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Japan with Jessi & The Reckless Optimists
Dates
Oct 6–12, 2025
Group Size
8–24 Travelers
Duration
7 days, 6 nights
Activity Level
Exploration
About This Trip
Meet Your Host
View Full Profile
Jessi Duley
I am a creator, a mother, an encourager, a founder, a CEO, a lunch maker, a list maker, a day maker, and a trouble maker. My favorite color is checkered (like my past) and I’ll literally do anything for a good story. I founded a company, created a brand, cultivated a community, and grew it all and in the same time span I also had 3 kids. So basically I hit the jackpot of lady awesomeness right? But then I hit rock bottom. Turns out a limitless state of mind is good - until it’s not. I’ve learned a lot over the last decade, how to build businesses and brands and blah blah blah, the most important thing I’ve learned is how to build self-respect and self-worth and through that I’ve learned how to build the life I’ve always dreamed without waiting for the other shoe to drop. I don’t have it all figured out, but I am ALL IN on sharing my wins, losses and hard lessons on my way to figuring out how to live a f*cking rad life full of contribution, impact, gratitude and inspiration. So that’s what I am here to do: to inspire possibility, to encourage potential, to foster connection, to live FULLY and TO LIVE OUT LOUD. And I am going to bring as many people with me as possible. ALL IN TEAM. Xoxo -JD
Trip Activities
Tea Ceremony
Asakusa Exploration
Meiji Jingu - Harajuku
Shibuya Exploration
Yanaka Food Tour
Zenko-ji Temple
Togakushi Taisha Day Trip
Togakushi Kamitsuge Onsen
Included in Your Trip
Double occupancy in 4-star hotels (limited single rooms available)
Local guide throughout trip
All city transfers
Not Included
Flights (except as noted)
Food and alcohol (except as noted)
Visas and travel insurance
Airport transfers
Tips & Gratuity
Itinerary
*All durations are approximate
Welcome to Tokyo!
dinner
You will be walking 10 minutes to the welcome dinner at a local Japanese izakaya. Your meal will typically be a set menu with water included. Additional food and beverages will be at your own expense. *Please note that Japanese cuisine frequently uses ingredients with animal products and/or gluten. For the included meals, vegetarian, vegan, gluten-free and shellfish-free diets CANNOT be accommodated.
The Celestine Tokyo Shiba
Overnight in Tokyo
Tokyo Landmarks & Tea Ceremony
breakfast
Breakfast at the hotel is included. Typical hotel breakfasts are continental full/American or buffet style. The exact breakfast offered will be determined by your finalized hotel. *Please note that Japanese cuisine frequently uses ingredients with animal products and/or gluten. For the included meals, vegetarian, vegan, gluten-free and shellfish-free diets CANNOT be accommodated.
Tea Ceremony
Learn about the techniques, history and importance of the Japanese tea ceremony with guidance from a tea master at a ceremony room in Asakusa, Tokyo. This small group immersive experience invites you to partake in the ceremony, kneeling and sipping green tea in the same way it’s been done for centuries.
Asakusa Exploration
In the afternoon, continue exploring the vibrant Asakusa District. You’ll arrive at Kaminarimon (Temple Sensoji entrance gates). Once an entertainment hub during the Edo era, featuring traditional theater like Kabuki, Asakusa has evolved from its historical role and is now a lively area filled with charming shops and restaurants. Nestled in the Taito ward of Tokyo, Japan, Asakusa seamlessly blends tradition with modernity. Its centerpiece is the iconic Senso-ji Temple, Tokyo's oldest Buddhist temple dating back to the 7th century. The district is famous for Nakamise-dori, a bustling shopping street that leads to the temple, offering an array of traditional goods, souvenirs, and mouth watering street food. Be sure to bring cash for souvenirs and food!
Meiji Jingu - Harajuku
After visiting Asakusa, you will travel across Tokyo on a 50 minute metro train ride to Meiji Shrine. Dedicated to the deified spirits of the former Emperor and his wife, Meiji Shrine is one of the most famous Shinto shrines in Japan. Enter through the 12-meter-high Torii gate into the tranquil grounds, where you'll wash your hands as per Shinto ritual of cleansing before entering this sacred space. Observe Shinto rituals and prayers as you walk through the area, connecting with the traditions of this unique culture. Then, you will have free time to explore one of the most funky streets of Tokyo: Takeshita-dori in Harajuku, a bustling and vibrant street that epitomizes Japan's unique and eclectic youth culture. Lined with an array of quirky and fashionable boutiques, Takeshita-dori is a haven for fashion enthusiasts seeking the latest trends, bold styles, and kawaii (cute) fashion. The street is also known for its diverse range of themed cafes, offering visitors a chance to experience the whimsical and imaginative side of Japanese pop culture.
