Japan Express: Tokyo, Kyoto, Nara & Osaka in 8 Days




Itinerary
When we think of a Japan itinerary in 8 days, what pops into mind? Neon lights in Tokyo, ancient temples in Kyoto, deer casually stealing your snacks in Nara… did we get it right?
Good. Because we’re doing all that — and a bit more.
This Japan group trip is the perfect mix of modern chaos and timeless calm. We start in Tokyo, where skyscrapers, ramen bars and karaoke nights will test your energy levels (spoiler: you’ll keep up). Then we hop on a bullet train — yes, the real one — and slow things down in Kyoto, among shrines, geishas and quiet streets that feel like a different century.
We’ll take a day trip to Nara (brace yourself: the deer have no boundaries), and wrap things up in Osaka, where food is basically a lifestyle and neon lights compete for your attention.
Eight days, four cities, countless memories. And yes, you’ll finally understand why everyone keeps talking about Japan.
Ready? Let’s go.


Tokyo: welcome to Japan
1 night: Tokyo
We made it
Jet lag? Probably. Excitement? Definitely.
You land in Tokyo, check in, and suddenly it hits: we’re actually in Japan. First meetup with the group, first awkward smiles (that will last about 7 minutes), and then straight into our welcome dinner (optional)
Sushi, ramen or something you’ll Google later — we start strong. If energy allows, we test Tokyo nightlife. If not… no worries, we’ve got time.

Neon lights & hidden temples
1 night: Tokyo
Balance is overrated (and Tokyo proves it)
We explore Tokyo: from Shibuya Crossing (yes, that one) to quieter temples where everything suddenly slows down.
Street food? Obviously. Random shopping you didn’t plan? Also yes.
And tonight: karaoke. Don’t worry, nobody here is a professional. That’s kind of the point.

Ueno Park
1 night: Tokyo
Getting lost is part of the plan
Today we lean into freedom, ready to explore more of the city's culture and history. We visit Ueno Park, one of the most popular parks in the city, home to many temples and shrines. The most notable is the Gojo Tenjinsha Shinto shrine, which can be reached by walking through a pathway lined with traditional red torii gates. Food is a fundamental part of any country's culture, so tonight's dinner will be no exception. We immerse ourselves in the vibrant streets of Ameyoko Market, near Ueno Park. Let's get our taste buds ready!
Museums, vintage shops, food hunts, or just wandering around like you live here — Tokyo works best when you stop trying to control it.
This is where the city starts making sense. Or not. Either way, you’ll love it.

Bullet train & slow vibes
1 night: Kyoto
From skyscrapers to shrines in a blink
We jump on the Shinkansen — yes, the famous bullet train. Fast, smooth, slightly unreal.
A few hours later: Kyoto.
Different pace, different vibe. Think wooden houses, quiet streets and a lot of “wait, this is beautiful”.
First walk around the city to soak it all in.

This is the Japan you imagined
1 night: Kyoto
Temples & tea
Kyoto day. The real one.
We explore temples, shrines, and neighborhoods that feel frozen in time. And then, we slow things down properly with a traditional tea ceremony — yes, the kind you’ve seen in movies, but better because you’re actually there.
Take your time. Kyoto deserves it.

Nara: deer have no chill
1 night: Kyoto
Day trip to Nara
We head to Nara for the day — and meet its most famous residents: deer. Friendly? Yes. Respectful of personal space? Not really.
Between temples, parks and snack-stealing moments, this is one of those days you won’t forget.
Back to Kyoto in the evening.

Kyoto → Osaka: food is serious business
1 night: Osaka
Eat, explore, repeat
We move to Osaka, where the vibe shifts again — louder, brighter, tastier.
This city doesn’t play around when it comes to food. Street food, local specialties, random stops just because it smells amazing — we’re doing all of it.
And at night? Neon lights and good vibes. Simple as that.

Osaka: sayonara
Goodbye Japan (the group chat will survive, don’t worry)
Last morning together. Breakfast, check-out, and the classic “how did this go by so fast?” moment.
e say goodbye — or better, see you soon somewhere else in the world.
What's included
7 nights hotel in twin room with private bathroom
Breakfasts
Tea ceremony in Kyoto with English speaking assistant
Train rides: Tokyo to Kyoto and Kyoto to Osaka
Group Leader services
Medical and baggage insurance - (coverage limits by destination country/region - €10,000 Italy, €20,000 Europe, €30,000 World, €50,000 USA/Canada)
What's not included
Roundtrip flight to/from destination
Food and beverages unless specified
Entrance fees for temples and attractions chosen by the group - approx. USD30-50
All souvenirs and extras that you wish to buy and will be able to squeeze in your backpack
Anything not mentioned in the "What's included" section
Optional activities
Please see below extra optional activities that you can experience during your trip. Your Group Leader will be happy to assist with organizing these activities for the group. Availability may vary depending on location and group preferences. Please note these activities are provided by third party suppliers and liability rests exclusively with these third party suppliers.
Foodie Tour & sake tasting in Osaka - approx USD130
Round-trip regional train to Nara - approc. USD15
Why WeRoad
Small groups, on average 11 people
Move or change your trip for free up to 31 days before departure
Book with $ 0. Pay the $ 100 deposit only once the trip is confirmed
The Group Leaders
Find your flight
For this trip, we recommend arriving and departing from these airports.

















