Japan, Singapore & Thailand: East Asia Meets Southeast Asia
East Asia meets Southeast Asia — bullet trains and temple gardens, the gleaming sophistication of Singapore, and a Thai finale of mountains or sea
From
£1,895pp
About this tour
This is the most aspirational of our grand tours — a fifteen-day passage from the refined traditions of Japan, through the gleaming modernity of Singapore, to the warm ease of northern Thailand. Three utterly different worlds, linked seamlessly, each a high point in its own right. You begin in Japan: Tokyo's energy and order, the hot-spring valley of Hakone beneath Mount Fuji, the temples and raked-gravel gardens of Kyoto, and the food halls of Osaka — travelling between them on the shinkansen bullet train, gliding past the countryside at 200mph in reserved comfort. Then a flight south to Singapore, the most sophisticated city in Asia: the Gardens by the Bay, the hawker centres, the colonial quarter and the rooftop bars. Finally, Thailand — and by default the gentle, temple-rich city of Chiang Mai in the northern hills, with its night markets, its mountain monasteries and its elephant sanctuary (Koh Samui's beaches are an easy alternative). Kenji, our Japan and Southeast Asia specialist, has built this itinerary for travellers who want range without exhaustion. The Japan leg is engineered around the rail network — luggage forwarded ahead, reserved seats, gentle daily distances — and the trip eases from the precision of Japan into the warmth of Thailand. It is, quite simply, a transformative three weeks.
Kenji Watanabe
Japan & Southeast Asia Specialist, 16 years in premium rail travel
Why this works for travellers over 50
- Japan explored by reserved-seat bullet train — fast, smooth and effortless between cities
- Luggage forwarded ahead in Japan so you travel between hotels with only a day bag
- Two internal flights replace the only long-haul hops between countries
- A premium itinerary kept under £2,000 with smart, comfortable 3-star and 4-star city hotels
- A choice of finale — temple-rich Chiang Mai (default) or the beaches of Koh Samui
- Single supplement waived on the cherry-blossom and November departures
Request a Callback
Price per person — based on two travelling together.
We respond within 1 working day · No obligation
Your journey
Day-by-day itinerary
1Arrive Tokyo
Tokyo, Japan
restDormy Inn Premium Asakusa, Tokyo
Arrive Tokyo
Tokyo, Japan
Your flight arrives in Tokyo, where our representative meets you and helps you to your hotel in the atmospheric Asakusa district by private transfer. The evening is free to rest, or for a first gentle wander to the lantern-lit Senso-ji temple gate nearby.
2Tokyo — Old & New
Tokyo, Japan
moderateDormy Inn Premium Asakusa, Tokyo
Tokyo — Old & New
Tokyo, Japan
A full day across the world's greatest city. The Senso-ji temple and Nakamise shopping street in old Asakusa in the morning; the Meiji Shrine, the crossing at Shibuya and the views from a skyscraper observation deck in the afternoon. Distances are kept gentle, with Tokyo's flawless metro doing the work.
3Hakone — Fuji & Hot Springs
Hakone, Japan
moderateYumoto Fujiya Hotel, Hakone
Hakone — Fuji & Hot Springs
Hakone, Japan
A morning train to the hot-spring valley of Hakone, in the foothills of Mount Fuji. A circuit of the area by mountain railway, cable car and the pirate-ship cruise on Lake Ashi, with views of Fuji on a clear day. Tonight, a traditional ryokan inn with a kaiseki dinner and your own hot-spring bathing.
4Bullet Train to Kyoto
Kyoto, Japan
moderateDormy Inn Premium Kyoto Ekimae
Bullet Train to Kyoto
Kyoto, Japan
Back to the mainline and aboard the shinkansen to Kyoto, gliding past the countryside (and, weather permitting, Mount Fuji) in reserved comfort. Afternoon in Japan's ancient capital: the golden pavilion of Kinkaku-ji and the Zen rock garden of Ryoan-ji, with their raked gravel and centuries of stillness.
