
TRIP OVERVIEW
Take Off With Us and experience the perfect blend of modern energy, historic charm, and cultural treasures on this unforgettable 10-day journey through Japan’s most iconic cities. From neon-lit streets to serene temples, this adventure captures the best of Tokyo, Osaka and Kyoto. Whether you’re marveling at Tokyo’s skyscrapers, indulging in Osaka’s culinary delights or finding serenity in Kyoto’s temples, this trip offers the perfect mix of turn up, culture and unforgettable memories!
**There are a limited number of spots, so reserve yours today to ensure that you don’t miss out. **
THE TOWT EXPERIENCE
We have carefully crafted an itinerary that is tailored to fully immerse you in the rich culture of Japan. You’ll join your favorite Travel Ambassadors, as we explore this magical land of contrasts. And the best part is - we've done all the planning and hard work for you.
Are you ready to experience Tokyo like never before? Let’s make this TOWT adventure one for the books!
YOUR INVESTMENT
TRIP ​PRICE:
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$350 Deposit to reserve your spot!
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Then 6 monthly payments of $500
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Pay in Full option available ($3,200)
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Prices are PER PERSON
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$100 discount for previous Take Off With Tiff Travelers. Early bird discounts also available!
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Price is for double occupancy hotel stays. Limited number of single occupancy rooms available - inquire for pricing. (Roommate matching available)
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Options to pay on website, PayPal, Zelle, Apple Pay or Venmo
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Travel insurance is not included.
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​***International Flights not included. Please do not purchase international airfare until you have received a confirmation email from Take off With Tiff confirming your reservations.***
WHAT'S INCLUDED
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Transportation to and from airport
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Roundtrip Bullet Train Ticket (for Domestic Travel)
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3-4 star hotel accommodations*
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A handpicked curated group of likeminded wanderlusters
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Some meals included
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Scheduled excursions and entry fees
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Welcome Dinner
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TOWT Welcome Gift
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*Accommodation are in a shared room with one other person. We also have a limited number of private rooms available on a first come, first served basis (for an additional fee). If you are interested in a private room, please contact us regarding availability.
WHAT'S NOT INCLUDED
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Flights (International flights to Japan)
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Passport Fees & Visa Fees
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Travel Insurance (Highly Recommended)
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Non-listed excursions and activities
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Some lunches and dinners
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Alcoholic beverages not included in the tour
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Tipping
PAYMENTS & PAYMENT PLANS
All payments to Take Off With Tiff are non-refundable and non-transferable. This is because Take Off With Tiff has contractual agreements with hotels, and other vendors that will not allow us to obtain any refunds. This way we can keep our package prices low and allow you to make monthly payments on your vacation.
Should you opt-in to our payment plan program, your invoice will clearly note your due dates and amount. We suggest you put this payment plan on your personal calendar.
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A $50 late fee will be applied to all payments made after the 3-day grace period. Your trip is subject to cancellation after two missed payments.
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Notes:
Traveling abroad requires a passport valid for six months beyond your travel dates. You must have a valid passport with an expiration date no SOONER than April 21, 2026.
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U.S. citizens carrying a tourist passport and in possession of an onward or return airline ticket do not require a visa to enter Japan. If you are not a US Passport holder, please check for the requirements for your specific passport.
FLIGHTS
Your gateway to our Japanese Adventure, is through Tokyo International - Haneda Airport (HND) or Narita International Airport (NRT).
To capitalize on early bird rates and secure your desired travel itinerary, we suggest booking flights roughly 3-5 months ahead of your departure date.
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International Flights:
Book roundtrip flights and plan to arrive by 3:00 p.m. local time on October 12, 2025.
Plan to depart after 12:00 p.m. local time on October 22, 2025​
It is the sole responsibility of the participant to purchase ALL of their international airfare.
If you need assistance with booking your flights, please contact the TOWT team at takeoffwithtiff@gmail.com and we’d be more than happy to assist you.
