Tokyo is overwhelming in the best possible way. Give yourself four full days to explore neighborhoods, shop, eat, and find your footing. The jet lag is real — lean into it. Go to bed early the first night, wake up naturally at 5am, and use that quiet dawn hour to wander before the city wakes.

AMAN TOKYO

84 ryokan-inspired rooms on the top floors of Otemachi Tower. The most celebrated hotel in Tokyo. Cathedral ceilings, washi paper screens, a legendary spa, and service that anticipates your every need before you ask. This is your base for the most electric city on earth.

SEE – Shinjuku Gyoen — Tokyo’s most beautiful cherry blossom garden. Arrive by 8am on a weekday for a near-private experience. Bring a blanket, get a coffee from a nearby conbini, and sit under the blossoms. One of those moments.

SEE – Meguro River at night — Hundreds of cherry trees lit by lanterns lining the canal. Walk this with drinks in hand on a warm spring evening. Unforgettable and incredibly romantic even for a girls trip.

SHOP – Amore Vintage (Omotesando) — The definitive stop for authenticated vintage Chanel, Hermès, Louis Vuitton, and Celine. The Omotesando location specializes entirely in rare Chanel pieces. English-speaking staff, tax-free shopping. Budget serious time and serious money.

SHOP – Allu (Ginza) — Five floors of pre-owned Hermès and Chanel. Five. Floors. If there is one stop for the bag lovers in the group, this is it. Prepare yourself accordingly.

SHOP – Shimokitazawa neighborhood — A full afternoon of vintage boutiques, indie shops, and wonderful cafés. The most charming neighborhood in Tokyo. No one will want to leave. New York Joe Exchange is the crown jewel — go on the first Sunday of the month for 50% off everything.

SHOP – Ginza — Tokyo’s luxury shopping district. Every major brand, stunning flagship architecture, and the most beautiful department stores you have ever seen.

DO – TeamLab Borderless at Azabudai Hills — The immersive digital art experience is genuinely one of the most spectacular things available anywhere in Japan. Book in advance, go in the evening. Your photos will break the internet.

EAT – Let the Aman concierge book dinner — The Aman team can get you into restaurants you could never book yourself. Hand this over to them for at least two nights and trust the process completely.

This is your official exhale. Two nights of doing absolutely nothing on any kind of schedule. Sleep in. Soak in your private onsen. Eat the most exquisite dinner of your life. Hakone sits at the foot of Mt. Fuji — on a clear spring day the views are breathtaking.

GORA KADAN

~85 MIN FROM TOKYO · ODAKYU ROMANCE CAR TRAIN (GORGEOUS) OR TAXI

Built on the grounds of a former imperial summer retreat. One of the finest ryokans in Japan. Your suite has a private outdoor onsen hot spring bath. A multi-course kaiseki dinner is served in your room by a personal attendant. You sleep on a traditional futon in a tatami suite. Rates from ~$1,100–$1,200 USD per night including dinner and breakfast.

SPA – Private onsen in your suite — Soak in your own outdoor hot spring bath overlooking the mountains. This is the Japan you dreamed about. The communal onsen are also spectacular and swap between male/female sections overnight.

SEE – Mt. Fuji views — Cherry blossoms framing Mt. Fuji in spring is one of the most iconic images in all of Japan. On a clear day from Hakone, you will understand why immediately.

DO – Lake Ashi cruise & Owakudani Ropeway — A beautiful boat ride with Fuji in the background, then an aerial tram ride over dramatic volcanic landscape. A genuinely fun afternoon before returning to the pure luxury of Gora Kadan.

Kyoto during cherry blossom season is simply the most beautiful place on earth. It is deeply atmospheric, incredibly romantic, and photogenic at every single turn. You will want to be dressed beautifully every single day here. The city moves at a different pace than Tokyo — slower, more considered, more intentional. Let it change you.

THE RITZ-CARLTON KYOTO

~2.5 HRS FROM HAKONE · SHINKANSEN BULLET TRAIN VIA ODAWARA

Nine consecutive Forbes Five-Star ratings — the only hotel in Kyoto to achieve this distinction. Riverside location on the Kamogawa River with views of the Higashiyama mountains. Asia’s first La Prairie Spa. Michelin-starred restaurants. Check-in begins with traditional Japanese tea. Four nights minimum — Kyoto demands it.

