The Hawaiian Islands aren’t just a destination, they’re a feeling. A slower rhythm. A warm breeze. A sense that, maybe for the first time in a while, you can actually exhale.
But with six unique islands to explore—each offering its own mix of natural beauty, cultural depth, and bucket-list adventures: planning your perfect Hawaiian escape can quickly turn into a full-time job.
I stop the overwhelm, second guessing, and analysis paralysis.
I design personalized Hawaii vacations that reflect your travel style—whether that means chasing waterfalls on Kauai, enjoying beachfront luxury on Maui, learning to surf on Oahu, or unwinding in a private bungalow on the Big Island.
Waking up to the sound of waves in Maui, sipping fresh Kona coffee on your lanai
Hiking through emerald green valleys on Kauai, then cooling off under a hidden waterfall
Watching the sunrise from Haleakalā, wrapped in a blanket and awe
Snorkeling with sea turtles in crystal-clear waters, then heading to a local food truck for the best poke of your life
Enjoying a laid-back beach day, followed by a romantic dinner with a view and a sky full of stars
Whether you’re planning a family vacation, honeymoon, anniversary, or once-in-a-lifetime escape, Hawaii is the kind of place that lives in your memory long after the sand is out of your shoes.
Because you want more than just a list of hotels. You want someone who gets it. Someone who’s walked those trails, swam those coves, and knows which resorts actually feel like paradise. I help you skip the stress and go straight to the wonder.
When we work together, you get:
Island matching based on your interests, vibe, and vacation goals
Custom itineraries that blend adventure, relaxation, and authentic culture
Curated resort and rental options that align with your style and budget
Excursion planning, car rentals, inter-island flights, luaus, and more
Insider tips on when to go, what to pack, and how to make the most of your stay
One-on-one support so you feel confident and cared for every step of the way
Oahu: Best for a mix of city life, history, surfing, and famous sights
Maui: Ideal for couples, beaches, luxury resorts, and scenic drives
Kauai: The “Garden Isle”—perfect for nature lovers and romantic escapes
Big Island (Hawai’i): Great for volcanoes, star-gazing, and adventure
Lanai & Molokai: Quiet, off-the-beaten-path gems for seasoned travelers
Don’t worry—you don’t have to figure it out alone. I’ll help you choose the island (or combo!) that best matches your dream.
Let’s plan a Hawaiian getaway that feels like it was designed just for you.
All you have to do is breathe in—and say aloha.
Find Your Wonder with Hillary
Copyright © 2025 Hillary Cummings, Find Your Wonder with Hillary
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