Thinking of canceling but will I regret it?

Question

Hello. I have an 8 day trip planned for August staying at the Andaz with husband and 14 year old son. This will be our 9th trip to Hawaii and it is my favorite place on Earth. I got really good prices for this trip both for the hotel and the plane tickets. However we come from Pennsylvania and I really hate the flight. I get anxious just thinking about it. I’m contemplating canceling and booking a trip to the Cayman Islands. However I’m afraid if I do bite the bullet and cancel I will regret it and I won’t get those prices back. The flight alone has doubled in price. And the Cayman trip will cost me pretty much the same as Hawaii. Anyone else ever substituted the Caribbean for Hawaii? Did you enjoy it? I feel blessed and fortunate every time I visit Hawaii and not sure anywhere else can compare. Thank you for all opinions. I always enjoy this forum.

Answer

It’s completely understandable to feel torn when you love Hawaii deeply but struggle with the long flight. Many travelers have the same conflict—heart in Hawaii, nerves in the air. Since you’ve been nine times already and call it your “favorite place on Earth,” your instinct that you may regret canceling is very reasonable, especially because you secured excellent prices that would be extremely hard to match now.

The Andaz Maui is one of the island’s premier resorts, and having eight days to enjoy Wailea with your husband and teenage son is something many people dream of. When the flight is the only major obstacle, it’s worth weighing the experience against the temporary discomfort. A long flight is tough—especially from the East Coast—but the payoff is an island that you already know fills you with joy, calm, and connection.

Many people have substituted the Caribbean for Hawaii. Some enjoy it, and others find it can’t quite replace what Hawaii offers. Here’s what you can realistically expect:

The Cayman Islands are gorgeous, with incredible beaches and fantastic snorkeling, but the cultural depth is different—more resort-focused, less tied to natural and spiritual heritage.
The Hawaiian scenery (volcanoes, lush mountains, waterfalls, unique beaches, energy of the land) is something the Caribbean simply can’t duplicate.
You’ve built emotional ties and memories in Hawaii—recreating that somewhere else may feel “nice,” but not the same.
If the price will end up almost identical, the savings of a shorter flight aren’t really financial—just comfort and convenience.

If flight anxiety is the real issue, there are ways to make the journey far more tolerable:

Split the flight with an overnight in Los Angeles or San Francisco—many East Coasters swear by this method.
Talk with your doctor about flight anxiety treatments, even short-term solutions.
Bring distraction tools: noise-canceling headphones, downloaded movies, a book you’ve saved specifically for the flight.
Remind yourself that the flight is temporary—the reward lasts eight days.

Ultimately, the question becomes: will the relief of avoiding the long flight outweigh the sadness of missing Hawaii?

For many longtime Hawaii lovers, the answer has been no—they regretted skipping the trip because nothing else felt like their “place.” You already know how Hawaii makes you feel, and you already have an incredible resort booked at a price you won’t see again. If your heart is telling you you’d miss it, that’s important.

If you decide to return to Hawaii, you’ll likely be grateful you pushed through the discomfort. If you decide to try Cayman, you’ll certainly have a beautiful vacation—but it may not bring that same sense of belonging you’ve described.

Whatever you choose, make sure it’s the option that aligns most with joy—not fear. In that case, you won’t regret it.