So you’ve booked your first trip to Japan, now what? Planning a trip to Japan can feel both exciting and overwhelming, especially if it’s your first time. Between Tokyo’s neon city lights, Kyoto’s serene temples, and Osaka’s street food paradise, it can be hard to know where to start. I first travelled to Japan as a solo female traveller with no clue on where to start. So I completely understand first-hand how difficult and overwhelming this can be!

From that personal experience, I decided to create this simple (hopefully), step-by-step guide to planning a 2-week Japan itinerary that balances travel, rest, and fun! ٩(ˊᗜˋ*)و ♡

— Step 1: Decide Your Travel Season ₊˚⊹ ᰔ

Japan offers something special in every season:

Spring (March–May) for cherry blossoms and mild weather
Summer (June–August) for vibrant festivals
Autumn (September–November) for crisp air and red leaves
Winter (December–February) for cozy onsens and snow festivals

Pick a season that fits your vibe (and budget!) since accommodation and flight prices can vary a lot depending on the season. Spring (March–May) is typically the peak period for travellers to visit Japan since many want to go see the beautiful cherry blossoms. However, if that’s not your priority, I’d personally recommend October or November, which is during the autumn season there. September and early October can still feel quite warm (maybe even hot!), as Japan is just moving out of their very hot and humid summer! November would be a bit cooler and will also have more of the beautiful autumn foliage.

— Step 2: Choose Your Route ₊˚⊹ ᰔ

So…hear me out first. You’re probably wondering, “Where should I go when I’m in Japan? Maybe Tokyo, Kyoto, Osaka, and Nara for the Deer Park?”. Well, no. While these destinations are popular spots (and also really amazing places), I want you to sit down and think about what you want to see, experience, or prioritise during this trip. Maybe you love cultural and traditional landscapes, architecture, and experiences? In that case, Kyoto would be a wonderful spot for you. And maybe you want to experience the bustling city life Japan has to offer? Well then, Tokyo it is!

A lot of first-time travellers who want to visit Japan, immediately think of your typical tourist destinations. But there are so many other beautiful and scenic places in Japan (That would also be less tourist-heavy!). For example, I’m personally not a foodie, so I haven’t had much interest in Osaka. And I love anime so I made sure to visit Akihabara and Ikebukuro for all my anime goods and merch. The idea is, make sure you plan a trip that YOU’RE interested in and would actually enjoy.

Here are just some of my personal favourite places to visit in Japan:

Hakone – Onsen towns, scenic views, and peaceful lake cruises
Yokohama – Harbor city vibes, shopping, and the famous Cup Noodles Museum
Kamakura & Enoshima – Coastal getaway, giant Buddha, and island cafes
Kichijoji – Cozy boutiques, Inokashira Park, and Ghibli-like charm
Daikanyama – Trendy cafes, bookstores, and stylish, quiet streets

*Motohakone Port in Hakone, Japan ⊹* ***࣪ ˖***

— Step 3: Book Accommodation Early ₊˚⊹ ᰔ

I’d recommend looking into accommodation early, ideally and at least a minimum of 3 months before your trip. Especially if you want to stay close to central Tokyo/Kyoto or in popular Tokyo/Kyoto areas like Shinjuku or Gion.

Accommodation within popular tourist areas can fill up very fast, and chances are, you may have to stay in a location that may have not been your first choice. Some accommodation options include:

Hotels & Ryokans: For comfort and local experience.
Sharehouses or Airbnbs: More affordable and good for longer stays.
Try to book near major train stations for convenience — especially if you’re carrying luggage.

My personal favourite are Airbnbs that allow self check-in. It makes the whole experience a bit more relaxing and comfortable, not to mention, you won’t have to worry about your card declining or not having enough cash on hand to pay for a room/place, since Airbnb requires payment beforehand. They do also allow for free cancellations up to a certain date.

— Step 4: Budget Your Trip ₊˚⊹ ᰔ

When planning a 2-week trip to Japan, setting a realistic budget early helps you enjoy everything without worrying about overspending. On average, you can expect to spend around ¥15,000–¥25,000 per day (roughly $150–$250 AUD) depending on your travel style.

This typically covers accommodation, meals, transport, and a few activities or shopping days. To stay organised, divide your budget into categories like:

Accommodation
Food
Transportation
Shopping/Souvenirs

If you’re planning to visit multiple cities, consider a Japan Rail Pass (JR Pass) for unlimited train rides, it’s an upfront cost but can save money long-term. However, if you’re only travelling from Tokyo to Kyoto, and back to Tokyo from Kyoto, then I wouldn’t recommend the JR Pass just because you’d end up paying more and not using it as much.

