For my wife’s birthday weekend, I decided to surprise her by going skydiving and relaxing at a gorgeous resort in Orlando, Florida.

My wife and I like to celebrate our birthdays in style, and I knew sky diving was high on her bucket list. I was less keen, but I knew it was what she wanted. We were on a budget, so I had been keeping an eye on Groupon deals. 

Planning a Great Birthday

I knew the best skydiving experiences were close to the beach, so when one showed up to Skydive over Cape Canaveral and the Kennedy Space Center, I knew I’d found just what we were after. My wife loves surprises, so other than gathering the courage to jump out of a plane, I also had to keep it a secret! Oh, and I had to fast from carbs for a month to drop my weight under 220 pounds and keep it there. The things we do for love!

American Icon Brewery
American Icon Brewery

At the time my wife, Danielle was working in Vero Beach, so I had her meet me at The American Icon Brewery for Dinner. They have really great food, so I recommend stopping in for a meal if you’re in the Vero area. I had dropped the news to her the night before that we would be jumping out of a plane for her birthday, but I still had another surprise up my sleeve.

Air BnB

After dinner we drove up to an Air BnB to stay the night, located somewhere between Orlando and Titusville. It was a nice enough place to stay, and we were only going to be there for the night. When we got up the next morning, there was a beautiful mist hanging in the air.

We drove out to Titusville and grabbed some breakfast on the way. Because we were excited and didn’t want to miss a thing, we got to the skydive center really early. They took us through a safety briefing and gave us death waiver forms to sign. I think that’s the only time where I’ve ever had to sign something that said, “You promise not to sue us if you die.”

The Pre-Flight Briefing

During the briefing they will also up sell you. We paid $229 for two of us jumping from 12,000 feet on Groupon. When you get to the Skydive Center they will let you know that you won’t have much free fall time from 12,000 feet, you’ll be jumping from a smaller plane, which means you may not be jumping together. Oh and by the way, you don’t just jump out the door of the smaller plane, you have to climb out below the wing and then jump.

So that sold me on the larger plane, higher jump. That, and Danielle was really keen on it. I had already factored some extra expense for her to get the video but it was at least double the price by the end of the day so make sure you factor that in.

The rest of the morning was sitting around in the hangar and waiting.

We played a couple of the games they had on the tables and we just tried to distract ourselves from the fact that we were about to strap ourselves to another grown man and jump out of a perfectly good aircraft 18,000 feet in the air.

Fly Time

As the guys started to suit up we were introduced to our jump buddy. They recorded interviews with us (just in case we wanted to buy the video) and then we boarded the aircraft. No seatbelts in this beast. You’re basically sitting in two rows with your legs either side of a bench right in front of your instructor. Normally I’m so excited to be going up in a plane, that I’m looking out the window and enjoying the scenery going by. After all, we were jumping from above the Kennedy Space Center. But not this trip, I don’t even remember seeing the Space Center – I think I said a few prayers in that flight.

Once at altitude, the instructor strapped himself to my back. There was no way for me to verify he had done it correctly. I just had to trust that he had my back, and the rest of me. There was a guy who was celebrating a birthday in his eighties who was jumping from our flight which was pretty cool to see. I was more concerned with my shoulder strap feeling loose though and worried that I was going going to slip out half way down. 


Danielle had elected to be the last one out of the plane which meant I was second last. I had assumed that there would be a fair bit of time waiting  for the other jumpers to go, but once that door slides up, the plane is like a Barrel of Monkeys being poured out. 

That said, it is not easy to get to the door. You have someone strapped to your back so it is really hard to move and stand up. I tried to grab the sides of the door to pull myself forward but the instructor kept telling me not to grab the door, so it was a bit awkward. Danielle was laughing at me, thinking I was trying to get out of jumping. But soon enough we were out the door and in free fall.

It’s an experience that is difficult to describe. I wasn’t ready for how loud the rush of wind past my ears was going to be. It’s also hard to figure out where to look, wanting to look out at the horizon but also wanting to look down at the ground rushing up toward you. All this while you are trying to coordinate your hands and legs to direct your body.

