Japan balances reverence and reinvention: thousand-year-old temples sit a subway ride from cutting-edge art, and quiet tea houses hide behind neon corners. In two weeks you’ll sample this full spectrum—from Tokyo’s skyscraper views and sushi counters to Kyoto’s moss gardens and lantern-lit alleys, finishing with Osaka’s sizzling griddles and late-night laughter.

Historically, the Tokaido Road tied these cities together; today, the shinkansen does it in hours. You’ll trace that route, pausing for a day under Mt. Fuji, strolling bamboo groves in Arashiyama, and grazing through markets that have fed locals for centuries.

Practical notes: pick up an IC card (Suica/PASMO/ICOCA) for effortless transit and carry a bit of cash for small shops. Book shinkansen seats during weekends and holidays. Spring cherry blossoms and fall foliage are wildly popular—reserve accommodations early and plan for crowds at marquee sights.

Tokyo

Welcome to a city of superlatives—18th-century shrines, Michelin-studded dining, and the world’s busiest crossing. Tokyo rewards curiosity: duck down an alley for yakitori smoke and laughter, then resurface for sky-high views and avant-garde retail.

Base yourself near Shinjuku, Shibuya, or Ginza to ride efficient trains everywhere and be steps from nightlife, shopping, and great food.

Days 1–5: Tokyo highlights, markets, and a Mt. Fuji day trip

• Classic Tokyo circuit: Meiji Shrine’s forested calm ➝ Omotesando’s design boutiques ➝ Harajuku Takeshita Street pop culture ➝ Shibuya Crossing (chaos since the 1930s streetcar era) and Hachiko statue. Cap with Shibuya Sky or Tokyo Skytree for sunset views.
• Old Tokyo: Asakusa’s Senso-ji (lantern, incense, and Nakamise snack street). Nearby, try a sit-down okonomiyaki at Sometaro (tatami mats, cast-iron griddles).
• Modern art & shopping: TeamLab digital art, Daikanyama book browsing, and Ginza’s depachika (food halls) for bento box perfection.
• Day trip to Mt. Fuji/Hakone: Cruise Lake Ashi, ride the ropeway over Owakudani, and return by bullet train to feel the country’s geography and genius for transit in one day.

Curated activities (book ahead):

• 1-Day Tokyo Bus Tour

  

  Efficient overview with Meiji Shrine, Skytree admission, and a bay cruise—ideal on Day 1 to orient yourself.

  
  
• Tokyo Tsukiji Fish Market Food and Culture Walking Tour

  

  Sample tamagoyaki, tuna, and regional pickles while learning how this market fed the city for generations.

• Tokyo Sumo Entertainment Show with Chicken Hot Pot and Photo

  

  In Ryogoku, watch wrestlers demonstrate technique, take photos, and enjoy a classic chanko-nabe hot pot.

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

  

  Reach Fuji’s 5th Station (weather permitting), cruise Lake Ashi, and speed back to Tokyo on the shinkansen.

Where to stay (Tokyo):

• Browse apartments and homes on VRBO Tokyo or hotels on Hotels.com Tokyo.
• The Peninsula Tokyo (Imperial Palace views, refined service, walkable to Ginza).
• Hotel Gracery Shinjuku (fun Godzilla head, compact but smart rooms in nightlife central).
• The Ritz-Carlton, Tokyo (Roppongi Hills panorama, sophisticated bars and spa).
• Aman Tokyo (serene minimalism and a destination onsen-style spa in Otemachi).

Eat & drink like a local:

• Coffee/breakfast: Fuglen (retro Nordic vibes, espresso and pour-overs), Onibus Nakameguro (neighborhood roastery with a canal stroll), and Kimuraya Ginza (since 1874—try anpan sweet bread).
• Lunch: Tonkatsu Maisen Aoyama (juicy kurobuta cutlets; go early), Uogashi Nihon-Ichi standing sushi (fast, quality nigiri), and Afuri (yuzu-shio ramen, bright and fragrant).
• Dinner: Kyubey Ginza (classic Edomae sushi—counter seats if you can), Nabezo Shinjuku (all-you-can-eat shabu-shabu with quality meats), and Omoide Yokocho yakitori (tiny grills, smoky lanes—bring cash).
• Night: Golden Gai’s micro-bars (each with a theme; small cover charges) or a highball in a hotel bar with skyline views.

