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In 2016, when it came time to plan another international family vacation, we once again asked our kids, ages 18 and 21, to come up with ideas. This time, we all decided to explore Japan. Since the kids were still in school, we needed to travel during their winter break, which allowed us to spend New Year’s Eve in another amazing location! Although it was wintertime, the temperatures were quite mild and comfortable. It was actually very pleasant not to be exploring with scorching hot temperatures!

My Itinerary

December 27

Fly all day

  • LAX to NRT 

December 28

Arrive at 6 PM

Pick JR rail passes

  • Make sure you order these before you go

    • You will still need to wait in a line, but it made it a little quicker

Take train to Tokyo

Get to hotel Grand Hyatt Tokyo at 9 PM

  • Beautiful hotel with wonderful views

Room service for dinner and sleep!

December 29

Breakfast at French Kitchen at Grand Hyatt Tokyo

Get train tickets 

Subway to Shibuya

Meiji Jingu Shrine

Late lunch at Hole in the Wall Spaghetti (unable to find site or link to location)

  • Across from Tokyo Plaza

  • Very good, fresh pasta

Cat café

  • Fun playing with kittens

  • There are several of these around

Walk on Takeshita Street

  • Lots of people!

See holiday lights in Shinjuku

Dinner at Roppongi Robataya

  • This was such a fun experience

  • You get to select what you want to eat and the chefs grill it right in front of you

  • It’s a small intimate restaurant

  • Good food, expensive

  • Reservation required

December 30

Clear AM and could see Mt. Fuji from Grand Hyatt Tokyo 

  • Such an impressive site!

Breakfast at Grand Hyatt Tokyo

Off to Hakone

Stop at Odawara Castle 

  • I would suggest doing this at the end of the day or a different day instead

  • Took up a lot of time, so we were limited on the later activities

Back on the train 

Lunch in Hakone

  • Soba at random noodle place we found after getting off of the train

  • It was fun trying to figure out what the restaurants in the area served by looking at the posted picturesNone of us speak Japanese!

Train to Gora

Hakone Open Air Museum 

  • Very interesting and unique art displayed in an outdoor space

  • There was even an exhibit with a foot pool that my children enjoyed trying out

Cable Car

  • This takes you to the gondola

Hakone Ropeway (gondola)

  • This takes you to the top of the mountain where you can see, and smell, the active volcano

  • See Ōwakudani

    • Volcano spot

    • If you are sensitive to sulfur, you may not want to spend a lot of time outside.

Get to Pirate Ship

  • Make sure to check the timetables

  • By the time we arrived, it was closed for the day 

  • This is the scenic way back down the mountain through the mountains

  • Since we spent too much time at our first stop of the day, we missed the last boat ride.  We had to take the bus down instead

    • Encountered a major traffic jam on the bus to train station 

    • Took a lot longer to get back and the bus was quite warm (since it was winter time, the trains and busses tended to keep the heat on high)

Trains back to Roppongi

Dinner at Rigoletto Bar and Grill

  • Good burgers 

December 31

Breakfast at Lauderdale (permanently closed)

Train to Kita-Kamakura Station

Walk along road 

Engakuji Temple

  • Beautiful views from the famous bell 

Kenchoji Temple

Tsurugaoka Hachimangu Shrine

  • Huge Shrine

  • Many people there for the New Year

Walk along Komachi Dori Avenue

  • Main shopping street/area

Kamakura Station

Eat lunch at Sometaro

  • Traditional Okonomiyaki pancake and Yakisoba

  • Cook on own grill 

  • This was a fun experience

Walk to Daibutsu (Great Buddha)

  • Second largest one 

  • The sheer size of the Buddha statue is breathtaking!  

Train back to Grand Hyatt Tokyo 

NYE dinner at Union Square

  • Good

Go to Tokyo Tower

  • It was lit up and we took the elevator up to the observation deck

  • Unfortunately, the firework show had been cancelled due to security issues

Back to Grand Hyatt Tokyo 

Oak Door Bar at the hotel for NYE celebrations 

  • Lots of champagne

  • Fireworks on the big TV screens!

