Japan has a way of folding centuries into minutes: a temple bell echoing over cedar forests, then a ramen slurp under neon. This 16-day itinerary anchors you in Osaka, Kyoto, and Tokyo—the classic trio—balancing food pilgrimages, serene hikes, spirited nightlife, and hands-on cultural experiences.

Osaka fuels the appetite with kuidaore—“eat until you drop”—and a reputation for humor and hospitality. Kyoto, the former imperial capital, invites you into tea houses, Zen gardens, and lantern-lit alleys where geisha glide at dusk. Tokyo is a universe of districts: shrines in the morning, art and coffee by day, izakaya and music by night.

Practical notes: pick up an IC card (ICOCA in Kansai, Suica/PASMO in Tokyo; mobile versions work on most phones), carry some cash, and wear easy-on shoes for shrine visits. Shinkansen seats between Kyoto and Tokyo run about ¥14,000 ($90–$110) one-way; local trains are inexpensive. Expect a mid-range daily food spend of ¥4,000–7,000 ($25–45) and use convenience stores for budget-friendly breakfasts.

Osaka

Osaka is Japan’s extrovert: billboards wink, grill smoke curls, and shouty vendors hand you skewers of crispy kushikatsu. Beyond the sizzle, you’ll find a powerful castle, riverside cycling, and a lush waterfall hike in Minoo Park perfect for photos and a taste of nature.

Base yourself in Namba or Umeda for easy train access and nightlife; head to Shinsekai for retro vibes and hearty eats. Foodies will love Kuromon Ichiba Market, while camera lovers get big-sky views from Umeda Sky Building’s Floating Garden.

Getting to Osaka (KIX/ITM) and around

• International/domestic flights: compare fares on Kiwi.com or Trip.com Flights.
• Airport to city: Nankai Airport Express to Namba (~45 min, ~¥1,000) or JR Haruka to Tennoji/Shin-Osaka (~35–50 min).
• Trains in Japan (for later legs): browse schedules/prices on Trip.com Trains.

Where to stay (mid-range friendly picks plus splurge and budget):

• Search apartments and homes: VRBO Osaka; hotels: Hotels.com Osaka.
• Splurge: The St. Regis Osaka (elegant, on Midosuji).
• Convenient: Swissotel Nankai Osaka (directly above Namba Station).
• Value near Dotonbori: Hotel Sunroute Osaka Namba.
• USJ area for theme-park fans: Hotel Universal Port or Universal Bay Condominium.
• Budget: Hotel Taiyo (simple, great for saving).

Days 1–5: Osaka base (street food, castle, hikes, nightlife) + day trips

• Dotonbori and Namba food crawl: Try takoyaki at Yamachan or Aizuya (original-style without sauce), okonomiyaki at Mizuno (griddle-front seating), and kushikatsu at Daruma (dip once!). Swing by Hozenji Yokocho’s stone lanes and mossy Hozenji Temple for atmospheric photos.
• Osaka Castle and park: Learn battle lore, the Toyotomi legacy, and climb the tower for city views. Pair with a riverside walk or a short cruise from Osaka-jo.
• Umeda Sky Building: Sunset over the metropolis from the open-air rooftop; nearby, Takamura Wine & Coffee Roasters for a refined pour-over or natural wine.
• Minoo Park hike: An easy, leafy 45–60 minute stroll to Minoo Waterfall; in season, snack on maple-leaf tempura from local stalls. Ideal for nature and photography.
• Shinsekai retro night: Neon, Showa-era arcades, and hearty skewers. For nightlife, venture to Amemura (America-mura) for craft beer at Beer Belly and cocktails at Bar Nayuta.
• Coffee/breakfast: Lilo Coffee Roasters (flight tasting), LiLo Coffee Kissa (kissaten vibe), LeBRESSO for thick-cut toast; Lunch: Endo Sushi at Osaka Central Fish Market (stand-up sushi), Tempura Tarojiro; Dinner: Kani Doraku (if you love crab), Torame Yokocho (multi-stall food alley), Harukoma Sushi in Tenma (lively, great value).

Osaka picks on Viator (book ahead)

• Food lovers: Osaka Private Food Tours by Local Foodies

  

• Iconic history: Osaka Castle Walking Tour + Tower Admission

  

• Theme-park thrills: Universal Studios Japan 1-Day Studio Pass + Express

  

• Hands-on culture: Samurai Show, Tea Ceremony, Traditional Activities

  

Optional day trips from Osaka: Nara (friendly deer, Great Buddha at Todai-ji), or Hiroshima & Miyajima (floating torii at Itsukushima). Consider Viator’s early-bird Nara tour to beat crowds, or the Hiroshima & Miyajima bullet train day trip.

