First Time Skydiving: What to Expect + Useful Tips to Know
I‘ve always wanted to go skydiving. But wanting and doing are two VERY different things, wouldn’t you agree? All I knew at the point I decided I wanted to skydive is that it HAD to be somewhere beautiful. Somewhere unforgettable. Somewhere extraordinary. So, when the time came to attend my friend’s wedding in Hawai’i, I realized this was my chance. If it’s your first time skydiving, there are things you need to know and expect. And, I’m sharing those “things” (or you know, tips) in this post. Hopefully, they are useful to you!
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First Time Skydiving?

Look, I hear you LOUD and CLEAR. This was my first experience as well. I would be lying if I said I wasn’t terrified. However, bucket list. Those two words, “bucket list,” are almost a verb in my world. My bucket list is a list of my life travel goals. So, I love to “bucket list”.
I like completing goals. Skydiving was a goal. Therefore, the math equation suggested a check mark appearing in the box beside skydiving on my bucket list. Just do it. Like me, some of you will have to “just do it”. Decision made. Check mark placed.
I am SO glad I “just did it”. SO glad I made the decision. Was it one of the best experiences of my life? Yes. Was it surreal? Yes. Was it beautiful? Yes. Would I do it again? Yes, in theory.
Wait…what? In theory? What does that mean?
We’ll get to that below. You know, the whole useful tips to know thing. But first…
What IS Skydiving?

Skydiving is jumping from an aircraft (usually a small, personal plane) and free-falling before launching a parachute and blissfully floating to the ground.
Yes, I said blissfully. It’s true. The post-parachute launch IS blissful. The nerve-wracking part is over, and you’re floating above (hopefully) gorgeous scenery without a care in the world.
Okay, that last part might be a stretch for some. However, it was true for me!
Simply put…
Yes, you’re choosing to willfully hurl yourself out of an aircraft, plunging to the unforgiving earth below. Not helping? Sorry. The drama took over!
Should I Skydive?
I can’t answer this one for you. As with everything in life, you must choose for yourself. There are pros and cons to each choice, and I’m here to highlight some of those.
Pros
- thrilling
- unique views
- “freedom” of flight
- conquering fear
- sense of accomplishment
- experience of a lifetime
Cons
- scary for some
- free-falling
- expensive
- equipment failure
- weather dependent
- not for those with certain medical conditions

Cons
We’ll skip the obvious cons as most everyone shares those fears. All I can say about that is you have no control over it, nor will you know what will or won’t happen ahead of time. It’s a decide-to-do or decide-not-to-do type of situation.
My Experience
The one con I do want to point out is the one I experienced. Even as an RN with awareness of my medical history and years of contemplating skydiving, I STILL didn’t think of this one.
If you experience inner ear issues, frequent ear infections, sinus infections, or have a history of motion sickness, please pay attention.
I had thought about motion sickness. Thankfully, if I’m actively taking part in the activity, I’m usually okay. It’s when I’m not moving (but everything else is) that gets me in trouble. So, I figured I was good here, and I was.

However, I failed to anticipate how fast that whole gravity thing works. Facepalm. My ears hurt within the first 15-20 seconds after jumping. Nothing to the point of thinking my drums were going to burst, but severe pressure issues nonetheless.
My friend Rita’s ears hurt initially as well, but hers went away a couple of hours later. Mine did not. I’ve had issues with my ears for years due to clear fluid occlusion. It’s hard to say how long mine were truly impacted, as I got COVID for the first time right after I returned home (after 4.5 years of avoiding it).
My point is, it affected my ears much longer than the average person.
My Decision
In hindsight, would it have changed my decision? NO. Was it possible I was already coming down with COVID, and this had something to do with it? Possibly, but I’ll never know. Most importantly, would I skydive again? YES. 100%.
Initially, I had decided, like ziplining or paragliding, I would like to skydive in every destination I visit with visually stunning scenery. Post-dive, due to my ears, I’ve peddled back on that.
Going forward, I’ve decided to skydive again. Once again, it will have to be a visually stunning destination like my first dive. If the ear thing happens again, I may have to decide that my second dive will be my last. 🙁
However, if it was due to the virus coming on and my ears are fine on the second dive, then I may continue. There still is that whole expensive cost thing though…
Where Should I Skydive?

