Fly with Senpai: Halloween in Tokyo [Week 1]

Tokyo, Japan

T
Tela
  • Email address verified
4 reviews
Oct 26 - Nov 1, 2025
Group size: 10 - 12
Fly with Senpai: Halloween in Tokyo [Week 1]
Tokyo, Japan

Tela
  • Email address verified
4 reviews

$2,850
Deposit: $500
Oct 26 - Nov 1, 2025
Group size: 10 - 12

About this trip

Hey friends! I want you to join me for an unforgettable 6-night stay in Tokyo, Japan! We’ll dive into the city’s vibrant culture and energy, staying in the heart of Akihabara—Tokyo’s iconic anime district.


I’ve handpicked some of my favorite experiences spanning over my many visits to Tokyo to share with you, from art and anime to nightlife and incredible adventures. Together, we’ll explore hidden gems and iconic spots, giving you a true local’s perspective—while also allowing your plenty of time to explore Tokyo your own way. Get ready for an immersive journey filled with creativity, flavors, and the dynamic spirit of Japan. I can’t wait to share this adventure with you!

What’s included

  • Local Boutique Stay
    Enjoy 7days/6nights at a boutique Japanese hotel, Hotel MONday, where you can rest as if you were in your own home. A 13 min walk from Akihabara Station, you'll be steps away from otaku culture.
  • Airport Transportation
    Let our team greet and escort you from the airport to the hotel. Please arrive at Tokyo International Airport (Haneda Airport) on October 26th between 2-5 PM (Tokyo time) to ensure a smooth arrival.
  • Daily Breakfasts
    Hotel MONday offers daily complementary breakfast buffet from 6:30-10 AM at their top floor restaurant with perfect views of the iconic Skytree.
  • Welcome Dinner
    A celebratory welcome group dinner with Taylor before MarioKart on the first full day.
  • Mario Kart Experience
    Race through the city in real-life go-karts, dressed as your favorite Nintendo characters. Drive past iconic landmarks for an unforgettable experience on Tokyo’s timeless streets.
  • VIP Private Shopping
    Treat yourself to an exclusive shopping experience in Harajuku with Taylor and Meg Thee Stallion’s former Private Guide to discover Japanese hidden boutiques
  • Sensōji Temple
    Spend a morning strolling and getting lost wandering around Sensoji Temple, one of Tokyo's most famous Buddhist temples in the Asakusa neighborhood. You might even discover some delicious warabimochi!
  • TeamLabs Planets
    Immerse yourself at one of the hottest IG spots in Tokyo for modern art, where you will walk through water, be surrounded by mirrored walls of fresh flowers and lie down in a dome of digital flowers.
  • Ghibli Museum & Tour
    This unique Ghibli film bus tour offers a guided visit to Ghibli Museum, a film screening, buffet lunch, and a tour of iconic architectural sites, evoking the charm of Spirited Away.
  • VIP Halloween Karaoke
    Sing your favorite all-time hits at karaoke in Shibuya for a once-in-a-lifetime, all-you-can-drink experience!
  • Farewell Dinner
    Before departing, enjoy a memorable farewell dinner before karaoke on Halloween to close your adventure.

What’s not included

  • International Flights
    While we cannot provide flights, our concierge team can help you find the best flight at an additional cost! If you rather book on your own, please arrive at Haneda Airport between 2 PM-5 PM.
  • Travel Insurance
    We require that all guests purchase travel insurance as all payments are non-refundable and cancellations fees apply. We recommend World Nomads or SquareMouth.
  • Additional Meals
    Although hotel MONday offers daily breakfast from 6:30-10 AM, we encourage guests to immerse themselves in Tokyo at local restaurants for most lunches and dinners on the trip.

Available Packages

[Early Bird]Double Occupancy
Deposit: $500
Available until April 1, 2025Sold Out

*Note: This rate is per person. Please have each roommate book this package individually. 

Room Description

This shared room features Two Deluxe Twin beds. While minimalist in style, this unique apartment-hotel is truly is equipped with with a kitchenette, refrigerator,  free wifi, washing machine and TV; giving you the feeling like you truly are a Tokyo local.

The "Fine Print" 

  • If selected without a roommate you will be matched with a roommate of the same gender. 
  • If no roommates are available to be matched, your package will be switched to single bed price.
  • If you have a requested roommate, please indicate at checkout

Cancellation Policy

  • All payments are final and non-refundable.
  • Late payments and cancellation fees will apply.
$2,850
Deposit: $500
[Early Bird] Single Room
Deposit: $500
Available until April 1, 2025Sold Out

*Note - This rate is for ONE person. If you would like to share the bed with a friend or as a couple, please have each guest individually book the double occupancy package.

Room Description

This private room features Two Deluxe Twin beds Pushed Together (Hollywood Twin). While minimalist in style, this unique apartment-hotel is truly is equipped with with a kitchenette, refrigerator,  free wifi, washing machine and TV; giving you the feeling like you truly are a Tokyo local.