January 1

Brunch at Lauderdale (permanently closed) again

Train to Asakusa

  • Crazy busy for the New Year

Context Travel walking tour in Asakusa

Walk around Ginza

  • Shops closed but still pretty (because it was New Year’s Day)

See Tokyo Station

  • Beautiful architecture

My birthday dinner at New York Grill at Park Hyatt

  • 52nd floor

  • Stunning 360-degree views, since you are so high up!

January 2

Breakfast at Grand Hyatt Tokyo

Check out of Grand Hyatt Tokyo

Shinkansen to Kyoto

  • 2 ½ hours

  • Scenic train ride

  • Saw Mt. Fuji along the way

Check into Citadines Apart'hotel

  • Comfortable rooms

  • Central location

Walk along Shijo-Dori

  • Lots of shops and people 

See the Yasaka Pagoda

Walk around Gion

Dinner at a hole-in-the-wall, small local chicken skewer place

  • We just happened upon it

  • Really good food

  • Tiny, counter-only place. Luckily there was an English menu

  • Cash only

January 3

Isetan Department Store

Meet Context Travel tour guide for Nara

Dinner at Nino Nara

  • Great little Italian restaurant

  • Owner, Nino, is the chef and his wife is the hostess

    • Such nice people!

  • When we arrived, the restaurant was full. While standing outside, the owner came out and said he made space for us at the counter. We had such a special, delicious, and memorable meal! We got to watch Nino cook and talk to him and his wife about where we were from. His wife then surprised us with hand-calligraphy prints of each of our names written in Japanese. We have these hung up in our home

January 4

Breakfast at Citadines Apart'hotel

Local bus travel today

Kinkakuji (Golden Pavilion)

  • Beautiful, truly breathtaking

Imperial Palace

  • Pretty park but palace was closed

Walk through the Gion

Lunch at Yushokutei

  • Fast food chicken and rice

  • Good

Maeda Coffee

Kodai-ji Temple

  • Amazing views 

Ryozen Kannon

  • Huge woman statue with zodiac signs

Higashiyama District

  • Shopping street

Kitomizudera Temple

  • Pretty orange pagoda

Dinner at Kushikura

  • Barbecue skewers and soup

  • Very good

  • We sat at a traditional table, which was low to the ground, and we sat on cushions. We needed to remove our shoes before going to the table

January 5

Breakfast at Le Temps at Granvia Hotel

Train to Osaka

Osaka Castle

  • Very interesting and beautiful

Lunch at Brasserie Monochrome (couldn't find correct link)

  • Difficult to order because of language but good food 

  • We walked until we found somewhere to eat. Upon entering, we didn’t realize there wouldn’t be any English menus. We were so hungry and didn’t want to walk more, so we decided to stay. After trying to point to order, the waitress ended up getting the chef who did speak enough English to help us order!

Sumiyoshi-Taisha Shrine


  • Lots of people, shops, and lights

Train back to Kyoto

  • Long and very crowded train

Late dinner at Gojo Paradiso

  • Mediterranean food (owned by an Israeli) 

  • We were a little concerned when we were the only ones there, but it didn’t disappoint! The food was delicious!

January 6

Breakfast at Citadines Apart'hotel

Check out

Shinkansen back to Tokyo

Train to The Royal Park Hotel Tokyo Haneda

  • Hotel at airport

  • It is literally inside the airport

Check into The Royal Park Hotel Tokyo Haneda

Get lunch at MOS Cafe in airport

  • Fast food chain 

Robot Restaurant in Shinjuku

  • Waiting area is like a Vegas lounge

  • Very unique

  • This is something you must do when there. There is truly nothing like it anywhere!

  • Buy your tickets ahead of time

Dinner at Casa Tequila Tokyo in Shinjuku

  • Good Mexican food 

Back to The Royal Park Hotel Tokyo Haneda

January 7

Breakfast at The Royal Park Hotel Tokyo Haneda

Long travel day home

Haneda to Osaka to LA

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