5Kyoto — Temples & Geisha District
Kyoto, Japan
moderateDormy Inn Premium Kyoto Ekimae
Kyoto — Temples & Geisha District
Kyoto, Japan
A full day in Kyoto. The thousand vermilion torii gates of Fushimi Inari in the cool morning, the Kiyomizu-dera temple and its wooden terrace, and the lanes of the Gion geisha district in the late afternoon, when you may glimpse a geiko or maiko hurrying to an appointment.
6Nara Day Trip
Kyoto, Japan
lightDormy Inn Premium Kyoto Ekimae
Nara Day Trip
Kyoto, Japan
A short train to Nara, Japan's first permanent capital, to see the Great Buddha of Todai-ji — one of the world's largest bronze statues, housed in a vast wooden hall — and the tame deer that roam the surrounding park. Afternoon free in Kyoto for the Nishiki food market or a tea ceremony.
7Kyoto to Osaka — Fly to Singapore
Singapore
lightHotel G Singapore
Kyoto to Osaka — Fly to Singapore
Singapore
A short train to Osaka and an afternoon flight south to Singapore. Our representative meets you and transfers you to your hotel in the stylish heart of the city. A free evening — perhaps a first drink overlooking the illuminated Marina Bay skyline.
8Singapore — Gardens & Colonial City
Singapore
moderateHotel G Singapore
Singapore — Gardens & Colonial City
Singapore
A full day in Asia's most sophisticated city. The Gardens by the Bay with their towering Supertrees and cooled conservatories in the morning; the colonial Civic District, the Raffles Hotel and a stroll through the old quarters in the afternoon. An evening hawker-centre dinner introduces Singapore's legendary food culture.
9Singapore — Chinatown, Little India & Quays
Singapore
lightHotel G Singapore
Singapore — Chinatown, Little India & Quays
Singapore
A morning exploring Singapore's cultural quarters — the temples and shophouses of Chinatown, the colour and spice of Little India, and the Arab Street district. The afternoon is free for the shops of Orchard Road, the Botanic Gardens, or rest before the onward journey to Thailand.
10Fly to Chiang Mai
Chiang Mai, Thailand
lightTamarind Village, Chiang Mai
Fly to Chiang Mai
Chiang Mai, Thailand
A flight north to Chiang Mai, the cultural capital of northern Thailand, cradled by forested mountains. Our representative transfers you to your hotel in the old walled city. A gentle late-afternoon orientation among the moat, the ancient gates and the lively night bazaar.
11Doi Suthep & the Old City Temples
Chiang Mai, Thailand
moderateTamarind Village, Chiang Mai
Doi Suthep & the Old City Temples
Chiang Mai, Thailand
A morning drive up the mountain to Wat Phra That Doi Suthep, the glittering golden temple that watches over Chiang Mai, with sweeping views across the valley. The afternoon visits the ancient temples within the old walls — Wat Chedi Luang and Wat Phra Singh — at a gentle pace.
12Ethical Elephant Sanctuary
Chiang Mai, Thailand
moderateTamarind Village, Chiang Mai
Ethical Elephant Sanctuary
Chiang Mai, Thailand
A day in the hills at an ethical elephant sanctuary, where rescued elephants are cared for rather than ridden. You'll feed and walk alongside them, learn their stories, and see them bathe in the river — a gentle, deeply moving day. Return to Chiang Mai in the late afternoon.
13Chiang Mai — Crafts & Cookery
Chiang Mai, Thailand
lightTamarind Village, Chiang Mai
Chiang Mai — Crafts & Cookery
Chiang Mai, Thailand
A relaxed day. Visit the craft villages famous for silk, silver and umbrella-making, or join an optional northern-Thai cookery class. The afternoon is free for a traditional Thai massage or the hotel pool before a final stroll through the Sunday walking-street market (or the night bazaar).
14Chiang Mai at Leisure
Chiang Mai, Thailand
restTamarind Village, Chiang Mai
Chiang Mai at Leisure
Chiang Mai, Thailand
A final, unstructured day to enjoy Chiang Mai at your own pace — a temple you wish to revisit, a last massage, the cafés of the Nimman district, or simply rest in the courtyard of your hotel. A gentle close to a richly varied journey.
