JJapan Trips

First Solo Trip to Japan – October 2025 (13 nights)

  • August 27, 2025

Hi all, I hope all is well

I went to Japan once before in 2023 with my girlfriend, but this time I’m going solo. I’m recovering from burnout and trying to figure myself out a little, learning to enjoy being alone, making my own choices, and hopefully meeting some people along the way.

I’m not really aiming for strict sightseeing this time since I already did most of that before. I just want to chill, eat amazing food, do some shopping, and enjoy the nightlife. During the day I like wandering around, checking out small shops and markets,fooooood, and relaxing in parks or cafés. At night, I love exploring the city, bar hopping, street food, and maybe even a little bar crawl.

Days 1–2: Tokyo (Shinjuku)

  • Day 1 (Oct 5): Arriving at Haneda around noon, then heading to my hotel in Shinjuku. Planning to explore Shimokitazawa for some shopping, grab a relaxed lunch, and wander around Omoide Yokocho in the evening.
  • Day 2 (Oct 6): Taking it easy in the morning, maybe Shinjuku Gyoen Garden or a good breakfast spot nearby. In the afternoon, I’ve got TeamLab Planets at 17:30 and might grab dinner in Toyosu afterwards if thats even a thing. Back to Shinjuku later, maybe a couple of late-night bars if there’s still energy, but not too much since my travel to Osaka the next day.

Days 3–6: Osaka

  • Day 3 (Oct 7): Taking the train to Osaka in the morning and checking in near Namba. Planning to explore Amerikamura for clothes since I’m packing light, have lunch at Kuromon Ichiba Market, and spend the evening in Shinsekai for kushi-katsu and izakaya hopping.
  • Day 4 (Oct 8): Visiting the Yamazaki Distillery in the morning for the Monozukuri Tour & Tasting, which I won the lottery for. Hoping to pick up a nice bottle to bring home. The afternoon’s open for wandering, and I’d love to check out some Kitashinchi whisky bars at night if I can still look at whisky by then haha. Definitely open to hidden bar recommendations here.
  • Day 5 (Oct 9): Umeda Sky Building in the morning, then Tenjinbashisuji arcade for snacks and lunch. Planning to explore the Tenma area in the evening for some proper izakaya hopping.
  • Day 6 (Oct 10): Keeping this flexible. I might do a Kyoto side trip for Nishiki Market and Pontocho Alley, or just stay in Osaka, grab some local food, and find a few small bars at night.

Days 7–8: Kobe

  • Day 7 (Oct 11): Taking the train to Kobe in the morning and checking in. Planning to visit Meriken Park, Harborland, and Chinatown during the day. I’ve got a reservation at Kobe Steak Ishida at 19:00, and after that I’d love to find some sake spots or bars.
  • Day 8 (Oct 12): Thinking about visiting Nunobiki Herb Gardens or Mt. Rokko if the weather’s good. The afternoon’s pretty open, maybe wandering Kobe’s backstreets and cafés. Probably want to end the day with a small local brewery or sake bar if I can find a good one.

Days 9–10: Kinosaki Onsen

  • Day 9 (Oct 13): Heading to Kinosaki and checking into a ryokan where breakfast and dinner are included. Planning to do the classic onsen-hopping route, take a seaside walk, and maybe try some sake tasting at Donmai.
  • Day 10 (Oct 14): Full chill day in Kinosaki with breakfast at the ryokan, more onsens, a few naps, and a slow evening, dinner back in the ryokan. And check out the festival that is supposed to be going on.

Days 11–13: Tokyo (Ueno)

  • Day 11 (Oct 15): Back to Tokyo and checking in at Ueno. Planning to browse Ameyoko Market, BerBerJin, Kapital, and Hinoya for vintage denim during the day. At night I want to check out Ebisu Yokocho for izakaya hopping, but I’m open to bar suggestions here.
  • Day 12 (Oct 16): Visiting Koenji in the morning for record stores, thrift shopping, and local cafés. Spending the afternoon in Shimokitazawa to wander food alleys and vintage shops. In the evening, maybe a proper bar crawl around Koenji, Ebisu, or Shibuya depending on the mood.
  • Day 13 (Oct 17): Exploring Nakameguro and Daikanyama for coffee spots and boutique shops. Planning an omakase dinner this evening, around ¥45,000 but not booked yet, and probably finishing with a final nightcap in Golden Gai or a hidden whisky bar with some jazz and maybe cigars.
  • Day 14 (Oct 18): Departure to home day 🙁 Spending the morning on last-minute souvenir shopping, probably Shinanoya, Liquor Mountain, and Don Quijote. Might do a final stroll through Ueno Park or Ameyoko Market before heading to Haneda for my flight.

Hope anyone can either give some heads up or wake me up and check if its a doable experience. I've planned most of this through my experience in 2023 and asked ChatGPT to assist in some other places I haven't been before (Kobe and Kinosaki) I really loved Osaka en Tokyo.

Thanks in advance!!!! And see you in Octoberr.

by YuriViroj