Shibuya Exploration
From Takeshita-dori in Harajuku, you’ll take an 8 minute metro train to Shibuya. The world-famous Shibuya Crossing, often referred to as the busiest pedestrian crossing in the world, is a mesmerizing spectacle as a sea of people converges from all directions. Surrounding the crossing, Shibuya is a hub of fashion, entertainment, and youth culture. The fashionable Shibuya 109 building stands tall as a symbol of the district's trendsetting fashion scene, offering a myriad of trendy boutiques and cutting-edge styles. Beyond fashion, Shibuya is also home to vibrant nightlife, trendy cafes, and a diverse array of shops and restaurants. You’ll then take a 25 minute metro train ride back to Shimbashi and walk 10 minutes to the hotel.
The Celestine Tokyo Shiba
Overnight in Tokyo
Yanaka Backstreets & Bullet Train to Nagano
breakfast
Breakfast at the hotel is included. Typical hotel breakfasts are continental full/American or buffet style. The exact breakfast offered will be determined by your finalized hotel. *Please note that Japanese cuisine frequently uses ingredients with animal products and/or gluten. For the included meals, vegetarian, vegan, gluten-free and shellfish-free diets CANNOT be accommodated.
Luggage Transfer
Today, your luggage will be transported separately from Tokyo to Nagano. One piece per person is included, additional luggage will be charged on the spot per piece based on size, payment must be made in cash - Japanese Yen. Don't forget to prepare a small go to bag before dropping off your luggage in the lobby. Your luggage awaits you in your next hotel.
Yanaka Food Tour
This morning you’ll take a 30 minute metro train ride to Yanaka for a food tour. You will explore the back streets and hidden gems in Yanaka, a rare taste of Tokyo's past. The local guide will take you through the charming area of Yanaka - one of the few remaining districts in Tokyo where the shitamachi (downtown) atmosphere- a feeling of Tokyo from past decades, still survives.You will have the chance to try local street snacks, stop by shops that are over 100 years old, see local shrines and temples and enjoy a regional lunch from the South of Japan, Kyushu. You will be making 6 food stops trying drinks and snacks that locals love such as senbei, menchikatsu, tayaki. You’ll then take a 30 minute metro train ride back to the hotel. *Please note that Japanese cuisine frequently uses ingredients with animal products and/or gluten, therefore vegetarian, vegan, gluten free diets and shellfish-free diets CANNOT be accommodated.
lunch
Lunch as a part of the Yanaka Food Tour is included. You’ll be making 6 food stops, trying 10-12 local dishes and drinks. Note that the menu may change depending on availability and seasonality. Additional food and beverages at your own expense. *Please note that Japanese cuisine frequently uses ingredients with animal products and/or gluten, therefore vegetarian, vegan gluten free diets and shellfish-free diets CANNOT be accommodated.
Bullet Train: Tokyo to Nagano
Take public transport to Tokyo Station, then board a Shinkansen bullet train to Nagano.
dinner
Dinner at a local establishment included
Kokusai 21 International Hotel
Overnight in Nagano.
Walking Tour to Zenko-ji Temple
breakfast
Breakfast at the hotel is included. Typical hotel breakfasts are continental full/American or buffet style. The exact breakfast offered will be determined by your finalized hotel. *Please note that Japanese cuisine frequently uses ingredients with animal products and/or gluten. For the included meals, vegetarian, vegan, gluten-free and shellfish-free diets CANNOT be accommodated.
