An 18,000 foot jump I’ll never forget

Every few weeks, I get an urge to jump on a plane and fly somewhere new. Occasionally, I get an urge to jump out of said plane. 

A couple months ago, I finally acted on that urge and convinced a friend to join in my recklessness. Here are my first-ever experiences with tandem skydive.


When I first tell someone I’ve been skydiving, here’s some of the first things I get asked – and what I think you should know before taking the jump.

“You can actually die from skydiving, right?”

Well, yeah. I chose to jump out of a plane 18,000 feet off the ground, and that comes with its own share of risks including death. They actually make you sign a comprehensive (read: very, very long) waiver to make sure you understand all the risks.

“What does it feel like?”

Have you ever stuck your head out the window while driving? You can feel the air pushing against your face, and it feels kind of windy even if it’s 100 degrees out? Now speed that up like 10x faster and that’s what it feels like.

“Were you scared?”

Honestly, I was more uncomfortable than scared. You wear a harness that awkwardly fits on your upper thighs and take off in a tiny plane, knee-to-back with the other passengers. When the time came to jump, I was honestly just glad to be getting out of the plane and into the air.

“How high did you jump from?”

18,000 feet off the ground. The highest option you can pick to jump from anywhere in the world! Call me adventurous or crazy – your pick.

Why Monterey?

I ended up choosing Skydive Monterey Bay, primarily for the breathtaking views and warm weather. I was able to find a $533 groupon for a Weekend VIP jump for two, so my base cost was around $277. That specific deal is currently expired, but you can find a few other options for Skydive Monterey Bay around the same cost.  I also chose to pay more and add on a photo and video package so my total cost came out to $477 ($277 base cost + $180 video package + $15 USB drive charge). 

If you have the means to do so, I highly recommend paying for a picture/video package to capture your once-in-a-lifetime experience (at least just for your first skydive if you’re adventurous enough to keep going). Unfortunately, you will not be able to bring your own camera, GoPro, etc. because there is a high risk it may fall off during the jump.

What to Wear

Skydiving is an extreme sport, but still a sport. So you need to dress accordingly. Depending on which location you choose, they may have their own requirements or restrictions. For the most part here are some general tips to follow:

  • Wear comfortable, athletic clothing.
    I wore a pair of Lululemon leggings, a cotton t-shirt and running shoes. 
  • Bring a light jacket.
    Even if you are in a warm city, it will still be much colder up in the air. It was around 90 degrees in Monterey the day I went, but it definitely felt more like 65 or 70 degrees in the air. I wore a thin Northface pullover and was very comfortable the whole jump. 
  • Avoid wearing any jacket with a hood.

What to Expect

Expect to spend at least a half-day. You should plan to be there for around 3-5 hours start to finish. When you book your reservation, you will be given a check-in time. Make sure you arrive early with enough time to fill out the extensive forms and waivers (I counted a total of 16 pages!) Keep in mind that skydiving has potential dangers, including injury and death, so you will have to sign off agreeing not to sue the skydiving company and equipment manufacturers in the case you do get harmed during the activity. 

After you fill out all the forms, you will be given your tandem instructor and broken off in different groups. Your instructor will help you get your eyeglasses and harnesses on.

In the Air

The plane is probably one of the most uncomfortable parts of the whole process. About 8-10 of you will be jumping out one after another, and after adding instructors and photographers, that totals to about 16-20 people crammed into a small plane. You are seated almost like you are going canoeing, expect no personal space. You are practically sitting on each other’s laps.

Once it’s time to jump, you somewhat waddle out to door and jump when your instructor tells you it’s time. It’s a really weird feeling, walking in your harness strapped onto someone else. I didn’t even feel like I actually jumped out of the plane. More like, walked off and fell.

Before you jump, you are told to maintain a “banana-like” position. I think I looked more like I was flailing in the air. While you are free-falling, it feels like a lot of wind and pressure is pushing up against you. I thought I could almost feel the skin on my cheeks flapping around (and the photos confirmed this).

Another thing they tell you is don’t try to grab onto your instructors hand. I’m not usually one for grabbing someone’s hand I just met so I laughed when they told me it’s more common than you’d think. And then my video came back where you could see me clearly reaching for my instructors hand as I was falling and him pushing my hand off. Twice. Oops!

The free fall lasts about 90 seconds (or so I was told – it definitely felt a lot longer). After this, your instructor pulls the parachute. You feel some pressure in your thighs from the harness pushing up against you until you slow down.

After your parachute is pulled, the rest of the journey is slow-paced. I really enjoyed this part for the incredible views. I could see the whole Monterey Bay Area from above – city, beaches, ocean and all! You drift closer and closer to the ground and land smoothly in a patch of grass.

Overall, it’s definitely a very strange experience that I definitely want to re-experience. Check out my entire experience in this incredibly cool and embarrassing video below! Highlights include:

  • Incredible scenic views of Monterey Bay
  • My face and cheeks flapping around as I free-fall
  • Footage of me reaching for my instructors hand and him pushing it away TWICE
  • Exclusive before and after interview with me!

Check out my one-sheeter to help you navigate through your first skydiving experience! If this is your second, third or even fourth time going, use it as a quick refresher!  (Coming soon!)

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