Japan blends ancient ritual with cutting-edge cool. From samurai-era shrines to LED-lit towers, this 14-day itinerary moves through three essential cities—Tokyo, Kyoto, and Osaka—linked by the ultra-punctual Shinkansen. You’ll taste regional specialties, explore serene gardens, and ride the rails like a local.

Tokyo offers big-energy neighborhoods and world-class museums; Kyoto slows the rhythm with cedar-scented temples and geisha lanes; Osaka turns up the flavor with sizzling grills and late-night snacks. Day trips—to Hakone’s hot-spring hills, Nara’s lantern-lined shrines, and Hiroshima’s moving memorials—deepen the story.

Practical notes: pick up a Suica/PASMO IC card for trains and convenience stores, and expect minimal tipping (it’s not customary). Book popular experiences (teamLab, tea ceremonies, high-demand restaurants) ahead, travel light or use luggage-forwarding, and time your visit for cherry blossoms (late March–early April) or autumn foliage (late Nov).

Tokyo

Days 1–6: Big-city icons, old-town lanes, and a Hakone escape

Arrive in Tokyo. Fly into HND (closer) or NRT. For flights, compare on Trip.com Flights or Kiwi.com Flights. From HND, the Tokyo Monorail to Hamamatsuchō is ~13 minutes; from NRT, the Narita Express to Tokyo Station is ~1 hour or the Skyliner to Ueno is ~41 minutes.

Classic Tokyo loop. Start in Asakusa’s Senso-ji (Tokyo’s oldest temple), then wander Nakamise shopping street for ningyo-yaki cakes. Cross the river to see the gleaming Asahi Beer Hall. Spend an afternoon in Ueno Park and the Tokyo National Museum for samurai armor and ukiyo-e. At sunset, head to Shibuya Sky for open-air views of a city that seems to go on forever, then descend to the famed Shibuya Crossing—organized chaos since the 1930s tram days.

Modern culture hits. Book teamLab Borderless (now at Azabudai Hills) for immersive digital art—plan ~2 hours. Stroll Omotesandō’s tree-lined avenue, pop into Nezu Museum’s quiet garden, then explore Harajuku from Takeshita Street’s crepe stands to the cedar forest of Meiji Shrine.

Old Tokyo neighborhoods. In Yanaka, pre-war lanes survived the 1923 quake and WWII—browse crafts on Yanaka Ginza and look for neighborhood cats. In Tsukiji’s Outer Market, arrive early to sample tamagoyaki, tuna skewers, and grilled scallops.

Day trip to Hakone (1 long day). Ride the Odakyu Romancecar from Shinjuku (85–90 min, ~¥2,400 reserved seat) or use the Hakone Freepass for loop transport on ropeways, pirate boats on Lake Ashi, and buses. On clear days, catch Fuji views near Togendai. Soak at a day-use onsen in Gora; respect tattoo policies (call ahead if needed).

• Breakfast & Coffee: Onibus Coffee (Nakameguro) for single-origin pourovers; Glitch Coffee (Jinbōchō) for light Nordic-style roasts; Bakery: Kimuraya Ginza’s anpan or Levain in Shibuya for sourdough.
• Lunch: Afuri (Harajuku) for citrusy yuzu-shio ramen; Tonkatsu Maisen (Aoyama Honten) with meltingly tender pork; Uogashi Nihon-Ichi (standing sushi) for quick, top-value nigiri.
• Dinner & Night: Bird Land (Ginza) for meticulous yakitori; Gonpachi Nishi-Azabu for convivial izakaya plates and a lively room; Tsukishima’s monjayaki at Iroha where you griddle your own savory batter at the table. For craft beer, try Popeye (Ryogoku) or Watering Hole (Shinjuku); for sake, ask for a junmai flight at Kurand Sake Market branches in Tokyo.
• Local gems: Omoide Yokocho’s tiny counter bars (go early); Kappabashi’s kitchen street for knives; Ghibli Museum in Mitaka (tickets must be prebooked well in advance).