Travel to Kyoto (morning, Day 6): Depart ~9:00 a.m. JR Special Rapid from Osaka Station to Kyoto Station in ~30 minutes (~¥590), or Shinkansen from Shin-Osaka in ~14 minutes (~¥1,420). Check times on Trip.com Trains.

Kyoto

Kyoto is where tradition lingers in the air: orange torii gates looping up a sacred mountain, tea whisked into froth, carp gliding beneath maple leaves. The city rewards early mornings, slow walks, and an eye for detail—kimono fabrics, incense smoke, a stone basin beaded with rain.

Explore by neighborhood: Arashiyama for bamboo and riverside gardens, Higashiyama for Kiyomizu-dera and old merchant lanes, and Fushimi for sake breweries. Evenings belong to Gion’s lantern-lit alleys and the slim restaurants of Pontocho.

Where to stay (great bases near subway/bus):

• Browse stays: VRBO Kyoto; hotels: Hotels.com Kyoto.
• Splurge riverside: The Ritz-Carlton, Kyoto.
• Stylish value: Hotel M's Est Shijo Karasuma, Hotel M's Plus Shijo Omiya.
• Classic comfort: Kyoto Tokyu Hotel, Kyoto Brighton Hotel.
• Budget/social: Piece Hostel Sanjo.

Days 6–9: Kyoto’s temples, tea, bikes, and night alleys

• Arashiyama morning: Walk the Bamboo Grove at first light, then Tenryu-ji’s landscaped garden and Okochi Sanso’s hilltop tea hut. Cross Togetsukyo Bridge and visit Iwatayama Monkey Park for city-overlooking photos.
• Fushimi Inari hike: Climb through thousands of vermilion torii to quiet viewpoints; detour to less-crowded trails near the summit. Reward yourself with coffee at Vermillion (great Inari views) and sample inari sushi nearby.
• Gion & Pontocho at dusk: Learn geiko and maiko customs, spot ochaya (tea houses), and dine on Kyoto-style kaiseki or yakitori. Respect local rules—no flash photos of geisha without permission and stay on public streets.
• Hidden Kyoto by e-bike: Glide to Kinkaku-ji (Golden Pavilion), Daitoku-ji’s mossy sub-temples, and back lanes where locals shop for pickles and tofu. It’s efficient and photogenic.
• Food & coffee: Breakfast at Smart Coffee (thick toast and Vienna coffee) or Inoda Coffee Main Shop (Kyoto classic). Lunch at Omen (udon near Ginkaku-ji) or Honke Daiichi-Asahi (ramen near Kyoto Station). Dinner at Gion Nanba (seasonal kyo-ryori), Yudofu near Nanzen-ji, or ramen at MENBAKA Fire Ramen (theatrical—and safe—flame-topped bowls).

Kyoto picks on Viator

• Arashiyama deep dive: Kyoto Arashiyama Walking Tour

  

• Tea and kimono culture: KYOTO Tea Ceremony with Kimono

  

• Evening flavors: Kyoto Night Foodie Tour in Gion (9+ dishes, sake)

  

• Two wheels, hidden lanes: Hidden Kyoto E-Biking Tour

  

Day trip options: Nara (Todai-ji’s Great Buddha, lantern-lined Kasuga Taisha) early in the morning for quieter photos; or northern Kyoto’s Amanohashidate “bridge to heaven” sandbar and thatched-roof Miyama village.

Travel to Tokyo (morning, Day 10): Nozomi Shinkansen from Kyoto to Tokyo Station ~2 hr 15 min; expect ¥13,500–¥14,500 ($90–$110) depending on seat/class. Reserve seats and check times on Trip.com Trains.

Tokyo

Tokyo is a mosaic of villages that grew into a galaxy. One minute you’re burning incense at Sensō-ji; the next you’re sipping a natural wine in Nakameguro or eating perfect shio ramen under a glowing lantern. It’s endlessly walkable and photogenic—especially at blue hour.

Plan by neighborhood: Asakusa for old Tokyo, Ueno for museums, Harajuku–Omotesandō for fashion and coffee, Shibuya for the crossing and clubs, and Odaiba/Toyosu for futuristic waterfronts. Save a day for Mt. Fuji and another for the beach at Kamakura/Enoshima if it’s warm.

Where to stay (near transit hubs):

• Search stays: VRBO Tokyo; hotels: Hotels.com Tokyo.
• High-end icons: The Peninsula Tokyo, The Ritz-Carlton, Tokyo, Aman Tokyo.
• Shinjuku convenience: Hotel Sunroute Plaza Shinjuku, Hotel Gracery Shinjuku, Keio Plaza Hotel Tokyo.
• For Disney days: Hilton Tokyo Bay.