Zenko-ji Temple
You’ll start the morning off with a 30 minute walk through Nagano passing through Nakamise street with shops on your way up to Zenko-ji Temple (You’ll also have an option to take a 15 minute metro train ride with a 10-15 minute walk to the temple). Having proudly hosted the Winter Olympic Games in 1998, this city is steeped in both modern sports history and ancient cultural significance. One of its most renowned landmarks is the venerable Zenko-ji Temple, a sacred site with a history spanning nearly 1400 years. The Main Hall of this spiritual haven is not only a testament to architectural prowess but is also designated as a National Treasure. Zenko-ji Temple is a repository of legends and myths, offering visitors a profound glimpse into the rich tapestry of Japanese history and spirituality. Take the opportunity to immerse yourself in the tranquil ambiance of the temple, exploring its sacred halls and absorbing the cultural significance that permeates the air. As you venture through the temple grounds, meander along the surrounding streets that lead to the main gate. Here, you'll discover quaint shops offering souvenirs and street food. You’ll then walk 30 minutes back to the hotel / or take the metro train. Remember to bring cash with you!
Kokusai 21 International Hotel
Overnight in Nagano.
Snow Monkeys & Yudanaka Onsen
breakfast
Breakfast at the hotel is included. Typical hotel breakfasts are continental full/American or buffet style. The exact breakfast offered will be determined by your finalized hotel. *Please note that Japanese cuisine frequently uses ingredients with animal products and/or gluten. For the included meals, vegetarian, vegan, gluten-free and shellfish-free diets CANNOT be accommodated.
Hotel to Togakushi Taisha
Take a private transfer from the hotel in Nagano to Togakushi Taisha.
Togakushi Taisha Day Trip
This morning, put on your most comfortable clothes and dependable shoes, and get ready to enjoy the beautiful Togakushi Taisha. Surrounded by nature and thousands of year-old culture, Togakushi is an area located in Mt Togakushi. The Togakushi trail is made up of 5 shrines. Your journey today will start in the lower shrine, Hokosha. Next up, is the Soba Museum, Tonkururin. Togakushi Soba used to be served to important guests, pilgrims, who rested in the area. Here you'll enjoy some free time to try out the Togakushi Soba (at your own cost) and roam around the shops. After, continue your hike towards Chusha, the middle shrine. On the way you'll stop to visit a ninja museum before continuing to the last (upper) shrine. Keep a look out for Zuishinmon, a red gate, as it marks the halfway point to the last shrine, Okusha shrine. The red colour of the gate provides a contrast with the trees and nature surrounding it. The total hike covers approximately 3 miles, offering a perfect blend of nature, culture, and relaxation.
Togakushi Kamitsuge Onsen
Finish up today's journey by hopping on the bus headed towards Togakushi Kamitsuge Onsen. Here, soak your fatigue away before going back to your hotel to rest and get ready for tomorrow's adventure.
Togakushi Kamitsuge Onsen to Hotel
Take a private transfer from Yudanaka Onsen Town back to the hotel in Nagano.
dinner
Dinner at a local establishment included
Kokusai 21 International Hotel
Overnight in Nagano.
Farewell Dinner & Karaoke Night
breakfast
Breakfast at the hotel is included. Typical hotel breakfasts are continental full/American or buffet style. The exact breakfast offered will be determined by your finalized hotel. *Please note that Japanese cuisine frequently uses ingredients with animal products and/or gluten. For the included meals, vegetarian, vegan, gluten-free and shellfish-free diets CANNOT be accommodated.
Luggage Transfer
Today, your luggage will be transported separately from Nagano to Tokyo. One piece per person is included, additional luggage will be charged on the spot per piece based on size, payment must be made in cash - Japanese Yen. Don't forget to prepare a small go to bag before dropping off your luggage in the lobby. Your luggage awaits you in your next hotel.
Bullet Train: Nagano to Tokyo
After breakfast, you’ll check out of the hotel and board a Shinkansen bullet train from Nagano back to Tokyo.
dinner
You will be walking 10 minutes to the farewell dinner at a local Japanese izakaya. Your meal will typically be a set menu with water included. Additional food and beverages at your own expense. *Please note that Japanese cuisine frequently uses ingredients with animal products and/or gluten, therefore vegetarian, vegan, gluten free diets and shellfish-free diets CANNOT be accommodated.
The Celestine Tokyo Shiba
Overnight in Tokyo.
Goodbye, Japan!
breakfast
Breakfast at the hotel is included. Typical hotel breakfasts are continental full/American or buffet style. The exact breakfast offered will be determined by your finalized hotel. *Please note that Japanese cuisine frequently uses ingredients with animal products and/or gluten. For the included meals, vegetarian, vegan, gluten-free and shellfish-free diets CANNOT be accommodated.