For budgeting apps, I recommend TravelSpend or Wanderlog’s expense tracker (my personal favourite), both of which make it easy to track spending in real time. And don’t forget to set aside a little extra for spontaneous finds! Japan’s charm often lies in the cute stores and cafes you stumble upon unexpectedly! (⸝⸝ᵕᴗᵕ⸝⸝)ﾉ♡

*Totoro Cream Puff @ Shirohige’s Cream Puff Factory in Shimokitazawa, Japan ⊹* ***࣪ ˖***

— Step 5: Plan Your Itinerary ₊˚⊹ ᰔ

I personally love using Wanderlog for all my travel trips and itinerary planning. It’s especially great when you travel in a group of people. When it comes to organising your Japan trip, having everything in one place makes a huge difference.

What I love most is how it lets you drag and rearrange days easily, so if you decide to swap a Tokyo shopping day for a Kyoto temple visit, it takes just a second. You can also pin locations directly from Google Maps, track estimated travel times, and even share your plans with travel buddies. For someone like me who enjoys a mix of structure and spontaneity, Wanderlog makes trip planning feel fun and creative instead of stressful.

It’s tempting to fill every day, but Japan has so many hidden corners worth slowing down for; A small shrine in an alley, a local bakery, or a themed café. Leave at least one “free day” in each city to explore spontaneously.

*Happy Pudding in Nakameguro, Japan ⊹* ***࣪ ˖***

— Step 6: Research & Plan Your Essentials ₊˚⊹ ᰔ

Before heading off on your Japan adventure, it’s important to sort out a few key essentials to make your trip smooth and stress-free!

*I personally love using Notion to categorise and organise my lists. This is just an example from my ‘Medicine’ category ⊹* ***࣪ ˖***

Below is a VERY SIMPLE checklist I’ve put together which can hopefully get you started. Keep in mind that this checklist may or may not be altered based on what you personally need.

— ₊˚⊹♡

🧳 Travel Documents

A valid passport
Flight tickets + hotel confirmations
Visit Japan Web QR codes
Travel insurance details
Photocopies of important documents

💻 Tech & Connectivity

Pocket Wi-Fi or SIM card
Phone charger + power bank
Japan plug adapter (Type A/B)
Camera + extra SD card
Portable tripod or stabiliser

🚄 Transport

Japan Rail Pass or regional pass
Suica/Pasmo card (You can get this at the airport, online, or on iOS)
Printed or digital itinerary (Wanderlog, Google Maps saved)
Cash (some smaller shops are cash-only)

🎧 Personal Care

Travel-size toiletries
Skincare + sunscreen
Makeup and beauty essentials
Medications
Mini first-aid kit

👚 Clothing

Weather-appropriate outfits (layers are best)
Comfortable walking shoes
Small foldable umbrella or raincoat
Sleepwear

— ₊˚⊹♡

🌐 Visit Japan Web: Pre-Arrival Preparation

Before flying to Japan, it’s also a good idea to set up your Visit Japan Web account. It’s a free online service that simplifies airport procedures once you arrive in Japan. Through this platform, you can complete immigration, customs, and quarantine forms in advance, which saves a lot of time upon arrival.

Once you’ve filled everything out, you’ll receive QR codes that you can show at the airport instead of paper forms. It’s quick, efficient, and highly recommended, especially if you want to breeze through the entry process after a long flight. Just remember to register a few days before your trip (or a month!) and keep screenshots of your QR codes handy (Wi-Fi might be spotty when you land). Setting up Visit Japan Web only takes around 10–15 minutes, a small step that makes your first day in Japan much smoother.

— Step 7: Have Fun! ₊˚⊹ ᰔ

Whether you’re vlogging, journaling, or scrapbooking, record your experiences. You’ll be surprised how much you’ll want to relive the small moments later, like a quiet train ride, a cozy konbini meal, or a trinket you found in a gacha machine!

(♡ˊ͈ ꒳ ˋ͈)

— Final Thoughts ₊˚⊹ ᰔ

Planning a Japan itinerary doesn’t have to be complicated. Focus on what truly excites you. It could be food, anime, temples, shopping, nature, and then create a schedule that feels balanced and joyful from there. Your 2-week trip will fly by, but the memories will linger long after you’re home. Happy safe travels! ദ്ദി(˵ •̀ ᴗ - ˵ ) ✧

Logging off now,

Dayze ⋆. 𐙚 ˚