Member Success Story: How Austin Saved $18,000 on His Dream Honeymoon to Japan
When Austin and his wife finally took their delayed honeymoon to Japan, they wanted it to be unforgettable — and thanks to smart points and miles strategies, it was. From Tokyo to Kyoto, Hakone to Osaka, they experienced luxury hotels, private onsens, and business class flights, all while saving nearly $18,000. Their story shows how a little planning and the right tools can turn a dream trip into reality.
Tell Us About Yourself
Hi! I’m Austin, and I live in Denver with my wife. I’ve always been savvy with credit cards and points, but about 3 years ago I became dedicated to the idea of free travel through points and miles. After learning I could’ve gotten 3–5x more value out of my Chase Ultimate Rewards® points on a Paris trip by using transfer partners, I dove headfirst into optimizing. Since then, I’ve embraced the Player 1 + Player 2 strategy (see this article for more information), growing our points stash and traveling like a true points savant!
Tell Us About Your Trip
We took a delayed honeymoon to Japan, aligning with my wife’s school holiday schedule. Over 2 weeks, we visited Tokyo, Hakone, Kyoto, Nara, and Osaka. We spent 4 nights in Tokyo, 2 at a boutique luxury ryokan in Hakone, 3 in Kyoto, 2 in Osaka, and wrapped up with 2 nights at the Andaz Tokyo.
We love immersing ourselves in the lifestyle and culture wherever we go — so we mastered Japan’s public transit, ate at hidden local spots, took a few half-day tours, and soaked up the safety, respect, and vivid nightlife that make Japan so special.
What Kind of Points Did You Use for This Trip?
We booked our flights using a mix of transferable points from several programs and relied heavily on PointsYeah alerts to catch business and premium class availability on our preferred departure dates.
Flights:
The best redemption to Japan for the dates we wanted was a direct flight from San Diego, which meant booking a positioning flight from Denver to San Diego. To avoid any travel hiccups, I used both Southwest and United miles to book 3 fully refundable positioning award flights (one the night before our flight to Japan and 2 the morning of). That foresight paid off—storms canceled our Southwest flight the night before, and our backup United flight the day of was delayed due to technical issues. Luckily, we pivoted to the Southwest flight the morning of, which cost only 7,500 points + $11.20 since my wife has a Southwest Companion Pass.
To get to Japan, we flew business class on Japan Airlines (JAL) from San Diego (SAN) to Tokyo (NRT). Our business flights were made possible by American Express Membership Rewards® transfers to Alaska Airlines via Hawaiian Airlines. (Note: this points transfer route is no longer available). Our business class seats were 60K miles per seat using Alaska miles (120K total), so we combined the Amex MR points with the points earned using a recently opened Barclays Hawaiian Airlines MasterCard.
For our return home, we flew premium economy direct from Japan (NRT) to Denver (DEN) for a total of 65K United miles using points from my wife’s Bilt Rewards Mastercard by Wells Fargo transferred to United airlines.
Hotels:
We used Chase Ultimate Rewards transferred to World of Hyatt® for 3 different hotels during our stay. For more unique hotel stays, we used Chase points for bookings within the Chase Travel℠ portal and Capital One Miles in the Capital One Travel portal.
- 4 night stay at Shinjuku Prince Hotel for 89K Capital One Miles in the Capital One Travel portal
- 2 night stay at Ryokan Hakone Gora Karuku for 154K Chase Ultimate Rewards points in the Chase Travel portal
- 3 night stay at Hyatt Regency Kyoto for 87K World of Hyatt points
- 2 night stay at Hyatt Caption Osaka for 19K World of Hyatt points
- 2 night stay at Hyatt Andaz Tokyo for 80K World of Hyatt points
How Much Money Did You Save Using Points and Miles for Your Trip?
We estimate we saved around $18,000 on this trip, which included:
- 2 business class flights.
- 2 premium economy flights
- 2 nights at the Andaz Tokyo (Hyatt)
- 4 nights of hotel stays via Capital One Travel portal
- 7 nights at other Hyatt properties
Since this trip was to celebrate our honeymoon, my wife and I took the last couple of years accumulating points from various cards. For example, we each applied and were approved for the Chase Sapphire Preferred® Card, and our side hustles made us eligible for Chase Ink Business cards. We also made sure we had access to other flexible point programs like Capital One and Amex for additional transfer partner options.
What Were Some of the Highlights of Your Trip?
One of the most memorable moments was checking into our boutique luxury ryokan in Hakone — Karaku, Gora. The experience was next-level: an immaculate lobby, a guest lounge stocked with sake, whiskies, snacks, and more, and our room was huge and luxurious with panoramic forest views and a private balcony onsen.
It blew my mind knowing we paid just $34.01 TOTAL for the 2-night stay thanks to points. Seeing my wife’s jaw drop over and over made it all worth it.
Other highlights included:
- Staying at the beautiful Andaz Tokyo
- Booking private onsens since my wife couldn’t use the public ones due to her tattoos
- Wandering hidden alleys and discovering local restaurants
- Experiencing Japan’s vibrant nightlife and unmatched hospitality
I cannot emphasize this enough — if you plan to travel to Japan, definitely experience Japan’s transit like a local — ride the subway, hop on a bullet train, and use tools like ChatGPT to plan ahead. We found the Suica card in our iPhone wallet made navigating Tokyo’s public transportation simple and convenient.
What Advice Do You Have for Someone Just Starting with Points and Miles?
Have faith in the process! At first, managing all the cards felt intimidating, but staying disciplined and tracking everything with the Travel Freely app made it easy.
Once you have a redemption in mind, don’t hesitate — use the points! The experiences you’ll unlock are truly priceless. Even when we couldn’t use transfer partners for everything, we still used the Chase and Capital One portals and didn’t regret it at all.
How Has Travel Freely Helped You Achieve Your Free Travel Goals, and What Do You Like Best About the App?
The Travel Freely mentor program has been a godsend — shout-out to Shawn for the expertise and guidance (Note: this service is no longer accepting new mentors). The app itself is amazing for card management, especially the alerts about annual fees and clear summaries of whether to cancel, downgrade, or keep a card.
It helped us stay organized, confident, and on track throughout the whole process.
Final Thoughts
This trip was everything we dreamed of for our honeymoon — full of beauty, culture, luxury, and unforgettable experiences — all without the stress of huge bills. From private onsens and luxury hotels to business class flights and late-night ramen, it was magical.
I’m so grateful for the tools, strategy, and support that made this possible. With the right cards and a little planning, anyone can make free travel a reality.
Cards that helped Austin and his wife experience their dream vacation:
Our #1 recommended personal card. Hands down the single best “starter card” for beginners and the MVP card for free travel. Note: New application rules as of June 2025 may affect your eligibility—click to learn more before applying.
Great "ultra-premium" card. Despite the big annual fee, the overall first year value is worth it for most people. This is due to the large signup bonus, extra benefits like Priority Pass, up to $300 annual travel credit and Global Entry/TSA PreCheck credit.
One of the very best business cards. A highly recommended business card for an incredible signup bonus and 3X categories.
A no-brainer, great business card. Your choice to receive 1.5% cash back or 1.5x points.
Great signup bonus for a business card with no annual fee, now with an extended timeline for hitting the spend requirement. Great for carrying a balance. 5x earning categories, and if paired with a premier Chase credit card (one that carries an annual fee), your points are worth even more.