Before I knew it, the instructor was pulling the rip cord. By far the worst experience of the day is when that parachute pulls and you feel the harness yank against your nether regions. Other than the discomfort, the next part of the flight was my favourite.  The feeling of gliding gently toward the earth, without the roaring noise of free fall, but with the certainty that the parachute was now open and functioning as it should. 

It had been nice and cool in the higher altitude but as we drifted down I could feel us drifting back into the reality of the Florida humidity and heat.  For landing I just had to bring my feet right up and we skidded to a halt on our bums. What a great experience!

The Next Surprise

After all that adrenaline it was time for some relaxation. We drove to Orlando. Most times when we visit Orlando, our time is packed with visiting friends, theme parks or shopping. I wanted this weekend to just be about relaxation and not going anywhere. I had booked us two nights at the Hyatt Regency Grand Cypress and Danielle had no idea. 

Hyatt Regency Grand Cypress Swimming pool and lake
Hyatt Regency Grand Cypress

As we pulled into the resort we drove through these beautiful gardens. When you walk into the main lobby you can see why they call this place Grand! You look up and you can see all the floors above. There’s water flowing through the lobby and you just have this incredible vacation feeling. They put us in a nice room and we were spent after our big morning so we took a nap and then explored.

The Pool

One of the first things I look at when booking a hotel is the swimming pool. This was no exception. The pool takes pride of place at the Hyatt Regency Grand Cypress. It is set out as two large pools with a river that runs between them through a man made chasm with water falls. It really is a beautiful thing. There is also a waterslide which I may have ridden a few times. The water was cold for August but I still had a lot of fun.

The pool at the Hyatt Regency Grand Cypress
The pool at the Hyatt Regency Grand Cypress

Lazing Around

Of course, if you prefer to just lay by the pool and relax, there are plenty of banana lounges where you can do that. Danielle enjoyed laying out and reading. There are also hammocks and other areas to relax down by the lake, a perfect place to watch the sunset. 

Tree of Lights at the Hyatt Regency Grand Cypress
Tree of Lights at the Hyatt Regency Grand Cypress


Your resort fee gets you access to plenty of activities. If you have kids they have rock climbing and plenty of other attractions to keep them engaged. Here are a couple of things we did…

Bike riding

At the time we didn’t have our own bikes so going for a cycle was a novel experience. We really enjoyed riding around and exploring the resorts extensive property. There are a couple of tracks you can take including one around a lake. 

Bike Riding at the Hyatt Regency Grand Cypress
Bike Riding at the Hyatt Regency Grand Cypress


If you prefer water sports, there are several boats you can take out on the lake. We opted for the kayaks and enjoyed finding a quiet spot and just floating on the water. 

Fitness centre

They have great fitness facilities. After all of the indulging we did, Danielle went in a few times to burn off some calories while I had a walk through. The fitness centre has numerous cardio machines, strength training machines and heaps of space to work on your own bodyweight exercises. Danielle enjoyed that they provided yoga mats, water, and towels just in case you didn’t bring your own.


As we weren’t leaving the property while staying at the resort, we made use of their onsite restaurants. 


We ate at the LakeHouse most often. They put on a delicious buffet breakfast. If you fill up then, you may not even need lunch. For dinners they put in a range of burgers, pizzas and let’s not forget their incredible milkshakes.

Milkshake from the LakeHouse
Milkshake from the LakeHouse


For a birthday celebration dinner we went to Hemingway’s which is higher end and more like fine dining. Danielle got a delicious looking dessert with a chocolate outer shell that you had to melt to reveal the treasure inside – it looked amazing.

On the Rocks Poolside Restaurant and Bar

Perfect for a drink or a snack, On the Rocks is super convenient if you don’t want to leave the pool area. I think we had lunch here on the first day and a couple of drinks during our time at the resort.

Hyatt Regency Grand Cypress
Hyatt Regency Grand Cypress

The thing I love about the Hyatt Regency Grand Cypress is that it is a resort. You can come here and just stay out without needing to go anywhere. I wouldn’t recommend staying here if you are going to the theme parks as I don’t think you’d get value out of all the amenities. We loved it for our weekend away.