So you’ve landed at the Daniel K. Inouye International Airport and need to find a way to your hotel. You walk to the nearby car rental and ask for a compact vehicle.

“Sorry, all our compact and sedan models are rented out at the moment. We can rent you a small SUV for $150 per day.”

That’s triple what you expected to spend. Better just call a cab for now. Arriving at your hotel and settling in, you’re eager to get out and do something fun. You whip out your smartphone, type in the search bar “fun things to do Oahu” and figure that ziplining is exactly what you want to do. You call up Kualoa Ranch to see if they’ve got a zipline open:

“Sorry ma’am, we’re fully booked for today.”

Alright, I guess it’ll have to be ‘Plan B’ for today, but what about tomorrow?

“I’m so sorry, but tomorrow’s totally full as well. We do have an open spot next Monday if you’d like!”

Sunday night is your flight back home, so that’s a no-go. By now you’re feeling a bit peckish, so you decide to go out and find a nice lunch restaurant. Walking around Waikiki, you spot an enticing place with a menu posted out in the front. As the hostess greets you, you can tell from her body language that this will be another disappointment.

“I’m sorry miss, but we’re really busy right now. If you want a seat, it will be a wait of maybe 60 to 90 minutes.” Sigh. What went wrong?

Here’s what you need to know when you want to start booking a trip to Hawaii.

1. "Last-minute" means "Last pick"

Last minute ticket booking
"Siri, how do I stop procrastinating?" © VELTRA

While it may seem fun to have a vacation that’s totally spontaneous, the reality is that a lot of things are too unpredictable to expect on the spot: rental cars run out, activities can get fully booked, and restaurants run out of seats.

Just like buying plane tickets, booking activities and tours in advance can ensure you get a seat when and where you want it, as well as save you money. Trying to book a same-day activity isn’t always possible for this reason, as tour providers may need to make arrangements (like food or equipment) beforehand.

Even if same-day bookings are available, during the busy seasons there might not be any availability left on the days or times you wanted. Making reservations well in advance will ensure you’ll get a spot exactly when you want.

2. Worry Now instead of Later

Young woman planning vacation trip and searching information or booking an hotel on a smart phone and laptop, Travel plan concept
© Shutterstock

Nobody wants to spend their vacation chasing after people to figure out if their North Shore horseback ride is still available or not. You definitely don’t want to drive all the way to your activity to find that there’s no spots left for your party.

Reserving your seats beforehand might seem like a chore, but figuring out your schedule is much better than trying to throw something together at the last minute (and perhaps not succeeding). You’re only here for a limited time, after all, so you should be spending that time actually doing things instead of searching for “fun things to do” on your phone.

3. Don't Get Caught by Surprise

Internet connection problem while booking
"I really wish I could switch network providers..." © Shutterstock

Sometimes, things happen. People make mistakes, errors pop up in digital systems—Murphy’s Law applies even during holidays. Things like spotty internet (you’re traveling, after all) when you’re trying to book an activity could compromise your reservation.

Booking early means you’ll have more time to catch any such errors or reorganize your schedule if it comes to that. It also means that you’re better able to change plans if something comes up: canceling early will often get you a full refund, whereas you’d be hard-pressed to get any money back for a last-minute cancellation.

4. Take Time to Prepare

Packing stuff before traveling
© Shutterstock

Some activities require preparation, whether due to certain restrictions or just by the nature of the activity. Imagine going on a guided snorkeling tour, but not having a snorkel and mask—you’d be forced to spend money on a gear rental or purchase on the day of the activity when you could have gotten a cheaper set if you knew earlier.

Maybe you thought you’d surprise your spouse with a 5-star Star of Honolulu sunset cruise, but neither of you brought appropriate attire for a high-class dinner. Planning ahead helps you pack exactly what you need and avoid bringing (or buying!) too much stuff. And honestly, it’s just less of a headache since you won’t be scrambling for whatever item you might have forgotten.

5. You Pay for Peace of Mind

keyboard red button book now travel holiday
© Shutterstock

Last-minute deals are tempting, but they’re always a gamble. Airlines, hotels, and other seat-based services tend to give out discounts at the last minute to fill up empty seats, which is the main reason why people like to wait before buying.

However, being able to get these lightning deals depends on the provider not being fully booked, which isn’t very common during busy season in Hawaii. It also means you’ll be left with whatever seats or activities aren’t as popular (why else wouldn’t they be taken by another traveler?). In the long run, planning ahead ends up saving you time, anxiety, and in some cases even money. You’re on vacation to get away from the stress, after all, so it’s best to just leave that all at home.

If you’re planning a trip to the tropical paradise of Hawaii, it’s essential to pick the right time for your visit. Our article about the Best Time to Visit Oahu provides an in-depth analysis of the best times to visit Hawaii, taking into account factors like weather patterns, crowd density, and seasonal activities. Whether you’re an active adventurer seeking the perfect wave or a relaxed traveler dreaming of serene beaches and vibrant sunsets, this article has the insights you need to plan your perfect Hawaiian getaway.