Valentine's in Japan: Exploring Tokyo & Kyoto Together

Japan was another one of those places that lived on our bucket list for years. We heard that winter was one of the best times to go since it's less touristy and still manageable weather-wise, so when we saw decently priced tickets, we booked it.

The Breakdown

Destination: Japan (Tokyo & Kyoto)
Trip Length: 9 nights
Trip Timeframe: Early February
Total Spend: $1,562.02 | ¥51,780
Booking Platforms:
- Flight: United Airlines & Japan Airlines
- Stay: Hilton
- Public Transportation: Suica Card & Shinkansen
First-Time Traveler Score: ★★★★★

First Impressions

Tokyo was bumpin' all day and night. We'd heard that winter would be less touristy, but there were still a lot of people everywhere, especially in Tokyo and at the shrines in Kyoto. We're usually in bed by or before 10 PM when we travel, but in Japan, we didn't get back until after midnight most nights. The energy just keeps going. If this was considered off season, we can only imagine what peak season looks like.

One thing that really stood out was how clean everything was. The streets were spotless, even in the busiest areas and we rarely saw any public trash. It was surprising considering how many people of all ages were out at all hours. We later learned that part of the reason you don't see public trash cans is due to security changes years ago, which means people carry their trash with them. It definitely contributes to how clean everything feels.

We also noticed how many Korean visitors were traveling in Japan as well as the Korean signage. It was interesting and comforting since it provided familiarity.

Despite the crowds and the cold, everything felt incredibly efficient. The train system was easier than we expected, and one thing we immediately noticed when we rode the train was how quiet everyone was. No loud conversations, no chaos. We quickly learned not to put your belongings on the seat next to you unless you want some disapproving looks. Hold it in your lap!

Our Stay

In Tokyo, we stayed at Conrad Tokyo, which was easily one of the best hotel experiences we've had.

Because we have Hilton Diamond status, we were upgraded to a King Suite on the 36th floor, just below the executive floor. The full bay view was unreal. Waking up to that skyline every morning was truly an experience.

The room details were also so memorable. The hotel provided the softest pajamas, a special Conrad Bear and Byredo Mojave Ghost amenities. Compared to how luxurious our stay was, the executive lounge breakfast was below our expectations with the variety of food options, but the views were amazing and it was very convenient since we saw there was always a long wait for the main breakfast buffet.

Our Tokyo stay was booked with points, totaling 130,000 Hilton Points+ 2 Free Night Rewards.

In Kyoto, we stayed at Hilton Garden Inn Kyoto Shijo Karasuma. We liked the location and the overall aesthetic, but unfortunately our room had a noticeable body odor-like smell that was hard to ignore. It was definitely not the same experience as our stay at the Conrad Tokyo.

Our Kyoto stay was booked with points, totaling 71,000 Hilton Points.

Activities

Our itinerary was structured city by city, with a mix of major sights, guided tours and built-in rest time.

Day 1: Arrival in Tokyo

After landing, we checked into Conrad Tokyo and immediately went shopping realizing we were underprepared for the weather. We went to ABC Mart to find a pair of women’s long boots but quickly learned how small the boots ran. That plan died quickly... Afterwards, we went to Uniqlo and bought a handful of things, including coats because it was much colder than we expected.

We ended the night at Ichiran Shimbashi. We got there around 9:30 PM but didn't eat until almost 10:45 PM. The food was good, but the experience was underhwhelming compared to our NYC Ichiran experience. Much to our dismay, there were no matcha beer or dessert options.

Day 2: Sightseeing in Tokyo

The second day, we started with breakfast at the executive lounge, which was fine but not amazing. Then, we went to the Imperial Palace, only to learn that you can't freely tour it without a guided reservation. Oops! We didn’t catch that in our research beforehand. We walked through the East Gardens instead, but since it was early February, most of the plants were dead. The bonsai trees were our favorite.

We didn't spend too much time at the palace or gardens and went straight to lunch. Let us tell you... we waited over 1.5 HOURS in the snow for Tsujihan in Nihonbashi. It was so cold and brutal, but what was so funny was how many Korean people were in line. It was almost as if we were all following the same Korean influencer who suggested this place. The food was very good, but we would never wait that long again especially in those weather conditions.

After lunch, we shopped in Omotesando, bought matching Onitsuka Tiger shoes and had our hair appointments at Canaan Omotesando, which was one of the best decisions of the trip. We used Google Translate most of the time, but the hair stylists were patient and so detailed. Women’s cut, color and treatment came out to be 22,000 yen and men’s scalp treatment and haircut was 15,000 yen. Our hair looked and felt so good.

Dinner ended up being at the Miyashita Park food hall after skipping another long wait elsewhere. It wasn't amazing, but the energy was fun and we chatted with a couple of other travelers next to us.

And last but not least, we finished the night with shopping at Mega Don Quijote. We kid you not, we still have their jingle stuck in our heads.

Day 3: More Sightseeing in Tokyo

Our third day seemed to work out better for us in terms of sightseeing and dining. We visited Meiji Shrine first thing in the morning and made a prayer but Yoyogi Park was closed due to weather. We headed to Shinjuku early, did some more shopping and ate lunch at Standing Sushi Bar, which was one of our favorite meals of the entire Tokyo stay. This time, we were one of the first in line at opening, at about 25 pieces each and only spent 9,010 yen total.

Afterwards, we visited the Tokyo National Museum, which was a bit underwhelming. We personally love museums, and was expecting to see and learn a lot, but we barely took two hours to see everything.

