A 6-day Japan itinerary featuring incredible food, charming backstreets, and a sublime selection of modern and traditional experiences.

This immersive private trip is designed especially for travelers who crave off-the-beaten-path experiences, amazing cuisine, and boutique accommodations.

Experience Tokyo from a local’s perspective, with insightful explorations, unforgettable outings, and mouthwatering meals. Then retreat to the countryside for an ultra-relaxing stay at a gorgeous traditional property where your worries will melt away.

5 nights / 6 daysUS $5,875 per person (based on double occupancy)Private trip based on your preferred travel dates

Itinerary Highlights

  • An immersive private itinerary, crafted with love by Boutique Japan
  • Tokyo, one of the world’s most exciting — and surprisingly charming — cities
  • A rejuvenating stay in the Japanese countryside
  • Beautiful accommodations
  • Unique private tours and experiences with fun and knowledgeable local experts
  • Amazing food
  • Seamless logistics and in-country transport
  • Extensive pre-departure information to help you prepare for your trip
  • Access to our in-depth Japan expertise, relationships, and firsthand experience
  • A Japan specialist to answer your questions, and thoughtful customer service

Asakusa Tokyo Japan

Effortless Planning

Unlike our usual custom trips, this is a set itinerary.

After all, some travelers relish the process of planning a custom trip, but many others love the simplicity of booking an amazing itinerary with the click of a button. All you need to do is decide when you’d like to visit (the trip is planned around your preferred travel dates).

Itinerary Overview

Fly into either of Tokyo’s airports, Narita (NRT) or Haneda (HND).

You can depart from either of Tokyo’s airports, or you may decide to spend additional time following the trip exploring Japan independently.

Day 1: Arrive in Tokyo, Japan
Day 2: Markets and Cuisine, Neighborhood Strolls, and Izakaya Outing
Day 3: Old-Fashioned Tokyo Backstreets, Ramen Lunch, and High-End Sushi Reservations
Day 4: Off-the-Beaten-Path Cycling Tour, and Final Evening in Tokyo
Day 5: Tradition and Luxury in the Japanese Countryside*
Day 6: Relaxing Morning at Leisure, and Departure

*For your time in the countryside, choose between two lovely areas: the lush Izu Peninsula (pictured at top of page) or the coastal town of Kamakura (see Day 5 for details).

Skyline Tokyo Japan

Itinerary Details

Day 1: Arrive in Tokyo, Japan

Welcome to Japan!

On arrival in Tokyo, you’ll be met and escorted to your private vehicle for the comfortable transfer from the airport to your stylish accommodations. Settle in, adjust to your exciting new surroundings, and get ready for your adventure ahead!

Depending on your flight’s scheduled arrival time we typically recommend keeping your first evening free, both in case of unexpected flight delays, and also to account for possible fatigue from the long journey.

Some people stay in after the flight to wake up re-energized the following morning, but in case you’d like to venture out we will include a short list of great suggestions, and the helpful staff at your hotel will also have insightful recommendations!

Your Hotel in Tokyo

Choose one of these small, stylish, and convenient hotel options for your stay in Tokyo:

Master izakaya Tokyo Japan

Day 2: Markets and Cuisine, Neighborhood Strolls, and Izakaya Outing

Ohayou gozaimasu (good morning)!

Today is your first full day to begin taking in the Tokyo metropolis. After a delicious breakfast at your hotel, you’ll meet up with your fun and knowledgeable private guide to begin your explorations.

What better place to start than Tokyo’s legendary Tsukiji Market, a must-visit for food and market lovers. While the wholesale section of the fish market moved to Toyosu in 2018, Tsukiji’s lively outer market — home to historic lanes and alleys packed with a colorful array of shops and small restaurants, not to mention atmosphere and charm to spare — remains an incredible place to immerse yourself in Japanese cuisine.

From Tsukiji, walk to the nearby Ginza district to pay a visit to a beautiful depachika (literally, “department store basement”), a dazzling food hall renowned for its gorgeous displays and breathtaking variety, including bento boxes filled with seasonal specialties, treats from Japan’s best patisseries, wagashi (Japanese sweets), and much more.

Following your morning explorations, your guide will take you to enjoy lunch at a casual yet charming restaurant offering fresh and delicious Japanese teishoku (lunch sets). After a healthy and filling lunch, your guide will direct you back to your hotel for some downtime.

You’ll have some time this afternoon to relax at your hotel and recover from any remaining jet lag you may have, or continue exploring independently. If you’d like to keep exploring without a break, you’ll also be able to take advantage of the pre-departure materials we provide you.

In the late afternoon, your guide will meet you once more and you’ll venture out on a great neighborhood stroll before dinner. Well beyond the urban clichés (think crowds and neon), Tokyo is full of quiet, stylish neighborhoods where you’ll find countless hidden gems in the form of attractive backstreets and wonderful little shops, cafes, and restaurants.