Days 10–16: Tokyo icons, art, food, nightlife, and day trips

• Asakusa & Ueno culture: Sensō-ji’s thunder gate and Nakamise shopping street for traditional snacks; then Ueno Park for the Tokyo National Museum. Nearby coffee: Bridge Coffee & Ice Cream or Glitch Coffee (Jinbōchō).
• Shibuya & Harajuku: Cross the famous scramble (a postwar symbol of neon-era Tokyo) and take in the view from Shibuya Sky. Harajuku’s Takeshita Street for fashion, Meiji Shrine for forest calm. Coffee stops: Koffee Mameya Kakeru (tasting flights), Fuglen (Nordic coffee/cocktails), Onibus Coffee Nakameguro (canal views).
• Odaiba/Toyosu art & waterfront: Experience teamLab Borderless (Azabudai Hills) or teamLab Planets (Toyosu) for immersive light art; stroll Odaiba Seaside Park at sunset for Rainbow Bridge photos.
• Nightlife: Shinjuku’s Omoide Yokocho (grilled skewers, tiny counters) and Golden Gai’s six-bar lanes (visit early to avoid cover charges). For clubs, WOMB in Shibuya draws global DJs. Craft beer fans: Watering Hole (Shinjuku) or YYG Brewery.
• Food highlights: Breakfast at Bread, Espresso & (Omotesandō) or City Bakery at Shinagawa; Lunch ramen at Fuunji (shio/tsukemen) or Afuri (yuzu shio); Dinner at Maisen Aoyama (tonkatsu), Uogashi Nihon-Ichi (stand-up sushi), or Han no Daidokoro (wagyu yakiniku).
• Spas: Thermae-Yu (Shinjuku) for late-night soak, Spa LaQua (Tokyo Dome City) for pools and saunas, or Tokyo Toyosu Manyo Club for modern onsen with bay views.
• Beaches & hikes: Day trip to Kamakura/Enoshima (sand beaches, Buddha of Kotoku-in, surfer cafés); or hike Mt. Takao (well-marked trails, summit soba, and views of Fuji on clear days).

Tokyo picks on Viator

• Mt. Fuji scenic circuit: Mt. Fuji & Lake Kawaguchiko 1-Day Bus Tour

  

• Market culture & tastings: Tokyo Tsukiji Fish Market Food & Culture Tour

  

• Izakaya night: Best of Shinjuku: Izakaya Food Tour (14+ tastings)

  

• Capture the crossing: Private Photoshoot at Shibuya Crossing

  

Suggested day blocks across the 16 days

• Days 1–2 (Osaka): Dotonbori, Namba, Osaka Castle, Umeda Sky; food crawl and Osaka Castle tour.
• Days 3–4 (Osaka): Minoo Park hike, Shinsekai night; optional Universal Studios Japan day with Express Pass.
• Day 5 (Osaka): Flex day—Tennoji and Shitenno-ji Temple, Sumiyoshi Taisha, or a sushi/ramen cooking class.
• Day 6 (Travel to Kyoto): Morning train; afternoon in Nishiki Market and Gion.
• Days 7–8 (Kyoto): Arashiyama morning, tea ceremony, e-bike to hidden temples, Pontocho dinner.
• Day 9 (Kyoto): Fushimi Inari hike and Fushimi sake district tastings; evening geisha stories walk.
• Day 10 (Travel to Tokyo): Afternoon Asakusa and Sumida riverside; ramen dinner.
• Days 11–12 (Tokyo): Shibuya/Harajuku/Meiji Shrine, teamLab; Shinjuku izakaya night and Golden Gai.
• Day 13 (Tokyo): Mt. Fuji & Kawaguchiko day trip (views, pagodas, lakes).
• Day 14 (Tokyo): Museums in Ueno or Roppongi; spa soak at Thermae-Yu or Spa LaQua.
• Day 15 (Tokyo): Kamakura/Enoshima beach day (summer swim; year-round seaside cafés) or hike Mt. Takao.
• Day 16 (Tokyo): Coffee crawl and last-minute shopping (Ginza, Daikanyama T-Site); depart via HND/NRT—compare flights on Trip.com Flights or Kiwi.com.

Budget & practicalities

• Mid-range budgeting (excluding lodging): Breakfast ¥500–1,000, lunch ¥900–1,500, dinner ¥1,500–3,000; local transit ¥600–1,000/day; attractions/tours as chosen.
• Passes: A nationwide JR Pass usually isn’t cost-effective for this route alone; buy point-to-point tickets and use IC cards for metros/buses.
• Tipping: Not customary; a polite bow and “arigatō gozaimasu” goes far. Many small restaurants are cash-preferred.

From the glow of Dotonbori to the hush of moss gardens and the electricity of Shibuya at night, this route captures Japan’s rhythm—eat well, walk far, and savor the details. You’ll leave with memory cards full, taste buds satisfied, and a list of reasons to return.