Tour overview

This 22-day small-group journey travels the length of the Thai peninsula and down through Malaysia to Singapore, combining history, rainforest, islands and three very different cities. Groups have up to 12 travellers aged 15 and over, with a leader throughout. You stay twenty-one nights: fourteen in hotels, four in resorts, two in guesthouses and one on an overnight sleeper train with curtained berths. Sixteen breakfasts, three lunches and two dinners are included, among them home-cooked dinners in Sukhothai and Huai Lan, a lunch on a raft house on Cheow Lan Lake and a community lunch in a fishing village near Trang.

From Bangkok you head west to Kanchanaburi, where the Hellfire Pass Memorial and a train ride along the Death Railway to the Bridge on the River Kwai tell the story of the prisoners of war who built it, with time to swim at Erawan Falls. Travelling north, you walk with rescued elephants at the Sappraiwan Elephant Sanctuary and cycle among the ruined temples of Sukhothai Historical Park, before reaching Chiang Mai to explore its largest fresh produce market.

Read more

A flight returns you to Bangkok for a cruise on its canals and a visit to Wat Pho's reclining Buddha, then an overnight train carries you south to Khao Sok National Park, one of the oldest rainforests in the world. A longtail boat crosses Cheow Lan Lake among limestone cliffs, with a trek to a cave of bats and streams. Near Krabi you paddle a sea kayak through mangroves and karst islands, with a free day for snorkelling or island hopping.

After a community visit near Trang, you cross into Malaysia to Penang and George Town, with its street art and shophouses. Kuala Lumpur brings skyscrapers and a mix of Malay, Chinese and Indian cultures, and in historic Melaka you tour the old port town by trishaw before a local bus takes you to Singapore.

The physical rating is medium, with some long travel days and transport that can be cramped. This trip suits curious travellers who want a varied overland journey with history, nature and food along the way. A single room is available on most nights.

Trip highlights

  • The Death Railway and Hellfire Pass (Day 3)
  • Walking with rescued elephants (Day 5)
  • Cycling around Sukhothai Historical Park (Day 5)
  • Cheow Lan Lake in Khao Sok (Day 11)
  • Sea kayaking near Krabi (Day 12)
  • George Town in Penang (Day 16)

Your route

16 stops from Bangkok to Singapore

22-day route: Bangkok – Kanchanaburi – Sukhothai – Chiang Mai – Khao Sok – Ao Nang – Penang – Kuala Lumpur – Melaka – Singapore
  1. Bangkok Days 1 & 8–9
  2. Kanchanaburi Days 2–3
  3. Hellfire Pass Memorial Day 3
  4. Wat Tha Sung Day 4
  5. Phitsanulok Day 4
  6. Sukhothai Day 5
  7. Chiang Mai Days 6–7
  8. Surat Thani Day 10
  9. Khao Sok (Phrom Lok) Days 10–11
  10. Cheow Lan Lake Day 11
  11. Ao Nang Days 12–13
  12. Trang Day 14
  13. George Town (Penang) Days 15–16
  14. Kuala Lumpur Days 17–18
  15. Melaka Days 19–20
  16. Singapore Days 21–22

Why choose this tour

Two countries and Singapore overland, from wartime history to rainforest. Small groups of up to 12, with an elephant sanctuary and sea kayaking included.

Best suited to

  • Travellers with time for a long trip
  • History lovers
  • Nature lovers
  • Solo travellers looking for a small group
Sea kayaking through limestone caves near Krabi

Day-by-day itinerary

22 days from Bangkok, Thailand to Singapore

  1. Day 1 · Bangkok Arrive in Bangkok

    A welcome meeting.

    Hotel
    Hotel
  2. Day 2 · Kanchanaburi Kanchanaburi

    Travel west to the River Kwai.

    Hotel
    Guesthouse
  3. Day 3 · Hellfire Pass, Erawan Falls Death Railway

    Hellfire Pass, a train ride and Erawan Falls.

    Hotel
    Guesthouse
  4. Day 4 · Phitsanulok Phitsanulok

    A long travel day north.

    Hotel
    Hotel
    Meals
    Breakfast
  5. Day 5 · Sappraiwan Elephant Sanctuary, Sukhothai Sukhothai

    Walk with elephants and cycle among temples.

    Hotel
    Resort
    Meals
    Breakfast, Dinner
  6. Day 6 · Chiang Mai Chiang Mai

    Travel via a Lanna village to Chiang Mai.

    Hotel
    Hotel
    Meals
    Breakfast, Dinner
  7. Day 7 · Chiang Mai Chiang Mai

    Explore the city's biggest fresh market.

    Hotel
    Hotel
    Meals
    Breakfast
  8. Day 8 · Bangkok Bangkok

    Fly back to Bangkok.

    Hotel
    Hotel
    Meals
    Breakfast
  9. Day 9 · Wat Pho, Chao Phraya River Bangkok

    A canal cruise, then the night train south.

    Hotel
    Overnight sleeper train
  10. Day 10 · Khao Sok National Park Khao Sok

    Free time in the rainforest.

    Hotel
    Resort
  11. Day 11 · Cheow Lan Lake Cheow Lan Lake

    A longtail boat across the lake.

    Hotel
    Resort
    Meals
    Breakfast, Lunch
  12. Day 12 · Ao Nang Ao Nang

    Sea kayaking through mangroves.

    Hotel
    Hotel
    Meals
    Breakfast, Lunch
  13. Day 13 · Krabi Ao Nang

    A free day for islands or snorkelling.

