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Explore vibrant cityscapes, serene nature, rich history, and iconic landmarks on this exciting 5-day journey across Tokyo, Hakone, and Osaka in the beautiful spring season.

Explore vibrant cityscapes, serene nature, rich history, and iconic landmarks on this exciting 5-day journey across Tokyo, Hakone, and Osaka in the beautiful spring season.
Free walking tours. Yes, actually free. No credit card needed. No catch.
Local guide, 2-3 hours
Major sights, hidden gems, local stories
100% tip-based
Guides earn only tips, so they give their absolute best
You tip what feels right
At the end, just tip whatever you feel is right
I've done these in dozens of cities and they've been the highlight of almost every trip. If you're visiting Japan, do this on your first day. You'll thank me later.

Start your day early at Senso-ji, Tokyo's oldest temple, located in Asakusa. Explore the temple grounds and the impressive Kaminari Gate.

Start your day early at Senso-ji, Tokyo's oldest temple, located in Asakusa. Explore the temple grounds and the impressive Kaminari Gate.

Walk through Nakamise Street, the shopping street leading to Senso-ji, for souvenirs and traditional snacks like freshly made ningyo-yaki cakes.

Walk through Nakamise Street, the shopping street leading to Senso-ji, for souvenirs and traditional snacks like freshly made ningyo-yaki cakes.

Head to the nearby Tokyo Skytree for panoramic views of Tokyo from the observation decks and visit the Solamachi shopping complex at its base.

Head to the nearby Tokyo Skytree for panoramic views of Tokyo from the observation decks and visit the Solamachi shopping complex at its base.

Visit the Sumida Aquarium located inside Tokyo Skytree Town for a relaxing experience viewing aquatic life including a large penguin exhibit.

Visit the Sumida Aquarium located inside Tokyo Skytree Town for a relaxing experience viewing aquatic life including a large penguin exhibit.
~2 hours
In the evening, roam streets in the Asakusa district to discover stalls and small shops selling local street foods like yakitori, kushikatsu and taiyaki pastries.
Exploring vibrant street food scenes offers a sensory adventure filled with mouthwatering tastes and enticing aromas. You'll typically sample diverse dishes ranging from savory skewers to sweet treats, gaining insight into local culinary traditions and street culture. Local guides often share stories behind each dish, enriching the experience with cultural context and insider tips.
Meals
Recommended traditional local cuisine

Find a café near Asakusa serving Japanese-style breakfast sets featuring onsen tamago, rice, miso soup, and grilled fish.
Onsen Tamago
Look for a sushi counter in the Tokyo Skytree Solamachi area and order fresh nigiri sushi with seasonal fish.
Sushi
Join a street food tour in Asakusa and sample kushikatsu, fried skewers of meat and vegetables, along with taiyaki, a fish-shaped cake filled with sweet red bean paste.
KushikatsuIdeal location to explore the day 1 itinerary with vibrant traditional atmosphere and good transit.

Spend the morning wandering this spacious park in Shinjuku with beautiful gardens and seasonal flowers. Enter via the Shinjuku Gate for easy access. Ideal for a peaceful stroll and photo opportunities.

Spend the morning wandering this spacious park in Shinjuku with beautiful gardens and seasonal flowers. Enter via the Shinjuku Gate for easy access. Ideal for a peaceful stroll and photo opportunities.

Visit this Shinto shrine near Harajuku Station. Explore the forested path and the main hall. Look for ema boards where visitors leave wishes.

Visit this Shinto shrine near Harajuku Station. Explore the forested path and the main hall. Look for ema boards where visitors leave wishes.

Explore Omotesando’s fashionable avenue for stylish cafes. Look for a place with terrace seating on the main street. Order a matcha latte and a light pastry to relax.

Explore Omotesando’s fashionable avenue for stylish cafes. Look for a place with terrace seating on the main street. Order a matcha latte and a light pastry to relax.

Experience the iconic scramble crossing in Shibuya. Best viewed from one of the surrounding buildings or the station overpass. Take photos and observe the bustling city vibe.

