⚡ Before You Go — Essentials
🍽️ Fine Dining in Tokyo — Book NOW
Tokyo's top restaurants book out weeks to months in advance. For Michelin-starred omakase and kaiseki, use Tableall.com, Omakase.jp, or Pocket Concierge immediately — these are the trusted English-language platforms for hard-to-book Tokyo restaurants. Sukiyabashi Jiro Honten requires an invitation via hotel concierge. Nihonryori RyuGin, Narisawa, and Quintessence can sometimes be booked 4-8 weeks ahead. Your hotel's concierge (especially at Park Hyatt or Aman) can often pull strings. Start booking the moment your travel is confirmed.
🏨 Where to Stay — Luxury Hotels
For a family of 3-4, we recommend: **Park Hyatt Tokyo** (Shinjuku, floors 41-52, "Lost in Translation" hotel — spectacular views, top-tier pool and spa, ¥60,000-90,000/night), **Aman Tokyo** (Otemachi, temple-like calm in the heart of the city, ¥120,000+/night), or **The Peninsula Tokyo** (Hibiya, Michelin-starred restaurant in-house, perfect for Ginza/Tsukiji days). All three provide concierge services that will help secure restaurant reservations and car transfers.
🌤️ May in Tokyo — Perfect Timing
May is arguably the best month to visit Tokyo. Daytime temperatures: 20-26°C (68-79°F), low humidity, clear skies. The city's parks are vivid green. Irises bloom in the Imperial Palace East Gardens. Yoyogi Park is at its most beautiful. Crowds are moderate compared to cherry blossom season (March-April). No typhoons yet (those come September-October). Pack light layers — evenings can be cool (15-18°C). One umbrella per family is wise; May has occasional brief showers.
🚇 Getting Around Tokyo
For a fine-dining family trip: use a mix of Tokyo Metro and taxis/private transfers. Get a Suica or Pasmo IC card at the airport for trains — tap in/tap out. For dinner evenings (especially after wine or sake), budget ¥1,500-2,500 per taxi ride — they're clean, reliable, and the driver will find any address. Your hotel concierge can arrange private car services for airport transfers and special evenings. Google Maps is flawless for navigation in Tokyo.
💴 Money & Tipping
Japan is still largely cash-preferring, especially at traditional and upscale restaurants. Hit a 7-Eleven or Japan Post ATM on arrival — they reliably accept foreign cards. Budget ¥50,000-80,000 per person per day (meals, taxis, shopping). Tipping is NOT done in Japan — it can even cause offense. Saying "oishii" (delicious) or "subarashii" (wonderful) is the correct way to compliment a chef. Fine dining restaurants may add a 10-15% service charge; check the menu.
Arrive in Tokyo — First Night Elegance
Touch down and check into one of the world's great hotels. Shinjuku is the natural home base for this trip — central, surrounded by food and culture, with the vast Shinjuku Gyoen garden nearby. Tonight's dinner is a statement: L'Effervescence in Nishi-Azabu, a French-Japanese restaurant that earns its Michelin stars on every plate. Your first night in Tokyo should feel like an arrival.
Arrive at Narita or Haneda — Transfer to Hotel
From Narita Airport, the Narita Express (N'EX) runs direct to Shinjuku in about 90 minutes — comfortable, punctual, perfectly designed. From Haneda, the Keikyu Line connects to Shinagawa, then Yamanote Line to Shinjuku (about 45 minutes). Your hotel concierge can arrange a private car transfer if preferred — book in advance. Check in, drop your bags, and let Tokyo begin.
Shinjuku Gyoen National Garden — Afternoon Walk
A 10-minute walk from the Park Hyatt, Shinjuku Gyoen is one of Japan's finest gardens — 144 acres of French formal gardens, English landscape lawns, and a traditional Japanese strolling garden. In May, the garden blazes with azaleas, irises, wisteria, and fresh green foliage. The French garden's central lawn is perfect for a post-flight rest — lie on the grass and let the jet lag dissolve.
Shinjuku at Twilight — Kabukicho Tower & Golden Gai
Before dinner, take a 30-minute evening walk through Shinjuku's contrasts. The Kabukicho entertainment district is spectacular at twilight — the new Kabukicho Tower rises 48 floors and its ground-floor entertainment zone is a spectacle worth seeing even without entering. Then find your way to Golden Gai — a tiny labyrinth of over 200 miniature bars packed into six narrow alleys. Each bar seats only 5-8 people. It's a Tokyo institution, and the atmosphere (neon signs, jazz floating from open doors, decades of history in every splinter) is unlike anywhere on earth.
