Five Reasons to Wait Before Booking Activities on Your Hawai‘i Vacation

By Kent Coules, Publisher

Americans are obsessed with planning. We plan everything—our careers, our retirement, our kid’s birthday parties—so why is it that when you ask someone what they’re doing over the weekend, they seem genuinely happy when they reply “Nothing”?

If you’re the type who has to map out everything and gets anxious when things don’t quite go as intended, let me offer you this personal tale:

Prior to moving to Hawai‘i, in 2011, my family was vacationing on Maui. We were taking our middle daughter to college at the University of Hawai‘i from New Jersey.

On our last day on Maui, we planned a snorkeling trip to Honolua Bay. I had the brilliant idea of taking my family via the “scenic route” I had discovered while running through the neighborhood a couple of days earlier. By the way, the roads in the neighborhood we were staying in were dirt. And, unfortunately, it had poured the entire night before.

The rains had created a river at the bottom of a precipitous portion of the road we were on, and I couldn’t get the rental car back to the top of the steep, muddy incline. 

While we struggled, a 20-year-old kid appeared at a gate adjacent to our car. He offered to open the gate so we could back into his property and get on to level ground, and we gratefully accepted his offer.

His father then appeared and we got to talking. It turns out that they had moved to Maui on a whim after falling in love with it while on vacation. His family and a friend had purchased the property we were standing on from Woody Harrelson a couple of years earlier. Furthermore, they moved from a goat dairy farm they owned on the mainland that was only 50 miles from where we lived.

We were stuck until the road dried out, and our gracious new friends offered to take us down to the beach. We hiked down to a private property on the cliffs above the ocean where we met another gentleman who was cutting down apple bananas with a machete. He was in his 70’s, a transplant from California, and in amazing shape. I mean, the man went down a makeshift wooden ladder bolted to the cliff with a cast on his lower leg and his dog in his arm! When we all got to the bottom we entered the water from the rocky beach, swam out to a tiny islet and jumped off the rocks for the rest of the afternoon.

The experience was unforgettable, completely unplanned and nary a mention on Trip Advisor!

If this anecdote is not enough to make you re-think your tendency to over plan, I offer five rational reasons to delay your activity decisions until you’re on island:

A Hawai‘i vacation will be greatly enhanced by doing your activities on the right day. For example, when planning a day trip to the North Shore during the winter months, wouldn’t one want to go on a day when the surf’s up? The North Shore’s waves can fluctuate from 10 feet to 50 feet or more in a matter of hours.

Similarly, planning a circle island drive or a snorkeling excursion on a rainy day will be a less than ideal experience.

If you wait until you get here, you’ll be able to match up your experiences with the best weather days for each. Does hiking in the pouring rain and touring the interior of ‘Iolani Palace on a beautiful, cloudless day make sense? That’s the risk you take when you book everything in advance.

Lastly, most activities are “rain or shine.” Zip lining in the pouring rain may safe, but would you still have done it if you hadn’t already paid the non-refundable fee?

2.  Your mood

People can get really ambitious when planning a Hawai‘i vacation. There are so many boxes to check that you run the risk of overbooking. Part of a vacation, especially one in paradise, is about relaxing. Give yourself a day or two to relax at the beach or by the hotel pool, reading the latest issue of This Week magazine. You’ll start to recognize your appetite for activities and schedule accordingly.

I had a niece come to Hawai‘i recently and she had multiple activities planned for each day. She didn’t always take into account travel time or delays. By the time they went home, they were exhausted. They literally slept for an entire day.

Relax. The activities will still be here when you arrive.

Sometimes you can save money when you book post-arrival. Visitor magazines (*ahem* like This Week), have coupon pages and special offers that are not available online. Many activity companies will offer better deals when you book direct.

Hotel concierges in Hawai‘i have a strong relationship with activity and tour companies. Meanwhile, brokers like Expedia and Pleasant Holidays have desks in many of the major hotels across all islands. These local experts can help determine the best options for you based on your individual needs.

In short, locals and local companies are generally the best resources for local information—especially with restaurants!

Hawai‘i has a ton of great events; check out our This Week Hawai‘i events pages to see what’s happening when you’re visiting. New events are being added regularly, and many of these events aren’t publicized until close to the actual day, so you’ll want to keep an eye out for what’s going on even after you arrive.

It should be noted that some activities do fill up early—tours for the USS Arizona Memorial , for example, can fill up two months in advance, with a limited number of tickets available at the door—so planning some of your activities ahead of time might be prudent.

Bottom line: don’t let your agenda rule your time off. You’re on vacation, after all. Allow room for flexibility and life’s happy accidents.

And on that note, happy planning! Or, more accurately, happy not -planning!