The former Wall Streeter-turned-"The Points Guy" travels the globe up to six months a year - and he does it for next to nothing, thanks to credit card rewards and frequent flyer miles. It all began in 2011, when he traded in his cubicle at Morgan Stanley to start his travel blog, The Points Guy.
Since, he's been around the world and back, from the streets of Havana, Cuba to the coast of Mykonos, Greece. We sorted through Kelly's Instagram to find some of the most awe-inspiring destinations he's visited.
Here's a glimpse into The Points Guy's full-time travel career:
Traveling the world can be exhausting, but with WiFi and plenty of leg room. Here's Kelly's business class setup on a JetBlue flight.
First class comes with its perks: Lufthansa Airlines served him champagne and caviar on a tablecloth during this trip.
On Kelly's $5.60 trip to Japan, he dined at the famous Robot Restaurant, where you get a 90-minute performance with your dinner.
From Tokyo, he took a two-hour trip on a high-speed bullet train that travels 200 mph to reach the heart of Kyoto, Japan.
Here's the beautiful Greek isle, Mykonos, 'where even the fish nets look pretty,' he writes on Instagram.
He found some stunning views in the Cape Winelands of South Africa.
And got up close and personal with the Parthenon on a tour of the Acropolis.
He went gorilla trekking in Rwanda, and tracked its famous — and rare — mountain gorillas.
And found some adorable monkeys in the Indonesian island of Bali.
Here's Istanbul, Turkey, where 'There's a photo opportunity everywhere you turn,' he writes.
He made it to the Mutianyu section of the iconic 5,500 mile long Great Wall of China.
And got a hot air balloon tour of Cappadocia, Turkey at sunrise. Here's his view from the clouds.
He stepped inside these caves in Guanayara park outside Trinidad, Cuba.
And made his way to Havana, Cuba, where 'the streets are an open museum for vintage cars.' Kelly hitched a ride in a 1957 Ford from Old Havana to Miramar (a 20 minute drive) for $20.
He spent 18 hours in Seoul, Korea on whirlwind trip. A $5,473.80 first class ticket with Singapore Airlines cost him just $203.30 thanks to rewards.
And said hello to the Eiffel Tower while strolling the Parisian streets.
It's hard to beat traveling the world, but the US has its moments — here's a shot from Kelly's trip to Maui, Hawaii.