14-Day Japan Itinerary for First-Timers: Osaka, Ise, Kyoto, and a Day Trip to Tokyo

I'm planning my first trip to Japan this mid-October. I’ll be traveling with my girlfriend, and we’ve mapped out a 14-day itinerary covering Osaka, Ise, Kyoto, and a one-day trip to Tokyo from Kyoto. I know it sounds a bit reckless to try and experience Tokyo in a single day, but we just couldn’t resist the chance to visit, especially since we’re flying out of Osaka at the end of the trip. We wanted to avoid checking in and out of hotels, dragging our luggage to Tokyo, so we opted for a day trip to keep things simple and experience the Shinkansen train.

The focus of our trip is Japan’s history and culture, which is why we’ve dedicated a lot of time to Kyoto. It's always been the aspect of Japan that’s fascinated me the most—its temples, traditional architecture, and historical sites. But I’m also a huge fan of Japanese food, landscapes, nature and festivals.

That being said, I grew up loving Japanese pop culture, anime, manga, and movies. While I’m definitely a fan, I’m not planning to spend much time hunting for action figures or merch that I know I won’t buy.

My girlfriend thinks the itinerary might be a bit too packed—especially with the number of temples I’ve included! I’m open to opinions, especially if you think there's something I should skip, or if there are any must-visit museums or hidden gems in these cities that I’ve missed.

Here’s the itinerary

Day 1 – Osaka

• Afternoon
  • Arriving at Osaka Airport around noon
  • Hotel Check-in and resting
  • Umeda Sky Building (sunset view. Tickets ¥2000 discount benefits with Enjoy Eco Card)
• Evening
  • Exploring Umeda 
    • Tsuyuno Tenjinsya/@34.6992668,135.5007309,17.24z/data=!4m15!1m8!3m7!1s0x6000e6ec86618ce5:0xc5f933b80be2029f!2sSonezaki,+Kita+Ward,+Osaka,+530-0057,+Japan!3b1!8m2!3d34.7002187!4d135.5010362!16s%2Fg%2F120lkgf6!3m5!1s0x6000e6ec63ebf97d:0xbc7a3186d97b154!8m2!3d34.6992683!4d135.5007629!16s%2Fg%2F122224v7?entry=ttu&g_ep=EgoyMDI0MDgyMS4wIKXMDSoASAFQAw%3D%3D) (small shrine)
    • Ohatsutenjin Urasando (tiny street with bars)

Day 2 – Osaka

• Morning
  • Kuromon Ichiba Market (open from 11 am)
• Afternoon
  • Nippon Bashi DenDen Town (anime, manga street)
  • Dotonbori, Ebisu-Bashi, Hozenji Yokocho
• Evening
  • Dinner at a fancy restaurant

Day 3 – Daytrip to Nara

• Morning
  • Train from Osaka Namba to Nara (Kintetsu Nara Station)
  • Visit the Historic Monuments of Ancient Nara
    • Kōfuku-ji (open from 9am)
    •  Tōdai-ji  (Great Buddha Hall tickets, ¥800)
• Afternoon
  • Kasuga Taisha (Shinto Shrine tickets)
  • Small hike in Mt. Kasuga Primeval Forest until the Uguisu Waterfall
  • Getting back to Nara station
• Evening
  • Travel back to Osaka

Day 4 – Osaka

• Morning
  • Minoh National Park and a small hike to Minoh Falls
• Afternoon
  • Katsuoji shrine (tickets ¥500)
  • Osaka Castle Park (just a look from the outside, unless we have enough time)
• Evening
  • Walking and dining in ShinSekai 

Day 5 – Ise

• Morning
  • Take the Train to Ise
  • Check-in in Ryokan 
• Afternoon
  • Ise Jingū
  • Kotai Jingu/@34.45501,136.725793,15z/data=!4m6!3m5!1s0x600450ebdf9f37f3:0xf009663753f60ca7!8m2!3d34.4550038!4d136.7254738!16zL20vMDJyX2c0?entry=ttu&g_ep=EgoyMDI0MDgyNi4wIKXMDSoASAFQAw%3D%3D)
• Evening
  • Dinner in fancy restaurant

Day 6 – Ise/Kyoto

• Morning
  • Breakfast in Ryokan at Ise
  • Train to Kyoto
• Afternoon
  • Check in Kyoto
  • Kiyomizu-dera (¥500, close at 6 pm)
• Evening
  • …

Day 7 – Kyoto

• Morning
  • Arashiyama Bamboo Forest (early morning)
  • Okochi Sanso Garden
• Afternoon
  • Jōjakkōji Temple (¥400)
  • Giōji (¥300, last entry 4.30 pm)
  • Adashino Nenbutsuji
  • Otagi Nenbutsuji Temple (¥400, last entry 4.15 pm)
• Evening
  • Rest

 Day 8 – Kyoto

• Morning
  • Demachi Masugata Shopping Arcade (lunch time)
• Afternoon
  • Nanzen-ji (¥500)
  • Philosopher Path
  • Higashiyama Jisho-ji (¥500)
• Evening
  • Rest

Day 9 – Tokyo Daytrip

• Morning
  • Shinkansen to Tokyo (early morning)
  • Asakusa
  • Senso Ji
• Afternoon
  • Yasukuni Shrine (close at 6 pm)
  • Shibuya & Meiji Jingu
• Evening
  • Shinjuku
  • Shinkansen to Kyoto

Day 10 – Kyoto

• Morning
  • Rest
• Afternoon
  • Kinkaku-ji (¥500)
  • Ryōan-ji (¥600)
  • Kyoto Botanical Gardens (¥200) Light Event (¥2000) from 6pm to 9.30pm (last entry 8.30pm) 
• Evening

Day 11 – Kyoto

• Morning
  • Kodaiji Temple (¥600)
  • Ishibe kōji
• Afternoon
  • Yasaka Shrine
  • Maruyama Park
  • Shogunzuka (¥600) (There is a light up event that begins in the fall following sunset)
• Evening
  • Pontocho

Day 12 Kyoto

• Chill day shopping for souvenir
• Recover something I missed in Kyoto

Day 13 Kyoto

• Morning

  • Kyoto

• Afteroon

  • Osaka

• Evening

  • Airport