Japan blends ancient rites with audacious modernity. Samurai strongholds evolved into glass-and-steel megacities; tea rituals whisper in the shadows of dazzling neon. From Edo-era alleys to bullet trains, the archipelago rewards curiosity with impeccable detail and surprising warmth.

September brings late-summer heat and the possibility of typhoons—pack a light rain jacket and breathable layers. It also means seasonal delights: early autumn menus, mountain hiking at its crisp best, and Tokyo’s September sumo tournament, a cultural spectacle you’ll talk about for years.

This 21-day itinerary mirrors your wishes: start with five nights in Tokyo, continue with two in Kyoto, then head into the Japanese Alps (Takayama area) before looping through Kanazawa, Osaka (with Nara), Hiroshima & Miyajima, and a calming onsen finale in Hakone—returning to Tokyo to fly home. Expect sightseeing, hiking, shopping, foodie finds, museums, and a few unique activities.

Tokyo

Days 1–5: Big-city energy, old-town soul, and unforgettable eats

Tokyo is a mosaic of neighborhoods: serene Meiji Shrine forests beside Harajuku style storms; sumo stables next to riverside craft shops; skyscrapers crowned with Michelin stars. Use your first days to adjust, browse depachika (department store food halls), and let the city’s rhythm carry you.

• Icons and viewpoints: Asakusa’s Senso-ji Temple at dawn; the kaminarimon gate’s giant lantern has greeted pilgrims for centuries. In the evening, gaze over an ocean of lights from Tokyo Skytree or the free Tokyo Metropolitan Government Building observatory.
• Neighborhood strolls: Shimokitazawa for vintage shopping and coffee; Daikanyama/Nakameguro for design boutiques and canal-side walks; Akihabara for retro gaming and otaku culture.
• Museums: Tokyo National Museum (Ueno) for samurai armor and Buddhist sculpture; teamLab Borderless (Azabudai Hills) for immersive digital art; Nezu Museum’s garden as a quiet reset.
• Unique evening: Shibuya Crossing’s theater of motion, followed by a tiny standing-only izakaya in Nonbei Yokocho or Omoide Yokocho for yakitori and sake.

Handpicked tours and activities (Tokyo):

• 1-Day Tokyo Bus Tour

  

  Great first-day overview with Meiji Shrine, Skytree admission, and a Tokyo Bay cruise when operating. Saves time and transit legwork.

  
  
• Tokyo: Shinjuku Food Tour (13 Dishes at 4 Local Eateries)

  

  Slurp, sip, and snack through backstreets you’d likely miss alone—ramen, yakitori, wagyu skewers, and more in a small group.

• Tokyo Sumo Wrestling Tournament Experience

  

  Held in September at Ryogoku Kokugikan—watch bouts, learn rituals, and feel the electricity of Japan’s national sport.

• Official Street Go-Kart in Shibuya

  

  A wildly photogenic, only-in-Japan thrill around Shibuya Crossing. Valid international driving permit required.

Where to eat and drink (Tokyo):

• Breakfast/coffee: Turret Coffee Tsukiji (rich espresso and caramel lattes); Onibus Coffee Nakameguro (single-origin pour-overs); Bread, Espresso & in Omotesando (butter-forward pastries).
• Lunch: Fuunji (shio tsukemen with a cult following); Tonkatsu Maisen Aoyama (pork cutlets so tender you can cut them with chopsticks); Uogashi Nihon-Ichi standing sushi bars (fast, fresh, affordable).
• Dinner: Kikanbo (spicy miso ramen with numbing pepper); Uomori in Kanda (old-school izakaya, charcoal-grilled fish); Horumon Dojo in Ueno (hearty offal-centric grills for the adventurous).
• Sweets: Kagari’s tamago sando at depachika; Asakusa’s melon pan stuffed with soft-serve.

Where to stay (Tokyo): Search citywide options on VRBO or Hotels.com. Mid-range favorites near great transit: Hotel Sunroute Plaza Shinjuku (easy trains, quiet rooms), Hotel Gracery Shinjuku (Godzilla-head rooftop), and Keio Plaza Hotel Tokyo (views, pool). For a splurge, Aman Tokyo or The Ritz-Carlton, Tokyo.

Getting to Tokyo: Book international flights on Kiwi.com or Trip.com. From Haneda: 20–30 min to central Tokyo by monorail + JR or Keikyu; from Narita: 60 min by Narita Express. For intercity trains later, browse Trip.com Trains.

