Japan
Over eight unforgettable days, we’ll move through Japan in a way that feels both elevated and deeply immersive. We begin in Tokyo, where ancient tradition and cutting-edge culture exist side by side, from serene shrines to world-class dining. From there, we slow things down in Hakone, soaking in hot springs and views of Mount Fuji, before continuing to Kyoto, the heart of Japan’s traditions.
Throughout the journey, we balance guided cultural experiences with free time to explore. We’ll bike through Tokyo’s neighborhoods, eat our way through hidden izakayas, walk through thousands of torii gates, and learn centuries-old traditions like tea ceremony and kintsugi. Along the way, we’ll share incredible meals, meaningful moments, and the kind of experiences that are hard to plan on your own.
This trip is designed to feel seamless, intentional, and full of discovery. It's equal parts adventure, culture, and connection!
$6,499.00
May 8-May 15, 2027
Per person based on double occupancy. Solo Rooms available.
Picture Yourself
- Sampling Tokyo's diverse food scene at numerous izakayas in Shinjuku
- Soaking in a private onsen surrounded by Hakone’s serene mountain landscape
- Participating in a traditional tea ceremony rooted in centuries of ritual
- Experiencing an intimate evening with a geisha in Kyoto’s historic Gion district
- Zooming through the Japanese countryside on the Shinkansen bullet train
Day by Day
Day 1: Arrivals
After arrival into Tokyo you'll be greeted for your private airport transfer and settle into your hotel near Shinjuku, one of the city’s most energetic neighborhoods. After a long journey, we ease into the rhythm of Japan with a welcome dinner nearby.
Shinjuku is a city within a city, where skyscrapers meet narrow alleys lined with tiny bars and late-night spots. It’s fast-paced and electric, with hidden corners that feel untouched by time. Tonight is about arriving, resetting, and stepping into a new environment. We’ll walk back together after dinner, taking in the lights and energy of the city as it comes alive at night.
Meals: D
Day 2: Meiji Shrine + Sushi Making Class
We’ll start the day with a peaceful morning visit to Meiji Shrine, a serene Shinto sanctuary tucked within a forest in the heart of Tokyo. From there, we’ll continue on foot to Omotesando, a stylish tree-lined boulevard known for its modern architecture, boutiques, and polished city energy.
After time to wander and take in the neighborhood, we’ll transition into a hands-on sushi making class, where a local instructor will guide us through the techniques behind preparing sushi before we sit down to enjoy the meal we’ve created together.
The afternoon is left open to relax or continue exploring the city on your own.
Those interested in an optional sushi experience, will gather in the evening to enjoy a premium omakase meal. Seated at an intimate hinoki wood counter, we’ll enjoy a refined progression of seasonal sushi paired with sake and wine, guided by expert chefs and sommeliers.
NOTE: this meal is available at additional cost
Meals: B, L
Day 3: Temples + Shinjuku Izakaya Food Crawl
We start the morning in Asakusa at Senso-ji, Tokyo’s oldest and most significant Buddhist temple, originally founded in the 7th century. As we walk through Nakamise Street, we’ll pass stalls that have been serving visitors for generations, offering traditional snacks like freshly made rice crackers and sweet ningyo-yaki cakes filled with red bean.
The rest of the day is yours to explore. You might wander through Harajuku’s colorful side streets, browse shops in Daikanyama, or seek out a tucked-away café or sushi counter. Tokyo rewards curiosity, and some of the best moments come from simply following what catches your eye!
In the evening, we'll head into Shinjuku to explore its hidden izakaya scene. Our local guide will navigate us through the narrow alleys to different izakayas often missed by visitors, each offering a different taste of Tokyo’s nightlife. It's a relaxed and immersive way to experience Tokyo's nightlife through authentic flavors and atmosphere!
Meals: B, D
Day 4: Hakone Ryokan + Onsen Experience
Today we'll leave the city behind and head to Hakone, a mountain region known for its natural hot springs and views of Mount Fuji.
We'll begin with a ride on the ropeway over Owakudani, an active volcanic valley shaped by a past eruption of Mount Fuji. You’ll see steam rising from sulfur vents and have the chance to try the region’s famous black eggs, boiled in the mineral-rich hot springs. Legend says eating one adds seven years to your life. From there, we cruise across Lake Ashi, where on a clear day, Mount Fuji appears in the distance, creating one of Japan’s most iconic views.
By late afternoon, we arrive at our ryokan, a traditional Japanese inn designed around relaxation and hospitality. Tonight, we'll experience Kaiseki, a multi-course dinner that is considered the highest expression of Japanese cuisine. Each dish is carefully prepared to reflect the season, with an emphasis on balance, presentation, and subtle flavors. Expect a progression of small, beautifully plated courses featuring fresh seafood, vegetables, and regional specialties.
