There’s something deeply moving about stepping into another culture. You start to see that joy, beauty, and connection live everywhere—just in different colors, flavors, and rhythms. Japan was exactly that for us. For 11 days, we wandered through neon-lit cities and quiet shrines, sipped cocktails high above the skyline, got lost in alleyways (more than once), and shared more laughs and bowls of ramen than we can count.
This trip was unforgettable. And even though it flew by, it gave us memories we’ll be carrying for a lifetime.
Day 1 – Touchdown in Tokyo
We flew out of ATL on a 14-hour flight to Japan, and after landing in Tokyo, we were picked up by an Uber car service that felt like a full-on limo and cruised to Shibuya Station and checked into the Shibuya Stream Hotel. That night, we ate at Wagyu Yakiniku Nikutarashi, indulging in eleven unforgettable courses. Every bite was buttery, smoky perfection. We had originally planned to head to Tableaux Lounge for live jazz, but after such a full day of travel and celebration, we turned in early—ready for rest and the adventures to come.
Day 2 – Rainy Streets, Street Food & Shibuya Crossing
We took the train to The Happy Pancake Shibuya to start our day—Tokyo’s rail system was beginning to feel more manageable! It was raining, so we made a quick stop at 7-Eleven for umbrellas before heading out. before braving Tokyo’s train system again—which, thanks to some colorful maps, we were finally getting the hang of. It was raining, so we made a quick stop at 7-Eleven for umbrellas and then shopped around UNIQLO (I picked up a few dresses, and Conner found a new sweatshirt). We saw Shibuya Crossing for the first time—a sea of people moving in every direction.
Later, Conner tried octopus balls from a street vendor (and loved them!), and we stumbled into シガーバー R261 CIGAR & ROCK, a local cigar bar before dinner at THE RIGOLETTO, an Italian restaurant. We had planned to go to SHIBUYA SKY, but it closed just five minutes before we arrived—rainy day problems!
Day 3 – teamLab, Arcades & Rooftop Drinks
After hotel breakfast, we shipped our luggage to Kyoto—and honestly, luggage transfer in Japan is a dream. It’s completely normal there, kind of like UPS for your suitcases. You just send it off the day before, and it magically arrives at your next hotel the next day. It meant we could explore all day without dragging our bags around, which made such a difference! and braved packed trains to get to teamLab. There was a bit of a mishap—we accidentally went to teamLab Planets when our tickets were actually for teamLab Borderless: MORI Building DIGITAL ART MUSEUM, but we eventually made it to the immersive art experience—and it was stunning. From there, we wandered through Akihabara, played arcade games, and even visited 隠れ家バー・カラオケバー Bar Mini Motto 秋葉原店, an underground bar where we were the bartender’s first customers.
We had a quick, silent, and delicious lunch at a hole-in-the-wall ramen shop before heading to a food hall at the Shin-Marunouchi Building with rooftop drinks and a view of Tokyo Station. In the evening, we visited the Imperial Palace (closed, but lovely to walk around), explored Nakameguro (adorable town vibes, roasted marshmallows at CABIN Nakameguro), and ventured into Shinjuku’s Golden Gai—a famous nightlife district made up of narrow alleys packed with tiny, quirky bars, each with its own unique theme and just a handful of seats—for some classic Tokyo bar hopping. Our feet were sore, so we called it a night with a drink at the hotel bar.
Day 4 – Bullet Trains, Temples & Gion Nights
We boarded a first-class Shinkansen to Kyoto (so fast and smooth!)—pro tip: book seats on the right side for the best mountain views. We also grabbed the famous bento boxes from the train station before boarding. Trains in Japan leave exactly on time, so don’t be even a minute late! And yes, we caught a glimpse of Mt. Fuji above the clouds. Once in Kyoto, we rented bikes and visited Kiyomizu-dera, a serene and historic temple. Riding through the narrow streets was a challenge, but beautiful.
We grabbed lunch at Yayoi Ken, it was our favorite quick food spot of the trip (we loved it so much, we had it twice!), explored downtown Kyoto, then checked into Sequence Kyoto Gojo. Gion district quickly became my favorite area for classy cocktail bars—we love beautiful atmospheres, and Gion delivered at every turn. That night, we bar-hopped through Gion—starting with ギオンプラネタリウムカフェアンドバーミソラキョウクウ, a space-themed bar, then Sui Cigar Bar, which was by far Conner’s favorite stop, and finally a cozy cocktail bar. We wrapped up the night with a stop at K36 (The Bar & Rooftop)—an iconic Kyoto rooftop. Typically, you need a reservation (and we recommend making one!), but we took our chances and they let us in for one perfect drink. Oh, and Conner found a mannequin dressed in Buffalo Bills gear holding a Pepsi—absolute perfection, considering he’s a huge Bills fan and practically runs on Diet Pepsi. Classic.
