Autumn 2025. We – Sam and Danny, Michel and Wille, and Timothy – are travelling to Japan for a quite classic tour of the Land of the Rising Sun. We are flying separately as we used miles. On the planning: Tokyo, Kanazawa, Shirakawa, Osaka, and Expo 2025, Hiroshima, Himeji, Miyajima, Kyoto, Nara, Nagoya, Hakone, and back to Tokyo. Three weeks plus some extra days.

Prior to the group trip, I – Timothy – am solo in Tokyo. Using artificial intelligence, I concocted a busy four days featuring Ito on the Izu Peninsula and Sawara, also known as Little Edo. I also end this Journey Across Japan with a solo spell in Minato, near Taito and Tamachi Station.  

Depending on how you want to count, I was four to five days solo in Tokyo before Danny and Sam landed in Haneda. AsI knew that long in advance, I did my research planned out these days.

Also, as I had already visited Tokyo back in 2013, I didn’t feel the need to tick off the stalwarts of tourism in the metropolis. I had already done that. 

2013 Japan Family Trip

1. JAPAN 2013 | Solo in Tokyo.
2. JAPAN 2013 | Tokyo ft. Ueno Park and the Shibuya Crossing.
3. JAPAN 2013 | Tokyo ft. Sensō-ji, Hamarikyu Gardens and the Imperial Palace East Gardens.
4. JAPAN 2013 | Meiji Shrine and Harakuju in Tokyo.
5. JAPAN 2013 | Tokyo ft. Tsukiji Fish Market, Ginza, Zōjō-ji Temple, Tokyo Tower and traditional restaurant Jomon in Roppongi.
6. JAPAN 2013 | Tokyo – Hakone by train.
7. JAPAN 2013 | Hakone Yumoto – Lake Ashi – Owakudani.
8. JAPAN 2013 | Hakone Yumoto Onsen Tenseien.
9. JAPAN 2013 | Kyoto’s Philosopher’s Path and Anraku-ji Temple.
10. JAPAN 2013 | Kyoto’s Ginkaku-ji or Temple of the Silver Pavilion.
11. JAPAN 2013 | Fushimi Inari Shrine in Kyoto.
12. JAPAN 2013 | Kiyomizu-dera Temple in Kyoto.
13. JAPAN 2013 | Kinkaku-ji or Temple of the Golden Pavilion in Kyoto.
14. JAPAN 2013 | Kyoto’s other temples: Eikando Zenrin-ji, Nanzen-ji, Chion-in, Shoren-in, Ninna-ji, Tenryū-ji.
15. JAPAN 2013 | Kyoto’s Arashiyama Bamboo Grove.
16. JAPAN 2013 | Impressions of Kyoto.
17. JAPAN 2013 | Looking back on and looking forward to a Japan trip.

Goals

My goals for this 2025 Journey Across Japan were seeing and visiting places I hadn’t twelve years earlier, to get outside the major cities… and also to hook-up with locals. That last one is hard to plan.

So I had conversations with ChatGPT. Many conversations. But it resulted in some interesting excursions. The Toei Animation Museum in Nerima. The Izu Teddy Bear Museum near Ito in Shizuoka Prefecture. Sawara, beyond Narita in Chiba Prefecture. Omotesandō in Shibuya. The Edo-Tokyo Open Air Architectural Museum in Koganei Park. 

I also had time for shopping and for hooking up. 

Travelling solo v. travelling with friends

Travelling solo has two main advantages: you can do what you want and you will do activities your travel mates are not interested in. You can also change plans à la minute. 

Travelling with friends has two main advantages. You will do activities which might be outside your usual scope, and this discover things you wouldn’t expect. You also don’t have to figure out and decide everything yourself, you can rely on others.

This Journey Across Japan combines both. 

Food 

I relied a lot on convenience stores or kombini for food. Maybe too much. At the end of the day I didn’t feel like researching potential nice restaurants. I did have Japanese-style breakfast and a few lunches. 

Also in the evening I was more browsing the hook-up apps looking ‘for fun’. So yeah. No regrets though.

Tokyo is solo-friendly

Tokyo is one of the world’s most comfortable cities for solo travellers — though it can feel overwhelming at first glance. Beneath the neon skylines and fast-moving crowds lies a culture of quiet efficiency and safety that makes exploring alone both easy and rewarding.

For a start, Tokyo is exceptionally safe. Street crime is rare, public transport is reliable, and the city functions with an understated sense of order. Travellers can wander through backstreets late at night, take the last train across town, or spend hours in cafés and arcades without worry. The city’s emphasis on etiquette and personal space means you are rarely disturbed, even in busy places.

Solo diners are warmly accommodated too. Many restaurants, from ramen counters and sushi bars to izakaya and family restaurants, are designed for single customers. Ordering via vending machines or touchscreens eliminates the stress of language barriers, and it’s not unusual to see locals eating alone. Convenience stores offer surprisingly good meals for those who prefer to eat on the go or in a park.

Accommodation is another plus. Capsule hotels, business hotels, and small boutique stays provide affordable and private options. Even higher-end hotels tend to be efficient and unintrusive, with staff who anticipate needs without fuss.