Dinner, however, redeemed the day. We went to Kuroge Wagyu Ichinoya Asakusa and got one of the last available spots before a line formed. The wagyu was served three ways and was incredibly tender.

Day 4: Even More Sightseeing in Tokyo

We started with a light breakfast and headed to the Tsukiji Outer Market instead of Toyosu. It was chaotic int he best way. We tried so many different types of food: shrimp tempera, rice cakes with soy sauce, buttered scallops, unagi on a stick, strawberry daifuku and fresh oysters. Our only regret was eating breakfast beforehand because we were too full to try even more.

After the market, we went back to Conrad Tokyo to enjoy a Valentine's Afternoon Tea, which doubled as an early birthday celebration. It was so pretty and very sweet. We spent a couple hours enjoying the pastries and tea before heading out to check out TeamLab Borderless. We loved how immersive and visually impressive it was.

The last highlight of the night was getting our lymphatic drainage massages at Facia Ginza. We received a facial massage and full body massage. It was really intense and painful but effective. We could feel and see noticeable differences especially in the face in pictures throughout the rest of the trip.

For dinner, we ended the night at Ginza Soba, which was tucked away downstairs and had a very peaceful atmosphere.

Day 5: Headed to Kyoto

We took our first Shinkansen to Kyoto. The ride was bumpier than expected and we forgot Dramamine, so felt pretty nauseous most of the 2+ hour ride.

Kyoto felt quieter immediately. We checked into the hotel, then had an omakase dinner at Kyoto Shijokawaramachi Kakida. It was kind of awkward at first since we were the only ones at the 6 PM reservation, but gradually eased up as more people came to dine. It was an interesting experience since it was marketed as an all you can eat omakase. We learned you can reorder your favorites after the initial set of 15, but only one time. We ordered about 5 extra each since we were already full after the set. Chef Masaki was really fun despite the language barrier and made the experience memorable.

Day 6: Photoshoot & Tea Ceremony

Of course, we booked another photoshoot. We started the day with a 7:30 AM photoshoot at Ninenzaka. It was raining all morning, so the shoot didn't go exactly as anticipated, but we still had a lot of fun.

After, we did a kimono tea ceremony at Maikoya Nishiki. They provided kimonos and also styled your hair for the ladies. It was educational and beautiful, though we returned the kimono early because it was freezing.

For lunch, we went to the Nishiki Market. It had more stores than expected despite midweek closures. We got to try more here than we did in Tokyo and both agreed that dining at markets is one of our favorite experiences while traveling. We also bought two prescription glasses made in under an hour, which still baffles us because you can't get that type of service in America.

Dinner was at Korean BBQ Vegetejiya Shijo-karasuma. We always crave Korean when we travel so thought we'd check this place out. As much as we wanted to enjoy it, it didn't taste Korean at all. Only the concept felt Korean. The only part we truly enjoyed was the all you can drink because the makgeolli was really good. We'll admit, we had a bit too much fun and drank more than we should knowing that we had a full day tour the next day.

Day 7: Full Day Kyoto Tour

We woke up slightly hungover, got a light breakfast and went out to meet our Viator Tour Guide for 10 Must-see Spots in Kyoto One Day Private Tour. If we haven't already shared, we love booking our Viator tours, especially for these long tours so we can maximize on the sightseeing!

Chihiro, our tour guide was so friendly and just wonderful to spend the day with. All the places we visited:

Kinkakuji Temple
Bamboo Forest
Tenryu-ji Temple
Togetsukyo Bridge
Arashiyama Kimono Forest
Fushimi Inari-taisha Shrine
Kiyomizu-dera Temple
Sannenzaka Ninenzaka
Yasakanoto
Gion

Our feet were definitely hurting after this, but soo worth it. We were supposed to end the day with dinner at Hikiniku To Come but it didn't work out because you needed a reservation, which was another planning fail on our end. If you didn't reserve online, you could also reserve in person starting at 9 AM the day-of, but since we didn't know we decided to go back to the hotel and order in.

We were actually craving something familiar, so ordered wagyu burgers and fries from Shogun Burger Gion-Shijo. It was honestly so good and the best decision especially after a tiring day.

Day 9: Return Home

Our last day was all travel. We flew from Osaka (ITM) to Haneda (HND) and then from HND back home.

Dining

Tokyo

Kyoto

For this trip, we had a mix of planned reservations and flexible meals. We bookmarked a handful of places ahead of time, but we stayed open to changing plans depending on wait times and how we were feeling.

One thing we learned quickly is that you don't need to chase only the viral or social media hyped spots in Japan. Some of our best meals were the ones we walked into without much planning. Even smaller, local places delivered incredibly fresh and well-prepared food. Also, there aren't a lot of advance reservation options so it makes it harder to plan if you're expected to wait long hours for meals.

Japan made it clear that quality is consistent everywhere, so if a place looks good and has locals inside, it's probably going to be good.

Things We Learned (So You Don't Have To)

Order currency through your local bank before your trip - This might be common knowledge, but we didn't know this was an option and always exchanged during our travel. For Japan, we ordered at our local bank prior to the trip and found the exchange rates were much more reasonable and was one less thing to worry about once we landed.
Add your Suica card to Apple Wallet before you go - You can set up your transit card directly in your phone and reload it instantly with Apple Pay, which made using trains and buses seamless. We didn't have to worry about buying physical tickets or finding machines every time we traveled.