15Chiang Mai — Onward Flight
Chiang Mai, Thailand
lightDeparture
Chiang Mai — Onward Flight
Chiang Mai, Thailand
A transfer to Chiang Mai airport for your onward flight, with the assistance of our representative. The end of a journey from the temples of Japan to the warmth of the Thai hills.
Like what you see?
Our specialists can tailor every day to your preferences.
Fitness & mobility
Pacing & accessibility
A premium three-country arc that moves with Japan's superb rail network rather than against it. The Japan leg uses comfortable, reserved bullet-train seats between cities; Singapore is compact and explored gently; and the Thai finale — Chiang Mai by default — is restful. Two internal flights connect the countries, and luggage is forwarded ahead in Japan so you travel unburdened.
Walking
2–4km per day, mostly flat and paved. The exceptions — the full Fushimi Inari circuit and Doi Suthep's steps — are optional, with shorter routes available. Japanese cities involve some stairs in metro stations, though lifts are widely available.
Transport
Reserved-seat shinkansen between Japanese cities (smooth, fast, spacious), two internal flights, and private air-conditioned vehicles with guides for city touring. Luggage is forwarded ahead in Japan.
Altitude
Tokyo, Kyoto, Osaka and Singapore are near sea level; Hakone sits around 700m and Doi Suthep around 1,000m, both reached by vehicle or cable car. No altitude concerns for any guest.
Heat / Climate
Departures avoid Japan's humid summer and Thailand's hottest months. October–November brings crisp Japanese autumn and cool, dry Thailand; the spring departures catch the cherry blossom with warm but bearable Thai weather.
Accommodation
Your hotels
Dormy Inn Premium Asakusa, Tokyo
★★★Asakusa, Tokyo, Japan · 2 nights
A spotless, superb-value hotel in the atmospheric old district of Asakusa, with a top-floor natural hot-spring bath, comfortable rooms and the Senso-ji temple moments away. A Japanese traveller's favourite.
- Top-floor natural hot-spring bath
- Atmospheric Asakusa location
- Steps from Senso-ji temple
- Excellent value and immaculate
Yumoto Fujiya Hotel, Hakone
★★★Hakone, Japan · 1 night
A welcoming hot-spring hotel in the Hakone valley with its own natural onsen baths, kaiseki dining and easy access to the area's mountain railway and Lake Ashi. A classic Japanese hot-spring night.
- Natural onsen hot-spring baths
- Kaiseki dinner included
- Hakone valley setting
- Gateway to Mount Fuji views
Dormy Inn Premium Kyoto Ekimae
★★★Kyoto, Japan · 3 nights
A comfortable, immaculate hotel moments from Kyoto Station, with a top-floor hot-spring bath and excellent transport links to the city's temples. An ideal, well-priced base for the ancient capital.
- Top-floor hot-spring bath
- Steps from Kyoto Station
- Excellent transport links
- Immaculate and great value
Hotel G Singapore
★★★★Singapore · 3 nights
A stylish, contemporary 4-star hotel in the lively Bugis district, within walking distance of the colonial quarter, Little India and the food streets, with smart rooms and a buzzy bistro. Excellent value for central Singapore.
- Stylish, contemporary design
- Central Bugis location
- Walking distance to the colonial quarter
- Great-value city base
Tamarind Village, Chiang Mai
★★★★Chiang Mai, Thailand · 5 nights
A serene Lanna-style heritage hotel built around a 200-year-old tamarind tree in the very heart of Chiang Mai's old walled city, with a lovely pool, a spa and a sense of calm just steps from the night bazaar.
- Heart of the old walled city
- Lanna heritage architecture
- Pool and spa
- Tranquil courtyard around an ancient tamarind tree
Enhance your trip
Koh Samui Beach Finale (in place of Chiang Mai)
+£from 195
Swap the northern-Thailand finale for the island of Koh Samui — five nights of beach and sea in place of the Chiang Mai leg, flying from Singapore to Samui. The premium relaxed alternative for those who want to finish by the water.
per person (supplement)
Tokyo Extra Night & Mount Fuji Excursion
+£from 295
Add a night in Tokyo and a full-day private excursion to the Fuji Five Lakes for the classic views of the mountain, with a lakeside lunch.
per person
Pricing
Holiday pricing
All prices are per person, based on two people sharing. We arrange departures throughout the year to suit your preferred dates.
