Tokyo & The North Experience

What’s Included in every Diamonds Experience

  • Complete trip planning & management

  • International flights to and from Japan

  • Private airport transfers

  • Full-time host & guide — Milky Diamonds

  • Private driver & luxury vehicle

  • Luxury hotel accommodations

  • All activities curated and arranged

  • Access to hidden towns & local gems

  • Flexible, on-the-spot adjustments

  • All activity equipment provided

  • Daily breakfast & locally sourced Japanese treats

  • Thoughtful photography moments

Every Diamonds Experience is fully bespoke, and the itinerary shown below is an insight into what we can create. We thoughtfully tailor each journey for your needs whether you’re family, have a longer stay or specific interests. Along your bespoke journey you’ll always have refined accommodations, a private driver, and Milky Diamonds as your dedicated host.

Nighttime scene at a parking lot with colorful cars, a woman and a person in a costume standing near the cars, and a crowd of people in the background illuminated by blue stage lights.

Day 1 — Touchdown + Tokyo Car Culture 

Theme: Settle in, relax, and ease into the adventure with car culture and Yokohama vibes.

Upon arrival, you’ll be picked up in a luxury van and taken to your Yokohama hotel to settle in and refresh before your first local experience. As night falls, your host introduces you to Tokyo’s after-dark car scene, before winding down with late-night snacks and a relaxed return to the hotel.

Nighttime city scene with illuminated billboards and pedestrians crossing the street.

Day 2 — Tokyo day & Northern Kanto

Theme: Experience lesser-known landmarks, food spots, and car culture

Begin the day at an easy pace with breakfast and a few local essentials before a scenic drive past Tokyo’s waterfront. As we make our way North curated activities such as local museums and flower parks will populate our journey.

As the day unfolds, you’ll leave the city behind and move through calmer, lesser-known areas that offer local experiences and flavor. Your evening ends with dinner near your hotel and time to unwind in true Japanese style.

Two people looking under the hood of a black and white sports car in a parking lot during late afternoon.

Day 3 — Oya Museum, Nikko Circuit, Bamboo Forest

Theme: Local life known only to residents, not tourists.

Ease into the day with coffee in a quiet local setting before visiting a museum tied to the area’s history and culture. The afternoon shifts gears at a local circuit where you’ll get up close with the cars, watch live track action, and enjoy ride-along experiences arranged by your host. Unwinding from the action, take in Japan's unique beauty in a bamboo forest for photos and matcha. Finally, enjoy local delicacies with dinner at a cozy izakaya.

Illuminated sign reading 'Funky Chicken Bar Morigen' with a cartoon woman singing into a microphone and an Afro hairstyle, located outside at night.

Day 4 — Culture Day: Temples, Hidden Towns, Local Markets

Theme: Authentic Japanese culture, peaceful nature, and rural beauty.

Spend the morning uncovering the cultural heart of Nikko, guided by your host who reveals traditions and local customs few visitors ever experience. In the afternoon, wander through a quiet rural town with stops at hidden markets, craft shops, and a tucked-away restaurant. optional experiences that offer deeper glimpses into local life. The day winds down with a traditional dinner and onsen visit for a calm, restorative evening, far from the usual tourist path.

Yellow hatchback and white racing car parked in a lot under a partly cloudy sky.

Day 5 — Gunma Mountain Roads & Sports Culture

Theme: Scenic driving, performance, and regional energy.

Depart Utsunomiya in the morning toward Gunma, stopping along the way for local snacks and treats. Upon arrival, take to the mountain roads in a sports car. Enjoy a carefully paced drive with stops at scenic viewpoints and quiet stretches of countryside. In the afternoon, attend a live sporting event or curated regional activity, before returning to Tokyo and settling into your final hotel of the journey.

Nighttime city street scene with lit-up buildings, advertisements, and pedestrians walking, some wearing masks.

Day 6 — Tokyo Exploration & Shopping

Theme: Iconic landmarks, flexibility, and a refined send-off.

Spend the day exploring Tokyo’s most famous districts and landmarks, traveling either by private vehicle or experiencing the city’s train system. This day is flexible by design, allowing for shopping, cultural stops, or additional activities based on your interests. The evening concludes with dinner at a special restaurant, thoughtfully chosen to commemorate the journey.

A busy city intersection filled with many pedestrians and high-rise buildings adorned with colorful advertisements and illuminated billboards.

Day 7 — Trip End + Omiyage

Theme: Slow and easy end to the trip while picking up Japanese gifts.

Begin the morning at one of Tokyo’s iconic Temples landmark and uncover the region’s rich cultural history. Along the way taste local specialties few travelers encounter. As the day unfolds, enjoy a scenic, unhurried drive through Japan’s countryside, taking in hidden corners and quiet landscapes before reaching the airport for your departure.


 FAQs

  • This experience starts from $10,000 (USD) + International Flights. Bookings are secured with a 10% deposit (non-refundable).
    The experience is bespoke to your wants and needs. Provide us with your budget, your bucket list or a bit of both.

  • What’s Included

    • Flights included in the final trip price

    • Private airport pickup and full-time luxury transport

    • Dedicated host and guide for the entire trip (Milky Diamonds)

    • Luxury hotel accommodations across multiple regions

    • Complete itinerary planning (including flights) and on-the-ground coordination

    • Curated experiences including hidden gems, car culture, track days and ride-alongs, cultural landmarks, small towns, local markets, nature spots, traditional experiences, scenic drives, and exclusive access beyond typical tourist routes

    • Breakfast and some meals when the activity provides

    • Optional cultural add-ons (tea ceremony, pottery making, festivals, kimono fitting with photoshoot, sake brewery)

    What’s not Included

    • Lunches & Dinners unless it’s a part of the activity

    • Shopping Expenses

    • Additional activities unless discussed beforehand

  • This package has been built with 2 people in mind. However, as a bespoke tour company we have flexibility to accommodate families or small groups.

  • Absolutely! Being Bespoke, we can alter and change activities to suit your family’s needs. We can even arrange (English speaking) childcare services if the adults are wanting some time to explore.

  • Just head on over to our contact form below. Once you have filled it out, one of our team will get back to you ASAP.

Get in touch.

Ready to discover a Japan most travelers never see?
Contact us to craft your bespoke journey; complete with small-town authenticity, local hobbies, luxury hotels, and your own dedicated driver and guide from start to finish.

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