Steele Street: What’s On The Points Guy’s #BucketList?

Brian Kelly, AKA "The Points Guy," and his dog Miles.

Disclosure: Sponsored by Capital One. The opinions expressed herein are those of the author and are not indicative of the opinions or positions of Capital One.

Over the past few weeks, I have been sharing what’s on my travel #BucketList over at Wise Bread, here at Steele Street, and on my Twitter page @SteeleStreet.

Recently, I had a chance to catch up with Brian Kelly, The Points Guy, one of America’s premier experts on reward travel. Even though I have met him several times and have been a contributor to his site since early 2012, I have always wanted to know how he emerged to be a leader in the industry, and what is on his own travel #BucketList. Just back from his latest trip to South Africa, he agreed to answer all of my questions.

First thing everyone reading this will want to know is, what is on your travel #BucketList?

I'm going on a cruise to Antarctica this December and doing Australia in February, which will complete all 7 continents. I am looking forward to seeing Sydney, visiting the Great Barrier Reef, and enjoying the beach during their summer and our winter I also want to explore more of Africa- from hiking with the gorillas in Rwanda to safari in Tanzania.

Did you grow up in a family that travels frequently, or was it something you got into later?

I started using my dad's points from his business travel to book our family of six on a trip to Grand Cayman every winter since I was 12, but beyond that and some domestic travel, we weren't a huge international traveling family. I didn't go to Europe until I hopped on a $300 mistake fare to Ireland and from that point on I was hooked, with later that year studying abroad in Madrid, which is one of my favorite cities to this day.

Were you always into earning travel rewards, or was there a moment when you realized how valuable travel rewards could be?

I started young, but then forgot about them when I moved to NYC after college and was just focused on paying rent! Then I got a job at Morgan Stanley traveling extensively and I saw the points and elite status rack up quicker than ever before. It was during the Great Recession in 2008 - 2010, yet I was still taking trips to the Seychelles for fun and jetting around the globe, which prompted just about everyone I knew to always ask me how I did it. That’s when I started ThePointsGuy.com and it has been an exciting ride ever since!

Vrede Lust Vinyards

So is it your love for travel or traveling with rewards that led to the launch of The Points Guy Web Site?

I first started it to offer an award booking service at $50 a ticket, which quickly grew to something bigger than I could handle while still working a full-time job. In June 2010, I started blogging and decided to write at least one post every day- something most other bloggers weren't doing at the time. Nine months later, Seth Kugel of the New York Times Frugal Traveler got in touch and wrote a really glowing piece about my site and the entire points world. That was the day I resigned at Morgan Stanley and knew that I was onto something bigger.

Your followers know that you have visited some of the best destinations in the world and have had some amazing travel experiences getting there along the way. How much of your travel is about the journey and how much is about the destination?

It is always about the destination. If I could teleport, I would do that to avoid flying, though luckily my miles/points allow me to travel in relative comfort. That being said, a bed in first class still pales in comparison to my own King size bed, or that of a suite at my favorite Park Hyatt. So for me it is always about the destination and meeting new people and trying new foods.

These days I don't mileage run (take flights for the sake of accruing miles) because my time is valuable and there are so many other ways to rack up points a lot easier.

How many places have you checked off your #BucketList?

I've been lucky to travel quite a bit, but I'm only 30 and there are so many more places to see! I haven't really explored the Middle East or the South Pacific yet, so they are still on my list. But some of my favorite #BucketList trips I've done so far have been South Africa (Cape Town, wine country and Kruger safari- probably my best trip ever), Seychelles, Paris, Easter Island, Hawaii (highly recommend Kauai), Tokyo, Cambodia and more.

What do you recommend to consumers who want to book a #BucketList vacation? Can you offer some tips to readers looking to book a #BucketList trip?

Don't think that anything is impossible. Where there’s a will, there’s a way- especially if you have the right frequent flyer miles and credit cards!

How do rewards cards help you get to a #BucketList destination?

Rewards cards drastically reduce the out of pocket cost- especially if you're flying in business or first class where fares can get astronomical when flying internationally.

What are your favorite gadgets and smartphone apps that make travel easier and more rewarding?

I always travel with my QuietComfort 15 acoustic noise cancelling headphones and of course, my Apple iPhone 5.

You just wrote about Cape Town being your new favorite destination, what are three things everyone must see there if they are taking a #BucketList trip there, either as a single traveler or with family?

South Africa’s Wine country is a must. My favorite winery is Vrede en Lust. It has both great history and wine! I also went diving with sharks at Gansbaii. For families, the table mountain cable car and hike is a great option.