After dinner, take time to unwind in the onsen, soaking in mineral-rich hot springs that have been part of Japanese culture for centuries.
Meals: B, L, D
Hotel: Hakone Ashinoko Hanaori
Day 5: Bullet Train + Geisha Experience
We'll enjoy a peaceful breakfast and onsen before boarding the Shinkansen, Japan's iconic bullet train and heading to Kyoto. Known for its speed, precision, and comfort, the Shinkansen is a symbol of modern Japan and one of the most efficient rail systems in the world.
After checking in, enjoy some free time to wander Gion, the city's most famous geisha district. With its preserved wooden machiya houses, narrow lantern-lined streets, and quiet teahouses, Gion feels like stepping into another era. This is where Kyoto’s traditions are still very much alive.
In the evening, we'll gather for a special cultural experience with a Maiko, an apprentice geisha trained in classical dance, music, and the art of hospitality. Over a beautifully prepared Kyoto-style dinner, we’ll learn about this centuries-old tradition and what it takes to dedicate years to mastering it. The evening includes interactive elements, including traditional games and conversation, offering a rare and personal glimpse into this world.
Meals: B, L, D
Hotel: The Blossom Kyoto
Day 6: Arashiyama + Tea Ceremony
This morning, we explore some of Kyoto’s most iconic and visually striking sites, starting in Arashiyama. As we walk through the bamboo grove, towering stalks surround us, creating a calm, almost meditative atmosphere that feels worlds away from the city.
We continue to Tenryu-ji, a UNESCO-listed Zen temple known for its beautifully designed garden that blends seamlessly with the surrounding mountains. From there, we visit Kinkaku-ji, the famed Golden Pavilion, where gold leaf reflects off a still pond in one of Japan’s most recognizable scenes.
In the afternoon, we slow things down with a traditional tea ceremony. Rooted in Zen philosophy, this experience is about mindfulness, precision, and presence. We’ll also have the opportunity to wear kimono, adding another layer of respectful, cultural immersion.
The evening is yours to explore. Whether you wander through Kyoto’s quiet streets, discover a tucked-away restaurant, or simply take in the atmosphere, this is your time to experience the city at your own pace.
Meals: B
Hotel: The Blossom Kyoto
Day 7: Fushimi Inari + Nishiki Market
We begin the day at Fushimi Inari Taisha, one of Japan’s most iconic and spiritual sites. Known for its thousands of vibrant red torii gates, the shrine is dedicated to Inari, the deity of prosperity. As we walk along the forested paths, the gates create a winding tunnel that feels both peaceful and symbolic, with smaller shrines and fox statues appearing along the way.
In the afternoon, we'll take part in a kintsugi workshop, learning the traditional art of repairing broken pottery with gold. Rather than hiding imperfections, kintsugi highlights them, reflecting a philosophy of resilience and transformation that is deeply rooted in Japanese culture.
Later, we explore Nishiki Market, often called Kyoto’s kitchen, via a guided food tour. As we move through the narrow, bustling stalls, we’ll sample a variety of local specialties, from fresh seafood to pickled vegetables and sweets. We'll conclude our tour with a relaxed farewell dinner to celebrate and remember our time together.
Meals: B, D
Hotel: The Blossom Kyoto
Day 8: Departures
After breakfast, we begin our journey home with a private transfer to Osaka’s international airport. As we make our way there, it’s a moment to reflect on the past eight days and everything we’ve experienced together.
From the vibrant streets of Tokyo to the tranquil landscapes of Hakone and the cultural depth of Kyoto, this trip has offered a layered and immersive look into Japan.
We leave not only with photos and memories, but with a deeper understanding of the country’s traditions, its attention to detail, and its way of finding beauty in both simplicity and complexity.
Meals: B
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Trip Length
9 days / 8 nights
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Activity Level
Moderate
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Perfect For
Culture Immersion + Food Lovers
Japan
Japan
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Spaces on tours are sold per person. Deposits are non-refundable. Ensure your payment option is as desired before checkout. If paying deposit only, remaining payments can be made via client portal until 60 days before departure. See our cancellation policy for details.
Love this tour but can’t make the dates? Click here to make this tour private.
Includes
- Accommodation (shared or solo, in premium boutique property)
- Private Airport Transfers + Shinkansen Tickets
- English-speaking local guides
- Meals listed on itinerary
- Gratuity for Damesly leader
- All Entrance Fees & Activities
Excludes
- International Flights to/from Japan
- Meals not listed
- Gratuities for local guides
- Travel Insurance (highly recommended)
Meet Your Trip Leader
Pamela Lau
Pamela was born and raised in the Netherlands but spent nearly ten years living in Singapore. She’s at her happiest when she’s meeting new people, enjoying great food, hiking through nature, and discovering new places — preferably all at once. Having visited over 40 countries, she has seen a...
