Tokyo Japan

Tokyo Japan

I invite you to follow along as I show you how my wife and I navigated a wonderful week away in Tokyo Japan staying in four distinctly different areas within this immense city!

Picture this: you’re walking around New York City except there is nobody else there… that’s what it felt like for us between the hours of 5am – 7am. It was eerie yet spectacular.

Among other things, we took long walks, ate local cuisines (Ramen = amazzzzing), interacted with locals, tried to navigate the subways, walked some more, and slept…too much (jet lag is a real thing = 14hr time difference).

See details and photos from our entire trip below:

What we paid approx.
as a percent of retail

How we did it

We had a vision, implemented a strategy I created and mastered, and used specific tools to take action and go on a vacation that cost us roughly 8% of the retail price. The tools are outlined below, but the most significant tools are credit cards: Amex Delta Platinum, Citi Hilton Reserve, Chase Marriott Rewards, Chase IHG, Chase Ritz Carlton.

It took me nearly 31 years to see Asia with my own eyes! That’s too bad because there is so much to see and it doesn’t have to be complicated or expensive. In this chapter of traveling more for less, my wife and I rocked two round-trip airline tickets, six nights in 4-5 star accommodations, and lots of free food and drinks for just under $500.

Back when I booked everything, I took screenshots of the dollar price for everything we booked with points/miles/free hotel certificates/etc etc and added it up and the total retail price came out to be roughly $6,500.

In my trip report for our trip to Wailea Hawaii back in May, 2017, I really detailed out a 10-step process that takes you on a visual day dream of how we went “door-to-door,” quite literally, paying pennies on the dollar.

For this trip report, I’ll keep things a bit more high-level, so you might focus on the big ticket items and get an idea of how you can do this too. I’ll break the trip down by “flights,” “accommodations,” and “food & drink.”

As always, I start off with some of our favorite photos and video from our trip. Enjoy, and always remember to travel more for less.


  • Summary: We coordinated a $3,700 round-trip flight for 2 on Delta Airlines from Denver, CO – Tokyo Japan for a net $0.
  • **as long as you agree that the annual fees on these particular credit cards are offset by all the perks that come with them, not including the sign-up bonus. Or, if you don’t agree, ask me how to get the Ritz Carlton annual fee removed :).
  • Breakdown: We used 70,000 Delta miles + $50 each. We used Ben’s Chase Ritz Carlton Visa card to cover the $100 as we get $300 reimbursed annually in travel related expenses. We used Ben and Ali’s 70,000 miles sign up bonus on our American Express Delta Platinum cards to cover the cost of the plane tickets and bags.


  • Summary: We stayed 6 nights in Tokyo Japan at a total of 4 hotels and paid a total of $100. Total value for the accommodations + the executive lounges food/drink in the hotels = about $2,800.
  • Breakdown: 
    • Night 1: Hilton Odaiba = 20,000 Hilton points + $100. We received a free upgrade to a bay view with a balcony which was HUGE. The retail price for the room we stayed in on the night we stayed, was just over $400.
    • Nights 2+3: Intercontinental ANA = FREE, Ali and I each used our Chase Anniversary free night that accompanies the Chase IHG credit card. The retail price for a standard room for the two nights we stayed there was about $550. We received a 1-level room upgrade based on Platinum Elite status, which also accompanies the IHG credit card.
    • Nights 4+5: Conrad Hilton = FREE, we used the two free weekend nights at any Hilton worldwide that accompanies the Citi Hilton Reserve credit card (Citi no longer offers this card as of a few months ago). We received a free upgrade to a deluxe, bay view room. The retail price for the room we stayed in on the nights we stayed was about $700 per night before taxes and fees.
    • Night 6: Prince Sakura Tower Autograph Collection = we used 40,000 Marriott points that are easily attained after being approved for the Chase Marriott Rewards credit card. We were given an upgrade to a deluxe room based on our Gold elite benefits, which also accompany the Marriott Rewards credit card. The retail price for the room we stayed in on the date we stayed was about $250.
    • *Note – looking back, if I did it over, I would have used one of our Hyatt annual free nights instead of using 40,000 Marriott points for night #6. You can’t win ’em all!

Food& Drink

  • We had access to the executive lounges for four of the six days and nights that we were in Tokyo Japan. This is attained with Diamond status with Hilton and Gold elite benefits or above with Marriott. Talk to me about how to status match to Diamond status and how to instantly get Gold elite benefits.
  • Ali and I don’t drink, but if we did, and we took advantage of the value from all the free booze – you better believe I would have put the overall value of the trip much higher than $6,500. Let’s just say, if you choose to indulge, this is definitely the way to go.
  • We enjoyed our choice of breakfast and brunch restaurants, in fact, we ate breakfast at one restaurant around 6am, then lunch at another at 10:30am. Then, they served food and drinks for “tea time” and again for “cocktail hour.”
  • Bottom line – we had to go out of our way to make sure we tried all the local cuisines in Tokyo Japan because the hotels were more than generous with their free offerings.