Roxy Jefferson
The Traveling Chucks
The Traveling Chucks Experience Japan- 2027
Oct 2, 2027 to Oct 9, 2027
Tokyo and Osaka
🇯🇵 JAPAN 2027
Tokyo • Mount Fuji • Osaka
October 2nd–9th, 2027
8 Days | 7 Nights | Hosted Experience
TOKYO LIGHTS. JAPANESE CULTURE. OSAKA NIGHTS.
Japan has been sitting on the bucket list long enough.
Over eight unforgettable days, we’ll experience the electric energy of Tokyo, escape the city for the beauty of Mount Fuji, and finish in Osaka with culture, incredible food, shopping, and nights worth staying out for.
This is Japan experienced with intention — iconic sights, immersive cultural experiences, great food, free time, and hosted moments you probably wouldn't plan on your own.
And because this is The Traveling Chucks, we're leaving room for a little after-dark energy too.
✨ THE EXPERIENCE
This isn't about rushing through Japan trying to see everything.
We've curated a balance of culture, food, exploration, nightlife, and free time so you can experience Japan without spending months figuring out the logistics yourself.
We'll handle the details.
You come ready to experience it.
✨ SIGNATURE EXPERIENCES
🌃 NEON NIGHTS: TOKYO AFTER DARK
Tokyo after dark deserves its own moment.
For our signature Neon Nights, we’re getting dressed and stepping into the electric streets of Tokyo surrounded by glowing signs, city lights, and that unmistakable Tokyo energy.
And we’re capturing it.
📸 Neon Nights Photoshoot
Think elevated street style, neon-lit streets, city energy, and photos that actually look like you went to Tokyo.
THE LOOK: Elevated Tokyo street style
THE VIBE: Neon. Stylish. Grown. Unforgettable.
More details about the theme and photoshoot will be shared with booked travelers.
🍸 COCKTAILS AFTER DARK
Japan isn’t only about what happens during the day.
We’re setting aside one evening for Cocktails After Dark — a hosted night to experience Japan’s bar scene, enjoy a few good cocktails, and spend time together without another tour on the agenda.
Good drinks. Good conversation. Japan after dark.
🛍️ SHOP OSAKA YOUR WAY
We’ve intentionally left room in the itinerary for you to experience Osaka your way.
And if shopping is on your Japan list, this is your time.
Vintage designer. Japanese fashion. Streetwear. Beauty. Souvenirs. Department stores. Or that completely unnecessary purchase that suddenly becomes very necessary because you’re in Japan.
Shop, explore, grab lunch, wander, or take the day in another direction entirely.
No group itinerary. No rushing. Just free time to enjoy Osaka your way.
🇯🇵 MORE JAPAN TO EXPERIENCE
Beyond our signature moments, your journey includes a mix of iconic sights, food, culture, and experiences throughout Tokyo, Mount Fuji, Kyoto, and Osaka.
🍣 SUSHI-MAKING EXPERIENCE
Get hands-on with one of Japan’s most recognizable culinary traditions during an authentic sushi-making experience.
Included | Lunch Included
🗻 MOUNT FUJI
Leave Tokyo behind for a full-day experience in the Mount Fuji area featuring beautiful scenery, scenic transportation, walking paths, and plenty of photo-worthy moments.
Included | Full-Day Experience
🚅 SHINKANSEN BULLET TRAIN
The journey becomes part of the experience as we travel from Tokyo to Osaka aboard Japan’s famous Shinkansen bullet train.
Included
⛩️ FUSHIMI INARI
Walk beneath the iconic red torii gates of Fushimi Inari Taisha and experience one of Japan’s most recognizable cultural landmarks.
Included
🍵 MATCHA TEA EXPERIENCE
Slow things down with a traditional matcha experience and another opportunity to connect with Japanese culture beyond sightseeing.
