A two-week journey through Japan is a dream come true — a perfect balance of time to explore multiple cities, immerse yourself in rich cultural traditions, and experience the country’s famous hospitality. But whether you crave the high-energy pace of Tokyo’s neon-lit streets, the elegance of Kyoto’s ancient temples, or the gastronomic delights of Osaka, you need an itinerary tailored to your interests to make the most of your time in this incredible country.
But in a nation as culturally and historically diverse as Japan, where do you even begin? That’s where we come in! At Wanderlust Jetsetter, we craft bespoke luxury travel experiences, ensuring every detail is thoughtfully curated. And as a specialist Japan travel agent, we make sure dream trips to the Land of the Rising Sun become a reality.
In this blog, we look at some of the main questions you must address first to make the most of your two-week trip to Japan. Once you have those answers, we can start to shape your vacation of a lifetime. Scroll down to get started — and please don’t hesitate to contact us if you have any questions.
Do You Want a Single-City or Multi-City Trip to Japan?
One of the first questions to consider is whether you’d prefer to stay in one city or explore multiple destinations. Of course, with two weeks at your disposal, a multi-city itinerary is totally feasible, highly rewarding, and offers a more comprehensive Japanese experience.
Single-City Stay: A Deep Dive into One Destination
A single-city stay allows for a more immersive experience, ideal for travelers who love to explore every corner of a destination at a leisurely pace. Tokyo or Kyoto are excellent choices, offering countless attractions, world-class dining, and cultural experiences. You could easily explore the wonders of the capital for two weeks without leaving the city — except for, say, a day trip to Kamakura or to see Mount Fuji in Hakone or Arakurayama Sengen Park.
On the other hand, Kyoto is much smaller but still densely packed with amazing things to see and do at an easy pace. But it also makes for a great base to enjoy day trips to Nara (get your photos with the famous deer), Uji (renowned for its matcha and green tea), Kobe (try authentic wagyu beef!), and Kurashiki (a dreamy town more akin to an open-air museum).
Staying in one city means less packing and moving between accommodations, and it minimizes transit time, allowing you to soak in the local atmosphere. However, you may miss out on Japan’s diverse regional cultures.
Is your Japan trip going to be your honeymoon? As expert honeymoon travel agents, we can add those all-important romantic touches to your itinerary to make it even more memorable.
Multi-City Japan Itinerary: See More Without Feeling Rushed
A two-week trip provides the perfect amount of time to visit multiple cities in Japan without feeling overwhelmed. Popular destinations on multi-city routes include:
- Tokyo – A dynamic metropolis blending ultramodern attractions with historic districts.
- Osaka – Japan’s culinary capital, famous for its vibrant nightlife and street food.
- Kyoto – The cultural heart of Japan, home to serene temples, tea houses, and geisha culture.
- Nara – A historical gem with stunning temples and free-roaming deer in Nara Park.
- Hiroshima – A poignant yet inspiring city known for the Peace Memorial Park and the floating torii gate of Miyajima Island.
- Sapporo – Perfect for winter travelers seeking snow festivals, skiing, and fresh seafood.
The Shinkansen (bullet train) runs between Japan’s major cities, making travel quick, easy, and comfortable. Riding this iconic high-speed train is also an unforgettable Japanese experience in itself. If you plan to take multiple Shinkansen rides, we can purchase a JR Pass on your behalf; that’s one less thing for you to worry about!
Are you an F1 fanatic? Find out more about our F1 travel packages and see if you can combine your trip with the thrilling Japanese Grand Prix at the Suzuka Circuit.
What Do You Want to See and Do in Japan?
Japan is one of the most diverse travel destinations in the world. There truly is something for everyone here! Ultimately, your ideal Japan itinerary depends on your personal tastes and preferences. To help shape your schedule, let’s look at some areas of interest that may appeal to you.
Japanese Culture and History
For those drawn to Japan’s rich history and tradition, Kyoto is a must-visit, with iconic temples like Kinkaku-ji (the Golden Pavilion) and the bold, vivid Fushimi Inari Shrine’s torii gates. Nearby Nara’s Todai-ji Temple houses a giant Buddha, while Hiroshima’s Peace Memorial Park provides a poignant historical perspective further afield. Tokyo is also home to many cultural and historical gems, including the Imperial Palace, Senso-ji, and Meiji Jingu.
Modern Attractions and Theme Parks in Japan
Tokyo’s Akihabara district is a haven for anime, gaming, and technology enthusiasts. Shinjuku and Shibuya offer dazzling skyscrapers and shopping. If theme parks are a priority, Tokyo Disneyland and Universal Studios Japan in Osaka should be on your list. Wanderlust Jetsetter is a theme park travel agent, so we can arrange everything you need for trips to these world-famous locations as part of your two-week Japan itinerary.
