Tailor-made Holiday · Japan
Japan luxury Trip: From Tokyo to Osaka
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Every trip built from scratch around your dates, pace and preferences.
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At a glance
Japan is a country of amazing contrasts, where ancient traditions and cutting-edge innovation exist in perfect harmony. This tailor-made journey has been designed to immerse you in the very best of the country, balancing iconic cities, cultural depth, serene landscapes and exceptional dining, all delivered with seamless comfort.
Begin in Tokyo, a dazzling metropolis where futuristic architecture, historic temples and world-class cuisine collide. From here, slow the pace in Hakone, surrounded by mountains and hot springs, where traditional ryokan hospitality offers a deeply restorative experience. Continue to Kyoto, the cultural heart of Japan, rich in timeless rituals, elegant streets and centuries-old craftsmanship. Your journey concludes in Osaka, a vibrant, food-loving city known for its energy, warmth and celebratory spirit.
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Throughout the trip, every detail has been thoughtfully curated. This is from luxury accommodation and private transfers to immersive experiences that reveal Japan beyond the guidebooks. This itinerary is ideal for travellers seeking a refined yet meaningful exploration of Japan, where moments of discovery are balanced with space to relax, indulge and connect.
Day by day
This is a sample plan, not a fixed departure. Days can be added, removed or reordered, and almost every client changes something. Prices are an entry-level guide; your quote will be exact.
Days 1–5: Tokyo
Set high above the city in the Otemachi Tower, Aman Tokyo offers a rare sense of calm amid the energy of Japan’s capital. Rooted in Japanese design tradition, the hotel features ikebana displays and washi paper doors with engawa platforms that create a seamless flow of space and light. Guest rooms echo the atmosphere of a contemporary ryokan, while the expansive Aman Spa is among the largest in the city. Dining is a highlight, with multiple restaurants presenting global cuisine from refined Italian cooking to masterful Edomae sushi, all delivered with Aman’s signature restraint and precision and service throughout stay.
Days 6–7: Hakone
Depart Tokyo this morning for a refreshing day immersed in the natural beauty of Hakone National Park, one of Japan’s most celebrated landscapes. Meet your private guide and driver before travelling to Hakone Machi-ko, where a scenic cruise across Lake Ashi offers sweeping views of the surrounding mountains. On clear days, Mount Fuji may appear in the distance, rising above the calm volcanic waters. Continue by cable car on the Hakone Ropeway to Owakudani, an active volcanic valley known for its steaming vents and dramatic terrain. Sample a local kuro-tamago before descending to Gora, where you transfer to your Hakone accommodation for a restful evening.
Days 8–11: Kyoto
Kyoto represents the essence of old Japan, defined by atmospheric temples, carefully tended gardens and traditional teahouses that continue to shape daily life. Once the imperial capital, Kyoto served as the seat of the emperor from 794 until 1868 and remains one of Japan’s largest cities, blending historic character with a contemporary rhythm. Despite centuries marked by war and fire, Kyoto survived with much of its cultural heritage intact. Owing to its exceptional historical significance, the city was spared destruction during the Second World War. Today, an extraordinary number of temples, shrines and culturally important structures remain, offering a rare and deeply authentic window into Japan’s enduring traditions.
Days 12–13: Osaka
If Kyoto reflects Japan’s imperial past and Tokyo its warrior spirit, Osaka has long been shaped by commerce and character. Traditionally the city of merchants, Osaka developed a reputation for openness and humour, with locals known for their expressive manner and playful approach to conversation. It is not conventionally beautiful, yet it is rich in atmosphere, with riverside views and streets illuminated by vibrant neon signage. Food is central to daily life here, and the best way to understand the city is through its cuisine and lively izakaya culture. Osaka’s unofficial motto, kuidaore, meaning eat until you drop, reflects a shared love of good food and good company.
Our Experts
Japan is often at the top of people's travel bucket-list, and for good reason. It's a country where you can find whatever it is you want, from the bustling cosmopolis of Tokyo to the luxury resort lined shores of the smaller islands.
The beauty of Japan is the amazing blend between old and new. You can enjoy the futuristic neon glow of Tokyo whilst also exploring some of the world's most culturally significant sites.
Stellar service. Stellar products. Stellar people and it gets so much better when you pick up the phone and call.
Anthony S.
Super client centred service. From first contact I have had warm, efficient, friendly and flexible service.
John
I’m confident in giving Out Of Office a 5-star review! They are one of the leaders in this space without a doubt.
Tiberiu
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Frequently asked questions
What does Out Of Office do?
Out Of Office is a luxury LGBTQ+ travel company specialising in tailor-made holidays and extraordinary journeys around the world. We create bespoke luxury holidays, LGBTQ+ honeymoons, safaris, cruises, beach escapes, private tours and group trips, with every itinerary designed around you. Our travel specialists combine global expertise, first-hand destination knowledge and trusted local partners to create seamless, highly personalised experiences.
Is Out Of Office a gay travel agency?
Out Of Office is an LGBTQ+ owned and run luxury travel specialist, with particular expertise in gay and LGBTQ+ travel. We understand the additional considerations that can come with travelling as an LGBTQ+ person or couple, from local laws and customs to finding genuinely welcoming hotels and experiences.
We welcome every traveller, including friends, families and allies. Many of our clients are not members of the LGBTQ+ community, but choose Out Of Office for our luxury travel expertise, personalised service and discretion.
Do you create tailor-made LGBTQ+ holidays?
Yes. Every tailor-made trip with Out Of Office is designed from scratch around your interests, travel style, budget and the way you want to experience a destination. We can arrange luxury hotels, private transfers, flights, guides, excursions, cruises and special experiences as part of one personalised itinerary. The journeys shown on our website are there to inspire you rather than restrict you; only clearly identified group departures operate as fixed itineraries.
How do you choose LGBTQ+ friendly hotels and destinations?
We combine first-hand destination knowledge with trusted local expertise to recommend luxury hotels, resorts and experiences where LGBTQ+ travellers can feel informed and welcome. We also consider the laws, customs and attitudes of each destination, because LGBTQ+ rights and experiences differ around the world. Our team regularly visit many of the properties we work with and where a destination requires greater awareness, we give you clear and considered advice so that you can make an informed decision about where and how you travel.
We plant trees for every booking
For every booking made with Out Of Office we commit to planting trees in your name to help reduce the impact of travel on future generations. You'll even get a link to see where your trees are planted in the world via our partner Ecologi.
We donate to Rainbow Railroad with every booking
Rainbow Railroad helps LGBTQ+ people escape state-sponsored violence and persecution. A donation goes with every trip we sell, funded by us and never added to your price.
Start Planning Your Trip
Tell us where you would love to go, when you are thinking of travelling and what kind of trip you have in mind. One of our LGBTQ+ travel specialists will create a tailor-made itinerary designed around your destination, style and preferences.
One named specialist, first enquiry to homecoming. No call centre, and nothing is charged until you decide to book.