Starting from
£1,895
per person · 2 sharing
Solo traveller supplement: +£625 pp
Travelling solo?
Single supplement: +£625 pp · Single supplement waived for solo travellers on the November and cherry-blossom April departures.
Full details
What’s included & not included
Included in your price
- 14 nights' accommodation in comfortable 3-star and 4-star city hotels, a Hakone hot-spring inn and a Chiang Mai heritage hotel
- Reserved-seat shinkansen bullet-train travel between Tokyo, Hakone, Kyoto and Osaka
- Luggage forwarding between Japanese hotels on the rail legs
- Private air-conditioned vehicle and English-speaking guide for city touring in each country
- Two internal flights (Osaka–Singapore and Singapore–Chiang Mai)
- Hakone ropeway, cable car and Lake Ashi cruise
- Visit to an ethical, no-riding elephant sanctuary near Chiang Mai
- Meals as specified (14 breakfasts, 2 lunches, 2 dinners including a kaiseki ryokan dinner)
- All airport and inter-city transfers
- ATOL-protected booking
Not included
- International flights into Tokyo and home from Chiang Mai (we can arrange from your local UK airport)
- Travel insurance
- Single supplement (waived on selected departures)
- Most lunches and dinners (Japan and Singapore are superb for independent dining)
- Gratuities (not expected in Japan; appreciated in Thailand)
- Personal spending, drinks and optional excursions
Your specialist
Who will plan your holiday
Kenji Watanabe
Born in Osaka and based between Kyoto and Bangkok, Kenji has spent sixteen years specialising in premium rail and multi-country travel across East and Southeast Asia. A devoted railwayman, he knows the shinkansen timetable by heart and engineers his Japan legs around reserved seats and forwarded luggage so that nothing feels rushed. Equally at home explaining a Zen garden, a Singapore hawker stall or a northern-Thai temple, he is calm, precise and quietly warm. He works with long-trusted guides in each country and is on hand throughout.
Tailor-made
Like this tour but want it adapted?
Extra nights, alternative hotels, private transfers — our specialists will build your perfect itinerary from scratch.
What our guests say
Guest reviews
The cherry blossom in Kyoto was a lifelong dream realised
“We chose the April departure for the blossom and it did not disappoint — Kyoto under a haze of pink is something we will never forget. The bullet trains were a joy, and the luggage being whisked ahead meant we never once struggled with cases. Singapore was a sleek, delicious interlude, and Chiang Mai a gentle, warm-hearted finish. A genuinely transformative three weeks, beautifully organised by Kenji.”
Charles & Diana Wexford
Surrey · 2025-04-18
Three countries, not a single stressful moment
“I was nervous about Japan as a solo traveller of 66, but the reserved seats, the forwarded luggage and the meeting at every step made it the easiest country I have ever visited. The elephant sanctuary in Chiang Mai brought me to tears. Singapore in the middle was the perfect sophisticated pause. Remarkable value given everything that was included.”
Patricia Holroyd
York · 2025-03-30
From raked-gravel gardens to golden temples
“The contrast was the whole point and it worked beautifully — the precision and quiet of Japan, the gleam of Singapore, the warmth of the Thai hills. We took the autumn departure and Kyoto's maples were ablaze. The Dormy Inn hotels in Japan were a lovely surprise, spotless and with those wonderful hot-spring baths. We would recommend it without hesitation.”
Brian & Sheila Forsythe
Glasgow · 2024-11-21
Before you go
Practical information
Visa requirements
No advance visa required for UK citizens: Japan (90 days visa-free), Singapore (up to 90 days), Thailand (up to 60 days visa-free, subject to current rules). Passport valid for 6+ months required. We confirm the latest rules on booking.
Currency
Japanese Yen, Singapore Dollar and Thai Baht. Cards are widely accepted in Japan and Singapore; carry some cash for Thai markets and smaller vendors. ATMs are plentiful throughout (in Japan, convenience-store ATMs are the most reliable for foreign cards).
