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Overview

Fly with Senpai: Halloween in Japan 2026
Tokyo, Japan
Oct 26 - 31, 2026
Tela image
Tela
$3,899
Deposit: $500

About your 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 Asakusa—Tokyo’s stunning historic 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 the boutique hotel MONday Asakusa, your home away from home. A 4 min walk to Sensōji Temple and Nakamise-dori shopping street, traditional Japanese culture is at your doorstep.

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 Asakusa offers daily complimentary breakfast buffet from 6:30-10 AM. With both Japanese and Western cuisine options, you can't go wrong!

Welcome Dinner

A celebratory welcome group dinner with Taylor on the first full day.

Monkey Kart Experience

Race through the city in real-life go-karts! Drive past iconic landmarks for an unforgettable experience on Tokyo’s timeless streets.

Day Trip to Kyoto

Enjoy a free day in Kyoto to explore with Taylor. The train will be departing early in the morning and returning to Tokyo in the early evening around dinner time. Roundtrip train ticket is included.

Sensōji Temple

Spend a morning strolling and getting lost wandering around Sensōji Temple, one of Tokyo's most famous Buddhist temples in the Asakusa neighborhood. You might even discover some delicious warabimochi!

TeamLAB Borderless

Immerse yourself in interactive displays of light, sound, and motion that respond to your movements and blur the lines of reality. This is one of the hottest IG spots in the city!

"Kill Bill" Final Dinner

Before departing, enjoy a memorable farewell dinner at the restaurant that inspired the famous fight scene in "Kill Bill." Then head to karaoke on Halloween to close your adventure.

VIP Halloween Karaoke

Sing your favorite all-time hits at karaoke in Shibuya for a once-in-a-lifetime, all-you-can-drink experience!

CYOA

Choose your own adventure! Explore the city OR head on a nerdy adventure with Taylor looking for rare collectibles and vintage finds at Nakano Broadway. End the night at a famous Tokyo muscle bar.

VIP Private Shopping

[Optional Add-on] Treat yourself to an exclusive shopping experience with Taylor and Meg Thee Stallion’s former Private Guide to discover Japanese hidden boutiques.

What's not included

International Flights

While we cannot provide flights, we will provide a round trip airport transportation service. Please plan to arrive at Haneda Airport between 2-5 PM and depart from Haneda Airport after 1PM.

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.

Oct 26: Arrival

Oct 26: Arrival image

Airport Arrivals & Welcome Experience

Day 1 | October 26

1-5 PM: Touchdown in Tokyo

We’re kicking off this adventure in style. After landing at Haneda (HND) between 1-5 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!

*As a reminder, only participants whose flights arrive at Haneda (HND) between 1-5 PM JST will be able to take the complimentary shuttle. If you will be arriving outside of this timeframe, we kindly ask that you make your own transportation arrangements to the hotel.

Welcome Drinks and Hors d'oeuvres: Meet Between 6-6:30 PM

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

After Welcome Drinks and Hors d'oeuvres: Relax and Dinner on Own

Ease into your first night in Tokyo with dinner on your own in Asakusa, whether you’re craving sushi, ramen, or something you spot on the street. Enjoy the town with Taylor on your first night!

Oct 27: Culture

Oct 27: Culture image

Sensoji Temple tour, Monkey Karts

Day 2 | October 27

6:30-8:30 AM: Morning Breakfast at Hotel

If you find yourself wide awake at the crack of dawn (due to jet lag) or just want to fuel up before our big day, hop on down to hotel MONday’s complimentary breakfast buffet.

 

9:00 AM: Meet in the Hotel Lobby to Go with a Guide to Sensōji Temple. Please be on time!

We’re kicking things off with a visit to Sensōji Temple, Tokyo’s oldest and most iconic Buddhist temple. Get lost in the charm of Asakusa, where ancient traditions meet vibrant street life. While you’re here, keep an eye out for warabimochi—a soft, chewy rice cake dessert (the matcha-flavored one is a personal favorite!). A photographer will also be joining you for about 4 hours while you are at Sensōji Temple as well to capture content and memories of your first full day in Tokyo!

 

Lunch: Explore Asakusa 

Have lunch on your own as you wander around Asakusa, Tokyo's historic district, and enjoy traditional snacks with Sensōji Temple in the background. The Uniqlo in Asakusa also offers custom Uniqlo embroidery (usually ready in 3 days). 

