14 Nights in Japan on Points: Final Thoughts, Mistakes, and Favorite Moments
This is Part 5 of 5 in our 14-night Japan trip on points.
In this final part: Our biggest surprises, favorite experiences, and the travel lessons we’ll carry into every future Japan trip.
Quick Hits - What We Loved Most
Best hotel experience: Osaka Station Hotel for the unexpected hospitality and amenity upgrades. Immediate access to Osaka Station was crucial for our city-hopping.
Best meal: Kaiten Sushi Ginza Onodera Kyoto - We eat here repeatedly, but our friends absolutely loved the ease of ordering and being able to choose everything you want to try.
This is important: So many people search Google or Reddit for the “best omakase experience.” But the reality is that with omakase, you give up a lot of control - some bites may completely blow you away, while others might just be okay or straight up weird.
We enjoyed both kaiseki and omakase with our friends, but especially for first-time visitors to Japan, I actually think a slightly high-end conveyor-belt sushi restaurant may be a better introduction. You can order exactly what you want, learn what you enjoy, and avoid feeling pressured to eat unfamiliar dishes you may not love. It also makes it easier to recognize and order those same types of sushi later in the trip.
Most memorable moment: I keep coming back to this, but it had to be the lounge at the Osaka Station Hotel. Unparalleled.
The “Oh yeah, I planned this trip perfectly” moment: Our award hotel stays were phenomenal. It gave us great access, amenities, breakfasts, and hospitality, making it easy to find everything we wanted and needed. And, it saved us cash!
Brian and Whitney bonded with an especially thoughtful concierge at the Conrad Tokyo, Peter, who helped them locate various things, facilitated restaurant reservations, and even arranged an emergency acupuncture appointment.
The biggest surprise I felt with our friends: They were absolutely crushed by jet lag. It was like watching your favorite athlete suddenly underperform and sputter out of energy - agonizing to witness from our normally bionic friends.
For a good time, they can push through almost anything. But multiple times, Whitney had to duck out early and miss bar-hopping - something normally unthinkable for her. And this was well into the trip, nearly six days in!
Biggest personal surprise: I was secretly against the idea of a matcha farm tour because I assumed it would be quite touristy and overpriced. It was a bit pricey, and I was the only Japanese person on the tour - but I ended up learning so much about sustainable farming, Japanese culture, and what it actually takes to start a matcha business.
Did D-Matcha have the best matcha we tried? Nope. But the tour sparked our obsession with matcha for the rest of the trip, and we tried it everywhere we went. Very thankful to Whitney for this one. Since returning home, this has been our biggest Japan-ritual we’ve kept up, even replacing our daily espresso with matcha. (Brian still thinks matcha tastes like grass - well, it is, so he’s not wrong. At least he tried everything, right?)
Cities We Didn’t Fully Cover (but loved)
Kurashiki, Okayama - We were pleasantly surprised that this was everyone’s favorite city! We have some mutual Boston friends who live there, and it was nice to travel with a true local, not just someone who looks Japanese (me). The city is a mixture of tradition and hipster - yes, an odd combo - but it makes for a very intriguing place to explore: jeans shopping, a beer garden with live music in Ivy Square, traditional food and drinks, strawberry matchas, beautiful glasswork, and age-old pottery known as bizen-yaki.
Sendai, Miyagi - This is our family time. We exchange souvenirs, and my older brother and his family often take us to their favorite shops and restaurants. It’s stress-free in that I have zero planning to worry about - a huge perk of visiting family or friends who know the local area inside and out. But even if you’re just visiting, it’s a great city to explore, with plenty of shopping, touring, and dining options to keep you busy for days.
We have yet to visit the Matsushima Bay, which is among the top three most beautiful scenes in Japan, Nihon Sankei, but we plan to do so on our next visit. A friend of ours tried a boat tour and remarked that it was the most stunning place she had ever visited, a place with an almost otherworldly feel.
Kobe, Hyogo - What’s not to love about Kobe? The people are open and kind, the food is amazing, there’s natural beauty everywhere, and there’s even hot springs!