The "Fine Print" 

  • If selected without a roommate you will be matched with a roommate of the same gender. 
  • If no roommates are available to be matched, your package will be switched to single bed price .

Cancellation Policy

  • All payments are final and non-refundable.
  • Late payments and cancellation fees will apply.
$3,450
Deposit: $500

Available Add-Ons

Extend My Trip | Double Occupancy
$160
Available until April 1, 2025

Choose Your Own Adventure 

If you wish to stay longer in Japan (and we don't blame you if you do), this optional day to add-onto your trip is all about that. Today is all about you and what you want to do on your final day in Tokyo. Whether it's doing some last-minute tax-free shopping, going back to your favorite café or local eatery, or visiting historic sites, like Tokyo Tower or the Imperial Palace, there is plenty to soak in before your flight.


Next Day Airport Departures

The next morning, bid farewell to Tokyo as you head to Haneda  Airport (in a complimentary ride) for your flight back to America. Relax and reflect on your trip and unforgettable memories and new friendships you have made along the way. May this experience stay with you and inspire you to explore more of Japan (and Asia) again in the future!

Fine Print 

*  Both roommates MUST extend the trip together .

* No preferred roommate? Please select the "Extend My Trip - Single Occupancy" option.

Extend My Trip | Single Occupancy
$310
Available until April 1, 2025

Choose Your Own Adventure 

If you wish to stay longer in Japan (and we don't blame you if you do), this optional day to add-onto your trip is all about that. Today is all about you and what you want to do on your final day in Tokyo. Whether it's doing some last-minute tax-free shopping, going back to your favorite café or local eatery, or visiting historic sites, like Tokyo Tower or the Imperial Palace, there is plenty to soak in before your flight.


Next Day Airport Departures

The next morning, bid farewell to Tokyo as you head to Haneda  Airport (in a complimentary ride) for your flight back to America. Relax and reflect on your trip and unforgettable memories and new friendships you have made along the way. May this experience stay with you and inspire you to explore more of Japan (and Asia) again in the future!

$2,850
Deposit: $500


Itinerary

Day 1: Arrival
Airport Arrivals & Welcome Experience

Touchdown in Tokyo

We’re kicking off this adventure in style. After landing at Haneda (HND) between 2-5 PM, grab your bags, a local SIM or pocket WiFi, and a Suica/Pasmo card for public transportation (trust me, you’ll need these). Then, we’ll hop on a private shuttle to our hotel—your home away from home for the week!


Welcome Drinks and Hors Devours

Settle in with complimentary champagne and hors d’oeuvres. Cheers to new friendships and all that Tokyo has to offer!


Relax and Dinner on Own

Ease into your first night in Tokyo with dinner on your own in Akihabara, whether you’re craving sushi, ramen, or something you spot on the street. If you’re feeling social, unwind at the hotel’s Skybar with a cocktail and city views before resting up for tomorrow.

Your Organizer


T
Tela
4 reviews
A travel design studio for visionaries

Reviews

AH
My recent trip to Guatemala was nothing short of transformational—a journey that was exactly what I needed to reset and begin the process of healing my nervous system. Every aspect of the trip was impeccably planned, with attention to detail that ensured a seamless experience. Each activity and experience felt thoughtfully tailored to align with the mission of the trip while addressing the unique needs of myself and everyone present. From grounding moments of tranquility to invigorating opportunities for connection and exploration, the atmosphere struck the perfect balance between calming and energizing. Morgan and Paige were the heart of this incredible experience. Their ability to co-create memories that will last a lifetime is unmatched. Their collaboration brought an unparalleled sense of care and intention to every moment, leaving me deeply grateful for their leadership. Without hesitation, I would join them on another journey at any time of the year. This trip was a gift to my soul, and I look forward to carrying its healing energy with me into the future.
By ANIYA H for "Unplug with Undone" Wellness Retreat on Dec 01, 2024
The good/great: -It was a beautiful venue - Logistics were organized/ran perfectly -Activities were fun -The itinerary was not overpacked -Communication was A1! Very well done!
By Jillian M for "Unplug with Undone" Wellness Retreat on Nov 26, 2024
From the start everything was intentionally curated! I truly appreciate the detailed thought and effort that took place to create a beautiful experience. My safety is always my main priority when traveling and I definitely felt safe during this trip down to the constant communication, accommodations and transportation. 10 out of 10 experience and would definitely do it again.
By Marjorie R for "Unplug with Undone" Wellness Retreat on Nov 21, 2024
Everything was so perfectly planned & executed! The villa couldn’t have been more stunning and comfortable. I loved the combination of down time to relax, wellness classes facilitated by Paige, and cultural-focused activities led by the local community. It was an ideal blend of rest, healing, exploration, learning, activity, and fun! Plus the house staff, breakfasts selections, fresh juices, champagne toasts… were all exceptional. Can’t wait for the next one!
By Jackie S for "Unplug with Undone" Wellness Retreat on Nov 21, 2024