Sharing a pretty detailed itinerary below. All of this is a result of me being an extreme googler/researcher — mainly I'd love to know if you guys think this is way too busy (we like a packed itinerary, but want to keep it do-able) and if anyone has experienced any of the things/places I have planned and recommends something different for any reason.

Also planning to propose when we get to Arashiyama (hopefully the cherry blossoms will be popping off!), so any recommendations location-wise there would be much appreciated.

Here we go:

Day 1 – Mar 29

Hotel: Cerulean Tower Tokyu (Shibuya, Tokyo)

• Lunch: Han no Daidokoro Bettei (A5 wagyu yakiniku).
• Explore Shibuya Crossing, Hachiko statue, and quirky cafés.
• Quick snack run at 7-Eleven.
• Dinner: Omoide Yokocho izakaya crawl → end with Tsurutontan Udon in Shinjuku.
• Drinks at hotel bar — early night to recover from jet lag.

Day 2 – Mar 30

Hotel: Cerulean Tower Tokyu (Shibuya, Tokyo)

• Breakfast and morning walk through Takeshita Street and quirky Harajuku cafés.
• Lunch: Tonkatsu Maisen Aoyama.
• Explore teamLab Planets digital art museum in Toyosu.
• Akihabara: arcade games + Super Mario Café.
• Dinner: Tempura Kondo (Michelin-starred, Ginza).
• Cocktails at SG Club back in Shibuya.

Day 3 – Mar 31

Hotel: Cerulean Tower Tokyu (Shibuya, Tokyo)

• Asakusa: visit Senso-ji Temple and Nakamise shopping street.
• Picnic under cherry blossoms at Ueno Park (grab bento lunch).
• Optional: Tokyo National Museum or more sakura strolls in Ueno.
• Dinner: Sushi Yoshitake omakase in Ginza.
• Golden Gai bar crawl — bring cash, explore tiny bars in Shinjuku.

Day 4 – Apr 1

Hotel: Suiran (Arashiyama, Kyoto)

• Travel to Kyoto and settle in.
• Dinner: Suiran kaiseki in Arashiyama.
• Evening: riverside cocktails.

Day 5 – Apr 2

Hotel: Suiran (Arashiyama, Kyoto)

• Sunrise walk through Arashiyama Bamboo Grove → Togetsukyo Bridge.
• Lunch: Yoshimura (soba + tempura) by the river.
• Visit Monkey Park + scenic riverside strolls.
• Dinner: Kyoto Kitcho Arashiyama — luxury kaiseki.

Day 6 – Apr 3

Hotel: Ace Hotel Kyoto (Central Kyoto)

• Transfer to central Kyoto.
• Lunch: Miyagawa Honten (grilled unagi).
• Philosopher’s Path → Maruyama Park → Gion District walk.
• Dinner: Monk — wood-fired tasting menu with pizza course.
• Drinks at Bar K6.

Day 7 – Apr 4

Hotel: Ace Hotel Kyoto (Central Kyoto)

• Day trip to Nara: Todai-ji Temple + Deer Park.
• Lunch: Kikusuiro — private tatami room with unagi bowls.
• Explore Naramachi Old Town.
• Return to Kyoto for casual izakaya dinner.
• Speakeasy drinks at L’Escamoteur.

Day 8 – Apr 5

Hotel: Ace Hotel Kyoto (Central Kyoto)

• Train to Kobe (~30 min).
• Lunch: Mouriya or Wakkoqu — Kobe wagyu.
• Afternoon street food grazing at Nishiki Market back in Kyoto.
• Light dinner near hotel.
• Drinks at Bar Rocking Chair.

Day 9 – Apr 6

Hotel: Asaba Ryokan (Shuzenji, Izu Peninsula)

• Travel to Shuzenji.
• Welcome tea at ryokan overlooking floating Noh stage.
• Private onsen soak + bamboo path strolls nearby.
• Dinner: in-room kaiseki feast.

Day 10 – Apr 7

Hotel: Asaba Ryokan (Shuzenji, Izu Peninsula)

• Morning bamboo forest walk + Shuzenji Temple visit.
• Relax in ryokan and onsen.
• Optional tea ceremony or guided walking tour.
• Dinner: final kaiseki feast at ryokan.

Day 11 – Apr 8

Hotel: Park Hyatt Tokyo (Shinjuku, Tokyo)

• Return to Tokyo → Shinjuku.
• Street food crawl: yakitori + ramen.
• Tiny bar hopping at Nonbei Yokocho.

Day 12 – Apr 9

Hotel: Park Hyatt Tokyo (Shinjuku, Tokyo)

• Relaxed morning spa + breakfast.
• Cherry blossom stroll through Nakameguro + boutique shopping.
• Fun lunch stop (e.g., Japanese McDonald’s).
• Dinner: world-class omakase in Ginza.
• Nightcap at New York Bar, Park Hyatt.

Day 13 – Apr 10

Hotel: Park Hyatt Tokyo (Shinjuku, Tokyo)

• Morning forest walk at Meiji Shrine.
• Lunch: Tonkatsu Maisen in Shibuya.
• Evening baseball game: Yakult Swallows at Meiji Jingu Stadium.
• Night: Golden Gai bar crawl, late-night Ichiran ramen.

Day 14 – Apr 11

Hotel: Park Hyatt Tokyo (Shinjuku, Tokyo)

• Final shopping day in Ginza & Shibuya — luxury brands, Don Quijote, quirky shops.
• Lunch: Flipper’s Soufflé Pancakes.
• Dinner: Narisawa or L’Effervescence.
• Drinks at Bar Benfiddich.

Day 15 – Apr 12

• Breakfast from 7-Eleven, pack up.
• Private car transfer to Haneda Airport.
• Flight home.