    Hotel
    Hotel
    Meals
    Breakfast
  14. Day 14 · Baan Mod Tanoy Trang

    A community visit and lunch.

    Hotel
    Resort
    Meals
    Breakfast, Lunch
  15. Day 15 · Penang Penang

    Cross into Malaysia.

    Hotel
    Hotel
    Meals
    Breakfast
  16. Day 16 · George Town George Town

    A walking tour of the old town.

    Hotel
    Hotel
    Meals
    Breakfast
  17. Day 17 · Kuala Lumpur Kuala Lumpur

    Travel south to the capital.

    Hotel
    Hotel
    Meals
    Breakfast
  18. Day 18 · Kuala Lumpur Kuala Lumpur

    A free day.

    Hotel
    Hotel
    Meals
    Breakfast
  19. Day 19 · Melaka Melaka

    A local bus to the old port town.

    Hotel
    Hotel
    Meals
    Breakfast
  20. Day 20 · Melaka Melaka

    A trishaw tour of the old streets.

    Hotel
    Hotel
    Meals
    Breakfast
  21. Day 21 · Singapore Singapore

    A local bus to Singapore.

    Hotel
    Hotel
    Meals
    Breakfast
  22. Day 22 · Singapore Trip ends

    The trip ends after breakfast.

    Meals
    Breakfast
A trishaw in George Town, Penang

Where you stay

  • Bangkok (1 night) Hotel
  • Kanchanaburi (2 nights) Guesthouse
  • Phitsanulok (1 night) Hotel
  • Sukhothai (1 night) Resort
  • Chiang Mai (2 nights) Hotel
  • Bangkok (1 night) Hotel
  • Bangkok to Surat Thani (1 night) Overnight sleeper train
  • Khao Sok (2 nights) Resort
  • Ao Nang (2 nights) Hotel
  • Trang (1 night) Resort
  • Penang (2 nights) Hotel
  • Kuala Lumpur (2 nights) Hotel
  • Melaka (2 nights) Hotel
  • Singapore (1 night) Hotel

Hotel names are indicative and may be replaced with a property of similar standard and location.

What's included

Included

  • Accommodation 20 nights in hotels, resorts and guesthouses, and 1 on a sleeper train
  • Meals 17 breakfasts, 3 lunches and 2 dinners
  • Private minivans, local buses, a sleeper train and a flight from Chiang Mai to Bangkok
  • Hellfire Pass, the Death Railway and Erawan Falls
  • Sappraiwan Elephant Sanctuary and Sukhothai by bike
  • Bangkok canal cruise and Wat Pho
  • Cheow Lan Lake longtail boat and sea kayaking near Krabi
  • George Town walking tour and Melaka trishaw tour
  • Leader throughout

Not included

  • International flights
  • Meals not included 4 breakfasts, 17 lunches and 19 dinners
  • Optional activities
  • Tips, travel insurance and personal spending
Temples and a lotus pond in Sukhothai Historical Park

This trip might not be for you if…

Honest disclaimer — please read

  • You want luxury — hotels are mostly standard
  • You dislike long travel days — there are several
  • You want a beach holiday — this is a touring trip
  • You want international flights included — they are not

Good to know

Meals by day Breakfast: Days 4–8 and 11–22 · Lunch: Days 11–12 and 14 · Dinner: Days 5–6
The Petronas Twin Towers in Kuala Lumpur, Malaysia

In pictures

Departures & prices

From £3,240 per person, twin share, tour only. 68 upcoming departures.

Frequently asked questions

How do I book this tour?

Tap any "Enquire" button on the page and one of our travel specialists will be in touch within 24 hours (often same day). We'll confirm availability on your preferred date, run through anything you need to know, and only ask for the deposit once you've decided.

What financial protection do I get?

Every Travelisto booking is 100% financially protected. Your money is held in a ring-fenced Trust account until you return from your trip, and we are members of the Protected Trust Services scheme (PTS 6035). Most tours also include ATOL protection where flights are part of the package.

Are there long travel days?

Yes, some days on the road are long, and some transport can be cramped and without air conditioning.

Can I have my own room?

A single supplement is available, except on the overnight train.

Is the elephant sanctuary ethical?

Yes, you walk alongside rescued elephants, with no riding.

Is the flight to Bangkok included?

Yes, the flight from Chiang Mai to Bangkok is included, though you take it without your leader.

Do I need visas?

UK visitors do not usually need visas for holiday stays in Thailand, Malaysia or Singapore. Check before you travel.

How many people travel together?

Up to 12 travellers aged 15 and over, with a leader.

Can you tailor the trip?

Yes — every escorted tour can be modified into a private tailor-made version with your own dates, adjusted pace, upgraded hotels and add-on extensions. Tell us what you'd like changed when you enquire and we'll quote it both ways so you can compare.

What if my flight is delayed or cancelled?

If your international flight is part of your booking through us, we re-book at no cost. If you've booked flights separately, the tour's local team holds your transfer slot until you arrive. We strongly recommend a comprehensive travel insurance policy that includes delay and cancellation cover.

ATOL protected 100% financially protected in a Trust bank account PTS 6035 4.7 on Trustpilot
Tailor-made option

Not quite the right fit? Make it tailor-made.

If this group tour doesn't match your ideal trip, our specialists will turn it into a private tailor-made journey — your own dates, your own pace, upgraded hotels where you want them, and the parts you don't love swapped out. Same destinations, just rebuilt around you.

Contact us for a tailor-made version of this itinerary
From £3,240
See dates & prices