Included
What's included in this trip:
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3 nights in 4-star accommodations in Osaka
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4 nights in 4-star accommodations in Tokyo
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Bullet train transfer from Osaka to Tokyo
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Group airport transfers on arrival and departure
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All ground transportation for activities included in the itinerary
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Daily breakfast
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2 hosted lunches
- Neon Nights Photoshoot
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Guided full-day Mount Fuji experience
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Authentic sushi-making class
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Traditional Matcha Tea ceremony
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Welcome cocktails
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Cultural tours and hosted group experiences in each city
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Swag bag with exclusive Traveling Chucks Essentials
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1 Traveling Chucks Host supporting the group throughout the journey
What's not included:
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International Flights
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Travel insurance
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Meals not listed
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Optional add-ons
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Nightlife entry fees
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Transportation to add-on activities
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Passport / visa fees
- Gratuites
Let's Drift through Japan
-Tokyo to Osaka Itinerary-
Day 1 – Arrival in Tokyo (10/02)
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Arrival at Haneda International Airport (HND)- (Depart on October 1st in order to Arrive on October 2nd)
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Group airport transfer
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Hotel check-in
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Welcome Cocktails
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Settle in, meet the group, and ease into Tokyo nightlife
DAY 2 — TOKYO CULTURE + NEON NIGHTS (10/03)
Tokyo, we’re outside.
We’ll begin with an authentic sushi-making experience before heading out to experience some of the neighborhoods and landmarks that make Tokyo one of the most fascinating cities in the world.
Today’s Highlights:
- Breakfast at hotel
- Authentic Sushi-Making Experience
- Imperial Palace area
- Shibuya Crossing
- Harajuku
- Time to return to the hotel and refresh
✨ TONIGHT: NEON NIGHTS
Get dressed.
Tonight we’re stepping into the lights for our signature Neon Nights experience + photoshoot.
Tokyo becomes the backdrop.
Activity Level: Moderate
Meals: Breakfast + Lunch
Day 3 – Mount Fuji Day Experience (10/04)
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Breakfast
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Full-day guided Mount Fuji experience:
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Scenic trains
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Ropeway sky tram
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Walking paths with breathtaking views
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Evening free for nightlife or rest
Activity Level: Moderate to Difficult
Meals: Breakfast, Lunch
Day 4 – Options- Tokyo Shopping & Street Karts or DisneySea Day (10/05)
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Breakfast at hotel
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DisneySea (Add on) or Temple visit, local markets & shopping
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Evening free to Explore Shibuya or Shinjuku
Activity Level: Moderate
Meals: Breakfast
Day 5 – Bullet Train to Osaka (10/06)
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Breakfast on the go
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Check-out
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The Famous Bullet Train from Tokyo to Osaka
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Check-in to Osaka accommodations
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Evening free to explore Dontonbori and Nightlife
Activity Level: Easy
Meals: Breakfast, Lunch
DAY 6 — CULTURE + COCKTAILS AFTER DARK (10/07)
Today brings us to Fushimi Inari Taisha, famous for its seemingly endless path of red torii gates.
Explore, take photos, learn about the significance of the shrine, and continue farther up if you’re feeling adventurous.
Then we’ll head back and get ready for another side of Japan.
🍸 TONIGHT: COCKTAILS AFTER DARK
Tonight, we’re heading out.
Good cocktails. Good conversation. A little exploring. And a chance to experience Japan after the sun goes down.
Activity Level: Moderate to Active
Meals: Breakfast
DAY 7 — SHOP OSAKA YOUR WAY (10/08)
It’s our final full day in Japan, and we’re leaving room for you to make it your own.
We’ll come together for our Matcha Tea Experience, then Osaka is yours.
Go vintage shopping. Hunt for Japanese fashion and beauty finds. Grab lunch. Explore. Pick up those last-minute souvenirs. Or simply wander and see where the day takes you.
There’s no group shopping itinerary and no list of stores to follow.
Shop Osaka your way.
