Itinerary: Two Weeks in Japan

What you need to know upfront:

  • Get the JR pass if traveling between Tokyo/Kyoto but be mindful of when you activate it and try to plan on getting the cheapest/shortest pass that will suit your itinerary. You wont need JR pass when in Tokyo itself, so don't activate it until you leave. Of note, this has to be done a few days in advance to allow for shipping to your address in the US. 
  • Get a pocket wifi (can order when you purchase JR Pass and pick up at the airport).
  • My favorite areas in Tokyo were Harajuku, Omotesando, and Takeshita Street, its touristy and over the top but really fun for young people with good shopping/food and plenty of instagrammable moments. In Kyoto, Pontocho Alley is a must for restaurants and hit the classic tourist sites, they are all worth it.
  • You must get the ramen at Ramen Takahashi in Tokyo (very tiny place, order from vending machine and wait in line, its sooo worth it! we went twice!).
  • I highly recommend staying at least 1 night at a traditional Ryokan with onsen, they are expensive but worth it for the experience. There are areas such as Hakone which are well known for this type of thing and a lot of fun sites to see around there. It's a nice stopover in between Tokyo and Kyoto.

Day 1

We arrived at Haneda Airport, picked up our pocket wifi, and had purchased airport transfer bus tickets online in advance from (where you also order your JR Pass, Pocket Wifi, and Hakone Free Pass). We decided to stay at an AirBnB in Tokyo because it was so much more affordable, reviews in general warn you that all the living spaces in Japan are really small, but we felt perfectly happy and comfortable in our tiny studio and it was just what we needed. This also allowed us to splurge on a few amazing hotels/experiences later in the trip. We spent the evening exploring our area of Shinjuku which has the most major train station you'll ever see, sort of like 2 mega malls combined with 3 train stations in one. We were fortunate enough to stumble upon one of the greatest treasure of our trip on the first night, which was Ramen Takahashi. Walked home and passed out. 

Day 2 - My made up walking tour from Shinjuku to Shibuya


Woke up early and set out on the 10-15 minute walk to Shinjuku train station, this became our daily morning routine and I looked forward to the walk and getting my steps in early while watching the commuters head to work. Stopped for breakfast at Sawamura Bakery, which had a small but interesting menu, ordered an egg that was cooked inside an avocado. The restaurant was chic, not very "Japanese," but felt like a good start to the day. Next up we headed to Meiji Jingu Shinto Shrine which is located in a huge, beautiful park. We walked around a soaked in the culture, focusing on the spirituality, reading the prayer sheets that are given out, and learning the clap, clap, bow, bow, clap technique when making a wish at the temples (you'll figure it out). Next we headed to Takeshita Street in the Harajuku area. Filled with colorful street art, fun fashion, owl/cat cafes, and a lot of chatshck - it was a blast. Try all the crepes and street food because, "why not? you're never coming back" became our trip motto. Along with "if there's a line for food, get on it and ask questions later." Next make your way to Omotesando Station to take pics under the mirrored plaza as you ride the escalator up and down. Have lunch at Harajuku Gyozou or the equally popular line out the door spot Chao Bamboo (Thai Food). If you have room for dessert, which we unfortunately did not, try Glaciel Omotesando. We then headed to the Shibuya area, where I had made my coveted nail appointment at Jill & Lovers (follow them on instagram and DM to make an appointment in English, at the time I did not know this and made my Japanese-speaking friend secure me appointment via their online website - very confusing and complicated and not recommended). I am obsessed with nail art and could not miss an opportunity to have my nails done in Japan! This place was super personalized, friendly, and amazing. Expect to pay about $100+ for intricate nail art. Stick around to watch the Shibuya Crossing at night, as thousands of commuters cross in what looks like a choreographed dance while obnoxious tourists such as myself stand in the middle taking pictures. While getting my nails did I researched for local spots for dinner. On a small, random blog there was an article about a Torikatsu Chicken spot (Tonkatsu is fried pork cutlet very commonly seen). The place was tucked away down a sketchy alley, inside an apartment building, with a fluorescent sign that I believe had "chicken" written somewhere on it. As you can imagine we were again the only tourists in the restaurant. Sat at the bar, no menu, watching a tiny, elderly woman drench, bread, and fry with chopsticks each individual piece of food. It looked like you could get chicken, pork, prawns, etc. We literally just nodded to the woman behind the counter who seemed to be facilitating the ordering process and she nodded back. For some reason, I felt very secure that we had just ordered and delicious food was on its way. Sure enough about 10 minutes later, we had two plates of fried chicken with a side of cabbage slaw and rice (balance right?). Tender, juicy, with a flakey panko crust. There was soy sauce and mustard to dip and dab and one genius patron ordered mayo on the side. I deferred, trying to remain "healthy" lol. We drank the weird tea and paid whatever we were told, probably no more than $8 per meal. Our pocket wifi died and we couldn't look up how to get home on the train, since we hadn't used any public transportation that day and had walked everywhere, we were newbies. The walk home would have been about an hour and I think we were 10miles deep that day, so we splurged on a taxi home, which I was very upset by because I thought it was such a waste, but my feet thanked me, and we passed out.

