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

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How to Travel Hack a $6,000 Vacation for Free

We do a fair amount of traveling. Travel costs were our second highest expense last year – at over $7,000, it was 18% of our $38k spending in 2016. This year, we mean to put a serious dent in those numbers through more extensive travel hacking. So far, we’re off to a good start. We booked a 9 day all-inclusive vacation to Jamaica – and we didn’t pay a dime for it.

A prior trip to Jamaica.

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Cheap Travel: Costa Rica After the Rain

I knew Costa Rica had changing seasons, but I didn’t realize the changes in the landscape would be so extreme. When we flew to Guanacaste, Costa Rica last March, I was surprised by how little green there was. Much like our Northeastern winters, most of the trees were bare, and the grasses were all dried up. But November is at the end of the wet season, and we arrived to lush green fields and forests.

Wet Season vs Dry Season in Costa Rica

Dry Season vs Wet Season in Guanacaste, Costa Rica

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Fighting the Fear Surfing In Costa Rica

The first morning in Costa Rica, I got up before Mrs. CK and grabbed my board to go catch the good surf. I had been anticipating this day for months and was full of excitement. I headed to the beach making my way down the narrow trail through the forest, watching the small lizards dart out of my path. As I got closer to the beach, I started to hear the roar of the waves. On a quiet morning with nobody in sight, the sound was deafening. It echoed deep in my gut, but I had my board in tow and there was no turning back – I was there to surf.


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You Won’t Expect What We Found: Bay of Fundy to Maine

We were thoroughly enjoying our stay on the lower part of Cape Breton Island. I could have stayed longer at our cottage on Bras d’Or Lake, but it was time to explore the Cabot Trail. So we packed up the Prius and hit the road again.


Eastern side of Cabot Trail

The Cabot Trail follows the coast around Cape Breton Highlands National Park. We knew we were getting close when we started to see mountains rise up against the Atlantic ocean. It was cold and rainy, but the rocky cliffs against the grey ocean made for epic views.

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It’s the Local Life for Me in Nova Scotia

Nova Scotia always sounded alluring – remote, cold, and untouched. It looks close on the map, but at 14 hours away from CT we couldn’t spare our precious vacation time to go explore during our working years. Now with unlimited vacation days, it was time to pack up the Prius and hit the road.

Driving Through Nova Scotia

Driving through Nova Scotia

We did minimal planning for this trip, only booking the first stay just across the border in Canada. We had no idea what we were in for and decided it would be best to get into Canada and ask the locals where to go. After randomly looking at towns just across the border, we found an Airbnb in St. Andrews. We knew nothing about the town, but at $44 USD a night, the price was right.

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Meet Lightning – Our $5,000 Prius


Ahhh, Lightning takes in the view

A few years ago, Mrs. Crazy Kicks was kicking ass and taking names as she climbed/ got pushed up the corporate ladder. She received several promotions within close proximity and was making bank. Many of her colleagues were into expensive cars – buying Porches and luxury Jeeps left and right. It seemed like something you needed to look professional at that level – just like you had to have fancy clothes to wear each day. While Mrs. Crazy Kicks did consider getting a new Audi or Tesla, she stayed true to the motto: “It’s not what you make, it’s what you keep.”

Mrs. Crazy Kicks decided to set a better example by getting an economical car that would look ridiculous next to the luxury vehicles bordering her assigned parking spot. Her mom wanted a new car, so Crazy Moms got a gently used Volvo, and we started the search for something practical. After considering a few options, we decided to target a Prius since they are fuel efficient, environmentally friendly, and great for road trips. The market wasn’t the greatest at the time – gas prices were still high, and we ended up looking for months. Continue reading

We Just Made $1000 Travel Hacking Our Vacation

Ever since I quit my job, new interesting opportunities seem to keep coming our way. It’s only been a month and I have had some really good luck sailingfishing, and going on a 2-week vacation to Colorado and New Mexico – all for free! On our vacation, we stayed in Colorado Springs, Taos NM, Pagosa Springs, Durango, Rico, Grand Junction, and Denver, and we actually ended up coming back $1000 richer than when we left. I am really not the best travel hacker, but the stars somehow aligned because with my best efforts, we were expecting the trip to cost us $1400.

Brazos Cliffs New Mexico

Brazos Cliffs, New Mexico

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