Japan, Singapore & Thailand: East Meets Southeast
East Asia to Southeast Asia in sixteen unhurried nights — bullet trains, garden cities and a beach to finish
From
£1,995pp
About this tour
Few journeys contrast the worlds of Asia as completely as this one. It opens in Japan — the bullet trains, the lantern-lit lanes of Kyoto, the cherry-blossom temples and the perfect cone of Mount Fuji seen from the hot-spring valley of Hakone. It moves on to Singapore, the most effortless city in Asia, where Gardens by the Bay glows after dark, the hawker centres serve some of the finest food on the continent, and Marina Bay frames a skyline that feels like the future. And it closes in Thailand, where the pace finally slows — a beach on Koh Samui or the temple-and-mountain calm of Chiang Mai, with nothing required of you but a long lunch and a longer rest. Sixteen nights, three countries, one carefully sequenced journey. Private transfers carry you door to door; in Japan your main luggage is forwarded ahead so you travel the bullet trains with only a day bag; and every hotel is chosen for comfort, location and a warm welcome rather than for a name on a brochure. This is Asia at its most rewarding and least tiring — designed, from first morning to last, for the traveller who has earned an unhurried pace.
“Designed by our East Asia and Southeast Asia specialists together — a journey that hands you off seamlessly from a Japan guide to a Singapore host to a Thai resort team, with every transfer pre-arranged.”
Why this works for travellers over 50
- Three of Asia's great destinations in a single, logically sequenced journey — no doubling back, no wasted days
- Luggage forwarding in Japan means you ride the bullet trains carrying only a day bag
- Private air-conditioned transfers throughout — no group coaches, no airport scrums
- A genuine beach or mountain rest in Thailand to finish, not a frantic dash home
- Every hotel is central, step-free where possible, with lifts and accessible bathrooms noted in advance
- A built-in free morning in each city to rest, repack or simply linger over breakfast
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
1Arrival in Tokyo
Tokyo
ArrivalHotel Niwa Tokyo
Arrival in Tokyo
Tokyo
Private transfer from Haneda or Narita to your central Tokyo hotel. The rest of the day is yours to rest and adjust. An optional gentle evening stroll through the lantern-lit lanes of nearby Shinbashi for a first bowl of ramen.
2Tokyo: Old Town & Imperial Calm
Tokyo
GentleHotel Niwa Tokyo
Tokyo: Old Town & Imperial Calm
Tokyo
A gentle introduction to the city — Senso-ji temple in Asakusa, the Nakamise shopping street, and the serene East Gardens of the Imperial Palace. Lunch is a relaxed tempura set. Afternoon at leisure.
3Tokyo: Gardens, Views & Free Afternoon
Tokyo
GentleHotel Niwa Tokyo
Tokyo: Gardens, Views & Free Afternoon
Tokyo
Morning at the Hamarikyu garden and a traditional tea house on its tidal pond, then up to a skyline viewpoint over the vast city. The afternoon is free — for the Ginza, a department-store food hall, or simply a rest.
4Hakone & Mount Fuji
Hakone
ModerateHakone Yutowa
Hakone & Mount Fuji
Hakone
Travel to the hot-spring valley of Hakone in the foothills of Mount Fuji. A cruise on Lake Ashi, the volcanic Owakudani valley by ropeway, and — weather permitting — Fuji itself in full view. Overnight in a hot-spring ryokan with private onsen options.
5Bullet Train to Kyoto
Kyoto
EasyNazuna Kyoto Gosho (machiya)
Bullet Train to Kyoto
Kyoto
Return to the rail line and board the Shinkansen for Kyoto — Fuji often visible from the window as the train glides past at speed. Your main luggage has been forwarded ahead. Check in to a machiya-style townhouse stay in the old quarter, then a first evening walk through Gion.
6Kyoto: Temples & Cherry-Blossom Lanes
Kyoto
ModerateNazuna Kyoto Gosho (machiya)
Kyoto: Temples & Cherry-Blossom Lanes
Kyoto
The golden pavilion of Kinkaku-ji mirrored in its pond, the rock garden of Ryoan-ji, and the Arashiyama bamboo grove with its riverside temples. In spring the whole city is wrapped in cherry blossom.
7Kyoto: Fushimi Inari & Free Afternoon
Kyoto
GentleNazuna Kyoto Gosho (machiya)
Kyoto: Fushimi Inari & Free Afternoon
Kyoto
An early visit to the thousand vermilion torii gates of Fushimi Inari — we walk only the gentle lower loop. The afternoon is free for the Nishiki food market, a tea ceremony, or rest before the journey south.