2:30 PM (Group 1) and 3:30 PM (Group 2): Monkey Karts

A "must-do" when in Tokyo,  experience the most thrilling activity by racing through Tokyo like a real-life video game character. To participate, you must have an international drivers license (IDP). Click here to obtain your IDP! 

Please note that for this activity, we will need to split up into two groups. Groups will be designated later closer to the day.

6:15-8:15 PM: Welcome Dinner with Taylor

Kick off your Tokyo adventure with a light, delicious welcome dinner with Taylor in a cozy, local Japanese restaurant near to your hotel. This dinner is complimentary.

Oct 28: Immersive Art

Oct 28: Immersive Art image

Free Day in Shibuya and Beyond!

Day 3 | October 28

6:30-8:00 AM: Morning Breakfast at Hotel

If you’re up early, head down to the hotel’s complimentary breakfast buffet and fuel up for what's about to be an incredible day. 

 

(Optional) 4:20 AM: Toyosu Tuna Auction

If you have ever been curious about Japan’s famous fish markets, this is your chance to experience one firsthand. Guests who opt in will meet the guide in the hotel lobby at 4:30 AM to visit the Toyosu Tuna Auction—a once-in-a-lifetime opportunity to witness the world's largest tuna auction. After the auction, you will eat breakfast on your own.

8:00 AM: Meet at the Hotel Lobby for teamLab Borderless

For those of you who wish to skip the tuna auction to sleep in or rest up, please meet your guide in the hotel lobby to head to teamLab Borderless!

9:00-11:30 AM: teamLab Borderless

Wander freely in a dreamlike world of digital artwork with no boundaries. Immerse yourself in interactive displays of light, sound, and motion that respond to your movements and blur the lines of reality. This is sure to be an unforgettable experience.

Enjoy a free afternoon in Shibuya and Beyond!

  • 2:00 PM Lunch at Ichiran 

    After all that exploring, what better way to recharge than with a bowl of rich, creamy tonkotsu ramen? Ichiran is famous for its customizable ramen and is one of Taylor's favorite spots! Choose everything from broth richness to spice level.

  • Shopping and Choose Your Own Adventure in Shibuya

    The rest of the day is all about exploring Shibuya at your own pace. Shop at Nintendo, the Pokémon Center, or Shibuya 109 (Tokyo’s legendary fashion mall that has unique pieces you won't find anywhere else)! Hunt for games, tech or beauty gadgets at Bic Camera and cross the infamous Shibuya Scramble! 

  • Dinner on Your Own

    You might want to stick around Shibuya for a bite or explore a new neighborhood to have dinner in that piques your interest!

Oct 29: Kyoto Day Trip

Oct 29: Kyoto Day Trip image

The City of Ten Thousand Shrines

Day 4 | October 29

Morning Breakfast at Hotel

If you grew up on dreaming about a trip to Kyoto, today is the day! But first-breakfast! Grab a plate at the hotel’s complimentary buffet from 6:30 AM – 10:00 AM before we head out to take an early train together to Kyoto.


Choose Your Own Adventure Day in Kyoto

The day is all yours to seize for wandering and exploring Japan's historic trip to Kyoto! Avoid the crowds at Fushimi Inari Taisha by going early in the morning, relax at a local café sipping matcha, or do some eclectic shopping downtown. 


We recommend checking out the Nintendo Museum, which can only be booked 3 months in advance. *This visit has the potential change, depending on availability. 


Choose Your Own Adventure: Back in Tokyo for Dinner

Around 8:00 PM, we’ll be back in Tokyo and you can have dinner: 

-Dinner on your own and go back to the hotel and rest up after a day in Kyoto.

-Optional: Golden Gai for drinks

Oct 30: CYOA

Oct 30: CYOA image

Choose Your Own Adventure: Tokyo!

Day 5 | October 30

6:30-10:00 AM: Morning Breakfast at Hotel

Taylor has shown you some of her favorite spots in Tokyo, but now it’s time to explore the city your way! First, fuel up with a delicious breakfast at the hotel’s complimentary buffet (open 6:30 AM – 10:00 AM) to prepare for a day filled with adventure. 

