Over the years, I’ve lost count of how many times I’ve touched down in Hawaii — but I can tell you this: every visit feels like the first. From waddling through Honolulu seven months pregnant, to chasing waterfalls with my family across three islands, to sailing in style on Norwegian and Oceania cruises, Hawaii always finds a new way to surprise me.
There’s no wrong way to do Hawaii. Every island offers its own rhythm — a different breeze, a unique flavor, a new memory. Here’s a personal island-by-island guide, curated from years of joyful discovery.
Oʻahu – The Heartbeat of Hawaii
Must-Sees:
• Pearl Harbor Memorial
• Diamond Head Hike• Waikiki Beach (sunset is non-negotiable)
• Iolani Palace and Honolulu’s historic co
Experiences:
• Surf lessons on the North Shore
• A traditional lūʻau at Paradise Cove
• Shopping in Honolulu, from farmer’s markets to luxury boutiques
Where to Stay:
• The Royal Hawaiian – historic pink elegance right on Waikiki
• Halekulani – understated beachfront luxury with exquisite service
• The Ritz-Carlton O’ahu Turtle Bay (formerly Turtle Bay Resort) – for a more relaxed, nature-framed North Shore experience
Big Island – Volcanoes, Stargazing & Soul
Must-Sees:
• Hawai‘i Volcanoes National Park
• Punaluʻu Black Sand Beach
• Mauna Kea Summit at sunset
• Kona Coffee Country
Experiences:
• Snorkeling with manta rays off the Kona coast
• Visiting the lava tubes and orchid farms in Hilo
• Wine tasting at Volcano Winery — yes, wine in Hawaii!
Where to Stay:
• Mauna Kea Beach Hotel – iconic, with timeless views
• Four Seasons Resort Hualālai – high-end, perfectly perched on the coast
• Volcano Village Inns – charming and cozy, right near the lava flows
Kauaʻi – The Garden Isle
Must-Sees:
• Nā Pali Coast (by air, sea, or trail)
• Wailua Falls
• Hanalei Bay & Valley
• Waimea Canyon – “The Grand Canyon of the Pacific”
Experiences:
• Helicopter tour over waterfalls and emerald cliffs
• Kayaking the Wailua River
• Hiking the Kalalau Trail (or at least the first two miles!)
Where to Stay:
• 1 Hotel Hanalei Bay – sustainable and spectacular
• Grand Hyatt Kauaʻi – classic luxury on the south shore
• Hanalei Colony Resort – remote, peaceful, soulful
Maui – The Valley Isle
Must-Sees:
• The Road to Hāna
• Haleakalā Sunrise
• Iao Valley State Park
• Lāhainā (rebuilding with grace and aloha)
Experiences:
• Whale watching (in season)
• Snorkeling at Molokini Crater
• Touring Upcountry farms and lavender fields
Where to Stay:
• Hotel Wailea – adults-only boutique luxury
• Andaz Maui – modern, vibrant, beachfront
• Ritz-Carlton Kapalua – secluded and serene
Molokaʻi – The Soul of Old Hawaii
Must-Sees:
• Kalaupapa National Historical Park
• Halawa Valley
• Papohaku Beach (one of Hawaii’s largest)
Experiences:
• Learning hula and lei-making from locals
• Exploring the island’s quiet, untouched beauty
• Immersing in community — there’s no resort wall here, just aloha
Where to Stay:
• Hotel Molokaʻi – laid-back and lovely
• Vacation rentals – your best bet for a true local feel
A Taste of Hawaii: Flavors You Can’t Miss
Hawaiian cuisine is a soulful blend of Polynesian roots, Asian influences, and fresh island ingredients — each bite tells a story.
Must-Try Dishes & Treats:
• Poke bowls – Fresh, flavorful, endlessly customizable. Try local ahi with limu and Hawaiian sea salt.
• Kalua pork – Smoky and tender, often served at a lūʻau or in a classic plate lunch.
• Loco moco – Comfort food at its finest: rice, a hamburger patty, fried egg, and rich brown gravy.
• Poi – A traditional Hawaiian staple made from taro root — earthy and unique.
• Huli huli chicken – Grilled and glazed, perfect beachside.
• Spam musubi – A surprisingly delicious snack found everywhere from markets to fine hotels.
• Malasadas – Portuguese-style donuts rolled in sugar (don’t skip the filled ones at Leonard’s in Oʻahu).
Don’t Miss:
• Farmers’ markets – For tropical fruits like liliko‘i (passion fruit), mango, and apple bananas.
• Shave ice – Especially from Matsumoto’s (Oʻahu) or Wailua Shave Ice (Kauaʻi), with real fruit syrups and a scoop of vanilla underneath.
From roadside stands to resort dining, the food in Hawaii is an adventure all its own — fresh, fun, and full of aloha.
Other Memorable Moments
Some of my most luxurious and soulful adventures have been aboard ships — like my Oceania cruise from Los Angeles to Singapore, with graceful pauses in the Hawaiian islands. Each arrival felt like a welcome home.
And yes, I even considered buying property here. It still tugs at my heart.
Final Thought
If you’re wondering which island to visit — don’t. You can’t go wrong. Each one offers something rare: space to breathe, beauty to behold, and a sense of being fully present.
Whether you’re a first-timer or a frequent flyer like me, Hawaii always has something new to show you. And I’d be honored to help you plan your own version of paradise.
Ready to craft your Hawaiian journey?