Food and Culinary Experiences in Japan
Japan’s food scene is unparalleled. Tokyo has the most Michelin-starred restaurants in the world, while Osaka’s Dotonbori district is famous for street food like takoyaki and okonomiyaki. Don’t miss out on a traditional kaiseki dinner in Kyoto or the freshest sushi you can imagine at Toyosu Market in Tokyo. Japan’s culinary world is seemingly endless and a joy to explore, so we can barely scratch the surface here.
Japan’s Natural and Scenic Beauty
Mount Fuji offers breathtaking hiking opportunities (and awe-inspiring views), especially in late summer. Japan’s stunning cherry blossoms add splashes of color in spring while autumn foliage in Kyoto and beyond creates stunning seasonal landscapes. If you prefer winter sports, Niseko in Hokkaido is Japan’s premier ski destination.
What Time of Year Do You Want to Visit Japan?
Each season in Japan offers a unique, unforgettable experience. Spring and autumn are the most colorful and comfortable; summer sees hot and sultry weather that eventually triggers the rainy season while the winter chill brings a cold snap and snowfall, especially in the north where the temperatures are lowest.
- Spring (March to May): Famous for stunning cherry blossom displays (sakura), spring has mild temperatures (50 to 70°F) ideal for exploring. Expect large crowds, especially in Kyoto and Tokyo around cherry blossom season.
- Summer (June to August): Summer in Japan is hot and humid (70 to 90°F), but great for hiking Mount Fuji and enjoying summer festivals with fireworks. The rainy season starts in June and lasts until around mid-July — but it doesn’t rain every day! The season begins in Okinawa’s islands around a month earlier.
- Autumn (September to November): A return to comfortable temperatures (50 to 75°F) with stunning fall foliage that is a joy to explore, particularly in Kyoto and Nikko. Seeking the most picturesque landscapes is so popular that it even has a name: Momiji-gari, which translates into “hunting red leaves”.
- Winter (December to February): Temperatures tumble in the winter (30 to 50°F), but these conditions are perfect for visits to onsen (hot springs), skiing in Hokkaido, and magical seasonal illuminations in Tokyo, Osaka, and other major cities.
What Kind of Accommodation in Japan Do You Want to Stay In?
Vacation accommodation is an integral part of any trip. It’s your home away from home, so it’s important to find the ideal balance between your own comfort levels and authentic cultural experiences. Fortunately, Japan has a wide range of accommodation options to suit every kind of traveler.
- Luxury Hotels: You’re spoilt for choice when it comes to luxury hotels in Japan. The Aman Tokyo, Ritz-Carlton Kyoto, and Park Hyatt Tokyo are just three examples of the world-class service and amenities you can expect in a country renowned for its outstanding hospitality.
- Traditional Ryokan: A stay at a high-end ryokan, such as Gora Kadan in Hakone, includes exquisite kaiseki meals and private onsen baths. If authentic overnight stays are high on your list of priorities, a traditional ryokan is a must!
- Boutique Hotels: Japan has a growing selection of stylish boutique accommodations that blend modern aesthetics with Japanese craftsmanship. These smaller hotels offer an appealing middle ground between luxury stays and traditional ryokan.
Brush Up on Japanese Customs and Cultural Etiquette
Japan has a deep-rooted sense of etiquette that enhances the travel experience. Here are a few key points to remember:
- Tipping is not expected – Excellent service is standard, so insisting on tipping may be considered awkward.
- Keep quiet on public transport – Speaking loudly is frowned upon — and showing the sole of a shoe to someone is considered rude, so stay mindful of how you sit.
- Remove shoes indoors – On the topic of shoes, many ryokan, temples, and private homes require you to remove shoes.
- Follow escalator etiquette – In Tokyo, stand on the left and walk on the right; in Osaka and the wider Kansai region, it’s the opposite.
- Respect queuing culture – Whether at train stations or restaurants, orderly lines are the norm, so join the back of the line.
Are you planning to travel to Japan with your kids? Organizing a two-week international vacation can feel overwhelming, especially when there’s a language barrier. But you can have peace of mind with Wanderlust Jetsetter. We’re a family vacation travel agent too, so you can count on us to take the stress out of planning your brood’s getaway.
Learn Basic Japanese Phrases Before You Arrive
While English signage is common, learning a few key Japanese phrases can enhance your experience. Here are a few to get you started:
- Arigatou gozaimasu (ありがとうございます) – Thank you.
- Sumimasen (すみません) – Excuse me / Sorry.
- Eigo o hanasemasu ka? (英語を話せますか？) – Do you speak English?
- Ikura desu ka? (いくらですか？) – How much is this?
- Onegaishimasu (お願いします) – Please (useful for ordering food or requesting help).
Let Us Craft Your Dream Two-Week Japan Itinerary
We hope this guide has given you a better sense of how to make the most of a two-week trip to Japan. At Wanderlust Jetsetter, we are the perfect combination of a Japan travel agent and specialists in bespoke luxury travel experiences. Let our all-star team bring your dream Japan vacation to life.
Let’s start planning! Simply get in touch and let us know your needs and wants — we’ll take it from there!