Your Day, Your Choice

  • Want a chill day? Relax at Yoyogi Park or take a day trip to Mt. Fuji. 

  • In the mood for a trendy theme café? Visit Sanrio, Kirby, or the Capybara Café.

  • For theme park thrills, spend the day at Sanrio Puroland, Tokyo Disney, or DisneySea. Reserve your tickets up to 6 months in advance.

  • Please note that for theme cafés and amusement park tickets must be purchased at least several weeks in advance and must be reserved on your own.

Or Join Taylor Senpai on a Nerdy Adventure!
Love anime, rare collectibles, and vintage finds? Join Taylor at Nakano Broadway—a quieter, hidden gem alternative to Akihabara with 4 floors of rare figurines, manga, and out-of-print books!


✨Bonus Stop✨ The Takashi Murakami Store

You'll arrive by 11 AM, then unwind at Coffee Zingaro, Murakami’s retro café filled with his signature colorful art. Enjoy a treat while browsing unique art pieces! 

Ikebukuro aka "Female Akihabara"

After Nakano, you'll do some anime shopping for women at Animate Ikebukuro (the largest anime/manga store in Japan), K-Books & Mandarake (rare BL, shoujo, and doujinshi), and Otome Road (this is THE spot for female anime/manga, cosplay gear, and unique collectibles).


Evening at Muscle Girl Bar OR Macho Man Bar (Optional)

After a day of anime shopping, join Taylor for an evening at either:

  • Muscle Girl Bar- the world's only female fitness-themed bar!

    OR

  • Macho Man Bar- where buff bartenders squeeze pineapples with their bare hands and flex on command.

The entry fee is around 5,000 JPY (about $33 USD) and includes 80 minutes of all-you-can-drink service. Tokyo's Macho Macho bars are the wildly unforgettable, only-in-Japan night out you didn't know you needed.

Oct 31: Turnt in Tokyo

Oct 31: Turnt in Tokyo image

Halloween in Shibuya: Kill Bill, Karaoke, & The Club

Day 6 | October 31

6:30 AM-9:00 AM: Morning Breakfast at Hotel

It’s nearing the end of our Trip in Tokyo and we’re going out with a bang! But first—breakfast. So fuel up before we dive into shopping, entertainment, and a fun Halloween night!

[Optional Add-On]

11:00 AM-3:00 PM: VIP Shopping with Taylor and Private Guide

For a VIP experience, come with Taylor and Meg Thee Stallion’s former private Tokyo guide! We’ll skip the touristy spots and explore hidden boutiques, exclusive Japanese streetwear, and unique fashion finds you won’t get anywhere else. This is the perfect chance to buy statement pieces for your wardrobe in Harajuku. Book this activity in the 'Add-ons' page.

5:00-7:00 PM: Farewell Dinner at the "Kill Bill" Restaurant

Before we head into our big night out, let’s slow down to enjoy a complimentary farewell dinner. This is the perfect time to relax, reminisce on our favorite moments, and soak in our last full night together.

7:45-9:45 PM: Group Karaoke in Shibuya 

Karaoke in the heart of Shibuya for an all-you-can-drink singing session. Whether you’re belting out Beyoncé, anime openings, or early 2000s throwbacks, this is going to be a night to remember. 

After Karaoke:

Shibuya Halloween is legendary—thousands of people in wild costumes filling the streets, clubs, and bars. If you’re feeling the energy, we can take it to the next level and hit up some clubs with Taylor to fully experience Japanese nightlife. This is our last night in Tokyo—let’s make it unforgettable! 

*Please note that new regulations prohibit foreigners from drinking in public and gathering around Shibuya Station on Halloween.

Nov 1: Departures

Nov 1: Departures image

Departure

Day 7 | November 1

6:30-9:00 AM: Morning Breakfast at Hotel

It’s your final morning in Japan, and while this week may have flown by, I hope it’s been unforgettable. Before heading out, take a moment to enjoy one last complimentary breakfast at the hotel and soak in the last bit of Tokyo’s magic.

10:00 AM Airport Departures
A complimentary shuttle will take you to Haneda International Airport for your return flight home.

For those who want to stay an extra day, select "Extend My Stay" in the Add-Ons to extend your experience. Airport transportation will be provided on Nov 2.

Location

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1. Tokyo, Japan

Tokyo, Japan

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