Luxury Holidays to Kyoto & Tokyo
Where Tradition Meets Tomorrow in Perfect Balance
Japan is a country of contrasts—and nowhere is that more breathtaking than in Kyoto and Tokyo. One whispers of geishas and Zen gardens, the other pulses with skyscrapers and sushi bars.
Together, Kyoto and Tokyo form a twin-centre journey that feels like time travel—with every moment framed by hospitality, detail, and deep cultural resonance.
Awake & Wander crafts seamless luxury experiences across both cities: tea ceremonies in private gardens, Michelin-starred omakase in the clouds, bullet train journeys in first class, and five-star ryokan stays where the past still lives beautifully.
Japan doesn’t ask for attention—it earns it with quiet wonder.
A Small Selection of our Latest Offers to Kyoto & Tokyo
These latest offers have been generated through our online booking system which is powered by our sister company , Jamie Wake Travel, and using our handpicked suppliers.
There will occasionally be times when offers will not show here. For example, where a destination may require more in-depth travel arrangements and will need to be tailor made by our team.
Prefer a more personal touch? We're always here to tailor your journey—simply get in touch and let us create the perfect luxury holiday to Kyoto & Tokyo for you.
Arriving in Japan: Effortless Access to Both Cities
Fly into Tokyo Haneda (HND) or Narita (NRT) for international arrivals, with optional connection to Osaka Kansai (KIX) if beginning your journey in Kyoto. Awake & Wander arranges business or first class flights, VIP airport service, and private transfers to your hotel or ryokan. For travel between the cities, we offer first-class Shinkansen bullet train tickets, private rail guides, or luxury chauffeur-driven options—each timed perfectly to maximise your time and peace of mind.
When to Visit Kyoto & Tokyo for the Best Experience
Japan’s seasons are legendary, each offering a unique palette of colours and festivals. March to April brings iconic cherry blossoms, best enjoyed with a private hanami picnic or traditional poetry reading. October to November sees brilliant autumn foliage, ideal for temple strolls and scenic train rides. Winter offers snow-dusted shrines and incredible food, while summer is festive and lively, especially in Tokyo. Awake & Wander will tailor your journey to your seasonal dreams—whether that’s sakura in Kyoto or summer fireworks over Tokyo Bay.
The Top 4 Unforgettable Experiences and Things to Do in Kyoto & Tokyo
In Japan, luxury is in the details: the warmth of a towel, the silence of a garden, the perfection of a single bite. These experiences bring that ethos to life in both cities.
1
Stay at a Ryokan in Kyoto with Private Garden and Kaiseki
Kyoto is the spiritual heart of Japan, and staying at a luxury ryokan is the ultimate immersion. Awake & Wander selects heritage inns with private gardens, tatami rooms, and discreet service. Enjoy multi-course kaiseki dinners served in-room, private onsen baths, and tea ceremonies led by cultural masters. It’s tranquillity wrapped in ritual.
2
Take a Private Architecture and Design Tour around Tokyo
Tokyo is a modern marvel—its skyline a gallery of glass, steel, and innovation. Explore with a private architect guide, visiting hidden residential masterpieces, fashion-forward districts like Omotesandō, and design museums like 21_21 Design Sight. We pair this with access to exclusive ateliers, artisan studios, or boutique hotels where form meets feeling.
3
Discover Kyoto’s Temples & Traditions with a Local
Skip the crowds and discover Kyoto’s quiet side with a private cultural expert. Visit Fushimi Inari Taisha before opening, enjoy a silent Zen meditation in a working temple, or learn calligraphy in a private home. Awake & Wander curates encounters that feel personal, not performative—designed for connection, not spectacle.
4
Dine in the Clouds with Tokyo’s Top Chefs
Tokyo has more Michelin stars than any city in the world—and we open the doors to the best. Awake & Wander secures private omakase reservations, rooftop dining with skyline views, or immersive kaiseki tasting menus in 10-seat restaurants known only to insiders. Add sake pairings, sushi masterclasses, or after-dinner jazz clubs for a full night of Tokyo indulgence.
Why Kyoto & Tokyo Are the Ultimate Japanese Pairing
One moves in silence. The other never stops moving. Together, Kyoto and Tokyo offer a complete picture of Japan—where heritage and hyper-modernity meet in a way no other country can replicate.
With Awake & Wander, this twin-city journey becomes more than a trip—it becomes a meditation on beauty, balance, and thoughtful living. Every temple, every bite, every lantern-lit street will stay with you. Because in Japan, luxury isn’t loud. It’s the quiet confidence of something done perfectly.
