5-Day Japan Holiday Itinerary: Tokyo to Osaka via Iconic Sights and Public Transport

Day 1: Explore Tokyo

Tokyo, Japan on June 10, 2025

8:00am

Breakfast at Tsukiji Outer Market

Enjoy fresh sushi and Japanese breakfast delicacies at Tsukiji Outer Market, which opens at 6am and is lively in the morning, perfect for avid food lovers.
JPY2000, 1h30m

9:45am

Visit Asakusa and Senso-ji Temple

Explore the historic Senso-ji Temple and stroll Nakamise Street for souvenirs. The temple grounds open from 6am to 5pm.
Free, 1h30m

11:30am

Lunch at Ueno Ameyoko Market

Taste street food and casual eateries around Ameyoko Market, offering various Japanese snacks and dishes.
JPY1200, 1h

1:00pm

Visit Ueno Park and Tokyo National Museum

Walk Ueno Park, then visit the Tokyo National Museum (open 9:30am-5pm) to witness Japan’s cultural heritage.
JPY1000, 2h

3:30pm

Shinjuku Gyoen National Garden

Relax in beautiful Shinjuku Gyoen, open until 4:30pm, a serene retreat in the heart of Tokyo.
JPY500, 1h

6:00pm

Dinner in Shinjuku Omoide Yokocho

Sample yakitori and traditional foods in this cozy alleyway famous for evening dining.
JPY2500, 1h30m
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Day 2: Hakone Hot Springs

Hakone, Japan on June 11, 2025

7:30am

Travel to Hakone by Odakyu Romancecar

Catch the Romancecar limited express from Shinjuku to Hakone-Yumoto, around 85 minutes journey, booking recommended.
JPY2070, 1h25m

9:30am

Hakone Open-Air Museum

Discover outdoor sculptures blended with nature and indoor Picasso Pavilion, open 9am-5pm.
JPY1600, 2h

12:00pm

Lunch at Gora Brewery & Grill

Enjoy local craft beer and grilled dishes in Gora town close to museum.
JPY2200, 1h

1:30pm

Hakone Ropeway and Owakudani

Ride scenic ropeway to Owakudani volcanic valley, famous for black eggs and views of Mt Fuji, ropeway operates 9am-5pm.
JPY1560 roundtrip, 2h

4:00pm

Relax in an Onsen

Book a visit or stay at Hakone Onsen ryokan to experience traditional hot spring baths.
JPY2000-5000, 2h

7:00pm

Dinner at ryokan

Enjoy kaiseki multi-course traditional dinner typically offered by ryokans.
Included or JPY4500, 1h30m
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Day 3: Kyoto Cultural Heritage

Kyoto, Japan on June 12, 2025

8:00am

Shinkansen from Odawara to Kyoto

Take the Tokaido Shinkansen from Odawara station to Kyoto, approx. 2 hours. Reserve tickets in advance.
JPY13910, 2h

10:30am

Fushimi Inari Shrine

Walk through thousands of vermilion torii gates at Fushimi Inari. Open 24 hours, no entry fee.
Free, 1h30m

12:30pm

Lunch at Nishiki Market

Sample Kyoto street food at Nishiki Market, the ‘Kitchen of Kyoto.’
JPY1500, 1h

2:00pm

Kiyomizu-dera Temple

Visit the iconic temple with views over Kyoto city. Opens 6am-6pm, admission JPY400.
JPY400, 1h30m

4:00pm

Gion District Stroll

Experience traditional Kyoto atmosphere and possibly spot Geisha in the evening.
Free, 1h

6:30pm

Dinner at Pontocho Alley

Dine at one of the many restaurants along Pontocho for authentic Kyoto cuisine and ambience.
JPY3500, 1h30m
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Day 4: Nara Day Trip

Nara, Japan on June 13, 2025

8:30am

Train from Kyoto to Nara

Catch the JR Nara Line rapid or Kintetsu train to Nara, about 45 minutes by public transit.
JPY710, 45m

9:30am

Visit Todai-ji Temple

Explore Todai-ji, home to the giant Great Buddha statue. Open 7:30am-5:30pm, admission JPY600.
JPY600, 1h30m

11:15am

Nara Park and Deer Feeding

Stroll around Nara Park, famous for friendly free-roaming deer.
JPY150 for deer crackers, 1h

12:30pm

Lunch at Nakatanidou

Try fresh mochi at this renowned mochi shop near Nara Park.
JPY800, 45m

2:00pm

Kasuga Taisha Shrine

Visit this notable Shinto shrine known for thousands of hanging lanterns, open 6am-6pm.
JPY500, 1h

3:30pm

Return to Kyoto

Train back to Kyoto to relax in the evening or explore more nearby spots.
JPY710, 45m

7:00pm

Dinner at Kyoto Station Ramen Street

End your day with hearty bowls of ramen at Kyoto Station’s famous ramen street, open until 10pm.
JPY1000, 1h
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Day 5: Osaka Highlights

Osaka, Japan on June 14, 2025

9:00am

Train from Kyoto to Osaka

Short train ride from Kyoto to Osaka via JR Special Rapid Service, approximately 30 minutes.
JPY570, 30m

10:00am

Osaka Castle

Visit iconic Osaka Castle and its museum, open 9am-5pm with entry fee JPY600.
JPY600, 1h30m

12:00pm

Lunch at Dotonbori

Enjoy takoyaki, okonomiyaki and street food in Osaka’s lively Dotonbori district.
JPY1500, 1h

1:30pm

Explore Shinsaibashi Shopping Arcade

Shop and explore one of Osaka’s largest shopping arcades featuring local and international brands.
Free to browse, 1h30m

3:30pm

Umeda Sky Building Floating Garden Observatory

Catch panoramic city views from the Umeda Sky Building open 10am-10:30pm, entry JPY1500.
JPY1500, 1h

6:00pm

Dinner at Kushikatsu Daruma

Experience Osaka’s famous kushikatsu deep-fried skewers at this popular chain with lively atmosphere.
JPY2500, 1h30m
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