Where to stay (Tokyo): Browse apartments and townhouses on VRBO Tokyo or compare hotels by neighborhood on Hotels.com Tokyo. Base in Shinjuku or Shibuya for nightlife and transit; Nihonbashi for quieter, refined stays near Tokyo Station.

Getting around: Trains and subways reach almost everywhere—tap in with Suica/PASMO. Consider a 24/48/72-hour Tokyo Subway Ticket for heavy sightseeing days. Taxis are clean and reliable but pricier; late-night surcharges apply.

Morning of Day 7: Tokyo → Kyoto. Take the Tokaidō Shinkansen from Tokyo or Shinagawa to Kyoto. Nozomi trains take ~2 hr 15 min; one-way fares typically ¥13,800–¥15,000 (~$95–$105). Reserve seats during peak seasons. Check times and book through Trip.com Trains. Use luggage-forwarding (takkyubin) for a smooth transfer (~¥2,000 per suitcase, overnight).

Kyoto

Days 7–10: Temples, tea, and riverside lanes

Temple highlights. Begin at Fushimi Inari Taisha—thousands of vermilion torii curve up Mount Inari; go early for quiet photos. Kiyomizu-dera’s wooden stage floats over a forested valley; continue through Sannen-zaka and Ninen-zaka stone lanes to Gion. Don’t miss Kinkaku-ji (the Golden Pavilion) and the zen rock garden at Ryōan-ji.

Arashiyama day. At dawn, the bamboo grove whispers; step into Tenryū-ji’s gardens, then stroll the Katsura River to the Iwatayama Monkey Park for panoramic views. In the afternoon, the Sagano Scenic Railway (retro train) is a delight, especially during autumn foliage.

Tea and traditions. Book a small-group tea ceremony (Camellia in Gion is intimate and English-friendly) to learn whisking techniques and etiquette. In the evening, wander Ponto-chō Alley’s lantern-lit restaurants; you may glimpse geiko and maiko moving between appointments in Gion.

Sake and Uji option. Head to Fushimi’s sake district for tastings and the Gekkeikan Okura Sake Museum. Or take a half-day to Uji (17 minutes by rapid train) for matcha, Byōdō-in’s Phoenix Hall, and riverside cafés.

• Breakfast & Coffee: % Arabica (Higashiyama) for espresso with a pagoda view; Inoda Coffee Main Shop for retro kissaten vibes; Vermillion café by Fushimi Inari for calm pre-hike cups.
• Lunch: Nishiki Market grazing—Miki Keiran’s rolled omelet, grilled eel skewers, and fresh yuba; Wajōryōmen Sugari for fragrant ramen in a renovated machiya; Yudōfu Sagano near Nanzen-ji for tofu-centric temple cuisine.
• Dinner: Gion Nanba for seasonal kaiseki (book ahead); Mishima-tei near Nishiki for sukiyaki with marbled wagyū; Menbaka Fire Ramen (near Nijō Castle) for a theatrical, smoky soy-broth show—secure a slot.
• Drinks & Night: Sake Bar Yoramu (natural-leaning list with guidance), L’Escamoteur for whimsical cocktails, and Beer Komachi for craft beer plus small plates.
• Local gems: Philosopher’s Path in cherry blossom season; Heian Shrine’s garden for irises in early summer; hand-dyed textiles and incense shops in Teramachi.

Where to stay (Kyoto): Traditional townhouses and family pads on VRBO Kyoto. For hotels from Gion to Kyoto Station, browse Hotels.com Kyoto. Staying near Sanjō/Kawaramachi offers easy dining; Kyoto Station is best for day trips.

Morning of Day 11: Kyoto → Osaka. JR Special Rapid trains reach Osaka Station in ~30 minutes (~¥570). The Shinkansen from Kyoto to Shin-Osaka takes ~14 minutes (~¥1,420) if you prefer reserved seating. See schedules on Trip.com Trains.

Osaka

Days 11–14: Street food capital, neon nights, and two powerful day trips

Feel Osaka’s energy. Start at Osaka Castle’s grounds and museum for a swift history of daimyo battles. Nearby, sample market snacks at Kuromon Ichiba—fatty tuna, sea urchin, and seared wagyū. At night, Dōtonbori’s giant signboards (crab, octopus, the iconic Glico runner) flicker above canalside promenades.