8Fly to Singapore
Singapore
EasyPARKROYAL COLLECTION Marina Bay
Fly to Singapore
Singapore
A relaxed morning, then a private transfer to Osaka Kansai for the flight to Singapore. On arrival, a smooth transfer to your hotel near Marina Bay. The evening is free to settle in.
9Singapore: Gardens & Marina Bay
Singapore
ModeratePARKROYAL COLLECTION Marina Bay
Singapore: Gardens & Marina Bay
Singapore
Gardens by the Bay — the Cloud Forest dome and the towering Supertrees — followed by the colonial quarter and a Singapore Sling at a heritage hotel. After dark, the Supertree light show. A hawker-centre dinner introduces the city's legendary street food.
10Singapore: Culture & Free Time
Singapore
GentlePARKROYAL COLLECTION Marina Bay
Singapore: Culture & Free Time
Singapore
A morning exploring the colour of Chinatown, Little India and the spice-scented lanes of Kampong Glam, with a guided hawker lunch. The afternoon is yours — for the orchid garden, the National Gallery, or a rest by the pool.
11Fly to Thailand
Koh Samui
EasyBanyan Tree Samui
Fly to Thailand
Koh Samui
A private transfer to Changi for the short flight to Koh Samui (a Chiang Mai alternative is available). On arrival, transfer to your beach resort, where the only task for the rest of the day is to do nothing at all.
12Koh Samui: Rest Day
Koh Samui
GentleBanyan Tree Samui
Koh Samui: Rest Day
Koh Samui
A full day at leisure on the beach. Optional spa treatments, a gentle swim, or simply a book under a parasol. Nothing is scheduled — this is the rest the journey has been building towards.
13Koh Samui: Island & Temple
Koh Samui
GentleBanyan Tree Samui
Koh Samui: Island & Temple
Koh Samui
An optional gentle island excursion — the Big Buddha temple, the fishing village of Bophut with its Fisherman's Village lanes, and a viewpoint over the bays. Back to the resort by early afternoon for more rest.
14Koh Samui: Free Day
Koh Samui
GentleBanyan Tree Samui
Koh Samui: Free Day
Koh Samui
Another unhurried day on the island. Perhaps a Thai cooking class, a long-tail boat trip to a quiet bay, or nothing more strenuous than choosing where to have lunch.
15Koh Samui: Final Beach Day
Koh Samui
GentleBanyan Tree Samui
Koh Samui: Final Beach Day
Koh Samui
A last full day to enjoy the resort and the sea. A farewell Thai dinner on the beach in the evening, with the lights of the fishing boats out on the bay.
16Departure
Koh Samui
Departure
Departure
Koh Samui
A final breakfast by the sea, then a private transfer to Koh Samui airport for your onward connection home, with your day-bag light and your luggage already forwarded. The end of three countries in one journey.
Like what you see?
Our specialists can tailor every day to your preferences.
Fitness & mobility
Pacing & accessibility
A three-country grand tour that moves with purpose but never rushes. Two internal flights and one bullet-train leg are arranged with private transfers and assisted check-in throughout; the Thai finale is built around rest. Sightseeing days are balanced with free mornings and a midpoint beach stretch.
Walking
1–5km/day; mostly flat city and garden walking with optional temple steps. Built-in free mornings and a five-night beach rest in Thailand.
Transport
First-class bullet train (Kyoto leg), two short internal flights, and private air-conditioned transfers throughout. Luggage forwarded within Japan.
Altitude
Sea level throughout; Hakone in low hills (around 700m at the ropeway).
Heat / Climate
Singapore and Thailand are hot and humid year-round (28–33°C); Japan is mild in spring and autumn. Mornings active, afternoons cool and optional.
Accommodation
Your hotels
Hotel Niwa Tokyo
★★★★Tokyo · 3 nights
A refined, garden-themed 4-star in central Tokyo near Suidobashi — quiet, traditional in feel, with lifts, Western beds and an easy walk to Akihabara and the Imperial Palace.
- Central, quiet location
- Japanese garden courtyard
- Lifts to all floors
- Western-style beds
Hakone Yutowa
★★★★Hakone · 1 night
A contemporary ryokan in the Hakone hot-spring valley with hot-spring bathing, a relaxed lounge and Western-bed rooms — onsen comfort without the formality.