Travel: Tokyo to Kyoto (morning of Day 6)

Ride the Tokaido Shinkansen (Nozomi) from Tokyo Station to Kyoto Station in about 2 hr 15 min; expect roughly $95–$120 USD reserved. Check schedules and seats via Trip.com Trains. Tip: Ship big luggage ahead (takkyubin) for about ¥2,000 per bag so you can travel light.

Kyoto

Days 6–7: Temples, tea, and time travel

Kyoto is a thousand years of imperial memory: torii gates climbing a mountain at Fushimi Inari, the gold leaf of Kinkaku-ji reflected in a mirror-still pond, and lantern-lit alleys where geiko still glide to evening appointments.

• Morning serenity: Kiyomizu-dera’s wooden stage before crowds; wander Sannen-zaka and Ninen-zaka lanes for artisan sweets and pottery.
• Arashiyama: Early-bird the bamboo grove, then cross the Katsura River and climb to Iwatayama Monkey Park or stroll the mossy gardens of Gio-ji.
• Culture and crafts: Ippodo Tea for a guided matcha tasting; Nishiki Market for snacks (yuba, pickles, sesame croquettes).

Handpicked tours and activities (Kyoto):

• PERFECT KYOTO 1-Day Bus Tour

  

  Efficiently covers Fushimi Inari, Kiyomizu-dera, Kinkaku-ji, and more—ideal for a short two-night stay.

  
  
• Kyoto Gion Geisha District Walking Tour

  

  Unravel the customs and stories behind Kyoto’s most enigmatic tradition as dusk falls over lantern-lined streets.

• Private Kyoto Tour with Licensed Guide & Vehicle

  

  Customize a full-day route to match your pace and interests—great for families or travelers who prefer fewer transfers.

Where to eat and drink (Kyoto):

• Breakfast/coffee: %Arabica Higashiyama (espresso with temple views if you go early), Vermillion near Fushimi Inari (calm garden setting).
• Lunch: Katsukura (panko-crisp tonkatsu with sesame grinding ritual); Okonomiyaki Katsu (Kyoto-style savory pancakes cooked on teppan).
• Dinner: Gion Namba (seasonal kaiseki), Musashi Sushi (belt sushi done right), and a cozy izakaya crawl in Pontocho Alley.

Where to stay (Kyoto): Explore VRBO or Hotels.com. Mid-range standouts: Hotel M's Plus Shijo Omiya (value, transit), Kyoto Tokyu Hotel (quiet wing around a water garden). Budget gem: Piece Hostel Sanjo. Splurge: The Ritz-Carlton, Kyoto or Kyoto Brighton Hotel.

Travel: Kyoto to Takayama (morning of Day 8)

Fastest is Kyoto → Nagoya (35–50 min by Shinkansen) → Takayama (Wide View Hida limited express, ~2 hr 20 min). Total ~3–3.5 hr; about $75–$95 USD. Check times on Trip.com Trains. Mountain rail views are superb—sit on the left from Nagoya for river scenery.

Japanese Alps: Takayama (base) + Kamikochi

Days 8–10: Old town lanes, Hida beef, and alpine air

Takayama’s preserved Edo streets (Sanmachi Suji) glow with cedar storefronts and sake breweries marked by brown sugidama balls. Morning markets along the Miyagawa River brim with pickles, miso, and hand-carved crafts.

• Culture: Hida Folk Village (Hida-no-Sato) for gassho-zukuri farmhouses and carp-filled ponds; Takayama Jinya for a rare look inside a shogunate-era government house.
• Sake crawl: Sip flights at Harada or Funasaka breweries; look for the seasonal namazake. Pair with hida-gyu beef skewers and croquettes from street stalls.
• Hiking day trip: Kamikochi (bus ~1 hr 30 min via Hirayu Onsen) for flat riverside trails between Kappa-bashi and Myojin Pond, or longer hikes toward Tokusawa—peak clarity in late September.

Where to eat and drink (Takayama):

• Lunch: Hida beef nigiri at the Sanmachi stalls; Center4 Hamburgers (local cult favorite); Menya Shirakawa (shoyu ramen).
• Dinner: Heianraku (Japanese-Chinese slow food from a beloved couple), Suzuya (Hida beef sukiyaki or ho-ba miso grilled on magnolia leaf).
• Snacks: Mitarashi dango (soy-glazed rice dumplings) warm off the grill.

Where to stay (Takayama): Browse VRBO or Hotels.com. Mid-range: Best Western Hotel Takayama near the station. Ryokan splurge: Honjin Hiranoya Kachoan (kaiseki dinners, onsen baths).

Travel: Takayama to Kanazawa (morning of Day 11)

Scenic route via Shirakawa-go: Nohi Bus (~50 min to Shirakawa-go; optional 2–3 hr village stop), then another ~1 hr 15 min to Kanazawa. Total bus time ~2 hr 15 min; about $27–$35 USD. Alternatively, train via Toyama (~2–2.5 hr). Compare options on Trip.com Trains.

