Planning your first (or twenty-first) trip to Hawaii

Avoid the internet rabbit hole

Contrary to popular belief, the internet hasn't made planning a trip easier. It's made it harder, especially when it comes to a dream vacation like Hawaii.

First it's a beach from Instagram. Then a resort saved on TikTok. A hidden waterfall from a travel blog. An island your friend insists you can't miss. Before long, you've got 47 things you're convinced you need to see, all because a stranger online told you to. Or maybe it was your next-door-neighbor's cousin's best friend.

When working with clients, I've noticed something interesting, especially when they are looking at Hawaii: after a little digging, sometimes they aren't even that interested in Maui or Oahu or Kauai, even though they think that's the island they want. Their dream has just been shaped by everyone else's opinions and viral videos.

But here’s the thing about Hawaii—you can't just pick an island out of a hat. They are completely different worlds. If you want bustling city energy mixed with surf culture, that’s Oahu. If you’re looking to totally unplug in a lush, quiet rainforest, you want Kauai. Maui gives you that classic, luxurious resort feel, while the Big Island is a massive, dramatic landscape of active volcanoes and black sand. They aren't interchangeable, and trying to force one island to be something it's not is a quick way to ruin a vacation.

So before you open another tab or try to island-hop three times in one week, stop and ask yourself what you actually want to experience.

Do you want to spend your days hiking through raw nature and stargazing? Or would you rather dive into local food, learn about native history, and just relax by a pool? Whatever consistently captures your attention, that is the island you should be looking at.

Fun fact: the Mona Lisa has been called “the world's most disappointing masterpiece.” The exact same thing happens to travelers who fight massive crowds at a viral Hawaiian beach just to take one photo. Popular doesn't mean worthwhile for you. Your itinerary should be built around what actually lights you up.

At the end of the day, a trip to Hawaii is a major investment of your time, money, and precious PTO. Don't waste it building someone else's dream vacation, or spending hours drowning in conflicting reviews online.

Instead, let me do the heavy lifting for you. Together, we’ll cut through the social media noise, pinpoint the exact island and pace that fits your style, and map out a custom itinerary that actually lights you up. Hit reply to this email, and let's start planning your perfect Hawaiian getaway!