- Hot-spring bathing
- Western-bed rooms
- Mountain setting
- Relaxed lounge
Nazuna Kyoto Gosho
★★★★Kyoto · 3 nights
A beautifully restored machiya townhouse stay near the Imperial Palace — private cypress baths, tatami-and-bed rooms and the atmosphere of old Kyoto on a quiet lane.
- Restored machiya townhouse
- Private cypress bath
- Old-Kyoto location
- Ground-floor rooms on request
PARKROYAL COLLECTION Marina Bay
★★★★★Singapore · 3 nights
A landmark garden hotel overlooking Marina Bay, wrapped in greenery with a vast atrium, a sky-level pool and a step-free walk to Gardens by the Bay and the Marina Bay waterfront.
- Overlooks Marina Bay
- Indoor garden atrium
- Rooftop pool
- Walk to Gardens by the Bay
Banyan Tree Samui
★★★★★Koh Samui · 5 nights
A hillside pool-villa resort above a private bay on Koh Samui's quiet south-east coast — an award-winning spa, buggy transport across the grounds and total beachfront calm to end the journey.
- Private pool villas
- Award-winning spa
- Secluded bay
- Buggy transport on call
Enhance your trip
Chiang Mai instead of Koh Samui
+£0
Swap the Koh Samui beach finale for the temple-and-mountain calm of Chiang Mai — Old City temples, the Doi Suthep hilltop sanctuary, an elephant-sanctuary visit and the night bazaar, at a comparable standard of 4-star boutique accommodation.
no supplement — like-for-like swap
Business-class international flight upgrade
+£on request
Upgrade your long-haul flights to and from Asia to business class for fully flat beds — a worthwhile comfort for the over-50s traveller on the longer sectors.
per person, subject to airline availability
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
£1,995
per person · 2 sharing
Solo traveller supplement: +£895 pp
Travelling solo?
Single supplement: +£895 pp · Single supplement waived on selected shoulder-season departures for solo travellers booking by the balance-due date.
Full details
What’s included & not included
Included in your price
- 16 nights in carefully chosen 4 and 5-star hotels and a ryokan
- First-class bullet train Kyoto leg with reserved seating
- Luggage forwarding within Japan
- Two internal flights (Osaka–Singapore, Singapore–Koh Samui)
- All private airport and inter-city transfers
- English-speaking local guides in Japan, Singapore and Thailand
- Meals as specified
- All listed entrance fees
- Japan IC transport card
- Mineral water on touring days
- ATOL-protected
Not included
- International flights to Japan and home from Thailand
- Travel insurance
- Single supplement
- Visas and entry fees where applicable
- Gratuities
- Optional excursions and spa treatments
Your specialist
Who will plan your holiday
James Whitfield
James has escorted multi-country Asia journeys for over a decade, coordinating the hand-offs between Japan, Singapore and Thailand so that each transfer is seamless and every guide is briefed on the group before arrival. He specialises in pacing trips for mature travellers who want breadth without exhaustion.
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
Three countries, and never once rushed
“We worried that three countries in just over two weeks would be exhausting. It was the opposite. Japan was a wonder — the bullet train with our bags sent ahead was a revelation — Singapore was effortless and clean, and by the time we reached Koh Samui we simply collapsed happily onto a beach for five nights. Every transfer was waiting for us. We are in our late sixties and not once did we feel hurried.”
Margaret & Roy Pemberton
Surrey · 2026-04-22
The pacing is the genius of it
“I have done escorted tours that march you off your feet. This one understood that a free morning is worth as much as another temple. Kyoto in the cherry blossom, the Supertrees in Singapore after dark, then a proper rest in Thailand. The accessibility notes for each day were genuinely useful for my wife, who uses a stick.”
Dr Alan Forsyth
Edinburgh · 2026-05-09
Autumn in Japan, summer in Thailand, all in one trip
“Travelling in November we caught the Kyoto maples at their peak and then flew south into warmth. The contrast was extraordinary. Our guides in all three countries clearly knew we were coming and knew exactly what we needed. The Singapore hotel overlooking Marina Bay was a highlight in itself.”
Jennifer Hale
Bath · 2026-11-30
Worth every penny and then some
“We chose the Chiang Mai alternative instead of the beach and loved the temples and the elephant sanctuary. The whole journey was beautifully organised — private cars, English-speaking guides, and a wonderful sense that someone had thought about everything in advance. We have already recommended it to two couples at our golf club.”