Again, this is a subjective answer and a personal decision. I do highly recommend somewhere very scenic. After you hurl yourself out of a plane, don’t you want to stare down at gorgeous scenery vs blah terrain?

I went skydiving in Hawai’i. I think I would also like to skydive in Dubai and Zermatt, Switzerland. But that’s me. You might be different.

Because you may only do this once, not to mention the cost, I would carefully contemplate where you want to have this dream experience.
In addition to Dubai and Zermatt, here are some other destinations on my bucket list: Key West, Florida; Sydney, Australia; Hong Kong; Rio de Janeiro, Brazil.

Skydiving in Hawai’i


Wedding Time – Hawaiian Style
Speaking of skydiving destinations, Honolulu, Hawai’i is a fantastic choice! I was heading there anyway for a friend’s wedding and stayed with another set of friends.
One of the friends I stayed with also wanted to skydive for the first time. Perfect, now I have a skydiving partner! After some research, Rita and I decided to dive with GoJump Hawai’i over the world-famous North Shore.
GoJump America recently merged with Pacific Skydiving Honolulu to create GoJump Hawai’i, so don’t get confused if you see both names during your booking process and jumping experience.
Our Experience

Rita and I had a 12:40 pm check-in for a 1 pm-ish (if I recall correctly) jump. From Honolulu, it was about an hour’s drive to the GoJump Hawai’i facility at the North Shore.


That morning, we went to a fantastic restaurant, Sweet E’s Cafe, for an incredible breakfast. We needed to eat, but wanted to have plenty of time to digest our meal before diving in early afternoon.
PRO TIP: Order the Kalua Pork Eggs Benedict and/or The Enchanting French Toast at Sweet E’s (although I feel like The Extreme Mess described me best that morning!)
After arriving and checking in, we met our tandem pilots and got geared up. Harnesses, more harnesses, goggles, plus that all-important clip (or whatever it’s called) to our pilot.

My tandem pilot, Dugan, and I all geared up
I know you’re thinking the parachute is the most important, and you’re right. Because the pilot is wearing the ‘chute, the clip to your pilot is your clip to the “all-important”.

Your pilot explains the entire process. Then you walk out (yes, willingly) to the plane. Don’t be surprised when the runway is short, not much is around, and the plane is small. That’s normal. These aren’t jets. You don’t need a long runway. You’re up in the air before most jets can even get themselves moving.
The Jump
Ready…
Nope, not really!
I’m an internalizer. I may be terrified inside, but you’ll never see it on my exterior. This was certainly one of those times. On the other hand, I love being in the air, and as always (on flights and slow climbs to that first, steep roller coaster dive), I did some of my best, calm, deep thinking on the ascent.

Then I snapped back to reality. I realized I had climbed into the plane with my pilot last. There was no one between me and the door. As the photographer threw the door open, it dawned on me.

Set…
I was jumping FIRST. Gulp.

Dear Lord, it’s me, Heather. Thank you for this day. Please allow me to see another one!
Ultimately, this was a good thing. Less time to anticipate and worry!

I hate the feeling of free-falling, but here we go. I had already told my pilot, Dugan, he was going to have to push me out of the plane. He responded with, “Luckily for you, I am here to do just that!” LOL!

D-I-I-I-VE!
Before I knew it, I was standing at the edge, and then I was out and free-falling. Initially, I held my breath in a “frozen” state (minus that whole hurdling to the ground thing. Never mind THAT).

First photo out of the plane

The wind was smacking me, putting more rolls on my face than a chubby toddler right before it starts walking. My ears were…what was happening with my ears?!? Honestly, I was just trying to get my bearings. No time to be scared (a good thing).

Dugan tapped me on the arm, reminding me the photographer was there. Right. All of a sudden, I smiled and made Shakas with both hands.