Read MoreAdditional Information
Flights: You'll fly into Tokyo (HND or NRT) and depart from Osaka (KIX). Arrive anytime before 4 pm on Day 1 arrival day, and depart after 12 noon on departure day.
Want us to advise on flights? Email us at info@damesly.com
Weather: May is one of the most beautiful times to visit Japan. Expect mild, comfortable weather with daytime temperatures in the mid-60s to mid-70s°F and cooler mornings and evenings. Spring greenery is at its peak, and conditions are ideal for walking, exploring temples, and being outdoors. Rain is possible but typically light and intermittent.
Packing: Think comfortable, polished, and versatile. Bring supportive walking shoes as we’ll be on our feet exploring cities and temples. Lightweight layers are key, including breathable tops, a light sweater or jacket, and a rain layer just in case. You’ll want outfits that feel elevated yet easy for group dinners and cultural experiences. Consider something slightly dressier for evenings like our omakase dinner or geisha experience. A small daypack or tote is perfect for daily outings, and don’t forget essentials like comfortable socks, sunscreen, and a portable umbrella.
For entry into Japan, you'll need:
- Passport (valid for 6+ months)
- Completed arrival procedures (Japan may require online immigration and customs forms prior to arrival)
At Damesly, our goal is to connect women through beautifully curated travel experiences.Â
Our trips feature a high level of customer support and a focus on cultural interaction and experiences. We’re dames who work hard, and travel often. So when you use your coveted PTO days, we want you to have the best trip possible! To do this, we hand-select boutique hotels based on location and service. We look for unique properties that we think of as hidden gems, which may or may not be 5-stars. Our itineraries offer a mix of adventure and relaxation. We’re not afraid to get a little dirty to have the most fun experiences, but if there’s an infinity pool or a great spa afterwards — we’ll meet you there!
Traveling the world comes with rewards and challenges. Our traveler is someone who is easy-going and open minded to new experiences and cultures, ready to get out of their comfort zone and understands that travel leads to personal growth, even on its toughest days. Join us if you’re adventurous, kind, open-minded and ready for the trip of a lifetime.Â
On this Japan journey, you can expect a thoughtful blend of cultural immersion, incredible cuisine, and moments of both energy and calm. From exploring centuries-old temples and walking through vibrant city neighborhoods to soaking in hot springs and learning traditional arts like tea ceremony and kintsugi, this itinerary is designed to give you a deeper, more meaningful experience of Japan.
Many of our days involve walking through cities, markets, and historic sites, so guests should feel comfortable being on their feet for extended periods. We move at a relaxed, manageable pace with breaks built in, but a general level of mobility will help you fully enjoy the experience.
As with any culturally immersive itinerary, timing, local conditions, and experiences may shift slightly. Japan runs with incredible precision, but flexibility allows us to embrace unexpected moments, whether it’s discovering a hidden café, catching a seasonal festival, or lingering a bit longer somewhere special. Come with curiosity, respect, and an open mind—often the most memorable moments are the ones you don’t plan for.
Will you match me?
Of course! If you choose a space in a shared room but you're traveling solo, we will do our best to pair you with a roommate. Roommates are matched based on arrival time and perceived compatibility. Sharing a room is a great way to save costs, and make a new friend! However, we ask you to approach the situation with an open mind, some grace, and maybe a little humor.
While 99% our travelers are amazing, we can't guarantee that you'll hit it off with your roommate, or that your sleeping styles will be compatible.
Is sharing right for you?
If you are a light sleeper, get easily irritated or just know that you need your own space, sharing a room might not be for you. Likewise, if you know that you snore, sleep with a CPAP machine or have other health conditions, sharing a room might not be the best fit.
What if I don't get along with my roommate?
If you've tried but you absolutely can't get along with your roommate and need to separate, your trip leader will either swap things around, or, attempt to get you your own room. If the latter, additional charges will incur.
What if I book a double room, and you can't match me?
We book a certain amount of hotel rooms before any tour, and are bound by their rules. In the event that we cannot find a roommate for you before the tour, and your room converts to a single room, there may be additional charges.
Small group trips require at least 4 people to run. We will confirm as soon as possible when the trip has met its minimum; up to 60 days before departure. For this reason, we recommend waiting until after a trip has been confirmed to purchase airfare. Any tour can be converted to a private departure when a trip does not meet its minimum. Additional costs may incur. Alternatively, apply your credit to any small-group tour departing within 12 months.Â
You'll receive an email from WeTravel after you book to set up your account and make payments according to your personal situation.
Email us at info@damesly.com if you'd like us to create a payment schedule for you. This is the easiest way to smooth out trip payments.
Tours must be paid in full 60 days before departure. See our cancellation policy here.
Still have questions? See our FAQ or Contact Us.
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