Activity Level: Easy
Meals: Breakfast
Day 8 – Departure (10/09)
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Farewell breakfast
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Hotel check-out
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Group transfer to Osaka Itami Airport (ITM)
(Mata aimashō — Let’s meet again)
ROOMMATE MATCHING REQUESTS ARE AVAILABLE
Want to experience Japan but don’t already have someone to room with?
After booking, you may request to participate in our complimentary Roommate Matching Service.
You’ll complete a roommate questionnaire that helps us learn more about your travel style, room habits, and preferences. If we identify a potential roommate, we’ll introduce you so you both have an opportunity to connect before agreeing to the match.
A few important things to know:
- Roommate matching is not guaranteed.
- Your reservation must remain active and current with all required payments to remain eligible.
- Roommate matching requests close 90 days before departure.
- If a roommate has not been confirmed by the deadline, you will be responsible for the applicable single-occupancy rate or single supplement, subject to availability.
The goal is to make joining the trip easier for travelers who are ready to go — even when their usual travel partner isn’t.
Flights & Transfers
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Arrival October 2, 2027: Haneda International Airport (HND) ....(NRT is available with added private transfer fee)
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Departure October 9, 2027: Osaka Itami Airport (ITM) ....(KIX available with added private transfer fee)
One group transfer is included on arrival.
One group transfer is included on departure.
Flights outside the designated transfer window incur a $50 additioinal per person fee for transfer. We will provide flight suggestions when it becomes available.
💳 INVESTMENT + BOOKING
$150 PER PERSON DEPOSIT
A $150 per person deposit secures your reservation.
- Monthly payment plans are available
- Final payment is due 60 days before departure
- All payments are non-refundable and non-transferable
Once your deposit is submitted, your monthly payment schedule will be generated automatically.
Because our international partners and suppliers have firm payment deadlines, timely payments are required to maintain your reservation.
If more than two consecutive payments are missed, your reservation may be subject to cancellation.
We understand that life happens. If something comes up, please communicate with our team as early as possible so we can assist where possible within our policies.
By booking this experience, you are agreeing to The Traveling Chucks’ Terms and Conditions, including our payment, cancellation, and refund policies.
🧾 How to Book
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Select your room type and any add-ons
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Enter traveler details
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Submit roommate information (or enter “N/A”)
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Review your booking details
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Submit your deposit or full payment
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A monthly payment plan will be automatically generated once your deposit is placed
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You’re booked
📩 Questions?
📞 901-501-6188
404-548-8125
📧 contact@thetravelingchucks.com
Available Packages
We Love Japan- Double Occupancy $2960 Per Person
Available until July 31, 2027
- 11 left
$2,960.00
Deposit: $150.00 per person
Double Occupancy Package
Please select this option for 2 guests sharing 1 room with 2 single beds (maximum 2 guests per room).
This package includes:
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Accommodations in 4-star hotels
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Included group activities & cultural experiences
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(1) In-country speed train ride (one-way from Tokyo to Osaka)
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Immersive experiences highlighting authentic Japanese culture
- Airport transfers with private group
Pricing is listed per person based on 2 guests sharing a room.
Please add one package per guest occupying the room.
BY BOOKING THIS EXPERIENCE YOU AGREE TO THE TRAVELING CHUCKS TERMS AND CONDITIONS
I Love Japan- Single Occupancy $3980
Available until July 31, 2027
- 3 left
$3,980.00
Deposit: $150.00 per person
Solo Occupancy Package
Please select this option for 1 guest occupying 1 room.
Room includes 1 double or twin bed for a solo traveler.
This package includes:
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Accommodations in 4 star hotels
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Included group activities & cultural experiences
-
(1) In-country speed train ride (one-way from Tokyo to Osaka)
-
Immersive experiences highlighting authentic Japanese culture
Pricing is listed per person for single occupancy.
BY BOOKING THIS EXPERIENCE YOU AGREE TO THE TRAVELING CHUCKS TERMS AND CONDITIONS