Peter & Susan Donnelly
Cheshire · 2027-04-18
A solo traveller made to feel at home
“As a woman travelling alone in my early sixties I was nervous about so much movement between countries. The waived single supplement on my departure was a lovely surprise, and James made sure every hand-off was smooth. I never once felt lost or alone. Singapore was my favourite — so easy and so beautiful.”
Hazel Crawford
Norfolk · 2027-05-28
Before you go
Practical information
Visa requirements
UK citizens: Japan and Singapore visa-free for short tourist stays; Thailand visa-exempt for tourist visits within the permitted period. We confirm current rules for your departure.
Currency
Japan: Japanese yen (JPY), cash still widely used — an IC card is provided. Singapore: Singapore dollar (SGD), card-friendly. Thailand: Thai baht (THB), cash useful for markets and tips. ATMs are plentiful in all three.
Tipping
No tipping in Japan; modest tipping is welcome in Thailand and at your discretion in Singapore. Guidance is provided in your travel pack.
Electricity
Japan 100V (Type A/B); Singapore 230V (Type G, UK-style); Thailand 220V (Types A/B/C). A universal adaptor covers all three.
Health & vaccinations
No vaccinations required for a standard itinerary; excellent private healthcare in all three countries. Bring any prescription medication in its original packaging with a copy of the prescription.
Flights
International flights not included: fly into Tokyo (Haneda or Narita) and home from Koh Samui or Chiang Mai, typically via Bangkok or Singapore. Two internal flights are included. We are happy to arrange your long-haul flights and upgrades.
Local transport
First-class bullet train on the Kyoto leg, two short internal flights, and private air-conditioned transfers throughout. Luggage forwarded within Japan.
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 tiring is a three-country tour at this pace?
Less tiring than most single-country tours, by design. The itinerary moves in one logical direction with no backtracking, every transfer is private and pre-arranged, your luggage is forwarded within Japan so you travel light on the bullet trains, and the final five nights in Thailand are pure rest. We build a free morning or afternoon into each city so you are never on your feet from dawn to dusk. The pace is rated Moderate and is comfortable for active travellers in their fifties, sixties and beyond.
Can I choose Chiang Mai instead of Koh Samui?
Yes. The Thai finale can be either the Koh Samui beach resort or the temple-and-mountain calm of Chiang Mai — Old City temples, the hilltop sanctuary of Doi Suthep, an ethical elephant-sanctuary visit and the famous night bazaar. The swap is like-for-like with no supplement. Tell us your preference when you enquire and we will confirm the matching accommodation.
What are the flights between countries?
There are two short internal flights included: Osaka to Singapore, and Singapore to Koh Samui (or Chiang Mai). Both are arranged with private transfers at each end and assisted check-in. Your international flights from the UK to Japan and home from Thailand are not included, which keeps the headline price low and lets us tailor your routing — we are happy to arrange these for you, including business-class upgrades.
Do I need visas for Japan, Singapore and Thailand?
For UK passport holders, all three are straightforward. Japan and Singapore are visa-free for short tourist stays. Thailand is visa-exempt for UK citizens for tourist visits within the permitted period. Requirements can change, so we confirm the current position for your departure and guide you through any online entry or arrival-card formalities before you travel.
What is the best time of year to go?
Japan is loveliest in spring (cherry blossom, late March to mid-April) and autumn (maple colour, late October to November), and our departures are timed accordingly. Singapore and Thailand are warm year-round; the Gulf coast of Koh Samui is at its driest and sunniest from roughly January to September, while Chiang Mai is best from November to February. Whichever season you choose, the journey is built to suit it.
How accessible is the tour for someone with limited mobility?
Every day in the itinerary carries an accessibility note, and the pace is gentle with optional elements clearly flagged. Singapore and Thailand are largely step-free; Japan involves some temple steps and traditional features, but we request ground-floor rooms, use lifts and ramps wherever possible, and arrange buggy transport at the Thai resort. Tell us about any specific needs when you enquire and we will tailor the daily plan around them.
What is the food like, and can dietary needs be met?
Food is one of the great pleasures of this journey — refined Japanese cuisine, Singapore's celebrated hawker centres, and fresh Thai cooking by the sea. Included meals are a mix of guided local experiences and relaxed hotel dining. Vegetarian, vegan, gluten-free and other dietary requirements are easily accommodated across all three countries; please let us know in advance so we can brief each guide and venue.
Is the trip ATOL-protected?
Yes. When we arrange your flights as part of the package the holiday is ATOL-protected under our licence (T7263), giving you full financial protection. We will explain exactly what is covered when you book.
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