One mini-story: Our friends really wanted an authentic Japanese experience, so we went to a local (but large) facility with indoor and outdoor hot springs. It was an amazing time, but we were literally the only tourists there. On the men’s side, everyone was polite and no one was staring at my 6’4” friend. On the women’s side, Whitney “abandoned” Cory and did her own exploring, which left Cory alone surrounded by Japanese women who kept saying, mezurashii, or wow, how unusual (for a foreigner to be there). Cory understands a decent amount of Japanese, so she turned even redder and did not know when to get out of the tub. Whilst she cooked in her tub, Brian and I were having a grand time hopping around the different outdoor hot springs and enjoying the 200F sauna and cold plunging.
The only lesson from this adventure was to plan transportation more carefully. After leaving the hot spring around 8:45 PM, we realized we could not find any taxis. We were only about 20 minutes from Kobe Station, but the nearest bus stop itself was a long walk away in the cold.
As we waited for a taxi app to accept our ride request, we slowly started to realize we might actually have to walk. Thankfully, after what felt like forever, a driver finally accepted the trip. He explained that tourists rarely visit the area we were in, and that we were lucky he happened to be dropping someone off nearby.
Lesson learned: don’t assume a taxi app will always save you in quieter local areas. On a map, the distance looked manageable, but in reality, we were fairly isolated with limited transportation options. After a relaxing evening in the hot springs, the idea of trekking through the cold at night would have completely killed the mood.
Osaka - Arguably the best shopping experience we had on this trip. We found more desirable and reasonably priced knives and souvenirs on Osaka’s kitchen street than in Tokyo’s (Asakusa area). We also stumbled upon gems like Ichiro’s Malt at list price - only 8,800 yen - whereas shops in Kyoto quoted us over 14,000 yen, if they even had it in stock.
Interestingly, luxury hotel cash rates in Osaka are noticeably cheaper than Tokyo, despite offering a very similar level of experience. In some cases, the hotels and rooms even felt newer and more modern. Staying at luxury brands like Waldorf Astoria or Four Seasons can realistically cost around $450+ per night in Osaka, while similar stays in Tokyo often climb well past $1,000 nightly.
What We’d Do Differently
Not plan dinners for the first week.
Book flights earlier (8-11 months out, not 3 months) - with award flights being more competitive than ever, we wish we had booked our friend’s flights earlier. Cory and I had a fairly comfortable plan but that’s because we had booked it 9 months out.
Not book business class just because - when I saw JAL business class seats from Osaka to Narita to San Francisco for 75k Alaska Air miles, I jumped on it. But the reality was a kind of rushed flight, a poor experience staying in San Francisco, and a seemingly long and tiring flight back to Boston in economy. Maybe we should have just booked a direct flight back home in economy or premium and called it a day.
The Japan Airbnb myth - I see from time to time that Japanese Airbnb’s have to abide by more rules and regulations so they are blah blah blah - But it’s not all that. We enjoyed the location of our Airbnb in an area of Kyoto we had never stayed in before, but was it worth $800 per family for three nights? Meh. It was a fun experience, but I would think that next time we will just stay in hotels and take advantage of their services, hospitality, and perks.
What We’d Do Every Time
-Plan five night stays in award hotels with free breakfast!
-Sauna amenity for the win! Truly the best way to detox after a long day, or to kick start a morning
-Plan just 1 or 2 things each day and leave the rest to exploring and spontaneity
-Fly direct and bring tons of snacks and goodies to last the flight
-Try at least one thing that is outside of my comfort zone (matcha tour)
-Plan one area that is not a major city/ touristy
-Load up digital IC cards for easy transit
-Bring enough luggage or do luggage shopping in Japan (Larger LOFT stores have reasonably priced options)
Final Reflection
Looking back, this trip had a little bit of everything: plenty of sweet moments together, a little bitter jet lag, some salty drama, flashes of heat from everyone’s hangry moments, and a whole lot of umami - the kind of unforgettable memories that linger long after the trip ends.
Despite some initial hiccups with our friends’ jet lag, it became one of our favorite Japan trips ever. They pushed us out of our comfort zone and encouraged us to try new things, while we got to introduce them to a country we obsess over - and their reactions absolutely did not disappoint.
The points-and-miles planning added an extra layer of magic and helped turn the trip into a true “once-in-a-lifetime” experience for our friends. But as sweet as this trip was, they’re already planning to return - because another Japan trip can still feel once in a lifetime when it’s done right.
Our next “solo” trip - just Cory and me - is coming up in September and is loaded with points-and-miles redemptions. It’ll be interesting to see whether we can ever recreate the same discoveries, laughter, and feeling of rediscovering Japan all over again.
