Mount Fuji rising behind a Japanese pagoda in spring, the opening chapter of a grand journey across Japan, Singapore and Thailand

Japan, Singapore & Thailand: East Meets Southeast

East Asia to Southeast Asia in sixteen unhurried nights — bullet trains, garden cities and a beach to finish

16 nightsModerateFrom £1,995 pp
ATOL ProtectedRefundable depositsPrivate specialist guideFlights included

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

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Your journey

Day-by-day itinerary

1

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.

Meals: DinnerWalking: approx. 1 kmHotel: Hotel Niwa Tokyo ★★★★
Specialist tip: Resist the urge to push through jet lag with a big first day. A quiet evening and an early night sets up the whole trip.
Accessibility: Step-free transfer; hotel has lifts to all floors and Western-style beds.
2

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.

Meals: Breakfast, LunchWalking: approx. 4 kmHotel: Hotel Niwa Tokyo ★★★★
Specialist tip: Asakusa is at its calmest before 9am — we start early to enjoy the temple before the crowds arrive.
Accessibility: Senso-ji approach is flat and paved; benches throughout the Imperial gardens.
3

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.

Meals: BreakfastWalking: approx. 3.5 kmHotel: Hotel Niwa Tokyo ★★★★
Specialist tip: The basement food halls (depachika) of Ginza's department stores are the easiest, most civilised lunch in Tokyo.
Accessibility: Hamarikyu has flat gravel paths; viewpoint reached by lift.
4

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.

Meals: Breakfast, DinnerWalking: approx. 3 kmHotel: Hakone Yutowa ★★★★
Specialist tip: Fuji hides behind cloud more often than not. Mornings give the best odds, so we time the lake cruise early.
Accessibility: Ropeway and cruise are step-assisted with staff help; ryokan has Western-bed rooms and private bathing.
5

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.

Meals: Breakfast, DinnerWalking: approx. 2 kmHotel: Nazuna Kyoto Gosho (machiya) ★★★★
Specialist tip: Sit on the right-hand side (Tokyo to Kyoto) for the Mount Fuji view about 40 minutes in.
Accessibility: Reserved bullet-train seats with luggage assistance; machiya has some traditional steps — ground-floor rooms requested for those who prefer.
6

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.

Meals: Breakfast, LunchWalking: approx. 5 kmHotel: Nazuna Kyoto Gosho (machiya) ★★★★
Specialist tip: Arashiyama's bamboo grove is magical at opening time and a crush by mid-morning. We go first thing.
Accessibility: Kinkaku-ji and Arashiyama have mostly flat paths; some temple gravel and gentle slopes.
7

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.

Meals: BreakfastWalking: approx. 3.5 kmHotel: Nazuna Kyoto Gosho (machiya) ★★★★
Specialist tip: Fushimi Inari never closes and is free — arriving by 8am means the first photogenic tunnel of gates almost to yourself.
Accessibility: Lower Fushimi Inari loop is paved and gentle; the full mountain climb is optional and not included.
8

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.

Meals: BreakfastWalking: approx. 1.5 kmHotel: PARKROYAL COLLECTION Marina Bay ★★★★★
Specialist tip: Changi Airport is a destination in itself — leave a little time for the Jewel waterfall if your flight allows.
Accessibility: Singapore Changi and the hotel are fully step-free with excellent accessible facilities.
9

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.

Meals: Breakfast, DinnerWalking: approx. 4 kmHotel: PARKROYAL COLLECTION Marina Bay ★★★★★
Specialist tip: The Supertree show is free and runs twice nightly — we time dinner so you catch it without a late finish.
Accessibility: Gardens by the Bay is step-free with shuttle buggies; the Cloud Forest is fully lift-served.
10

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.

Meals: Breakfast, LunchWalking: approx. 3.5 kmHotel: PARKROYAL COLLECTION Marina Bay ★★★★★
Specialist tip: Singapore is hot and humid year-round — we keep mornings active and afternoons cool and optional.
Accessibility: All neighbourhoods are flat and walkable; the MRT is fully accessible if you prefer to ride.
11

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.

Meals: BreakfastWalking: approx. 1 kmHotel: Banyan Tree Samui ★★★★★
Specialist tip: Koh Samui's airport is open-air and charming — one of the most relaxing arrivals in Asia.
Accessibility: Resort has buggy transport across the hillside grounds; flat villas can be requested for those with mobility needs.
12

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.

Meals: BreakfastWalking: approx. 1 kmHotel: Banyan Tree Samui ★★★★★
Specialist tip: Book a spa slot for the late afternoon — a sunset treatment is the best way to ease into the Thai pace.
Accessibility: Buggies on call; beach access via gentle ramped paths.
13

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.

Meals: Breakfast, LunchWalking: approx. 2.5 kmHotel: Banyan Tree Samui ★★★★★
Specialist tip: Fisherman's Village is best in the late afternoon when the heat softens and the cafés open onto the water.
Accessibility: Big Buddha has a flight of steps to the statue; the lower terrace and views are step-free.
14

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.

Meals: BreakfastWalking: approx. 1.5 kmHotel: Banyan Tree Samui ★★★★★
Specialist tip: A half-day cooking class is a lovely, low-effort souvenir — you go home able to recreate the trip's best meal.
Accessibility: All activities optional; boat trips are weather-dependent and step-assisted by crew.
15

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.

Meals: Breakfast, DinnerWalking: approx. 1 kmHotel: Banyan Tree Samui ★★★★★
Specialist tip: Ask the resort to set your farewell dinner table at the water's edge — they will, and it's the photograph everyone keeps.
Accessibility: Beachfront dining reached by ramped path; buggy on request.
16

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.

Meals: BreakfastWalking: approx. 0.5 km
Specialist tip: Most homeward flights connect via Bangkok or Singapore — we hold a day room option if your layover is long.
Accessibility: Step-free transfer and assisted check-in arranged.

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

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 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

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

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

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

4.9/ 5 — 27 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.

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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Japan, Singapore & Thailand Tour | 16 Nights for Over 50s | Private Escorted | Holidays to Asia | Holidays to Asia