Tailor-made Vacation · Japan
Luxury Japan Tour in Winter – Tokyo, Nagano & Snow Monkeys
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At a glance
Winter changes the shape of a trip to Japan. Tokyo turns cold and often clear. Nagano disappears under snow, and the hot springs at Yudanaka become one of the main reasons to go this time of year.
By the time you reach Kyoto, the cherry blossom and autumn crowds have thinned out. The city feels more accessible.
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This 12-day trip starts with a few days in Tokyo, then heads north into Nagano Prefecture. The centerpiece is Jigokudani Monkey Park, where the macaques sit in the hot springs surrounded by snow, sometimes with steam rising off the water. You stay nearby in a traditional ryokan, with time built in for an onsen and a kaiseki dinner before moving on to Matsumoto.
From Matsumoto, the route turns south to Kyoto. The mountains give way to temples and old neighborhoods, the kind of sites that take a full day each to see properly.
There's enough time in Kyoto to settle into it rather than rush through, plus a separate day trip to Nara so you're not cramming both into one exhausting day.
The point of building the trip this way is the contrast. You get the postcard version of Japan in winter, snow monkeys and mountain onsen, without giving up the cities and temples that make the trip feel complete.
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.
Day 1: Arrival in Tokyo
Arrive in Tokyo, where a private driver will meet you at the airport and take you to Park Hotel Tokyo.
The rest of the day is deliberately left open. After a long flight, you can stay at the hotel or head out for a first look at the city if you have the energy.
Day 2: Discover Tokyo’s Historic & Modern Contrasts
Meet your private guide for a full day in Tokyo.
Begin in Asakusa at Senso-ji, Tokyo’s oldest Buddhist temple, before walking through the surrounding streets and Nakamise shopping street.
Later, cross the city to Meiji Jingu, set within a large wooded area beside Harajuku. From here, continue toward Omotesando, where contemporary architecture and Japanese fashion offer a very different side of Tokyo from the morning.
Return to Park Hotel Tokyo for the evening.
Day 3: Sumo Morning & Tokyo’s Pop Culture Scene
Start early with a visit to a sumo training stable, where you can watch wrestlers during their morning practice.
The rest of the day is devoted to modern Tokyo. Your guide can take you through Shibuya and Harajuku before continuing to Akihabara if anime, gaming or Japanese pop culture is of interest.
It is a busy day, so the exact balance can be adjusted rather than trying to cover every district.
Day 4: Into the Mountains – Hakone & Mount Fuji
Leave Tokyo for a day in Hakone.
Visit the Moto-Hakone area and take a cruise across Lake Ashi. Weather permitting, this part of Hakone can give you some of the best views of Mount Fuji on the trip.
You can also take the Komagatake Ropeway before returning to Tokyo in the evening.
Mount Fuji visibility always depends on the weather, so we would never build the whole day around the assumption that the mountain will be visible.
Day 5: Tokyo to Yudanaka
Leave Tokyo by Shinkansen for Nagano, then continue by private transfer to Yudanaka.
Tonight you stay at Issanokomichi Biyunoyado, a traditional ryokan close to the snow monkey area.
The ryokan experience is an important part of the day. Dinner is served kaiseki-style, with a sequence of seasonal dishes, and you will also have time to use the hot spring baths.
Day 6: Jigokudani Snow Monkeys and Matsumoto
Visit Jigokudani Monkey Park, one of the best-known winter wildlife experiences in Japan.
Reaching the monkeys involves a walk through the forested valley, which is often covered in snow during the winter months. The Japanese macaques live wild in the area and are particularly famous for using the park’s hot spring.
After the visit, continue to Matsumoto and check into Matsumoto Hotel Kagetsu.
Day 7: Matsumoto Castle
Spend the day exploring Matsumoto.
The main reason to stop here is Matsumoto Castle, whose original wooden keep survives from the late 16th and early 17th centuries. Its black exterior makes it immediately recognizable and very different from the white facade of Himeji Castle farther south.
After the castle, walk through Nakamachi, an old merchant district where several traditional kura storehouses remain.
Day 8: The Art of Wasabi & Journey to Kyoto
Before leaving Nagano Prefecture, visit Daio Wasabi Farm near Azumino.
Wasabi requires very particular growing conditions, and the farm gives you a useful look at how the plant is cultivated in spring water before it eventually reaches restaurants around Japan.
Afterward, travel south to Kyoto and check into Kyoto Tokyu Hotel.
Day 9: Kinkaku-ji and Northern Kyoto
Spend the day with a private guide in northern Kyoto.
Begin at Kinkaku-ji, the Golden Pavilion, before continuing to Ryoan-ji and its famous rock garden.
Later, visit Kitano Tenmangu and walk through Kamishichiken, one of Kyoto’s traditional geiko districts and considerably smaller than Gion.
Day 10: Fushimi Inari’s Torii Gates & Kyoto’s Timeless Icons
Start at Fushimi Inari, where thousands of vermilion torii gates climb the slopes of Mount Inari.
Continue to Sanjusangen-do, best known for its hall containing 1,001 statues of Kannon.
The day finishes at Kiyomizu-dera, whose wooden terrace looks across eastern Kyoto. Depending on the time of year and opening hours, we can arrange the sequence to avoid some of the busiest periods.
Day 11: A Journey to Nara’s Ancient Temples & Sacred Deer
Travel to Nara for the day.
Visit Todai-ji, home to the enormous bronze Daibutsu, before continuing through Nara Park toward Kasuga Taisha.
The deer that roam through the park have become one of Nara’s signatures, but the city is worth visiting for much more than that. As one of Japan’s early capitals, it contains some of the country’s most important Buddhist and Shinto sites.
Return to Kyoto after the visit.
Day 12: Departure
A private transfer will take you from Kyoto to Kansai International Airport for your flight home.
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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.
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Frequently asked questions
What does Out Of Office do?
Out Of Office is a luxury LGBTQ+ travel company specializing in tailor-made vacations and extraordinary journeys around the world. We create bespoke luxury vacations, 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 personalized 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 traveling as an LGBTQ+ person or couple, from local laws and customs to finding genuinely welcoming hotels and experiences.
We welcome every traveler, 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, personalized service and discretion.
Do you create tailor-made LGBTQ+ vacations?
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 personalized 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+ travelers 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.
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