Add-Ons
Private Accommodation
Pre-Trip Accommodation
Post-Trip Accommodation
Airport Transfer
Insurance Policy
Physical Activity Level:Exploration
These trips require some movement, but slow and steady is the name of the game. Maybe a mid-length walking tour or at-your-pace sightseeing. No rush.
Essential Travel Information
Cancellation Policy
We get it—life happens. Here's how cancellations work depending on where you're at in the process:
Spot Pending
Spot Confirmed With 91 or More Days Before Your Trip
Spot Confirmed With 90 or Fewer Days Before Your Trip
HIGHLY RECOMMENDED: Protect Your Adventure-Invest in Peace of Mind
After booking, you'll receive a personalized recommendation for coverage tailored to your trip. For full details on our cancellation policy, please refer to our Terms & Conditions.
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FAQ
Traveling with TrovaTrip
What's it like to travel on a Trova Trip?
Trova Trips are curated group travel experiences designed to help you see the world, meet new people, and connect over shared interests. Each trip is hosted by a community leader you know and trust, and run by professional local Operators who handle the logistics. Expect meaningful experiences, authentic activities, and a like-minded group to share it all with.
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- The Host is your community leader—the person who brings the group together, sets the vibe, and curates the overall experience. They may lead a workshop or activity during the trip, but their main focus is connection and community, not logistics.
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In short: The Host shapes the experience and brings the vibe, the Operator runs the trip, and we make it all happen. Read more about who does what here.
What's the difference between the Host, the Operator, and Trova?
Great question! Each plays a key role in bringing your experience to life:
- The Host is your community leader who brings the group together, fosters connection, and perhaps leads a workshop or two. They're there to bring the vibes, not the logistics. That's the Tour Operator's job.
- The Operator is the professional travel company that runs the trip on the ground. They handle it all—accommodations, local Guides, activities, and safety. Every Operator we partner with is licensed, insured, and vetted to deliver high-quality group travel.
- TrovaTrip is the platform who connects it all. We help design the trips, partner with Hosts with Operators, and support you before and during your journey to ensure everything runs smoothly.
In short: The Host brings the vibe, the Operator runs the trip, and we make it all happen. Read more about who does what here.
I'm nervous to book. How can I feel more confident?
First, let us say—it's totally understandable, and you're not alone! Travel can feel intimidating, but we built Trova to take the guesswork out of group travel and earn your trust every step of the way:
- Every trip is run by licensed Tour Operators with vetted local Guides.
- Hosts are there to foster connection, meaning you'll arrive solo but never feel alone.
- Itineraries are clearly outlined so you know what to expect, including activity level, example accommodations, and what's included.
- Our team is available to support you pre-departure, and Operators—plus your local Guide—are on the ground to assist during the trip. And rest assured, all our Operating partners are trained in crisis management.
- We always recommend travel insurance for extra peace of mind, whether you're traveling with Trova or solo. It can cover medical issues, lost luggage, or even cancellations.
We know it takes trust to book a trip with new people, and we're here to make sure you feel ready, supported, and excited!”
Can I book solo?
Absolutely! As of 2025, almost 84% of TrovaTrip Travelers go solo. (And yes, we may be a little biased, but we think group travel is one of the best ways to meet new people!) You'll have your own bed and the option to book a private room on most trips. Plus you'll be traveling with others who are just as excited to explore and connect.
What if I need to cancel?
We understand that life happens. Our cancellation policy is designed to provide flexibility while balancing the logistics of group travel:
- Spot pending – 100% refundable. Not confirmed yet? No worries. You can cancel at any time for a full refund.
- Spot confirmed with 91 or more days before your trip – Partially refundable + credit towards a future trip. You'll receive a future trip credit for the amount of your down payment (minus a $100 cancellation fee per Traveler). This trip credit is valid for one year from the date it is issued. Additionally, any payments made beyond the original 25% down payment will be refunded to your original form of payment.
- Spot confirmed with 90 days or fewer before your trip – Non-refundable. At this point, all payments are non-refundable because your experience is already in motion behind the scenes. By this time, our operating partners will be working with local businesses to secure your accommodations and finalize your activities.
HIGHLY RECOMMENDED: Protect Your Adventure–Invest in Peace of Mind
We strongly encourage purchasing travel insurance with trip cancellation coverage to safeguard your investment. With travel insurance, you're covered in case of unexpected events–from illness to emergencies–that could affect your plans. Life is unpredictable, but your dream trip doesn't have to be.
