produce from its own organic farm. And the patio at AMA is a delightful spot to enjoy ramen and other Asian dishes made with — what else? — locally sourced ingredients. Make sure to make a reservation in advance. 

Maui

Maui has always been popular, but now it’s as busy as ever, courtesy of season two of The White Lotus, which was filmed at the Four Seasons Resort Maui at Wailea. Expect lots of fellow visitors, but that doesn’t mean you still can’t have an amazing vacation. 

There are several areas of the island to explore. A top recommendation is Haleakalā, a nearly two-mile-high dormant volcano that beckons hikers, bikers, horseback riders and stargazers. In 2023, fires devastated the town of Lahaina, on Maui’s northwest coast. The town is still re-building, and now it’s as important as ever to support the area’s local businesses.

Image courtesy of Andaz Maui at Wailea Resort

Where to stay on Maui

Four Seasons Resort Maui at Wailea: A luxe oasis with some fantastic dining options, right on Wailea Beach.

Fairmont Kea Lani, Maui: This ultra-family-friendly resort has just been treated to an extensive renovation; expect an open-air lobby, redesigned rooms and suites, a new cultural center and more.

Andaz Maui at Wailea Resort: Sleek and modern, with cascading infinity pools and farm-to-table dining.

Montage Kapalua Bay: A sophisticated stay with residential-style suites, where everything is a celebration of Maui’s local culture.

What to do on Maui

The famed Road to Hana is among the most scenic drives you’ll experience (although inexperienced drivers will want to enlist the help of someone comfortable with hairpin turns, narrow stretches and other tricky obstacles). Make sure to allow time for several stops to take in the stunning scenery (waterfalls, rainforests) along the way. Along the trail is the black-sand Pa‘iloa Beach, located within the beautiful, biodiverse Waiʻānapana State Park (reservations are required here). Off of Wailea Beach, you’ll find Molikini, a sunken crater that makes for great snorkeling. Explore the local shops and restaurants in Pā’ia, a charming town on Maui’s North Shore, and, as mentioned, don’t miss a hike or bike ride on Haleakalā (Haleakalā National Park boasts five different climate zones!).

Where to eat on Maui

Mama’s Fish House, in Pā’ia, is a fun (and very popular) local haunt with tight connections to local fisherman and farmers. In Wailea, Monkeypod Kitchen champions locally sourced, organic ingredients, served in a chic laid-back setting. In Lahaina, I love Leoda’s Kitchen and Pie Shop for homemade comfort food. Ka’ana Kitchen, at the Andaz, serves a curated menu of farm-to-table, Japanese-inspired fare in a stylish open-air space. And don’t miss a meal at Ferraro’s Restaurant & Bar, at the Four Seasons, where expertly crafted coastal Italian cuisine is paired with ocean views and, oftentimes, soothing live music.

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This may be information overload, but that’s where I come in. Above is just a taste of all that Hawaiʻi offers. Connect with me for a tailored trip. I’ll work to understand your vibe and what you’re after, and design your dream Hawaiʻian getaway, complete with VIP perks and priority status at the state’s best hotels.