When I walked up to the parasailing booth on Sunday I was a little nervous.

Maybe it was the anticipation of waiting for the boat, or the fact one of the tourists on the previous boat got seasick, or perhaps because my friend of over a decade, Tomo, told me for the first time that he gets seasick on boats and hadn’t brought any Dramamine with him.

For reference, me and Tomo were set to do the 1000-foot, tandem parasail, meaning any puke would have a long way to fall.

As we boarded, the crew of Hawaiian Parasail were very helpful, taking pictures of us “just in case” and reassuring us that sharks usually couldn’t jump high enough to attack.

As it happened, there were only six people on that boat when it went out: the captain & a crew member, me & Tomo, and two other visitors.

The boat ride itself was surprisingly smooth. It was around 4:15 pm when we went out, so ocean conditions were fairly calm. Tomo focused on the horizon to reduce the feeling of motion sickness.

I always enjoy being out on a boat off Waikiki—the view of the city skyline with Hawaiian mountains and valleys in the background is simply amazing.

A panorama of Waikiki
Click for full-size panorama

We got suited up with a life vest and harness support system while the captain asked us how much we were willing to get wet. The others pointed at their feet. We held our hands somewhere around neck level.

We were gonna get wet.

When it was time for our flight, me and Tomo scooted over to the landing pad, got clipped to the sail, and floated up into the sky.

Me and Tomo on the launch pad

Tomo and I leave the boat in the most epic way possible

Tomo and I begin our parasail flight

Parasailing wasn’t nearly as frightening as I thought it would be. In fact, once we got up to max length it felt rather peaceful.

Shaka from da sky!

Floating 800 feet in the sky above miles of ocean, Waikiki and Diamond Head waiting a comfortable distance away as the sun sinks behind you: that’s parasailing in Waikiki. We couldn’t hear anything but the ocean breeze blowing past us.

I felt like I was far above anything that could bother me: sharks, worries, taxes—all of that seemed incredibly distant.

I think everyone should experience that feeling at least once in their lives.

We were attacked by a giant shark at one point.

The parasail held us steady in the air without jerking or dipping suddenly, and the view was gorgeous. If seeing the city skyline from the ocean is awesome, seeing it when you’re level with the tops of the high-rises is phenomenal.

Things got a bit more exciting when we were reeled in.

Descending, we approached the water steadily

At first, the captain pulled us in gradually towards the boat, causing Tomo to remark that perhaps he had forgotten about dipping us.

Not a second later, the captain gave our line some slack, causing us to plunge into the cold water for a second before getting pulled back up. I barely finished saying “That was refreshing” before getting dunked like a basketball once again.

We are the basketball. The HP guys are LeBron.

Whether it was the captain’s experience in dipping parasailers or the sail and life vests holding us up, we weren’t submersed above our necks, so it didn’t feel dangerous or uncomfortable.

Washed up and hung out to dry

After we were reeled in, we got to relax in the boat as others took their turn before we headed back to the harbor.

I was even more impressed with the captain’s skills as the two other visitors were dipped in no higher than their knees, as requested. These guys definitely knew what they were doing and how to have fun doing it!

Parasailing is often thrown in with other water sports, but it’s much more relaxing and hands-off as an activity: you don’t really have to do anything other than sit down and enjoy the view.

Going up and coming back down is exciting, especially if you get dipped, but otherwise, parasailing is a relaxing joyride that anyone can (and should!) experience.

We had fun with Hawaiian Parasail

Tips for prospective parasailers:

  • While the wind & waves were calmer in the late afternoon, if you want great pictures the best time to go would be between 9 am and 2 pm.
  • Getting dipped is optional. Hawaiian Parasail (and most other parasailing companies) can do a dry landing, meaning you’ll never have to touch the water.
  • Tandem flights are available for up to three people. Someone on our boat suggested a 2-person tandem flight could be a romantic idea for a date (just make sure your date doesn’t get seasick).
  • The entire experience lasts about an hour, but can be longer or shorter depending on how many people are on your boat.
  • Hawaiian Parasail offers pictures on request; you can buy an SD card with your photos after the ride for $30. The pictures used in this post were taken by them!
  • Kids can parasail, too! Hawaiian Parasail’s age limit is 5 years & over.

Without a doubt, everyone should try out parasailing, whether you’re into water sports or not. It’s an awesome experience that’s definitely worth it—and Tomo didn’t even get seasick!

Some parasailing companies even allow you to fly in a tux or evening gown, making it an awesome experience for honeymooners.

If you’re on Oahu, there are a bunch of parasailing companies conveniently located on the south shore. If you’re on the neighbor islands, Maui has a couple of flights available on the west side, while the Big Island has a parasail that departs from Kailua-Kona.


Have you been parasailing before? Planning to go but unsure? Share your experience with us in the comments!