Kanazawa

Days 11–12: Gardens, samurai lanes, and gold leaf

Kanazawa escaped wartime bombing, preserving districts that feel like walking through woodblock prints. Kenrokuen Garden is among Japan’s “three great gardens,” a composition of borrowed scenery, reflective ponds, and stone lanterns.

• Don’t miss: Kenrokuen at opening for mirror-still waters; Kanazawa Castle Park; Nagamachi Samurai District’s earthen walls and Nomura-ke house.
• Market lunch: Omicho Market for ocean-fresh bowls—try Mori Mori Sushi’s conveyor delights or a piled-high kaisen-don.
• Arts: 21st Century Museum of Contemporary Art (playful installations) and traditional gold-leaf workshops.

Where to eat (Kanazawa): Curio Espresso & Vintage Design (Australian-Japanese coffee haven), Itaru Honten (lively izakaya), and Fuwari (seasonal small plates and local sake).

Where to stay (Kanazawa): See VRBO or Hotels.com. Mid-range: Kanazawa Tokyu Hotel (walkable to Kenrokuen). Upscale: Hotel Nikko Kanazawa. Budget: Guesthouse Nagonde near the station.

Travel: Kanazawa to Osaka (morning of Day 13)

Take Hokuriku Shinkansen to Tsuruga then Limited Express to Osaka (about 2 hr 45 min–3 hr). Expect $50–$70 USD; check departures via Trip.com Trains. Seats with power outlets are common—charge up and plan your foodie forays.

Osaka (+ Nara day trip)

Days 13–15: Street-food capital, neon nights, and a deer-filled detour

Osaka is swagger and hospitality rolled into one. Dotonbori’s giant signs (crabs, gyoza, the Glico runner) beckon toward takoyaki, okonomiyaki, and skewers galore. By day, explore a surprisingly rich museum scene; by night, eat your way down alleyways.

• Core sights: Osaka Castle Park, Umeda Sky Building’s floating garden, and the Nakanoshima museum district.
• Food crawl: Dotonbori and Shinsekai for kushikatsu (try two-dip rule: never double-dip). Kuromon Market for toro cubes, grilled scallops, and fresh fruit.
• Nara day trip (40–50 min by Kintetsu): Meet the bowing deer in Nara Park; visit Todai-ji’s Great Buddha; stroll Naramachi’s machiya townhouses.

Foodie experience (Osaka):

• Osaka Food Tour - 13 Delicious Dishes at 5 Local Eateries

  

  Guided grazing through true local haunts, from takoyaki to kushikatsu and regional sake—ideal for hungry explorers.

Where to eat (Osaka): Chibo for fluffy okonomiyaki, Daruma for classic kushikatsu, Endo Sushi at the fish market for dawn nigiri, and Tsuboya for hearty udon when you need a reset.

Where to stay (Osaka): Explore VRBO or Hotels.com. Mid-range: Hotel Sunroute Osaka Namba steps from Dotonbori. Upmarket: Swissotel Nankai Osaka above Namba Station or The St. Regis Osaka on Midosuji. Budget: Hotel Taiyo. Families: Universal Bay Condominium.

Optional Nara overnight (if you extend): Historic Nara Hotel, or value picks Super Hotel Lohas JR Nara Eki, Hotel Nikko Nara, and Guesthouse Nara Komachi.

Travel: Osaka to Hiroshima (morning of Day 16)

Shinkansen from Shin-Osaka to Hiroshima is about 1 hr 30 min; roughly $70–$100 USD depending on train type. Reserve seats via Trip.com Trains. Stow luggage in the carriage end or ship ahead to your Hiroshima hotel.

Hiroshima & Miyajima

Days 16–17: Reflection and island beauty

Hiroshima’s Peace Memorial Park and Museum are deeply affecting—plan unhurried time. Nearby, Okonomimura layers three floors of stalls specializing in Hiroshima-style okonomiyaki with noodles.

• Miyajima (Itsukushima): Ferry from Miyajimaguchi to see the “floating” torii gate, walk to Daisho-in Temple, and ride the ropeway toward Mount Misen for inland sea panoramas.
• Local bites: Grilled oysters, momiji manju (maple-leaf cakes), and lemon-infused sweets from nearby Setouchi.

Where to stay (Hiroshima): See VRBO or Hotels.com. Convenient picks: Sheraton Grand Hiroshima Hotel (by the station), RIHGA Royal Hotel Hiroshima (central), waterfront Grand Prince Hotel Hiroshima, or budget-friendly Santiago Guesthouse Hiroshima.