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![]() Image by Denys Nevozhai | ![]() tokyo5 | ![]() tokyo6 |
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![]() tokyo7 | ![]() Image by Matt Ketchum |
ITINERARY
Day 1: (October 12th) Welcome to Tokyo
Welcome to the World’s Most Exciting City! After touching down in Tokyo, you’ll check into your hotel in the vibrant Shinjuku neighborhood. Get settled into your hotel room and freshen up, explore the neighborhood, grab a bowl of ramen – a perfect intro to Japan’s food culture, meet the rest of the TOWT crew, or just catch up on some sleep. Today is all about settling and gearing up for an adventurous trip.
For those with energy we’ll hit up the late-night Shinjuku party scene.
Included meals: None
Key highlights: Arrivals
Day 2: (October 13th) Intro to Tokyo
Dust off your walking shoes, today we get a quick tour to help familiarize you with the bustling city! Our tour guide will bring us all around the city, showing us the ins and outs of Tokyo’s sprawling public transportation system and teaching us a few key Japanese phrases. Consider this your intro to Tokyo!
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Later that evening we meet up for our (themed) TOWT Welcome Dinner.
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As night falls, we’ll venture into the Golden Gai area in Shinjuku—a maze of tiny, themed bars where each drink tells a story. Remember, what happens in Tokyo, stays in Tokyo!
Included meals: Breakfast, Dinner
Key highlights: Walking Tour, Welcome Dinner
Day 3: (October 14th) Timeless Traditions in Asakusa
This morning, we step back in time at Senso-ji Temple, Tokyo’s oldest Buddhist temple. We’ll walk through the iconic Kaminarimon Gate and explore Nakamise Street, where vendors sell everything from kimono fabric to freshly made melon bread.
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Afterwards we head to tour the iconic streets of Asakusa, as we drive custom built go karts. Dress up as your favorite character to add an extra layer of excitement as we go on an exhilarating ride through Tokyo’s bustling streets. ** A Driver’s License is required for this activity. As well as an International Driving Permit (IDP). We will provide details on how to easily obtain one. A limited number of alternative vehicles are available for non-license holders**
After our fast and furious adventure, it’s time to slow things down a bit! We make our way to participate in a traditional Tea Ceremony, complete with wearing a kimono as we experience an integral part of Japan’s rich cultural heritage. Afterwards we’ll continue our journey at the nearby Samurai Museum, where we will explore fascinating samurai and ninja activities, complete with ninja star-throwing!
Included meals: Breakfast, Tea
Key highlights: Go Karts, Tea Ceremony
Day 4: (October 15th ) Culture Meets Cool
Begin your day in serene bliss at the Meiji Shrine, nestled in the lush greenery of Yoyogi Park. Then, we’ll step into the vibrant world of Harajuku, where Takeshita Street overflows with quirky fashion, playful accessories, and must-try snacks like rainbow cotton candy.
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Afterwards we’ll head over to Shibuya to visit the world's busiest pedestrian crossing, with as many as 3,000 people crossing at a time – Shibuya Crossing. While in Shibuya, we will pay a visit to one of Japan’s unique cafés - here you can relax, sip on a drink and spend quality time with an adorable animal. From cats and owls to hedgehogs and even capybaras, these unique cafes offer an unforgettable way to interact with animals in a cozy and friendly environment.
After our cute and cuddly animal interactions, it’s time to chase sunsets! We make our way up to Shibuya Sky - Tokyo’s newest and most breathtaking observation deck. Here we’ll watch the sunset with 360-degree panoramic views of Tokyo’s iconic skyline, stretching all the way to Mount Fuji on clear days!
The night is still young, time to unleash your inner superstar! We’ll make our American Idol debuts, as we hit up one of Tokyo’s infamous Karaoke spots.