Experience the iconic scramble crossing in Shibuya. Best viewed from one of the surrounding buildings or the station overpass. Take photos and observe the bustling city vibe.
~2 hours
Find a local Izakaya in Shibuya backstreets. Order kushikatsu, deep-fried skewered meat and vegetables that are popular here, along with sake or shochu.
You'll typically settle into a lively, casual spot where small plates, charcoal-grilled skewers, and seasonal dishes encourage sharing and conversation, creating a relaxed evening of tasting and socializing. Local guides often explain ordering customs and recommend pairings with local drinks, helping you discover flavors rooted in tradition alongside inventive modern twists. The city's mix of narrow alleys, historic neighborhoods, and neon-lit nightlife makes every stop feel like a cultural snapshot, ideal for travelers who want an authentic, sociable food experience.
Meals
Recommended traditional local cuisine

Grab breakfast at a bakery near Shinjuku Gyoen and try dorayaki, a sweet red bean pancake sandwich, along with a cup of coffee.
Dorayaki
Look for an Izakaya in Shibuya and order kushikatsu, deep-fried skewers with various fillings, paired with sake or shochu for an authentic local experience.
KushikatsuClose to evening activities and easy access to other parts of Tokyo for next day.
Take the JR Tokaido Shinkansen from Tokyo Station to Odawara Station, then local transport to Hakone. Booking tickets in advance online is recommended for the best fares.

Explore the Hakone Open Air Museum located near Kowakudani Station. Enjoy outdoor sculptures and Picasso Pavilion. Wear comfortable shoes for walking through large grounds.

Explore the Hakone Open Air Museum located near Kowakudani Station. Enjoy outdoor sculptures and Picasso Pavilion. Wear comfortable shoes for walking through large grounds.

Board the Hakone Ropeway from Sounzan to Togendai for panoramic views of Mount Fuji and volcanic valleys. Get off at Owakudani for sightseeing.

Board the Hakone Ropeway from Sounzan to Togendai for panoramic views of Mount Fuji and volcanic valleys. Get off at Owakudani for sightseeing.

Walk through Owakudani Valley to see volcanic activity and sulfur vents. Try the famous black eggs boiled in hot springs. Stay on marked trails for safety.

Walk through Owakudani Valley to see volcanic activity and sulfur vents. Try the famous black eggs boiled in hot springs. Stay on marked trails for safety.
~2 hours
Choose a traditional onsen resort near Hakone Yumoto for rejuvenating baths. Many offer outdoor hot springs amid nature. Check for facilities with private baths if preferred.
Relax in natural hot spring baths at a traditional onsen resort.
~3 hours
Travel from Hakone to Osaka by Shinkansen bullet train from Odawara Station to Shin-Osaka Station. Reserve seats in advance and store luggage in station lockers for easy transit.
Meals
Recommended traditional local cuisine

Look for a restaurant near Togendai Station and try Soba Noodles, a local specialty featuring buckwheat noodles served hot or cold.
Soba Noodles
Dine at an onsen resort restaurant and order Kaiseki Ryori, a traditional multi-course Japanese dinner that showcases seasonal ingredients.
Kaiseki RyoriStaying in Hakone Yumoto places you close to the hot springs and easy access to the ropeway and museum.
Take the Shinkansen from Odawara Station to Shin-Osaka Station. Book seats in advance during spring travel season for best availability.

Explore the historic Osaka Castle and its extensive grounds in Chūō-ku. Visit the castle museum inside and enjoy views from the top floor.

Explore the historic Osaka Castle and its extensive grounds in Chūō-ku. Visit the castle museum inside and enjoy views from the top floor.

Walk through Kuromon Ichiba Market for fresh seafood and local snacks. Try grabbing a takoyaki or kushikatsu from street vendors.

Walk through Kuromon Ichiba Market for fresh seafood and local snacks. Try grabbing a takoyaki or kushikatsu from street vendors.

Stroll along Dotonbori street famous for vibrant neon lights and iconic billboards. Check out shops, cafes, and photo ops by the canal.