Day 5 – Nishiki Market, Shrines & a Rainy Night Walk
We slept in (no regrets), and Conner, being the sweet husband he is, had scheduled me a Japanese massage at 8 Elements Spa Kyoto—which honestly might have been the best massage of my entire life. while Conner grabbed coffee and wandered. Rain pushed us indoors, so we explored Nishiki Market, where Conner braved mystery meats and I stuck with steak and strawberries.
We visited Yasaka Shrine, bar-hopped through Pontocho Alley (we loved walking this vibrant street), and honored my dad’s tradition with a drink at the Hard Rock Cafe Kyoto—he’s traveled over 3 million miles in the air and collects Hard Rock pins wherever he goes, then had ramen for dinner. One of our favorite stops that night was BAR LIQUOR MUSEUM Osakenobijutsukan Yasakajinjamaeten, where we had the best time chatting with the bartenders. We ended the night with a long, rainy walk back to the hotel, laundry, and drinks nearby.
Day 6 – Bike Struggles & Fushimi Inari
After a lovely hotel breakfast, we made the bold decision to bike to two shrines based on advice from ChatGPT (which promised a flat route—lies). After struggling up hills and navigating busy streets, I crashed (minor scrape!) and we rerouted straight to Fushimi Inari Shrine. And it was absolutely breathtaking—pro tip: walk further back into the gates and you can capture some incredible photos without the crowds.
We hiked through thousands of red torii gates, grabbed street food (steak for me, crab for Conner), and cooled off with ice cream. By the end of the day, we had biked an unbelievable 20 miles. One of the highlights, though, was seeing Kyoto’s neighborhoods up close during our ride. We cruised alongside rivers, through quiet streets, and really got a sense of local life. After logging 20 miles on our bikes, we returned them, then headed back to the Gion district for a pre-dinner drink at ATLANTIS—one of our favorite cocktail spots of the trip. Then we did laundry and prepped for our final Kyoto evening
Day 7 – Hello, Osaka & the 40th Floor
We took the train to Osaka and dove into the shopping district. I headed to a traditional head spa at MOD Beauty Salon Osaka—such a unique and truly amazing experience—while Conner explored and made some local bar friends—they chatted using ChatGPT! We checked into Candeo Hotels Osaka The Tower and immediately extended our stay. Osaka completely stole my heart—it ended up being my favorite city of the trip! The vintage luxury shopping here was some of the best I’ve ever seen—I even left with a beautiful new wedding band from Cartier and was so happy with it. Our corner suite on the 23rd floor had us sold.
We ended the night with world-class cocktails at 40 Sky Bar & Lounge on the 40th floor, made by a bartender ranked #89 in all of Asia. The drinks were absolutely incredible, and the bartender even took the time to chat with us after preparing them—which made the whole experience even more special. Osaka had already stolen our hearts.
Day 8 – Universal Studios & a Street Food Finish
After getting hilariously lost in Osaka Station, ChatGPT helped us find the right train to Universal Studios. We soared through Hogwarts at Harry Potter World (Conner = Viktor Krum), and rode the park’s biggest coaster before deciding to leave early and skip our evening Super Mario entry. Honestly, neither of us are the biggest theme park people, so leaving early made perfect sense—and gave us the whole afternoon to enjoy Osaka in a different way.
Conner was also on a mission today: tracking down a very specific bottle of whisky called Gold & Gold. It belonged to his grandfather and has since been discontinued, making it incredibly hard to find. We turned the rest of the day into a full-blown treasure hunt, visiting probably 11 different liquor stores—but came up empty-handed.
Back in Osaka, Conner got a haircut (including pre-and post-washes—a first!), and we shopped, dressed up, and searched for dinner. Our hotel restaurant was closed, so we landed at Barbacoa Umeda (バルバッコア 梅田店)—incredible. We ended the night with wine and whiskey from 7-Eleven, jazz music, and skyline views. Oh, and McDonald’s—I was sad about the no ranch or ketchup, but it still hit the spot.
