A Look Back on Our Travels for this Decade

It’s impossible to only highlight one moment for each year. But as the new decade approaches, we’ll look back on some of our travels that defined us this past 10 years.

2009 – Chase Freedom / Chase Preferred Travel Combo Earnings Introduction

Ah yes, when Preferred came out it was a game changer for us. We were immediately hooked in using the two cards to our advantage in optimizing points. Back then, Chase Freedom clients used to earn triple reward points back in any top 3 spending categories… even motorcycles. 

3x UR points on old Freedom card (even on motorcycles) back in the day!

After the earnings, we then used our Preferred card for our travels and made our first “mistake” execution with our points redemption — using the Ultimate Rewards booking portal to get a mere 25% bonus on an economy class ticket to Asia…. at least the Reserve card now gives you 50% bonus…

To this day, Miki & Paul still cringe in hindsight on spending over 200,000 UR points on two roundtrip eco tickets to Taiwan & Thailand. Nevertheless, they were still super happy and grateful to be in Asia for the first time for “FREE”.

Taiwan 2009
Thailand 2009

2010 –  Hello! I’m Chai Bear 

From 2007-2010, I used to work remote in a 100 square feet apartment in Philly. In 2010, Miki & Paul started to take me on their travels and I started to meet friends and finally see the world.

Hello world!

My favorite airline program used to be Southwest (anyone remember the fly four segments regardless of distance and get one segment anywhere free?) and American Airlines. Remember this logo back in the day?

American Airlines 2010

2011 – First International Business Class

Cathay Pacific has a special place in our travel hearts. To this day, we still remember our giddiness in flying Cathay Pacific Business Class for the very first time!

before 1st Business Class flight…

By the time we landed in Hong Kong, we pretty much felt like kings and queens. The expressions in the before/after pic of the flight cracks me up 😉

after Business Class flight

2012 – Start of W Taipei New Years tradition

Back in the good old SPG days, this hotel used to be only a category 4 hotel when it first opened in late 2011. From 2012 – today, we try to make it an effort to celebrate New Years in Taiwan at this hotel.

NYE 2011-2012
NYE 2018-2019

2013 – Miki & Paul Wedding

Since we love travel, we had our destination wedding in Bangkok, Thailand!

Miki & Paul wedding 2013

The whole trip spanned over 3 weeks — it was epic.

2014 – Canada Surprise

Would you rather have a gift that’s an experience or material? In 2014, we surprised Paul’s parents to a luxe trip to Vancouver, Canada! We stayed at the Fairmont Pacific Rim and Tony (Paul’s brother) pretended to dress up as a butler to surprise them.

Fairmont Pacific Rim

It was a very very fancy hotel.


2015 – Singapore Suite

The very first post of Chai Bear World… Singapore Suite Class!

Singapore Suites

And Paul’s reaction to us taking the most expensive nap in the world….


2016 – Cathay First Class Birthday Surprise

One of the most popular posts on Chai Bear World…. how Cathay Pacific went above and beyond in surprising Miki for her birthday in Cathay Pacific First Class!

Cathay Pacific First Class Surprise

2017 – Emirates First Class (Drunken) Fun 

There’s a special glitzy aura to Emirates. The airline is just so fun to fly. Just look at the bathroom where you can take a shower in the sky.

Yes… no shame in recording it 

is this real life?

The flight attendants makes the flight realllllly fun too.

Paul’s buzzed

2018 – ANA First, Chloe’s 1st Flight! 

This flight was very special… Chloe’s 1st flight with Japanese hospitality in ANA First Class. Look how small she was… pretty much the size of me!

ANA First Class to Asia

2019 – Singapore New Suite Class



Singapore New Suite Class

Overall, this was quite an eventful decade. There were so many more moments I wanted to share in this post, but it’s extremely hard to summarize 10 years of travel in one article!

Cheers to another decade of travel.

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