My AWESOME Vacation for 2014 (How I Booked It)


I will be taking an extended vacation around the world in August. To fund the trip, I made use of my travel hacking points. Through three credit cards: Chase Sapphire (40,000 bonus points), Chase Bold (50,000 bonus points) and the Chase United Explorer (55,000 bonus points), I was able to merge points together, and fund this 130,000 point round-the-world excursion. The Sapphire and Bold Ultimate Reward points were converted to United points.

Round-Trip Flight to Japan

Because the points were used to purchase seats in business class (not cheap!), naturally, you would want to extend your trip so that you could fly as many times as possible, and travel as many miles as possible.

To illustrate, let’s suppose that I only wanted to travel round trip from San Jose, CA to Tokyo, Japan on business class.

Using the United points chart below for business class, I could purchase a round trip flight for 120,000 points (60,000 points each way).


In total, the round trip flight to Tokyo and back home would cover 10,308 miles. For 120,000 points, this is still a pretty good deal because a business seat to Tokyo from San Jose probably costs around $4000, each way.

SJC to NRT and back:


Round-the-World Modification

However, thanks to certain perks in place, individual airlines allow travelers a certain degree of freedom. As it pertains to United Airlines, a passenger is allowed (2) open jaws, (1) stopover and segmented 24-hour layovers. This allows you to create flexibility in your flights, and the potential to travel more destinations. The best part, you can do all this and not have to spend any more points than your original flight.

By working within the guidelines, I was able to piece together a more elaborate trip, covering more destinations and miles. My trip in August is detailed below:

First Flight: San Jose, CA to Tokyo, Japan (Business on ANA All Nippon Airways)

Second Flight: Bangkok, Thailand to Frankfurt, Germany (First Class on Thai Airways); layover/connecting to Rome, Italy (Business on Lufthansa)

Third Flight: Rome, Italy to Toronto, ON Canada (Business on Air Canada)

Fourth Flight: Toronto, ON Canada to San Francisco, CA (Business on Air Canada)

Round-the-World Trip:


First Open Jaw

An open jaw is a break in the itinerary, when you depart from a different city than the one you first arrived in. My first open jaw occurs after I land from San Jose to Tokyo. The open jaw is created due to the fact that my departure flight back home is now from Bangkok, and not Tokyo. To get to Bangkok, I have to find my own means… The open jaw can be for as long as I want. In this case, I’ll be in Thailand for about a week.


From Bangkok, through the use of the first open jaw, I am able to resume my flight back home, first passing through to Rome, Italy. Technically, I will first be landing in Frankfurt, Germany, but I don’t plan on doing anything there. Going to Frankfurt will be a short layover since it is only needed to connect me to Rome, which is my stopover destination. I connected in Frankfurt because there were no direct flights from Bangkok to Rome that fit my needs/schedule.

Rome is where I will use my first stopover. United allows one stopover, which is simply when you stop at a destination for longer than 24 hours before resuming your flight to its final destination. I will use this stopover to vacation for one week in Rome.


On the way back home, I will fly from Rome to Toronto, ON Canada. This is where I will use a layover, which allows for a stay in a city for less than 24 hours, before you have to resume your flight. I will travel in Toronto for one day (pushing the layover as close as possible to 24 hours), and visit Niagara Falls. The very next day, it’s back on the plane to get home.

Second Open Jaw

From Toronto, the final flight will take me to San Francisco. Because I will be landing back home at a different airport (city) than where I departed from, this again creates the second open jaw in the flight plan. For my trip, it is simply more convenient to fly back to the Bay Area via San Francisco than San Jose.


By making use of open jaws, stopovers, and layovers, I am able to extend my trip for the same amount of points. Even though I will be taking four distinct flights, they won’t cost me anything more. They are all considered a part of the original round-trip itinerary (San Jose to Tokyo and back home). The best part? Because the original round-trip flight was booked on business, I am able to get a business seat on each of the flights. Score!

For this trip, the total miles traveled will span 18,023 miles. This is almost double that from the original example, which is what I mean about getting more bang for your buck (points).

So, why is my round-the-world trip 130,000 points instead of 120,000 points? On the leg home (Thailand to Frankfurt), I decided to upgrade to First Class (Thai Airways), which costs an extra 10,000 points. 😉

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Fast Weekly
6 years ago

Quite incredible FI. You literally can say you’ve “been around the world”, when this trip is over. Not many people have!

FI Pilgrim
6 years ago

That’s very cool! I’ve GOT to look into travel hacking a bit more, it seem incredible to me that you can put that trip together based only on points.

Michelle @fitisthenewpoor

This is insane. I am in awe of this. I am totally new to the idea of travel hacking, but by the looks of it, you are far and away rocking it.

Done by Forty
6 years ago

Great trip! We’re trying to do something similar for our trip to Europe this year and have the hotels covered, but don’t think we’ll have enough time to churn cards for flights. There’s always next year though!

The First Million is the Hardest

Wow, thats pretty badass. Sound’s like an amazing trip!

6 years ago

Wow that’s a ton of points! I am holding onto my Chase Freedom points since they’re actually Chase Ultimate Rewards points that can be transferred to airlines if I want. I’m going to investigate if that’ll be more valuable than using them directly. Also, doing the Chase Sapphire Preferred for a year to collect more points might not be a terrible idea!

6 years ago

That’s freaking awesome bro, I’m jealous. I look forward to the photos and stories from your travels.


[…] As it pertains to yen or euros? Darn, I only wish I had booked vacations to Japan and Italy NOW instead of in late 2014!!! […]