Stroll along Dotonbori street famous for vibrant neon lights and iconic billboards. Check out shops, cafes, and photo ops by the canal.
~2 hours
Join a guided or self-guided street food tour around Namba and Dotonbori. Sample street foods like okonomiyaki, takoyaki and kushikatsu.
Exploring vibrant street food scenes offers a sensory adventure filled with mouthwatering tastes and enticing aromas. You'll typically sample diverse dishes ranging from savory skewers to sweet treats, gaining insight into local culinary traditions and street culture. Local guides often share stories behind each dish, enriching the experience with cultural context and insider tips.
~3 hours
Travel from Osaka to Tokyo via Shinkansen bullet train. Book tickets early for best prices, the ride lasts about 2.5 hours.
Meals
Recommended traditional local cuisine

Find a café near Osaka Castle and order a light Japanese-style breakfast with green tea and mochi sweets.
Mochi
Try fresh sushi at a market eatery in Kuromon Ichiba Market, focusing on seasonal fish for authentic taste.
Sushi
Look for a street food vendor in Dotonbori serving okonomiyaki, a savory pancake with cabbage, meat, and seafood.
OkonomiyakiStaying near Namba puts you close to Dotonbori street life and convenient for next day's travel to Tokyo.
Book tickets in advance for best fares; depart from Shin-Osaka station to Tokyo station.

Arrive early at teamLab Planets in Toyosu to avoid queues. Explore immersive digital art installations where you can walk through water and light. It is best accessed via Shin-Toyosu Station on the Yurikamome Line.

Arrive early at teamLab Planets in Toyosu to avoid queues. Explore immersive digital art installations where you can walk through water and light. It is best accessed via Shin-Toyosu Station on the Yurikamome Line.

Walk or take a short JR Chuo Line ride to lively Kichijoji. Stroll through Inokashira Park's ponds and shaded paths. Check out small shops and cafes along Sun Road shopping street.

Walk or take a short JR Chuo Line ride to lively Kichijoji. Stroll through Inokashira Park's ponds and shaded paths. Check out small shops and cafes along Sun Road shopping street.
~2 hours
Seek out a tea house in Kichijoji or nearby Mitaka offering hands-on tea ceremony sessions. Reservations are advised. Learn about matcha preparation and Japanese etiquette.
Experience a moment of tranquility as you engage in a ritual that emphasizes harmony, respect, purity, and tranquility. You'll typically observe meticulous attention to detail and elegant movements, guided by local experts who explain the cultural significance behind each step. Most classes include hands-on participation, allowing travelers to savor matcha tea prepared with traditional tools in an authentic setting.
~2 hours
Head to a nearby small izakaya in Kichijoji or along the train lines toward Shinjuku. Order kushikatsu, fried skewers, and try local shochu or sake for drinks.
You'll typically settle into a lively, casual spot where small plates, charcoal-grilled skewers, and seasonal dishes encourage sharing and conversation, creating a relaxed evening of tasting and socializing. Local guides often explain ordering customs and recommend pairings with local drinks, helping you discover flavors rooted in tradition alongside inventive modern twists. The city's mix of narrow alleys, historic neighborhoods, and neon-lit nightlife makes every stop feel like a cultural snapshot, ideal for travelers who want an authentic, sociable food experience.
Meals
Recommended traditional local cuisine

Look for a soba noodle shop near Inokashira Park and order cold soba with dipping sauce, a refreshing and traditional dish.
Soba Noodles
Find a local izakaya in Kichijoji and try kushikatsu, fried skewered meat and vegetables paired with shochu.
KushikatsuStaying in Kichijoji keeps you close to your evening activities and offers a relaxed atmosphere after a busy day.
Get your trip plan as a PDF with maps and a CSV spreadsheet.
Accommodation is approximately $80 per night. Food budget includes restaurant meals averaging $15 per day. Transport includes local metro, JR lines, and taxis averaging $20 per day. Activities budget is estimated at $25 per day.
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