Begin your walk in Naka-Meguro, a neighborhood best known for its pleasant canal district. From here walk up to the adjacent Daikanyama area, a fashionable little district full of unique shops, including the stunning Daikanyama T-Site.

End by strolling into the nearby Ebisu neighborhood, legendary in Tokyo for its lively small bars and restaurants. Here you’ll drink and dine with your guide at a casual and authentic izakaya, where you can enjoy a quintessential Japanese-style atmosphere, and sample a delicious and eclectic variety of Japanese food and drink.


Restaurant Tsukiji Market Tokyo Japan

Day 3: Old-Fashioned Tokyo Backstreets, Ramen Lunch, and High-End Sushi Reservations

After breakfast at your hotel, your guide will meet you and you’ll head to the historic Asakusa district, best known as home to Tokyo’s oldest temple, Senso-ji. After paying a visit to the impressive temple, leave the crowds to explore the area’s vibrant backstreets, filled with old-school kissaten (coffee shops) and retro Tokyo charm.

Continue to Yanaka. Largely spared during World War II, Yanaka is a beautiful and well-preserved old neighborhood. Today it is home to quaint streets, small temples and shrines, traditional mom-and-pop shops selling Japanese sweets and rice crackers, and up-and-coming galleries and cafes run by young creatives.

Finally, walk into nearby Ueno, a bustling yet old-fashioned district best known for Ueno Park and its various museums. End your stroll at Ameyoko-cho, a boisterous open-air marketplace where you can find everything from fresh fruit and seafood, to clothing shops and yakitori stalls.

From here you’ll head with your guide to a spectacular little ramen shop for lunch. Afterwards, your guide will direct you back to your hotel for some downtime, or elsewhere in the city if you’d prefer to keep exploring. After an afternoon at leisure — with ideas on how to spend your time from our pre-departure materials and your guide — this evening prepare for a splendid sushi dinner.

A quintessential Tokyo experience, for tonight we’ll be making special reservations for you at a fantastic sushi-ya (sushi shop), where you can enjoy spectacular cuisine in unpretentious (and non-touristy) surroundings, dining at the intimate counter of an unsung sushi master. For this sublime experience, you will simply need to pay on the day (we will select a sushi shop that matches your preferred budget range for this evening).

Following dinner, make your way back to your hotel, or head out on your own to enjoy more of Tokyo’s legendary nightlife!

Sushi chef Tokyo Japan

Day 4: Off-the-Beaten-Path Cycling Tour, and Final Evening in Tokyo

With your final full day in Tokyo, you’ll have the chance to explore yet another fascinating side of this rich and layered city.

In the late morning, you’ll meet your private cycling guide (urban cycling experience not required!). After being fitted for your bicycle and helmet, you’ll embark on a leisurely cycling tour, winding your way slowly through the quiet backstreets of delightful, off-the-beaten-path neighborhoods where tourists are rarely seen.

Prefer not to cycle? This cycling experience can be swapped out instead for a private walking tour taking in an irresistible mix of backstreets featuring marvelous vintage or antiques shops.

End at a local favorite lunch spot specializing in tonkatsu. Afterwards, you’ll have the remainder of your final day in Tokyo at leisure.

You may choose to visit any remaining neighborhoods, places, or museums of interest; sample any other culinary specialties on your personal must-eat list; or while away a few memorable hours checking out only-in-Tokyo shops and boutiques (don’t forget to leave some space in your luggage!).

Restaurant Asakusa Tokyo Japan

Day 5: Tradition and Luxury in the Japanese Countryside

After a few thrilling days exploring the many charms of Tokyo, today you’ll get away from it all with a luxurious stay in rural Japan. But first, enjoy one last lovely breakfast at your hotel.

In the late morning, your private driver will meet you to take you to the station. At the massive station your private escort will lead the way, dropping you off right at your impeccably clean train, where you’ll take your comfortable seats for the journey.

(As you know if you’ve been to Japan, riding the trains is an experience in and of itself. The cleanliness, the speed and efficiency, the etiquette — and the pleasure of watching the landscape speed by.)

Before you know it, you’ve arrived. Right as you step off the train, you’ll be greeted by your driver and escorted to your private vehicle. Shortly thereafter you’ll arrive at your destination: a stunning traditional property with gorgeous Japanese aesthetics.

Step inside, where you’ll exchange your shoes for slippers and be led into your beautiful Japanese room. After making sure you’re comfortable and serving you tea, staff will leave you to settle into your serene surroundings.

Shed your street clothes and put on your traditional yukata. Savor a healing soak in the aromatic wooden bath, kick back with a book, or head for a leisurely stroll around the property and surrounding area.

Following an afternoon of pure relaxation, prepare for a magnificent multi-course dinner, another essential ingredient of the countryside experience.