After booking, you'll receive a personalized recommendation for coverage tailored to your trip. For full details on our cancellation policy, please refer to our Terms & Conditions.
What's included in the trip cost?
Most trips include accommodations, daily activities, ground transportation, some meals, and a dedicated local Guide. Because Travelers are coming from all around the world, flights to and from your destination are not included. Each trip page breaks it all down for you.
Does my Host make money from hosting?
TL;DR: Sometimes! Many Hosts earn income from leading trips, but not always.
Every trip on Trova is uniquely shaped by the Host. They choose the destination, curate the itinerary, and rally their community to come along for the adventure. It’s a big effort (and a rewarding one, or so we hear!).
A Host’s earnings depend on the trip price they set and how many Travelers join. Trova provides the tools, support, and platform—but ultimately, income isn’t guaranteed.
Will I have free time?
Yes! While we pack in incredible experiences, most itineraries include built-in free time so you can relax, wander, or check out personal must-sees.
What do the activity levels mean?
Every trip has a physical Activity Level from 1 to 5 so you can find the right fit for your travel style:
- Level 1 – Relax + Unwind: Minimal movement (spa days, beach lounging, local markets)
- Level 2 – Low-Key Movement: Light, easy-paced activity (snorkeling, boat tours, gentle hikes)
- Level 3 – Moderate Activity: Ready to move (multi-day hikes, skiing, camping)
- Level 4 – Get Your Heart Rate Up: More intense movement (long hikes, biking, active days)
- Level 5 – Extreme Adventure: High-adrenaline travel (challenging hikes, dives, technical climbs – experience may be required)
You'll find the Activity Level clearly listed on each trip page, and a more in-depth explanation of each level here.
Who can I contact with more questions?
Our support team is here to help! Visit trovatrip.com/company/contact-us to reach out. You can expect to hear back within 2 business days, but probably sooner—our Trova elves are pretty speedy!
Accommodations
What does "or similar" mean next to the accommodations?
When we say “or similar,” it means the hotel listed is an example of what you can expect—not always the exact spot you'll be staying. Sometimes Operators adjust accommodations due to seasonal availability or group size. But rest assured: the quality and comfort will match what's shown.
Why would the accommodations change from time of booking?
Flexibility allows Operators to choose the best-fit accommodations closer to your trip—based on availability, logistics, and what works best for the group (like the number of Travelers and room configurations). This ensures a smooth experience without sacrificing comfort or quality.
Finalized hotel info is typically shared about 30 days before departure in your Traveler Portal, along with your final itinerary.
Trip Operations & Compliance
Who actually runs my trip, and how does Trova keep things safe?
Your trip is operated by licensed, certified Tour Operators who manage all trip logistics and safety—from accommodations and local Guides and day-to-day logistics. All trips comply with local legal and regulatory standards. We vet each Operating partner carefully so you can travel with confidence.
Who do I talk to if I have questions about safety or compliance?
If you have any questions about safety protocols or trip compliance, reach out to us at safety@trovatrip.com. We're here to help.
General Travel Questions
Do I need any documentation to travel?
It depends on where you're headed. Though it is not a universal requirement, many countries require that your passport be valid for at least six months beyond your arrival date. This ensures Travelers have sufficient time to return home even if their visas are extended or if unexpected circumstances arise.
Some destinations may also require a visa. Check our visa page to consult your country's travel resources.
Do I need any vaccines?
It's always best to check with your healthcare provider or a travel doctor before your trip. You can also visit the CDC website (or your local government's travel health resource) for destination-specific vaccine guidance. Health and safety first!
Are flights included in the trip cost?
Because our Hosts and Travelers are coming from all around the world, flights to and from your destination are not included. Some trips include internal flights (like a short domestic hop), and those details will always be listed on the trip page if applicable.
Can you accommodate my dietary needs?
We’ll do our very best! Our Operators aim to accommodate dietary restrictions, though availability varies by destination. For example, some places offer plenty of vegan and vegetarian choices, while others might be quite limited. The earlier you let us know—through your trip form or by contacting our support team—the better we can prepare. Once you arrive, be sure to remind your local Guide about any allergies or restrictions so they can help you enjoy your meals safely and comfortably.