SEE – Philosopher’s Path — A stone walkway lined with hundreds of cherry trees along a canal. Walk it before 8am with coffee and no agenda. One of the most beautiful walks on earth.

SEE – Fushimi Inari Shrine at sunrise — Thousands of vermillion torii gates winding up a forested mountain. Go at 5:30am. The photos look like nothing anyone has ever posted on Instagram and the hike in quiet dawn light is magical.

SEE – Gion District at dusk — The geisha district. Lantern-lit wooden townhouses, atmospheric tea houses, the most beautiful streets in all of Japan. Walk it as the sun goes down and find somewhere wonderful for dinner nearby.

DO – Kimono rental for the group — Rent kimonos together and spend the day in Gion. It sounds like a tourist thing and it absolutely is — and it is also one of the most joyful experiences of the whole trip. The photos are extraordinary.

DO – Private tea ceremony — Book a private ceremony for your group. Intimate, serene, and one of those cultural experiences that stays with you long after you’re home.

SHOP – Nineizaka & Sannenzaka — Ancient stone-paved lanes lined with the most beautiful traditional shops. Lacquerware, ceramics, fans, handmade textiles. Budget a full afternoon and bring an extra bag.

SPA – La Prairie Spa evening at the Ritz — Book a group spa evening after a day of temple-walking. Asia’s first La Prairie Spa hotel. Follow with dinner at one of the hotel’s restaurants. The perfect Kyoto night in.

SHOP – To-ji Temple Flea Market (21st of month) — If your dates align, do not miss this. One of the best flea markets in Japan — vintage kimono, textiles, ceramics, and treasures everywhere.

After the serenity of Kyoto, Osaka’s energy hits like a welcome shot of espresso. The city is louder, funnier, and completely food-obsessed — and for a girls trip that is a very good thing. Osaka runs on food, fun, and a brilliant sense of humor. Your only job here is to eat as much as possible and have an absolutely great time doing it.

WALDORF ASTORIA OSAKA

~15 MIN FROM KYOTO · SHINKANSEN BULLET TRAIN

Hilton’s most prestigious brand making its Japan debut — opened April 2025. Brand new, perfectly located in the Grand Green Osaka development next to Osaka Station. Rooms from 53 sq meters, butler service, rooftop teppanyaki and sushi on the 29th floor, spa, and an indoor pool. The most coveted address in Osaka right now.

EAT – Dotonbori on your first night — The neon-lit entertainment district. Giant moving crab signs, street food on every corner, energy that is completely infectious. Get takoyaki, okonomiyaki, and fresh ramen. Walk this with drinks in hand and let the city wash over you.

EAT – Kuromon Ichiba Market — Osaka’s famous covered food market. Fresh seafood, grilled wagyu, incredible produce vendors. A morning here is a highlight of the entire trip.

EAT – Michelin-starred farewell dinner — Osaka has more Michelin-starred restaurants per capita than almost any city in the world. Let the Waldorf concierge book your group somewhere truly unforgettable for your last big dinner in Japan.

DO – Day trip to Nara — 45 minutes from Osaka. Hundreds of freely roaming deer in a beautiful park surrounding ancient temples. Feeding deer in your kimono with your girlfriends is an absurdly fun afternoon and the photos are absolutely adorable.

~2.5 HRS FROM OSAKA · SHINKANSEN TO TOKYO

Return to Tokyo for your final two days. Use this time for anything left on the wish list — one last sweep through Ginza, a final morning under the cherry blossoms, anything you didn’t get to do the first time around. Ask the Aman concierge to hold something special for your farewell dinner. Raise a glass to each other. You just did Japan together.

DO – Luggage forwarding (takuhaibin) — Japan has an extraordinary service where your hotel can ship your suitcases ahead to your next hotel, so you travel the bullet train with only a day bag. Your luxury hotels will arrange this. Use it for every move. It is a game-changer.