Day 3


Today we made our daily walk to Shinjuku Station and had breakfast at Mr. Farmer. The cutest, instagrammable spot on a little shopping side street tucked in between the train station. Next up was Shinjuku Gyoen National Garden to see the first buds of cherry blossom season (go in March to see the full bloom, but be prepared for Hanami in Japan - it is described as a contact sport). Next we headed to the Ginza area known for shopping and being kind of high end. We had lunch at Itamae Sushi Tokyo which was simple and fab. We shopped at the largest Uniqlo in the world, I think there was even a plus size section, but I was mostly there to rest my feet and watch my boyfriend try on clothes, he's obsessed. We were debating what to do next, when a wave of sheer exhaustion came over me and we headed home, passed out at 6pm and skipped dinner. It happens. Would recommend Yoyogi Park or Golden Gai for some afternoon fun/night life.

Day 4

Headed to Sensoji Temple one of the oldest in Tokyo. By this time we were temple pros and knew the customs for wishing, washing, praying etc. Shopped along the touristy streets leading to the Temple, somehow missed the Kardashians by a day - shame. Eat lunch at Sometaro Asakusa, you have to sit on the ground so make sure your comfortable/flexible enough in a cross-legged position. They invented their own thing called Osome-Yaki which is a cool pancake creation topped with meat, veggies, noodles, egg, and decorated with yummy sauces. Next up was Akihabara for entertainment, arcades, and Club Sega. It's very loud inside the arcades and casinos and tbh I kinda hated this area. Made a reservation at Fukuzushi for dinner, seemed like a mid-high end range sushi spot, very friendly towards tourists, mostly populated with business people. The fish was excellent and preparation superb, but I felt like it was missing the cool vibe/character I was looking for.

Day 5

If you're die hard, head to Tsukiji Market (Tokyo's premiere fish market - closed WED/SAT/SUN) at like 4am to watch the tuna auction and get on line for Sushi Dai for breakfast. I have to admit that sadly I did not make it here, probably my biggest and only regret from the trip. Instead, we slept in and made our way to Shinjuku station to travel to Hakone via Hakone Free Pass tickets on Odakyu Line to Odawara. We decided to spend one night at a traditional Ryokan called Yama No Chaya. The most famous and expensive one in this area is called Gora Kadan, but it was not in our budget. I wanted one with the full dining experience along with private bath and Yama No Chaya was perfect. Take the Hakone Tozan Train to Tonosawa and walk to Yama No Chaya. Amazing, professional, attentive service, spent the afternoon soaking in private onsen baths, and luxuriating in the spa facilities. You get to wear these amazing kimonos but sadly I didn't fit into the ones they had, they were very accommodating and tried to bring me a million different ones to try on, but let's face it, they don't build them like me in Japan. So I just lounged in my comfy pants and shawl and decided to not let it phase me. Dinner was pre-scheduled for 7pm after our private onsen experience and served in our room on the floor. There were literally what felt like 10-20 courses of traditional kaiseki offerings, beautifully presented and thoughtfully prepared by a talented chef. I tried what felt like a million tiny appetizers, bursting with flavor, delicate textures, and barely made it through the meal sitting up. Slept on the ground on traditional tatami mats and futons.


Day 6

Breakfast was another luxurious meal at Yama No Chaya, opt for the traditional Japanese breakfast, it may be your only opportunity. We checked out at 10am and took a bus to the Odawara train station where you can leave your luggage in lockers as we were off to explore Hakone. This is where the Hakone Free Pass kicks in and gives you access to all the different transportations around the area as well as discounts at the museum and gift shops. We took the train headed to Gora, but make sure to stop at the Hakone Open Air Museum to see amazing sculptures and Picasso exhibit. Then back on the train to Gora, stop for a snack while waiting for the cable car to Sounzan. Get off and transfer to the ropeway which is a gondola to Owakudani and stop to see the interesting volcanic, sulfur activity. Eat the black eggs (supposed to add 7 years to your life) and the black ice cream (no health indication here, just cool ice cream). Views of Mt. Fuji on clear days. Continue on the gondola to Togendai for your sightseeing cruise back to the mainland and then bus back to Odawara. Here we activated the JR pass and were off to Kyoto. Again we stayed at an AirBnB in Kyoto, this time we were joined by our friend Emma and had a pretty spacious pad. Dinner at a kinda disappointing local sushi restaurant, our fault for not really researching this one, went home and passed out.

