If I ever was on an airplane that had lost both engines, I’d want to go down in the warm blue waters of the Caribbean. Maybe I could get some snorkeling in while waiting for the rescue boats. The airport at Montego Bay has a beach side airstrip. One minute it looks like you are going to land in the ocean, and a moment later you touch down on the beach. We had to deplane at the gate rather than evacuating straight into the Caribbean, but I was eager to don my board shorts and start enjoying some sun, surf, and sand.

Picture of Carribean.I love the warm blue waters of the Caribbean

This was our 5th trip to Jamaica, and our hotel for the next 9 days was the fanciest one we’ve stayed at. Our room had a great view of the ocean, an all inclusive minibar, all inclusive 24-hour room service, and was finished with fancy modern American sensibilities. I still can’t believe we got this free vacation just by hacking a few credit cards.

Picture of ocean view.The view from our room

The Hyatt Zilara has lots of water sports

The North Coast of Jamaica has a rockier coast line. It’s also more exposed to the steady trade winds that blow from the northeast. Most all-inclusives on this part of the island are equipped with an array of free water sports. The Hyatt Zilara had a few of our favorites including sailing, snorkeling, kayaking, windsurfing, and stand up paddle boarding.

Just before we arrived, a storm had passed through the area. The water was choppy, and it was windy. They weren’t letting any boats out, and the water was too churned up for snorkeling. The second day, things lightened up and they started letting out the sailboats and windsurfers.

Some heart pounding fun racing boats in Jamaica

Without wasting any time we hopped on a Hobie sailboat to scope out the waters around the resort. It was a wild ride heading out through the waves, and we were immediately drenched by the aqua blue bath water breaking over our bow. As we passed the crashing waves, we started picking up speed. Passing over the shallow reef and into the deeper dark blue waters where the swells were no longer breaking, but quite large.

Picture of rough surf.Conditions were too rough for any water sports on the first day

We weren’t the only ones having some heart-pounding fun, the resort crew were out giving other tourists rides. Caught up in the excitement, we got to racing our small catamaran with them. With huge grins all around we let out some hollers back and forth shouting “Whoop whoop!” and “Yeah Mon!” as our boats flew over the swells in close formation chasing each others heels. I’m glad we took the opportunity to learn to sail for free years ago.

As we were racing back to shore I spotted a nice size set of waves. My new surfing instincts kicked in and I steered our boat into the path of a large oncoming wave. We had enough speed and the skids on our boat started to vibrate and groan as we slid down the face of this wave. “Holy shit!” We were surfing in Jamaica, and couldn’t help but let out a few more whoops and hollers.

A new milestone windsurfing in Jamaica

After our wild ride on the sailboat, I started getting anxious about windsurfing. These were the windiest and choppiest conditions that I’d tried to windsurf in, but I took comfort that there were lifeguards and a rescue boat – also free of charge 🙂 The equipment at the resort was also quite nice. In addition to the trainer boards, they had a much sleeker board that looked like it could rip through the water pretty good.

My system flooded with adrenaline when I hit the water. I hopped on the board and managed to get the sail up and flying. It was catching so much wind that I had to hang from it using all of my body weight to keep it in the wind. I started picking up speed and bouncing over the swells when I felt the force on the board change a bit. I looked down and realized I’d gained enough speed for the board to get up on plane. “No way!” I was surfing while hanging from this sail which I was flying like a hang glider.

After a few more wild runs, I ended the end of the day battered and exhausted. I had a few good wipe outs where I collided with the board and sail leaving some newly earned bruises. But I was just too stoked about reaching a new milestone in windsurfing to care.

For the rest of our trip, the windsurfing wasn’t as adrenaline pumping. The conditions calmed down over the days, and were much better for practicing without taking a beating. Mrs CK even got some cool pictures from her kayak.

Picture of windsurfing.Mrs CK got some shots from the kayak on a calmer day

Learning to windsurf at the Hyatt Zilara in Jamaica

I wasn’t the only one to hit a new milestone in windsurfing on the trip. After some prodding from one of the staff, Mrs CK agreed to some free lessons. This guy had a real knack for teaching, and within a day Mrs CK was up on the trainer board making loops around the cove.

Picture of windsurfing.Mrs CK picked up windsurfing faster than I did

Can you go surfing in Jamaica?

Toward the end of the trip, the wind disappeared. We started switching up our activities to snorkeling and paddle boarding. I noticed that as the tide was changing in the late afternoon, and some waves were still forming around the mouth of the cove. I took the paddle board out, and after a few tries started catching some of the small waves. They weren’t big, but broke over a long time giving me a bunch of sweet rides. Again, I got to do some unexpected surfing in Jamaica. Mrs CK joined in on the fun catching some waves in a kayak.

Picture of surfing.I even caught some small waves with the paddle board

How not to take advantage of an all inclusive

We were busy every day having a ton of fun in the water, yet I couldn’t help but notice a lot of people who were looking longingly at us from the beach. A few came out and joined us trying to catch the breaking waves. But there were a lot of people who would only go as far to ask about the activities. After inquiring, they would say “I’ve seen all the people falling down, I’m not gonna embarrass myself.”

Here were grown people, at an expensive resort with awesome free activities, and they just couldn’t let go and have fun. I pitied those people and what their egos cost them. But then, when I though about it some more, I realized I often do the same thing. Whether it’s trying new exercises at the gym or getting up and dancing at a party, sometimes my ego holds me back. I think I’ll try and embarrass myself more in the future. I don’t want to risk skipping out on the opportunity of a lifetime just to avoid embarrassment.

A great adventure, and on to the next one

I thought this would be a lazy beach vacation. But every day was spent out on the water flailing around with our sails, paddles, and snorkels. And each night we threw back our fair share of Red Stripes while chowing down on delicious Jamaican food. I still can’t believe we got to do it all for free.

Picture of Tony in robe.A man could get used to this

A man could get used to a life like that. But for now we are back in CT, and I need to finish travel hacking our next trip – Barcelona, Spain.