Sacred Tokyo — Senso-ji, Old Edo & Kaiseki at RyuGin
Today is Tokyo's oldest soul. Rise early and arrive at Senso-ji Temple in Asakusa before 8am — the city's oldest temple complex, golden and incense-filled, belongs to early risers. Walk Nakamise shopping street, cross the river to the Sumida River walk, and then spend the afternoon in Ueno. Tonight is a pinnacle: Nihonryori RyuGin, where chef Seiji Yamamoto has held three Michelin stars for years and runs the most creative kaiseki program in Japan.
Senso-ji Temple Complex — Asakusa at Dawn
Tokyo's oldest and most magnificent temple. Enter through Kaminarimon (Thunder Gate) with its enormous red and black lantern, walk the 250-meter Nakamise shopping street, and arrive at the main temple hall where incense smoke curls into the sky. Early morning is essential — by 9am the crowds are thick; by 7am you may have the temple courtyard almost to yourself. The light at dawn through the incense smoke and ancient wooden structures is one of Tokyo's great visual experiences.
Nakamise Shopping Street & Surroundings
The covered shopping arcade leading to Senso-ji has 89 shops selling traditional crafts and souvenirs — the best in Tokyo for quality traditional items. Look for: handmade tenugui (cotton hand towels with beautiful woodblock-print designs), traditional lacquerware, Japanese fans, and genuine ningyo-yaki (small sponge cakes shaped like Senso-ji symbols, filled with red bean paste). Walk the side streets behind the shopping street — the backstreets of Asakusa feel like old Edo-era Tokyo.
Tokyo National Museum — Ueno Park
The Tokyo National Museum is one of the world's great museums — and in May the Ueno Park setting is at its most beautiful. The museum's 110,000-object collection spans 5,000 years of Japanese art and cultural history. The Honkan (Japanese Gallery) main building is essential: samurai armor that makes you stop breathing, Buddhist sculpture of heartbreaking beauty, ancient ceramics, and calligraphy scrolls. The Heiseikan gallery's archaeological exhibits show Japan from the stone age to the imperial era. Give it 2-3 hours.
Yanaka — Old Tokyo Backstreets
A 20-minute walk from Ueno, Yanaka is one of Tokyo's best-preserved old neighborhoods — it survived both the 1923 earthquake and the WWII firebombing, and its wooden temple alleys and shotengai (old shopping street) feel like 1960s Japan. Yanaka Ginza is a covered street with local butchers, tofu makers, ceramic shops, and the most neighborhood-local atmosphere in central Tokyo. Cats sit in doorways. Old women tend flower pots. It's everything.
Roppongi Hills — Pre-Dinner Walk
Take a 30-minute stroll through Roppongi Hills before dinner — the development built around the Mori Tower is one of Tokyo's most sophisticated mixed-use neighborhoods. The Mori Art Museum (floors 52-53 of Mori Tower) is often spectacular. The outdoor Tokyo City View observatory gives a 360-degree look at the glittering city at dusk. Roppongi is also where RyuGin is located, so you're already in the right neighborhood.
Meiji Shrine, Harajuku Energy & Narisawa
A day of beautiful contrasts: the ancient forest silence of Meiji Shrine, the exuberant kawaii culture of Harajuku, the architectural elegance of Omotesando, and one of the most interesting lunch experiences in Asia — Narisawa, where chef Yoshihiro Narisawa has invented his own cuisine called 'innovative Satoyama.' The evening brings Shibuya's legendary scramble crossing, and dinner at the intimate, thrilling Florilège.
Meiji Jingu Shrine — Forest Walk
One of Tokyo's most peaceful and profound experiences. The 70,000 trees surrounding Meiji Shrine — donated from across Japan when the shrine was built in 1920 — have grown into a forest so tall and dense that it feels impossible this is central Tokyo. Walk the gravel path from the outer torii gate through the trees to the main shrine complex. In May, the iris garden (Kitanomaru side of the shrine) is in spectacular bloom — 1,500 irises of 150 varieties. Dedicated to Emperor Meiji and Empress Shoken, the shrine has a profound, meditative quality.