Day 7

Started the day with my favorite breakfast of the trip at Café Matsunosuke. Order the yogurt, granola, fruit bowl and thank me later. Then on to Nishiki Market for great shopping and gifts to bring home to the people you actually care about. Headed to Murayama Park, wandered around and found a cool abandoned monk hideaway in the hills, up some steps. Pit stop at the Yasaka Shrine. Then head to Gion, the geisha district and try and spot the real ones. Have dinner at literally any restaurant on Pontocho Alley or drinks along the river. 

Day 8

Major day of sightseeing lined up. Take the train to Arashiyama Bamboo Forest, be bold and photoshoot it up! Remember the "why not? you're never coming back" motto. Continue walking on uphill towards the Okochi Sancho Gardens, pay the admission fee and transport yourself to the peaceful quiet gardens of the former Japanese actor. Take a short loop hike for some cool views and drink the tea while you plan the rest of your day. Walk around the whole area of Arashiyama, shop, eat, enjoy. Eat really dope soba noodles for lunch at Arashiyama Yoshimura. Then off to Kinkaku-Ji Golden Temple (pretty much have to cab from bamboo to here as no good public transpo options). Finally time to club it up at World Kyoto. This club literally feels and looks like you're in a 1990s movie staring Freddie Prince Jr, with cool vaulted ceilings, it's somehow not overcrowded, and there are high top tables on the dance floor which don't really make sense, but you can picture the key conversation between the main characters going down here. "I think I love her, man." Make friends, dance, go home and pass out.

Day 9

We were lucky enough to be traveling with a close best friend who's work sponsored us for one night at The Four Seasons Hotel in Kyoto. As far as luxury hotels go, this spot is absolutely top of the line. Also expect to see a slew of celebrities, The Kardashians, Jenna Fischer, and football star Tony Gonzalez were all spotted at our hotel the week we stayed. We basically did not leave the hotel for the next two days because the food and amenities are so phenomenal. If splurging on a night here is not out of the question, enjoy the pool, outdoor spaces, amazing breakfast, and spa amenities.

Day 10

We managed to pull ourselves away from the Four Seasons to see the much anticipated Fushimi Inari Shrine, also referred to as the red gates, although they are really more orange. The place is crowded and touristy but also magical and well worth the trip. Catch the light shining through the gates and keep climbing as far as you can until it gets less crowded. Some people even climb all the way to the top, I guess that's a thing, however we did not attempt. Afterwards walk through the market spaces around the gates, grab some street food, or sit for a casual meal.

Day 11


Today was a big travel day as we made our way to Gala Yuzawa Snow Resort for a surprise ski trip arranged by my boyfriend. To give him credit, he had really done his homework, as this place rents you everything from skis and boots, to snow pants/jackets/gloves and more. Of course the whole way there I was mentally preparing myself that nothing was going to fit me and it was going to be so embarrassing. While the resort does try and be inclusive to larger sizes, things in Japan are just not made to fit my body, I think they have sizes up to 6XL but everything was wrong in terms of fit, too big in certain areas, too long, or too tight in others. I ended up being more comfortable wearing long underwear purchased at Uniqlo the day prior (they also have extended sizes in Japan), with two layers of workout pants, and my winter jacket. The whole look somehow worked and we had an amazing time on the slopes. Views were out of this world and if you're up for a little adventure and maybe some pre-planning, a ski trip in Japan is not out of the question, even as a quick day jaunt.

Day 12

Back in Tokyo for one night, we had another hotel splurge, this time using AMEX points for a night at the Ritz-Carlton in Tokyo. As obnoxious as this sounds, after The Four Seasons, this hotel did not blow me away. The location is cool at the top of the cities tallest building and lots of great indoor shopping and exploring to do, which paid off on the rainy day. Facilities are lovely, spent a lot of the time at the gym, pool, and relaxation room within the spa. Service was excellent of course. Tonight's meal was also a major event as we had booked in advance a reservation at Sushi Masuda. A 6 seat omakase restaurant by one of the famous apprentices of Jiro Ono from "Jiro Dreams of Sushi" with a price tag of around $250pp. I did a lot of research to find a place where I would feel comfortable and Masuda had stellar reviews. We booked through the concierge service at the Ritz which is another reason to spend at least one night at a fancy hotel. When we arrived, my foodie friend and I were whispering to each other, thinking that the small quiet space could not handle our booming voices. The Sushi Master himself, asked us why we were whispering and told us "big voices." We laughed and from then on felt so comfortable, asking questions, taking pictures, and hearing stories about what it was like training under Jiro and working with "the crazy" Nakazawa. The food, as expected, was once in a lifetime quality.

Day 13

Flight back to USA!