Japan is a love story between old and new: a place where thousand-year-old shrines share the map with neon towers and perfect bowls of ramen. In five days, this itinerary traces a romantic arc from Tokyo’s glittering skyline to Kyoto’s lantern-lit lanes, with a delicious detour into Yamanashi’s vineyards to taste Japan’s signature Koshu wine.

Food and drink are the throughline. Think morning pour-overs at destination coffee bars, lunch among market stalls, and evenings that wander from izakaya grills to craft breweries and natural wine bars. You’ll ride the Shinkansen, glide past rice fields, and tuck into kaiseki that condenses seasons into a dozen small marvels.

Practical notes: Reserve popular restaurants and tastings in advance—spaces are small and coveted. Load a mobile Suica/PASMO for transit, carry some cash for markets, and plan for luggage delivery between cities if you like to travel light. Spring and autumn are peak; in any season, pack layers and comfortable shoes for temple steps and market strolls.

Tokyo

Tokyo thrills: soaring viewpoints, alleyway eateries, and a specialty coffee scene that treats beans like fine wine. Shibuya’s famous scramble funnels thousands across every light cycle, while quieter corners—Nakameguro’s canal, Daikanyama’s boutiques—set the mood for hand-in-hand wandering.

Food here ranges from counter sushi to modern izakaya that reinvent bar snacks with finesse. The city also leads Japan’s craft beer revival, and its natural wine bars are intimate, buzzy, and perfect for date night conversation.

• Don’t miss: Shibuya Sky’s 360° rooftop, Asakusa’s Senso-ji, a Sumida River glimpse, and an evening in memory-laden Omoide Yokocho.
• Coffee hits: Koffee Mameya Kakeru (curated tasting flights), Onibus Coffee Nakameguro (canal-side), Glitch Coffee (competition roasts).
• Craft beer & wine: Hitachino Brewing Lab (taps by the tracks), Baird Beer Harajuku, Yona Yona Beer Works; for wine, Ahiru Store (natural wine bistro) and Winestand Waltz (standing bar).

Where to stay (mid-range picks): Look for central bases in Shibuya, Ginza, or Tokyo Station for easy transit. Browse stays on VRBO Tokyo or compare hotels on Hotels.com Tokyo.

Getting in: Fly into HND (closest) or NRT and take rail into the city. Search flights on Trip.com Flights or Kiwi.com. From HND to central Tokyo: ~30–40 minutes by train; from NRT: ~60 minutes by express services.

Day 1: Arrival, Canal Strolls, and Skyline Romance

Morning: In transit to Tokyo.

Afternoon: Check in and ease into the city with a Nakameguro canal walk. Grab a cappuccino at Onibus Coffee (tiny roastery with a cedar facade) and share a seasonal pastry at Higuma Doughnuts just nearby.

Evening: Head to Shibuya. Time sunset at Shibuya Sky’s open-air deck for jaw-dropping views—on clear days, you’ll spot Fuji. Dinner at Uogashi Nihon-Ichi (stand-up sushi; fresh, fast, affordable) or try an izakaya such as Toriyoshi in Shibuya for charcoal-grilled yakitori and small plates. Cap the night with craft beer at Baird Beer Harajuku (Japanese ales; balcony seats) or a couple of pours at Winestand Waltz (tiny, romantic, natural wines).

Day 2: Markets, Temples, and teamLab After Dark

Morning: Dive into Tsukiji Outer Market for tamagoyaki skewers and seared tuna belly; for sit-down sushi without splurge, Sushi Daiwa’s successors nearby or Sushisei counters deliver quality at mid-range prices. Follow with a curated tasting at Koffee Mameya Kakeru, where baristas talk processing and terroir like sommeliers.

Afternoon: Explore Asakusa’s Senso-ji and the Nakamise arcade for rice crackers and ningyo-yaki cakes. Lunch at Tempura Daikokuya (light, sesame-oil tempura) or Menya Musashi for a ramen detour. Stroll to Kuramae—dubbed “Tokyo’s Brooklyn”—and sip a pourover at Leaves Coffee Roasters.

Evening: Immerse yourselves at teamLab Borderless (Azabudai Hills)—interactive light art that feels like walking through a dream. For dinner, slide into an izakaya in Roppongi like Warayakiya (seared bonito over straw fire, smoky and theatrical). Finish with Hitachino Brewing Lab in Akihabara for Japanese-style ales or TY Harbor’s riverside taps if you prefer a waterside walk.

Day 3: Yamanashi Wine Day Trip (Koshu Country)

Morning: Take a JR Limited Express from Shinjuku to Katsunuma-Budōkyō (1.5–2 hours; ~¥2,500–3,500 each way; reserve seats for comfort). Pre-book tastings at two to three wineries: Chateau Mercian Katsunuma (museum-like grounds and flights highlighting Koshu’s citrus-mineral profile), Kurambon Winery (small, family-run; intimate tastings), and Aruga Branca/Katsunuma Jozo (benchmark Koshu styles).