Tokyo also offers the solo traveller plenty to do without needing company. You can spend a morning exploring the calm of a Shinto shrine, an afternoon in an art museum or bookshop café, and an evening wandering the illuminated streets of Shinjuku or Akihabara. The city’s vast public transport network means you can navigate easily, whether heading to cultural districts like Ueno and Asakusa or seeking quiet neighbourhoods such as Kagurazaka or Nakameguro.

That said, Tokyo’s politeness can sometimes feel isolating. Locals are friendly but reserved, and spontaneous conversation with strangers is rare. It’s a city that lets you observe rather than participate — perfect for introverts, less so for those craving social connection.

Still, for many, that is precisely Tokyo’s charm. It’s a place where solitude feels normal, even luxurious — where you can disappear into the crowd, find a quiet café corner, and simply exist amid the hum of the city. For solo travellers, Tokyo offers the rare combination of anonymity, safety, and endless fascination.

Hooking up

I was apprehensive about my chance on the hook-up market in Japan. I’m consciously not using ‘dating market’ as I was’t looking for conversations over drinks, but for action. 

The gaijin (foreigners) are not necessarily loved. The Japanese have this slight xenophobic reputation when it comes to dating and hooking up. 

The reality was different. I stayed in Asakusa and on Grindr I found men willing to hook up. I was 44 in autumn 2025 and I’m stocky to chubby. I do not have that Instagrammable body. 

Deep Throat Men

I hooked up with C. from Taiwan; an anonymous person at a dedicated gay bathhouse called 24 Kaikan and with T. from Tokyo. We met up at Deep Throat Men in Shinjuku, a glory hole bar. You pay a cover charge of 2,000 yen, which includes a drink. There’s a bar area and a cruising area. You receive a bracelet telling if you want to give, receive or both. It’s all very practical. 

Later, when I moved hotels to stay in Minato, near Tamachi Station. There I had even more success. But that’s for later. 

So? 

I had a swell time travelling solo in Tokyo. Tokyo is single-friendly. But I was also glad to welcome Danny and Sam, as it would mean the proper start of the trip. 

Gay adventures of the homosexual kind

• GAY TOKYO | 24 Kaikan in Asakusa (+ Ueno and Shinjuku).
• GAY SEOUL | Jongno 3-ga ft. Bar MoU.
• GAY ITAEWON | Homo Hill = Usadan-ro 12-gil (우사단로12길) in Seoul, South Korea.
• The best cities for gay cruising? London, Berlin, Paris, Madrid and Barcelona.
• QUEER KOREA | Beomil-ro, Busan’s gay street.
• GRAN CANARIA | 11 takeaways to enjoy Winter Pride Maspalomas to the fullest.
• The best cities to visit as a gay solo traveller.
• Gay Hong Kong.
• Heading for the sun in gay destination Torremolinos.
• QUEER ANDORRA | Entre Nous, the only gay bar in the village.
• Queer Iceland & Rainbow(baiting) Reykjavík.
• Manchester’s gaybourhood around Canal Street.
• Pride in Valladolid, Yucatán and queer encounters in Mexico.
• FLORIDA SOLO ROAD TRIP | Eye-opening encounters in Miami.
• FLORIDA SOLO ROAD TRIP | Fort Lauderdale.
• Drag queen bingo at Pride of our Footscray Community Bar.
• LGBTQ+ get-together on Majestic Princess.
• Gays failing at being gay? ‘LGBTQ Mix & Mingle’ on Royal Caribbean’s Serenade of the Seas lacked enthusiasm.
• Gay Tel Aviv: pinkwashing or genuine?.
• Gay Taipei with misterb&b.

2025 Journey Across Japan

1. Japan’s Superconducting Maglev train breaks world speed record at 603 km/h.
2. Japan’s maglev bullet train delayed to 2035 or later as costs rise to ¥11 trillion.
3. QUESTION | Should you be stressed about travelling to Japan, and fear of missing out?.
4. Brussels Airport to Milan Malpensa with Brussels Airlines, operated by Air Baltic, ft. the 2025 check-in and boarding software hack.
5. REVIEW | Sala Montale Exclusive Lounge and Sala Gae Aulentin Premium Lounge at Milan Malpensa Airport, extra Schengen.
6. REVIEW | All Nippon Airways (ANA), Business Class, Boeing 787-9 Dreamliner to Tokyo.
7. REVIEW | Toei Animation Museum in Nerima, Tokyo.
8. JAPAN | Tokyo Station, its Character Street and Pokémon Store.
9. REVIEW | Onyado Nono Asakusa Hotel in Tokyo.
10. TOKYO | Asakusa ft. Sensō-ji Temple.
11. JAPAN | The Odoriko train from Tokyo to Ito on Izu Peninsula.
12. PHOTOS & REVIEW | The Izu Teddy Bear Museum in Izu-Kōgen.
13. JAPAN | A visit to Ito on Izu Peninsula in Shizuoka Prefecture.
14. REVIEW | Japan’s Saphir Odoriko in Premium Green Car from Ito on Izu Peninsula to Tokyo Station.
15. GAY TOKYO | 24 Kaikan in Asakusa (+ Ueno and Shinjuku).
16. TOKYO | Sawara in Chiba Prefecture, ‘Little Edo’ beyond Narita.
17. TOKYO | Omotesandō in Shibuya – AEON Shinonome –  Uniqlo – Muji.
18. PHOTOS | The Edo-Tokyo Open Air Architectural Museum in Koganei Park.