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Included meals: Breakfast
Key highlights: Shibuya, Karaoke
Day 5: (October 16th ) C'Mon n' Ride The Train!
All Aboard!! Today we board a Shinkansen (bullet train) to head to Osaka. Japan’s third-largest city, it’s a vibrant metropolis renowned for its dynamic nightlife, exceptional street food, and rich cultural heritage. It’s often referred to as “Japan’s Kitchen.”
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After checking into our hotel room, we head out to see with all the food fuss is about! We roll up our sleeves and try our hands at a Japanese cooking class.
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Later that evening, we’ll hit up the Dotonbori District to experience the energetic night life, neon lights and late-night bites.
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Included meals: Breakfast, Lunch
Key highlights: Bullet Train Travel to Osaka
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Day 6: (October 17th) Finding our Zen
Today we ditch the city and embark on an enchanting journey through Kyoto, the cultural heart of Japan. Renowned for its timeless temples, serene gardens and traditional tea ceremonies. Here we’ll stroll through the iconic bamboo groves of Arashiyama, wander the endless red gates at Fushimi Inari Shrine and explore the stunning Golden Pavilion.
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Later that evening, back to the Dotonbori District for our final night of partying in Osaka.
Included meals: Breakfast
Key highlights: Kyoto
Day 7: (October 18th ) Best of Both Worlds
The first half of the day is yours to explore Osaka on your own.
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Head back to Chinatown, check out the ramen noodle museum, visit the Umeda Sky Building. Just don’t venture off too far, later in the afternoon we board the Shinkansen (bullet train) to head back to Tokyo, to finish up the rest of our Tokyo explorations!
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Once back in Tokyo, we'll check into our hotel and the rest of the evening is yours to explore Tokyo on your own.
Included meals: Breakfast
Key highlights: Bullet Train Travel to Tokyo
Day 8: (October 19th) Anime, Arcades, and All Things Geeky
Today is all about the future! We start this fun and geeky day with a visit to TeamLab Borderless, where digital art comes alive in mesmerizing displays.
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Afterwards we dive into the heart of geek culture in Akihabara. Here we’ll spend the day exploring multi-level arcades, anime shops, and collectible stores. For lunch, we will experience the quirky charm of a maid café where your meal is served with a side of playful theatrics.
The night is yours to explore Tokyo on your own.
Included meals: Breakfast
Key highlights: TeamLab
Day 9: October 20th (Monday) Disney Magic
Time for us to don some Mickey Mouse ears! Today we’ll embrace our inner child as we spend the day at Tokyo DisneySea, widely regarded as the best Disney parks in the world! Here we’ll experience thrilling rides, whimsical parades, and Disney magic with a Japanese twist. And who can forget about Disney’s evening fireworks— its sure to be pure magic under the Tokyo sky!
Included meals: Breakfast
Key highlights: Disney
Day 10: October 21st (Tuesday) Your Last Hurrah!!
The morning is yours to do as you wish. Revisit your favorite neighborhood, grab last-minute souvenirs, hit up that Ramen shop one last time, or sip matcha at a tranquil café before heading to the airport for your departure flight.
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Farewell Tokyo! We know if feels like you just got here, but it's time to say good-bye....until the next TOWT adventure!
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Included meals: Breakfast
Key highlights: Free Morning, Departure
​Notes:
**Schedule/events subject to change**​​
TRIP CANCELLATION & REFUND POLICY
Trip Cancellation & Customer Refund Policy
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All bookings are subject to approval.
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If you are approved and cannot attend, you can cancel by May 31st and be refunded all money minus non-refundable deposit and any transaction fees.
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All prices are listed for individual booking. Each registrant will need to apply individually.
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All payments are subject to platform processing fees of 3% per transaction.
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You must have a Passport that is valid for at least 6 months from the intended date of travel. Refunds will not be given for invalid/expired passports.
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Refunds will not be given to travelers who fail to obtain the necessary travel documents for entry into Japan.