Afternoon: Enjoy a winery lunch—many offer light plates or nearby cafés serve hoto noodle stew and grape-fed pork. Tasting flights typically run ¥500–¥2,000; designate a driver or stick to taxis between wineries (walkable clusters exist, but hills are real). If time allows, soak your feet at a public footbath in nearby Isawa Onsen for a romantic pause.

Evening: Train back to Shinjuku. Dinner at Ahiru Store in Shibuya (natural wine blackboard list, rustic pâtés, house-baked bread; expect a wait) or Uobei for a fun, budget-friendly conveyor experience. Nightcap at Goodbeer Faucets (broad tap list) before packing for Kyoto.

Kyoto

Kyoto whispers rather than shouts. Wooden machiya townhouses glow in Gion, shrine gates climb mountainsides, and tea houses fold time like origami. The city rewards early starts and meandering walks more than checklists.

Culinarily, Kyoto leans seasonal and delicate: kaiseki, temple shōjin ryōri, and obanzai home cooking. The craft beer scene is lively too, with taprooms and bottle shops tucked into covered arcades and quiet streets.

• Essentials: Higashiyama lanes, Kiyomizu-dera, sunset by Yasaka Pagoda, and the Philosopher’s Path if you love contemplative strolls.
• Coffee & bites: % Arabica (Higashiyama/Arashiyama), Weekenders Coffee (courtyard roaster), Kurasu Kyoto (beans and toasties).
• Brews & bars: Kyoto Brewing Co. Taproom (weekends), Beer Komachi (tiny, delicious), Bungalow (craft beer and natural wine under an awning—great for standing dates).

Where to stay (mid-range picks): Base in Gion, Kawaramachi, or near Kyoto Station for transit. See options on VRBO Kyoto or compare on Hotels.com Kyoto.

Getting from Tokyo to Kyoto: Ride the Tokaido Shinkansen (Nozomi ~2 hr 15 min; ¥13,910–¥14,500 one way). Book seats via Trip.com Trains. Flying is possible but rarely faster center-to-center.

Day 4: Shinkansen to Kyoto, Higashiyama Romance

Morning: Depart Tokyo by Shinkansen around 8–9 a.m. and arrive before lunch. Drop bags at your hotel and head for a coffee at % Arabica Higashiyama, where the bar faces the street—great for people-watching.

Afternoon: Walk the preserved lanes of Ninenzaka and Sannenzaka to Kiyomizu-dera; the wooden stage overlooks a sea of maple and cherry trees. Lunch on obanzai at Omen Kodaiji (udon with seasonal sides) or Okutan for tofu-focused temple cuisine.

Evening: Reserve a counter at Giro Giro Hitoshina (inventive multi-course kaiseki at friendly prices) or dine riverside along Pontocho Alley. After dinner, sip Kyoto-made ales at Beer Komachi (cozy, couple-friendly) or taste both sake and beer at Kizakura’s bar in the Fushimi area if you’re keen to compare flavors.

Day 5: Arashiyama Dawn, Fushimi Gates, and Departure

Morning: Go early to Arashiyama’s bamboo grove for a near-private walk, then visit Tenryu-ji’s gardens. Espresso at % Arabica Arashiyama before a romantic riverside brunch—Shoraian offers a refined tofu course with Katsura River views, while Yudofu Sagano keeps it simpler and gentler on the wallet.

Afternoon: Head to Fushimi Inari Taisha; climb through vermilion gates as far as time allows for sweeping city views. If schedules permit before your flight/train, swing by Kyoto Brewing Co. Taproom (open afternoons on weekends) for a shared flight, or pick up station ekiben lunch boxes for the journey.

Evening: Departure day—plan for an afternoon exit. For flights from Kansai (KIX) or Itami (ITM), browse Trip.com Flights or Kiwi.com. If you’re continuing by rail, book seats via Trip.com Trains.

Budget notes (50/100, mid-range): Expect ~¥12,000–¥18,000 per person per day for meals, coffee, and drinks depending on splurges; tastings add ¥1,000–¥4,000. Shinkansen Tokyo–Kyoto is ~¥14,000 each way. Free sights abound; save for one or two marquee dinners and the winery day.

Reservations to make: Shibuya Sky sunset slot, teamLab Borderless timeslot, Yamanashi winery tastings, Giro Giro Hitoshina, and any tiny natural wine bars you’ve set your heart on.

In five days you’ll taste Japan from bean to barrel: meticulous coffee, sushi and tempura, Koshu whites among the vines, and Kyoto’s seasonal plates. Between Tokyo’s glitter and Kyoto’s grace, this romantic route balances flavor, culture, and just enough travel to keep things exciting.