Views and retro corners. Rise to the Umeda Sky Building’s Floating Garden Observatory for sunset panoramas. In Shinsekai, try nostalgic games around Tsūtenkaku Tower, then dip into kushikatsu shops where deep-fried skewers are dunked into communal sauce—no double-dipping.

Day trip: Nara (12th day or 13th morning). JR or Kintetsu trains reach Nara in 35–50 minutes (~¥570–¥720). Visit Tōdai-ji’s Great Buddha, wander Nara Park with (polite) deer crackers, and walk the lantern-lined path to Kasuga Taisha. Lunch at Edogawa Nara (grilled eel over rice), sweets at Nakatanidō (lively mochi-pounding), and coffee at Rokumei Coffee Roasters.

Day trip: Hiroshima & Miyajima (full day). From Shin-Osaka, the Shinkansen to Hiroshima is ~1 hr 25 min on Nozomi (~¥10,500–¥11,500 one-way). Take the tram to the Peace Memorial Park and Museum (powerful, sobering). Then ferry to Miyajima (10 minutes, ~¥200) to see the vermilion torii of Itsukushima Shrine rising from the sea; ride the ropeway to Mt. Misen for Inland Sea views. Try Hiroshima-style layered okonomiyaki at Nagataya or Mitchan Sohonten, and oysters at Yakigaki no Hayashi on Miyajima.

• Breakfast & Coffee: Endō Sushi (Osaka Central Fish Market) opens early—order the 5-plate set; LiLo Coffee Roasters (Americamura) for balanced espresso; Mel Coffee Roasters (Kitahama) for light-roast pour-overs.
• Lunch: Dōtonbori takoyaki at Aizuya or Wanaka; okonomiyaki at Mizuno (long lines, worth it) or Ajinoya (fluffier style); ramen at Jinsei JET (shoyu-chicken base) or Hanamaruken (melting braised pork rib).
• Dinner & Night: Kushikatsu Daruma (Shinsekai classic), Izakaya Toyo (Kyōbashi) for blowtorched tuna and banter, and Beer Belly (Higobashi) for Minoh craft brews. For a refined finish, Takamura Wine & Coffee offers rare bottles with a stylish warehouse vibe.
• Local gems: Sumiyoshi Taisha’s arched bridge; teamLab Botanical Garden Osaka (Nagai Park) after dark; Nakazakichō’s indie boutiques in preserved alleys.

Where to stay (Osaka): For nightlife, base near Namba or Shinsaibashi; for transit, consider Umeda/Osaka Station. See apartments on VRBO Osaka and hotels on Hotels.com Osaka.

Departing Japan. From Osaka, fly out of KIX or Itami (ITM). Compare fares on Trip.com Flights or Kiwi.com Flights. Nankai’s Rapi:t from Namba to KIX is ~38 minutes (~¥1,450); JR Haruka from Tennoji to KIX is ~35–40 minutes.

Suggested 14-Day Flow (by blocks)

• Days 1–6: Tokyo — Asakusa, Ueno museums, Shibuya/Harajuku/Meiji Shrine, teamLab Borderless, Yanaka, Tsukiji + Hakone day trip.
• Day 7 (AM): Tokyo → Kyoto by Shinkansen; Days 7–10: Kyoto — Fushimi Inari, Kiyomizu-dera, Gion/Ponto-chō, Arashiyama bamboo, Kinkaku-ji, tea ceremony; optional Uji/Fushimi sake.
• Day 11 (AM): Kyoto → Osaka by JR; Days 11–14: Osaka — Osaka Castle, Dōtonbori, Umeda Sky, Shinsekai; Nara day trip and Hiroshima & Miyajima day trip.

Two weeks in Japan gives you Tokyo’s creative charge, Kyoto’s contemplative calm, and Osaka’s delicious swagger—plus day trips that show the country’s range. You’ll return with temple bells in your ears, neon in your camera roll, and a new obsession with noodles.