Harajuku & Takeshita Street
A 5-minute walk from Meiji Shrine, Takeshita Street (竹下通り) is the most concentrated expression of Japanese kawaii culture on earth — a 350-meter pedestrian alley packed with crepe stands, rainbow cotton candy, idol merchandise, and fashion that defies categorization. For families, it's joyful and genuinely fun. Try a Harajuku crepe from the Marion Crepes original location (since 1976). The energy is infectious and the people-watching is spectacular.
Omotesando — Architecture & Shopping
A 5-minute walk from Harajuku, Omotesando is Tokyo's most architecturally significant boulevard — a wide, zelkova-tree-lined avenue flanked by flagship stores designed by the world's top architects. The buildings alone are worth the walk: Prada by Herzog & de Meuron (glass mesh), Dior by SANAA, Tod's by Toyo Ito (concrete trees). The side streets (Ura-Harajuku, Minami-Aoyama) contain Tokyo's best concept stores, galleries, and cafés.
Shibuya Crossing & Scramble Square Observatory
The Shibuya Scramble Crossing is the most famous intersection on earth — up to 3,000 people surge from all directions simultaneously when the lights change. Experience it at street level (it's gentler than it looks), then head up to Shibuya Sky (the Scramble Square skyscraper's rooftop observatory at 229m) for an aerial view of the crossing and the entire city. In late afternoon, the view from the outdoor rooftop as the city lights turn on and the sky shifts from gold to indigo is unforgettable.
Tsukiji Morning, Ginza Afternoon & Omakase Night
Today's crown jewel is the evening: an omakase sushi dinner at one of Tokyo's top counters — 20 courses of nigiri composed piece by piece in front of you by a chef who has spent decades perfecting each cut. But first: the legendary Tsukiji Outer Market at its best hour, followed by the Imperial Palace East Gardens in May bloom, and Ginza shopping in the afternoon. teamLab Planets as a digital interlude before the main event.
Tsukiji Outer Market — Premium Seafood Breakfast
The Inner Market moved to Toyosu in 2018, but the Outer Market remains one of Tokyo's great food experiences — a dense grid of stalls selling the freshest seafood, tamagoyaki, pickles, dashi, and premium ingredients. Arrive at 8:30-9am when stock is freshest. This is a premium grazing experience — budget ¥3,000-4,000 per person and move from stall to stall. The ritual of eating fresh uni (sea urchin) on a spoon from a Tsukiji stall is something you carry with you forever.
Imperial Palace East Gardens
A 15-minute walk from Tsukiji, the Imperial Palace East Gardens are built on the site of Edo Castle's inner compound — the most historically significant land in Japan. In May, the gardens are spectacular: irises in the traditional Japanese garden, peonies and roses along the main paths, and the ancient stone foundations of Edo Castle's towers overgrown with soft moss. The Ninomaru Garden pond reflects the ancient trees above. This is one of Tokyo's most beautiful and underrated spots.
Ginza — Serious Shopping
Tokyo's most prestigious shopping district — the Fifth Avenue of Asia, but better curated and more interesting. The anchor stores (Mitsukoshi, Matsuya) have excellent basement food halls (depachika) that are themselves worth visiting. Essential stops: Itoya (12-floor stationery paradise), Ginza Six (rooftop garden + every luxury brand), Dover Street Market Ginza (the most interesting fashion concept store in Tokyo), and the craft-focused Okuno Building where independent artists and designers rent tiny galleries.
teamLab Planets — Digital Art Immersion
Book your timed ticket in advance online — teamLab Planets is the world's most extraordinary immersive art experience and sells out weeks ahead. You enter barefoot and wade through shallow water into rooms where the digital art surrounds you completely: a universe of floating flowers, shimmering light spheres you can bat with your hands, a mirrored room where infinity reflects in every direction. The 'floating flowers' room in spring/summer mode is particularly stunning — cherry blossoms replaced by seasonal arrangements. Absolutely unmissable for families.
Farewell Morning — Nakameguro Canal & Final Kaiseki
Your last morning in Tokyo belongs to Nakameguro — a neighborhood of narrow canal paths, impeccable coffee shops, and some of the city's most beautiful boutiques. In May, the Meguro River canal is lined with lush green trees and the neighborhood hums with a relaxed, creative energy. Store your bags, take one last long walk, have a final fine farewell lunch, and then make for the airport. Tokyo doesn't let go easily.