Getting in & around:

• Flights to Tokyo (NRT/HND): Compare on Trip.com Flights and Kiwi.com. Typical round-trips from North America run ~$700–$1,300 depending on season.
• Airport to city: Narita Express or Keisei Skyliner to central Tokyo (about 40–60 minutes). Haneda is closer via monorail or Keikyu line.

Kyoto

Kyoto is the keeper of Japan’s classical arts. Over a thousand temples and shrines hide in its folds, from vermilion gates to moss gardens. Even the air seems slower—best enjoyed on foot or by bicycle along narrow lanes.

Split time between the eastern hills (Higashiyama, Gion) and the western hills (Arashiyama) to feel the city’s balance of ritual and nature.

Days 6–10: Temples, tea, and lantern-lit lanes

• Morning Day 6 travel: Tokyo ➝ Kyoto by Tokaido Shinkansen Nozomi (~2 hr 15 min). Unreserved/Reserved seats from ~¥14,000–¥15,500 (about $95–$105). Book seats on Trip.com Trains. Consider forwarding luggage (takkyubin) to your Kyoto hotel.
• East Kyoto day: Kiyomizu-dera’s stage, Sannen-zaka and Ninen-zaka stone lanes, Yasaka Pagoda, and sunset around Gion’s tea houses. Keep an eye out for apprentice geiko (maiko) on their way to evening appointments—observe respectfully.
• Fushimi Inari: Start early for quiet under thousands of torii gates. Reward yourself after with espresso at Vermillion Cafe or tea tastings in nearby Fushimi.
• Arashiyama: Dawn in the Bamboo Grove, Tenryu-ji’s gardens, and the Katsura River. If time allows, hop a romantic Sagano scenic railway ride.
• Markets & crafts: Nishiki Market for yuba (tofu skin), croquettes, and pickles; Aritsugu for chef knives; tea town Uji for matcha and Byodo-in’s Phoenix Hall.

Curated activities (book ahead):

• PERFECT KYOTO 1-Day Bus Tour

  

  Hit headline shrines and temples efficiently, including Kiyomizu-dera and Fushimi Inari.

• Kyoto Gion Geisha District Walking Tour

  

  Local guides explain geiko/maiko traditions as you wander lantern-glow lanes and wooden machiya houses.

• 10 Must-see Spots in Kyoto One Day Private Tour

  

  Customize a perfect day with a pro guide—ideal for families or small groups wanting flexibility.

Where to stay (Kyoto):

• See options on VRBO Kyoto or compare hotels on Hotels.com Kyoto.
• The Ritz-Carlton, Kyoto (Kamo River, impeccable service, great base for Higashiyama).
• Hotel M's Plus Shijo Omiya (value, transit-friendly, walkable to Nishiki).
• Kyoto Tokyu Hotel (quiet elegance near Nishi Hongan-ji).
• Piece Hostel Sanjo (social, design-forward, excellent for solo travelers).

Eat & drink like a local:

• Coffee/breakfast: % Arabica Higashiyama (single-origin espresso with a pagoda view), Vermillion Espresso at Fushimi Inari (post-hike pick-me-up), and Iyemon Salon (Japanese-style breakfast sets).
• Lunch: Honke Owariya (buckwheat soba since 1465), Katsukura (panko-crisp tonkatsu with mortar-ground sesame sauce), and Musashi Sushi (fun conveyor-belt spot when you need a quick bite).
• Dinner: Tempura Endo Yasaka (light, seasonal tempura courses), Pontocho Alley izakawa hop (small plates, river views), and Gion Nanba (kaiseki emphasizing Kyoto’s delicate flavors—reserve ahead).
• Sweet stops: Nakamura Tokichi (Uji matcha parfaits) and traditional wagashi near Yasaka Shrine.