Travel: Hiroshima to Hakone (Odawara) (morning of Day 18)

Long but doable: Hiroshima → Shin-Osaka → Odawara by Shinkansen in ~4–4.5 hr; about $140–$170 USD. From Odawara, use the Hakone Tozan lines or bus to your ryokan. Check options on Trip.com Trains.

Hakone (Fuji Region)

Days 18–19: Onsen time, volcanic valleys, and art outdoors

Hakone is your exhale—onsen baths, cypress-scented air, and views of Mt. Fuji on clear days. The classic “loop” includes the Hakone Ropeway over Owakudani’s steaming vents, a pirate boat cruise on Lake Ashi, and the quirky, photogenic Hakone Open-Air Museum.

• Tips: Start early to beat lineups; try kuro-tamago (sulfur-black eggs) in Owakudani; book a room with private onsen if modesty or tattoos are a concern.
• Food: Yamashita’s soba near Gora for buckwheat noodles; bakery cafés by Miyanoshita for mountain-view lunches; kaiseki dinners at your ryokan.

Where to stay (Hakone): Browse options on VRBO or Hotels.com. Look for Gora or Hakone-Yumoto areas for easy transport and dining.

Travel: Hakone to Tokyo (evening Day 19 or morning Day 20)

From Hakone-Yumoto, take the Odakyu Limited Express “Romancecar” (~1 hr 20 min) or local lines via Odawara to Tokyo/Shinjuku (~1.5 hr). Budget about $15–$25 USD. For trains and timetables, see Trip.com Trains.

Tokyo Finale

Days 20–21: Last looks, last bowls

Use your final days to shop and savor: Ginza’s flagship stores and art galleries, Kappabashi for kitchen knives and ceramics, and Daikanyama T-Site for beautifully curated books and magazines.

• Museums/venues to fill gaps: Edo-Tokyo Museum (relocated exhibits update—check current status), Sumida Hokusai Museum (ukiyo-e masterworks), or a second neighborhood wander in Koenji for thrift and live music.
• Farewell eats: Afuri (yuzu-shio ramen), Tempura Kondo (reservation required), or a casual yakitori lineup at Torikizoku to keep things affordable and fun.

Extra Tokyo tours if you want more structure:

• Tokyo 6hr Private Tour with Government-Licensed Guide

  

  Tailor your last day: antiques in Yanaka, architecture in Omotesando, or culinary deep dives in Tsukiji Outer Market.

Where to stay (Tokyo — last nights): Re-visit Hotels.com or VRBO, or consider Disney-adjacent fun at Hilton Tokyo Bay for an easy-breezy last day.

Why this pacing works for you

You asked to start with five nights in Tokyo, then two in Kyoto, and head into the Alps—done. We added Kanazawa for a smooth exit from the mountains, Osaka for urban eats (with optional Nara), Hiroshima & Miyajima for history and island beauty, and Hakone to unwind before your flight home. With a mid-range budget, this route keeps most transfers under three hours and balances paid tours with free wander time.

Ballpark transport costs and passes

• Point-to-point tickets: Your route is well-suited to buying individual tickets; expect roughly $400–$600 USD total per person in long-distance rail.
• Seats: Reserve during busy times (Fri/Sun, holidays). Pack light or ship bags between hotels.
• Weather note (September): Warm and humid; monitor typhoon forecasts, especially for coastal or mountain days. Flexible plans help.

Optional Mt. Fuji day from Tokyo (earlier in the trip if skies look great):

• Mt Fuji and Hakone 1-Day Bus Tour Return by Bullet Train

  

  Clear-sky flexibility: lock this in when the weather looks best during your first Tokyo block.

Final flight out: Book return flights from Tokyo (HND or NRT) via Kiwi.com or Trip.com. Aim for a late-day departure on Day 21 to enjoy a leisurely final breakfast and souvenir run.

Accommodations quick links by city (browse and filter by budget):

• Tokyo: VRBO | Hotels.com
• Kyoto: VRBO | Hotels.com
• Takayama: VRBO | Hotels.com
• Kanazawa: VRBO | Hotels.com
• Osaka: VRBO | Hotels.com
• Hiroshima: VRBO | Hotels.com
• Hakone: VRBO | Hotels.com

In three weeks you’ll taste Tokyo’s futurism, Kyoto’s history, the mountain air of the Japanese Alps, Kanazawa’s artistry, Osaka’s joyful appetite, Hiroshima’s resilience, and Hakone’s restorative calm. It’s a route that respects your pacing and budget while delivering the breadth that makes Japan so addictive.