Nakameguro Canal Walk
The Meguro River runs through one of Tokyo's most beautiful residential neighborhoods. The canal-side path is lined with zelkova trees and flanked by independent coffee shops, design boutiques, and excellent restaurants. In May the trees are fully leafed — a green canopy over the water. This walk is the opposite of Shibuya's scramble: narrow, quiet, deeply Tokyo in a different register. Walk from Nakameguro Station south toward Daikanyama — about 1.5km, flat, unhurried.
Daikanyama T-Site — The World's Most Beautiful Bookshop
A 10-minute walk from Nakameguro, Tsutaya Books Daikanyama is one of the world's great bookstores — a sprawling garden campus with three connected buildings housing books, music, a café, and curated lifestyle products. The architecture is beautiful, the garden between the buildings is peaceful, and the Anjin café (a vintage international magazine library where you drink coffee surrounded by decades of Vogue, National Geographic, and Life) is the perfect final Tokyo moment.
Head to Airport — Haneda or Narita
After farewell lunch, collect your bags from the hotel, and make for the airport. Give yourself generous time — international departures need 3+ hours for check-in and security at Tokyo's airports.
💰 Budget Breakdown
| Category | Budget | Midrange | Luxury |
|---|---|---|---|
| Luxury Hotel (per night) | ¥15,000–25,000 | ¥30,000–60,000 | ¥80,000–150,000+ |
| Fine Dining (per person per meal) | ¥8,000–15,000 | ¥20,000–35,000 | ¥40,000–70,000 |
| Attractions & Experiences | ¥2,000–5,000/day | ¥5,000–12,000/day | ¥15,000+/day |
| Transport (metro + taxis) | ¥1,000–2,000/day | ¥2,000–4,000/day | ¥5,000+ (private car) |
| 5-Day Total (3-4 people, fine dining) | ¥400,000–600,000 | ¥800,000–1,500,000 | ¥2,000,000+ |
🍽️ Restaurant Reservations — Act Now
- Use Tableall.com and Pocket Concierge for English-language bookings at Michelin-starred Tokyo restaurants
- Nihonryori RyuGin and Quintessence: book 6-8 weeks in advance minimum
- Narisawa and Florilège: 4-6 weeks, sometimes available 2-3 weeks out
- Sushi Sawada: 6+ weeks via Pocket Concierge or hotel concierge
- Your hotel concierge (Park Hyatt, Aman, Peninsula) can often access reservations that the public cannot — use them
🏨 Recommended Hotels for This Trip
- Park Hyatt Tokyo (Shinjuku): floors 41-52, "Lost in Translation" hotel, ¥60,000-90,000/night — the classic luxury Tokyo choice
- Aman Tokyo (Otemachi): minimalist Japanese luxury, temple-like calm, ¥120,000-200,000/night — the finest hotel in the city
- The Peninsula Tokyo (Hibiya): in-house Michelin-starred restaurant, perfectly located for Ginza and Tsukiji, ¥70,000-120,000/night
- Mandarin Oriental Tokyo (Nihonbashi): 38th-floor location, stunning city views, impeccable service, ¥80,000-130,000/night
- All four hotels have concierge services that can assist with restaurant bookings — this alone is worth the price premium
✈️ Getting There & Around
- Haneda Airport (HND): closest to Tokyo — 35 min by Keikyu Line from Shinagawa, or private car (¥15,000-25,000)
- Narita Airport (NRT): 60-90 min via N'EX express — ¥3,250/adult, ¥1,630/child to central Tokyo
- IC Card (Suica/Pasmo): get at the airport, add ¥5,000-10,000 per person — covers all trains, buses, and convenience stores
- Taxis: plentiful, clean, metered, always honest — essential for evenings after fine dining when you're not counting coins
- Private car service: book via hotel concierge for airport transfers and special evenings
🛍️ Shopping Guide — Fine Goods to Bring Home
- Ginza Itoya (stationery): Japanese handmade washi paper, Mont Blanc pens, hand-bound notebooks
- Nakamise (Asakusa): genuine quality traditional items — tenugui, fans, lacquerware, ningyo-yaki
- Ginza Six basement food hall: premium Japanese pantry — yuzu kosho, dashi packs, fine matcha, regional sake
- Isetan Shinjuku (basement depachika): the finest food floor in Tokyo — wagashi, bento, premium produce
- Tokyo Station Gransta: Tokyo Banana (custard cake), Toraya yokan, Shiroi Koibito, matcha KitKats — the essential omiyage