Day 9 – Castles, Bao Buns & a Whisky Miracle
We shipped our luggage to Tokyo, rented e-bikes (much easier than Kyoto), and rode to Osaka Castle. The grounds were peaceful and full of history. Then we wandered through Namba, snacked on bao buns, and headed to the Umeda Sky Building for unreal views.
We wrapped up our night with drinks and street views. Just outside one of the bars, we stumbled upon a random liquor shop—and there it was. A single armored bottle of Gold & Gold whisky. It felt like fate, and Conner couldn’t have been happier. We were ready to rest up for one more full day in Osaka.
The area near our hotel was dripping in luxury—Birkin bags, Chanel, Rolls-Royces, and private security every few feet. We ended the night with dinner at the most authentic Japanese restaurant of the trip—hidden in a basement, ordering off an iPad, surrounded by locals.
Day 10 – Suit Shopping, Skyline Dinners & Goodbye for Now
We took the Shinkansen back to Tokyo and hit the ground running in Ginza, checking into The Royal Park Canvas Ginza 8. Our mission? Find Conner a Japanese suit. After a marathon of fittings, we found the perfect one—and I might have done a little shopping too. One of my favorite stops was LE LABO Ginza Six Store where I picked up a gift for my mom. It’s a must-visit in Japan—really anywhere that lets you make your own personalized perfume scent.
Even crazier? Conner found another bottle of his grandpa’s rare whisky—one of the last four in Tokyo. We discovered it at M Whisky Shop Ginza / M Whisky Museum Ginza, located on the sixth floor—highly recommended for any whisky lovers. A cherry-on-top kind of moment.
That evening, we met our photographer @ippei.janine in Akihabara for a photoshoot before heading to Restaurant Luke with Sky Lounge on the 47th floor. The view? Incredible. Mt. Fuji in the distance, city lights glowing. The meal turned out to be a 7-course seafood tasting menu (surprise!), but the anniversary dessert they brought out totally made up for it.
We ended the night bar hopping, then grabbing Japanese fast food because… that seafood didn’t exactly fill us up.
Day 11 – Packing Up & One Last Adventure
Lastly packed up and headed out for some last-minute shopping at the iconic Don Quijote. We even bought an extra suitcase to carry all our treasures home—definitely a sign of a successful trip. After slurping down one last bowl of ramen, we made our way to the airport.
My Take on Each City
Tokyo is a true CITY—it never sleeps. The energy is electric, there’s so much to do, and so many people. You could get lost (in the best way) every day and never see the same thing twice.
Kyoto was Conner’s favorite. It’s full of rich history and traditions, with the feel of a charming small town. The shrines, temples, and peaceful streets give it a totally different vibe than Tokyo.
Osaka had my heart. It’s perfect for those who love shopping and modern city life—it feels like a more high-end, stylish version of Tokyo. We loved the vibe, the skyline views, and of course, the vintage luxury finds.
What We Learned & Travel Tips
This country is amazing—and we were blown away by how kind and helpful everyone was. Don’t be afraid of the language barrier; so many people speak English, and even if they don’t, technology bridges the gap beautifully. Our favorite apps were Payke (for understanding product labels) and Papago (a fantastic translation app).
Be sure to download your Suica Card to your Apple Wallet for quick train access—you don’t even need to open your phone, just hold it up to the scanner. And if you ever feel unsure, don’t hesitate to type your question into Google Translate or Papago and show it to someone. People are more than happy to help.
A few more tips:
Most people dress modestly, and I would recommend that. I wore a lot of long skirts and dresses. Conner wore pants the majority of the time—not only because we didn’t see many people in shorts, but also because he has a large leg tattoo we wanted to keep covered out of respect for the culture.
Be respectful: don’t talk on trains, carry your trash with you (very few public bins!), and avoid eating while walking.
Carry cash—especially for local markets and street food. Any 7-Eleven has an ATM.
Use the luggage transport service—it’s around $30 and totally worth the convenience. Most hotels offer this service right at the front desk, and if they don’t, they can usually point you to a nearby location that does.
Save your shopping for the end, especially if you’re doing luxury shopping. Check multiple stores and go in with something in mind or it can get overwhelming!
Wear comfortable shoes. We both wore our OnClouds the entire time and were so thankful.
And finally: know you can’t see everything. It’s a whole country. Be present, soak it all in, and enjoy every moment.