If you aren’t aware, the Shaka is the official state hand greeting in Hawai’i, signifying the Aloha spirit of “don’t worry, don’t rush”. Some refer to it as the “thumb and pinky salute”.
Then, all of a sudden, something miraculous happened.
The Float
The free-falling sensation went away. Everyone told me it would. It’s physics. You know, simple physics. (Side Note: Physics is one of two reasons I am an RN and not an MD.) I got a physics lesson that day. One that I could actually wrap my head around. We won’t go into the boring details; let’s not ruin the moment.
All of a sudden, I was floating BEFORE the parachute deployed. Over the North Shore. In Hawai’i. It was peaceful, beautiful, and an experience I wouldn’t change. An experience, I’m SO glad I did. A bucket list experience.
This part of the dive was so relaxing, I was able to have a whole conversation with my pilot. “Where are you from?” “Oh, really? I’m from Birmingham, not too far from your part of Florida. How long have you been here? How many dives have you done?” “Oh look, do you see xyz down there?” “Yes, I do!”
Small talk while skydiving. Who would have thought?
The Landing
And just like that, landing time arrived. That was quick! The entire process, if you’re the first diver as I was, is only about 20-25 minutes, from takeoff to landing. Obviously, if you’re the last diver, the time will differ.
I was a bit anxious about the landing. I didn’t exactly stick my landing in Zermatt, so naturally, I was worried about sticking it here. However, for whatever reason, this time was much easier. I tucked, Dugan landed, and then I just put my feet on the ground as instructed.

Ta-Dah! I’m grounded!

That hair, though! 😆
Post-Dive
My friend, Rita’s partner, was videoing and shooting us, and he got several good photos. Rita came in after me then we got photos together with the GoJump Hawai’i photographer.


Have to admit, we were on a high. Exhilaration. Feelings of accomplishment. 100% ecstatic, we just did it. I just did it!

And then, we were on our way back to Honolulu, making a stop at Hale’iwa Bowls for incredible, tropical smoothies/bowls along the way. This blue beauty is the way to go! It’s pretty, isn’t it?

The Blue Cloud consists of bananas, dates, brazil nuts, coconut butter, blue majik spirulina, collagen peptides, and almond milk? SO. GOOD. 10/10 recommend.
Had I not gotten this, my second choice would have been the Mauna Kea (mango, pineapple, strawberries, coconut sorbet, coconut milk). Just pure (literally) tropical goodness.
The Skydive Stats
- Jumped from 14,000 feet (highest altitude available without oxygen)
- 50-60 second free-fall at 120 mph
- $199 price
- Included certificate of jump, signed and dated by your tandem pilot
- $98 – $378 additional for optional photo/video packages
- PRICELESS experience of a lifetime!!!
Tips for First-Time Skydivers
If you are a first-time skydiver (whether booked or contemplating), please read these tips first!
First-Time Skydiver Tips
- Wear fitted, athletic clothing and athletic shoes (no open-toed). You will be in a tight-fitting harness that, ahem, invades your privates, er, I mean private space, and believe me, you want that harness to fit well. 😉
- Leave all the jewelry at the hotel. There will be a locker for personal belongings if you don’t have someone to leave them with, as we did.
- If you have long hair, secure it not just in a ponytail. Tie it down so it doesn’t whip your face.
- Unless you know your stomach and KNOW this absolutely won’t work, do try to have something on your stomach even if a few hours prior (recommended). You don’t want to pass out from low blood sugar or anxiety.
- Use the restroom just before instruction time. Common sense, and some people’s bladders work overtime during moments of anxiety.
- Listen to your instructor. Pay close attention to what they’re saying and follow instructions. For the love, follow instructions. They have a purpose. There’s a reason they’re given. Follow them.
- The parachute does jerk you up (like in the movies), but it isn’t painful.
- Don’t forget cash to tip your instructor and photographer (if you choose to add one). Some of them offer Venmo options (ours did), but I can’t speak for all of them.
- Think about time of day, especially for photos. At certain times of the year, they offer a sunset “ultimate” experience from 18,000 feet and 80 seconds of free-fall. It’s pricey, though, and likely requires extra prep (like oxygen, for starters). For full details, contact GoJump Hawai’i for the full details.
- There are offerings of round-trip transportation for great prices ($18 at time of publish)!
- For more tips, see this additional first-time guide.
PIN IT!




I hope these tips help all different groups of people. If you’re in the “currently-deciding-on-skydiving” group, I hope you’ve decided to do it. If you’re in the “want-to-do-it-but-will-I-won’t-I” group, I hope this helps give you the…ahem…gentle nudge you need. If you’re in the “definitely-am-skydiving-but-where” group, I hope you’ve found the place!
Have you gone skydiving before? If so, what are your tips for first-time skydiving? Share them below so everyone can be better prepared and have the best experience ever!
‘Til next time…
Trimm Travels,



