After dinner, enjoy a drink, or simply unwind and breathe in your rejuvenating surroundings before a restful evening.

Your Lovely Traditional Accommodations

For your rural stay, choose one of these traditional yet forward-thinking Japanese-style properties within easy reach of Tokyo, where you can savor tranquil surroundings and quintessential Japanese hospitality:

  • Asaba (Japanese-Style Room with Hot Springs), located in the lush Izu Peninsula (~2 hours from Tokyo)
  • Kishi-ke (Luxury Private Villa), located in the coastal town of Kamakura (~1 hour from Tokyo). Please note that this property specializes in elegant plant-based cuisine.

Ugetsu Room Asaba Shuzenji Onsen Izu Japan

Day 6: Relaxing Morning at Leisure, and Departure

Today marks the conclusion of your travels with us. You’ll be free until departure to luxuriate in your idyllic surroundings and enjoy a beautiful breakfast.

When it’s time to depart, you’ll be transferred back to the station for your journey by rail back to Tokyo. Back in Tokyo you’ll be met on arrival for your private transfer to your departure airport.

Please Note: If you plan to spend additional time exploring Japan independently, we will adjust today’s transport accordingly.

More Details and How to Book


US $5,875 per person based on double occupancy. If you have a different party size, just let us know when inquiring below.


This is a private trip, planned around your preferred travel dates. Because we work with small boutique properties, and top private guides, availability is limited.

Simply complete the below, letting us know your dates, and we will proceed to confirm availability. If your dates are flexible (or not yet set), just indicate approximate dates and we can take it from there.

After we’ve confirmed availability for your dates, a deposit of US $1,000 per person will be due to confirm your services.

Garden Tokyo Japan

What’s Included

  • Immersive, one-of-a-kind itinerary crafted with love by Boutique Japan, designed through our in-depth Japan expertise, relationships, and firsthand experience
  • Accommodations as indicated
  • Daily breakfast at accommodations
  • Lunch on days 2, 3, and 4
  • Dinner on days 2 and 5
  • Private tour of Tsukiji and Ginza as indicated (including lunch)
  • Private tour of Naka-Meguro, Daikanyama, and Ebisu as indicated (including dinner)
  • Private tour of Asakusa, Yanaka, and Ueno as indicated (including lunch)
  • Private cycling (or walking) tour as indicated (including lunch)
  • Private transfer from arrival airport in Tokyo to hotel
  • IC transport cards pre-filled with 3,500 JPY (about 35 USD) of initial credit
  • Travels from Tokyo to countryside as indicated (round-trip)
  • Private transfer to departure airport in Tokyo
  • Expertly-planned logistics for peace of mind and convenience
  • Pre-departure materials featuring free-time ideas ranging from recommended neighborhoods to explore to sights worth seeing, as well as fantastic places to eat and drink
  • Extensive Japan-specific travel tips including advice on money, packing, etiquette, tipping, Wi-Fi, language, food, and more
  • A Japan specialist to answer your questions, and thoughtful customer service
  • 24/7 emergency assistance during your trip

Not Included

  • Services or arrangements before or after the trip
  • Flights (while we don’t book flights in-house, we can provide input on airlines, routes, etc.)
  • Tours, experiences, meals, or any other services other than those specified
  • Personal expenses such as, but not limited to, drinks (e.g., coffee, alcohol, etc.), snacks, laundry, luggage forwarding, visa fees, etc.
  • Travel insurance
  • Charges incurred as a result of changes beyond the control of Boutique Japan
  • Any other services not specified

“Zuleta’s Boutique Japan is a small company that eschews volume and spends more time customizing each trip to offer travelers a fresh, creative approach to Japan – something that discerning travelers seek out after learning of Zuleta’s deep immersion into the Japanese language and culture from years of living in Tokyo, Kyoto and Osaka.” — Condé Nast Traveler

At Boutique Japan, we have unusually high standards when it comes to private guides. After all, few things in travel are more disappointing than a boring guide.

Even though there are plenty of guides throughout Japan, very few meet our standards, and we’ve personally developed a network of amazing guides and local experts around the country. It’s about far more than just having knowledge: we seek out truly engaging individuals who are not only bright and knowledgeable, but also fun and flexible.

As part of your trip, transport during tours and outings will be a combination of walking, public transit, and taxis. Tokyo is extremely well connected by its outstanding trains and subways, taxis are wonderfully clean and efficient, and the city is also surprisingly walkable despite its size.

To give you the best possible experience by giving your guides the freedom to tailor things to you in real time, transport costs during tours and outings are not pre-included. This provides an added degree of flexibility: for example, you may decide to walk if the weather is particularly nice, or take a taxi if you want to give your feet a rest.

We’ll be happy to help if you have any questions, please just contact us.