Tipping
No tipping in Japan — it is not part of the culture and can cause confusion. Tipping is not expected in Singapore (a service charge is usually included). In Thailand, tipping is appreciated: a little for guides, drivers and at restaurants. Your guides will advise.
Electricity
Japan uses 100V with Type A/B plugs; Singapore uses 230V with the UK three-pin (Type G); Thailand uses 220V with Type A/B/C sockets. Bring a universal adapter for the trip; UK appliances work in Singapore without one.
Health & vaccinations
No mandatory vaccinations for UK travellers; routine jabs should be up to date and Hepatitis A is sometimes advised for the Thailand leg. Healthcare is excellent in all three countries. Comprehensive travel insurance with medical cover is essential.
Flights
International flights are not included. We arrange flights from your local UK airport into Tokyo and home from Chiang Mai, plus the two internal flights (Osaka–Singapore and Singapore–Chiang Mai) which are included in the tour.
Local transport
Reserved-seat shinkansen bullet trains between Japanese cities, with luggage forwarded ahead. Two internal flights link the countries. Private air-conditioned vehicles with English-speaking guides for city touring and excursions throughout. Japan and Singapore also have superb, accessible public metros your guide may use for speed.
Travel with like-minded people
Join a Small Group Departure
Prefer to travel with a small group of fellow over-50s rather than as a couple or solo? Our fixed-departure group tours put you alongside eight to twelve like-minded travellers with a dedicated tour manager for the entire journey.
- Maximum 12 travellers — intimate by design
- Dedicated tour manager throughout
- Social dinners and shared discoveries
- Single supplement waived on selected departures
- Like-minded over-50s travellers
- No single friends needed — just arrive and enjoy
Register Your Interest
Tell us your preferred dates and travel companions — we’ll match you with the right departure and send full details.
Our team will respond within 1 working day.
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Common questions
Frequently asked questions
How does the bullet-train travel work — is it difficult with luggage?
It is wonderfully easy. We book reserved seats on the shinkansen for every inter-city leg in Japan, so you always have a guaranteed spacious seat. Crucially, your main luggage is forwarded ahead from hotel to hotel (a service Japanese travellers use constantly), so you board the train with only a small overnight bag. The trains are smooth, punctual to the minute and have generous legroom. Your guide handles the tickets and platforms. It is, for many guests, a highlight rather than a chore.
Can I finish on a beach instead of in Chiang Mai?
Yes. The standard itinerary finishes in Chiang Mai, the temple-rich cultural capital of northern Thailand, which we find offers the richest contrast to Japan and Singapore. But if you would rather end by the sea, we offer a Koh Samui beach finale in place of the Chiang Mai leg (see add-ons) — flying from Singapore to the island for five nights of beach and relaxation. Either way, the first ten days remain the same.
Do I need a visa for Japan, Singapore or Thailand?
For UK citizens, none of the three requires a visa in advance for a tourist stay of this length. Japan grants a 90-day visa-free entry, Singapore up to 90 days, and Thailand up to 60 days visa-free (subject to current rules). You simply need a valid passport with at least six months' validity. We confirm the latest entry requirements for all three countries when you book.
Is the elephant sanctuary ethical?
Yes — this matters greatly to us. We only ever use genuine, no-riding sanctuaries near Chiang Mai that exist to rehabilitate rescued elephants and prioritise their welfare. You feed and walk alongside the elephants and watch them bathe, but you do not ride them and there are no performances. It is one of the most moving and responsible wildlife experiences in northern Thailand.
Why is a premium trip like this under £2,000?
The price is land-only — your international flights are arranged separately from your local UK airport. Within the tour, we keep the cost down with intelligent hotel choices: the excellent-value Dormy Inn Premium hotels in Japan (immaculate, with hot-spring baths) and smart 4-star city hotels elsewhere, rather than five-star throughout. You still travel by reserved-seat bullet train, stay a night in a hot-spring ryokan, and finish in a lovely heritage hotel in Chiang Mai. It is a genuinely premium experience at a carefully managed price.
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