Our Free Adventures in Jamaica

If I ever was on an airplane that had lost both engines after ingesting some large birds, 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.

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.

Hyatt Zilara Ocean View Jamaica

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.

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.

Windsurfing Hyatt Zilara Montego Bay Jamaica

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.

Windsurfing Lessons Hyatt Zilara Montego Bay Jamaica

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.

Surfing small waves in Jamaica

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.

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.

27 thoughts on “Our Free Adventures in Jamaica

  1. I think I may go for that Hyatt card next. There’s an intimidation factor with some of these cards, especially with meeting the minimum spend, but going with that Hyatt seems pretty easy. It’s just spend the $1k, get your two free nights, and book the most expensive, baller Hyatt hotel you can, right? Are you planning to cancel that card once the fee comes due or hang onto it?

    • It looks like the terms for the Hyatt card have changed around a bit. I just checked, and it’s 2k spend over 3 months now. We only needed 1k of spend, and they were waiving the fee for the first year when we got it. I still think it’s worthwhile with the current deal considering what you can get with the free nights.

      The spending usually isn’t too bad since its over 3 months, and we time new cards to coincide with larger expenses like car insurance payments. I do plan on cancelling the card before paying any fees.

      Good luck with the hacking, it’s totally worth the effort 🙂

  2. That’s so amazing, what a fantastic travel hack, and maximizing each opportunity on your vacation, it’s inspiring! Your writing style is engaging and I have been enjoying your blogging adventures, and learning about all your pursuits. Thanks for the great detailed posts! Keep them coming.
    By the way your pizza dough recipe is the absolute best! It has ruined me for all other pizzas.
    Ok water sports…I am not a strong swimmer so I may not be a great candidate for water sports. Do you suggest a simpler water sports to start with? I have gone kayaking and snorkeling…Armed of course, with many flotation devices! Great travel.hacking post. Looking forward to hearing about Spain! Nurse pkj

    • Thanks! It’s comments like yours that keep me writing 🙂

      Kayaking and snorkeling were our gateway drug to water sports. I actually never did much paddle boarding until this trip. It’s a great workout, you get to see a lot in the water, and you get some good board skills that should translate well to surfing. If you get a chance I would give it a whirl, just don’t forget your life jacket 🙂

  3. It sounds like a great trip, and I love the lesson at the end. How many people waste what might be super enjoyable for fear of being embarassed. Carpe deim… if I had the opportunity to learn sail boarding for free I’d do it.

  4. Sounds like a great trip Mr. CK and looks like you guys had some water sport fun.

    I always read about travel hacked trips like this and wonder how you guys do it…

    I see you used the Chase Ultimate rewards signup bonus. How did you manage to spend that much cash in 90 days? Offhand, I believe the requirement was $5k.

    • The largest spend we had to meet was for the Chase Sapphire card, and it was 4K in 3 months. Most of our spending goes onto credit cards, and our credit card bills average just over 1k a month. We also time larger spend cards to coincide with big payments like our 6 months of car insurance or travel expenses.

      If we had trouble meeting the spend, I would probably just buy some gift cards from our grocery store. But we haven’t run into that situation yet. Good luck with the hacking!

  5. This is a great trip, especially it was free!
    I learned from your post. ” I don’t want to risk skipping out on the opportunity of a lifetime just to avoid embarrassment.” touched me.
    Every trip, we should learn new knowledge and skills or try new sports.
    Jamaica is also my dream place.
    Have a nice trip to Barcelona, Spain!

  6. Sounds like a great trip! We went to Jamaica once around 1999. It was a lot of fun, but seems like a lot of poverty too. Our group got a driver and went all over the place. The Caribbean has great weather and we’d like to visit other islands too. It’s just a bit far from the west coast. Someday…

    • The Caribbean has some ideal weather. We’ve also been to Barbados and Puerto Rico. Both are better suited for making up your own trip and driving around. There are still a lot of other islands we want to check out as well 🙂

  7. I have windsurfing on my to-do list for this summer; great post! I love the part about ego; I can’t dance to save my life, but I often make a total fool of myself anyway. Guess who’s most likely having the most fun at that party? Yep, the silly one that can still laugh at herself despite her horrendous moves.

  8. When my wife and I went to Aruba a few years ago we tried all the activities as well. It was a blast and at first I was self conscious about falling but then I thought, I’ll never see these people again. What did I care? It made for an incredibly memorable trip plus we got some awesome photos of us in action 🙂

  9. Love Montego Bay! My brother got married there in 2007 and it was an awesome trip. I also ’embarrassed’ myself regularly trying various activities (not sure that word applies when your 25, multiple drinks in, and don’t give a crap). I’ve been to a number of islands in the Caribbean, though we’ve kind of settled on Cayman Islands as our favorite. Been there several times now. Last year I travel hacked a mostly free 10 days. I kick myself that I only discovered travel hacking a couple years ago, but hey, better late than never right? 🙂

    • Ha! I believe they call it liquid courage 😉

      I’ve also just started travel hacking in the last couple years. I didn’t think I had time while working, but it’s a lot more lucrative, and easier than I originally thought. At least we are getting our free trips now 🙂

    • Most of the waves on the North part of Jamaica are usually pretty tiny, but there was a storm passing through while we were there. The waves weren’t very big, but the biggest I’ve seen in that area. The paddle boards are pretty floaty so it’s easy to catch smaller waves with them.

      While most of it is quite calm, the Caribbean does have some surf breaks. I’ve hear there are some breaks on the east coast of Jamaica. The waves in Barbados are decent, and the surf can get quite large in Rincon, Puerto Rico. I need to get back to those islands soon 🙂

  10. I have seen you like to raise chickens, who do you pay and how much do you pay to take care of them for 9 days? We have chickens and other pets and it cost us about $40 per day when we vacation, which is a good hit to the vacation budget.

    Keep up the good life.

    rick, Battle Ground WA

    • Hey, Rick. My mother in law lives next door. She has no trouble feeding the chickens and collecting the eggs for us while we are travelling. Otherwise we would probably do something like what you do and pay a friend.


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