Osaka

Osaka is Japan’s culinary soul—a place where the motto is kuidaore, “eat until you drop.” Friendly, outspoken locals, neon-lit billboards, and markets that never seem to sleep make it a perfect finale.

Base near Namba or Umeda for easy trains and a short walk to Dotonbori’s canal and the giant mechanical crab you’ve seen in photos.

Days 11–14: Street food, castles, and coastal day trips

• Morning Day 11 travel: Kyoto ➝ Osaka. JR Special Rapid (~30 min, about ¥570) or Shinkansen to Shin-Osaka (~15 min, ~¥1,420). Trains searchable/bookable via Trip.com Trains.
• Food crawl: Dotonbori for takoyaki and okonomiyaki; Shinsekai for retro vibes and kushikatsu (deep-fried skewers—dip once!).
• Culture & views: Osaka Castle’s museum, Umeda Sky Building’s floating garden observatory, and Amerika-mura’s indie fashion.
• Optional day trips: Himeji Castle’s brilliant white keep (about 1 hr by train), or Kobe’s Nada sake district for brewery tastings and marbled beef.
• Departure options: Fly out of KIX (Kansai International) via Trip.com Flights, or return to Tokyo by shinkansen (~2 hr 30 min, from ~¥14,500) if your flight departs there.

Curated activities (book ahead):

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

  

  Featured by Netflix—taste takoyaki, okonomiyaki, and more with a guide who knows the backstreets.

• Hungry Osaka Street Food Tour: 15 Dishes & 3 Drinks

  

  Award-winning evening feast through Shinsekai’s retro arcades—come hungry.

• Osaka Kickstart: Hotspots and Hidden Gems

  

  Get oriented fast—perfect for your first afternoon to bookmark neighborhoods and snack stops.

Where to stay (Osaka):

• Search stays on VRBO Osaka or Hotels.com Osaka.
• The St. Regis Osaka (Butler service on Midosuji, refined rooms near premier shopping).
• Swissotel Nankai Osaka (on top of Nankai Namba Station—airport and subway at your feet).
• Hotel Sunroute Osaka Namba (good value steps from Dotonbori).
• Hotel Universal Port (family-friendly base for Universal Studios Japan).

Eat & drink like a local:

• Coffee/breakfast: LiLo Coffee Roasters (serious beans in a tiny shop), Takamura Wine & Coffee Roasters (warehouse-chic), and A Happy Pancake (extra-fluffy soufflé pancakes).
• Lunch: Ajinoya or Mizuno (okonomiyaki on a steel teppan, order a mix with pork, squid, and shrimp), Endo Sushi (fresh cuts at the market), and Takoyaki Yamachan (gooey octopus balls with dashi-rich batter).
• Dinner: Kushikatsu Daruma (house rules on dipping, addictive skewers), Kani Doraku (crab set menus under the famous moving sign), and Hozenji Yokocho’s small izakaya lanes near a mossy temple.
• Late night: Stand-up bars in Tenma for craft beer and sake flights; sweets at Rikuro’s cheese cake if you crave dessert.

Logistics at a glance

• City order & trains: Tokyo (Days 1–5) ➝ Kyoto (Days 6–10) ➝ Osaka (Days 11–14). Book shinkansen and JR seats on Trip.com Trains. Tokyo–Kyoto ~2 hr 15 min (from ~¥14,000). Kyoto–Osaka 15–30 min (¥570–¥1,420). Osaka–Tokyo ~2 hr 30 min (from ~¥14,500).
• Flights: Fly into Tokyo (HND/NRT) and out of Osaka (KIX) to minimize backtracking; compare on Trip.com Flights or Kiwi.com.
• Transit tips: IC cards (Suica/PASMO/ICOCA) work on trains, subways, and convenience stores. Peak bloom and foliage seasons require early reservations for tours and restaurants.

Two weeks in Japan will sharpen your senses: temple bells at dawn, sizzling griddles at dusk, and a shinkansen whispering past tea fields in between. You’ll leave with a camera full of vistas and a palate tuned to umami, already planning a return to the lanes you didn’t finish wandering.