Thailand Itineraries

The first-timer’s week. Two days in the capital, two in the north, three on a beach, with the overnight train saving a hotel night and a direct flight south avoiding a return to Bangkok. Pick the island by season: Phi Phi or Ko Lanta from Krabi between November and April, Ko Samui from June to September.

Pace: fast but not frantic, since the train and the flight do the long distances while you sleep or eat. The only hard day is Day 2, so skip Ayutthaya if you land late on Day 1 and spend the day on the river instead: the orange-flag Chao Phraya Express (16 THB a hop) strings together Wat Arun, the flower market at Pak Khlong Talat and Chinatown without a single taxi. In Chiang Mai, book the elephant sanctuary before you arrive, since the reputable no-riding places sell out days ahead in high season, and choose a cooking class that starts with a market tour. On the island, the longtail trips leave around 9am and the afternoon light is better for swimming than for photographs, so do the boat first and keep the second afternoon free.

Cost: about 20,000-40,000 THB ($600-1,200) per person, of which the Chiang Mai to Krabi flight is the biggest single line. Rooms run 1,200-2,500 THB in Bangkok and Chiang Mai and 2,000-4,000 THB on the beach in high season; food, songthaews and temple entry add 800-1,500 THB a day.

Adds Chiang Rai and a second island, and slows the beach half to five nights. This version uses the sleeper north and flies Chiang Mai to Phuket, then works south down the Andaman coast.

Pace: moderate. Days 5 and 6 involve the most moving; if that is too much, drop Chiang Rai and give Chiang Mai three nights, using the spare day for Doi Inthanon or the Chiang Dao caves. Chiang Rai itself is worth the detour for Wat Rong Khun, the White Temple, which is at its best at 8am before the coaches arrive, and for the night market’s Lanna food court. On the Andaman side, Phi Phi and Ko Yao Noi are opposites: pick Phi Phi for the Maya Bay cliffs and a party, Ko Yao Noi for rubber plantations, empty beaches and a bicycle. Railay is reached only by boat and has no roads, which is the point.

From May to October swap the Andaman half for Ko Samui and Ko Tao: fly Chiang Mai to Surat Thani with AirAsia (90 minutes), take the Lomprayah combined bus-and-catamaran to Samui (3 hours) and the catamaran on to Ko Tao (2 hours), where the dive schools around Sairee Beach run three-day Open Water courses. Cost: 30,000-55,000 THB ($900-1,650) per person, with the Chiang Rai to Phuket flight and the Phi Phi ferries the expensive legs.

Two weeks lets you add the ruins at Sukhothai, the mountain town of Pai and both an Andaman and a Gulf stop, or a slower run down one coast. This version goes clockwise: central ruins, north, Andaman, Gulf, back to Bangkok by sleeper.

Pace: steady, with Days 4-5 and 9-11 the heavy travel days. Sukhothai is the stop people drop, and the one they most regret dropping: the park is quieter and better kept than Ayutthaya, and cycling it at 6am with the lotus ponds reflecting Wat Mahathat is one of the best hours in the country. Pai is the opposite case; if winding roads make you ill, replace it with a second night in Chiang Mai and a day trip to Lamphun’s Wat Phra That Hariphunchai. Khao Lak is chosen over Phuket’s west coast beaches deliberately: the same Andaman water, a third of the crowds and the Similan boats leave from its piers.

Two weeks is also where the alternative routes open up: swap Days 9-13 for Ko Samui, Ko Pha-ngan and Ko Tao in the mid-year months, or replace Sukhothai and Pai with the Mae Hong Son Loop (600 km over four days by rented car, 1,200-1,800 THB a day, with nights in Mae Hong Son and Pai). Cost: 40,000-80,000 THB ($1,200-2,400) per person, roughly 3,000-5,500 THB a day once the two flights and the sleeper are paid for.

For a second visit, or anyone who wants sand rather than temples. Fly straight to the coast that is in season and keep Bangkok to a single night at the end. The Andaman version runs November to April; the Gulf version in brackets runs January to September.

Pace: relaxed, with every move by boat and most under two hours. The order matters: Phi Phi is the busiest and loudest stop, so it comes early while you still have energy, and Ko Lipe or the Trang islands close the trip because they are the quietest and the furthest from an airport. Divers should swap Days 3-4 for three nights on Ko Tao in the Gulf version, where an Open Water course costs 10,000-12,000 THB including accommodation. Snorkellers get the most from Ko Lipe’s Adang archipelago and from Ko Kradan, where the reef starts a few metres off the beach.

Cost: 35,000-60,000 THB ($1,050-1,800) per person; islands cost 30-50% more than the mainland for the same room, and speedboats and longtail charters are the other big line. Bring cash: ATMs on Phi Phi, Railay and Ko Lipe charge 220 THB a withdrawal and run out of notes over long weekends.

• First-timers: stick to the 7-day shape even with 10 days; use the extra nights to give Bangkok and Chiang Mai three each rather than adding a fourth destination. Three nights is the minimum at which a place stops being a transit stop.
• Families: replace the sleeper train with a morning flight (children under 12 struggle with the 07:15 arrival), choose Ko Lanta, Khao Lak or Hua Hin over Phi Phi and Ko Pha-ngan, and book rooms with pools for the 2-4pm heat. Elephant sanctuaries, Kanchanaburi’s Erawan waterfalls and the Ayutthaya bicycle day all work with children over six.
• Monsoon season (June to October): keep the north and Bangkok as they are (afternoon storms, lush hills) and move the beach days to the Gulf: Ko Samui, Ko Pha-ngan and Ko Tao are at their driest from June to August. From October to December reverse it and use the Andaman routes. Avoid Andaman speedboat trips from May to October and build a spare day in before any international flight in case ferries are cancelled.
• Slow travel and digital nomads: make each stop a week. Chiang Mai for a month, Pai or Ko Lanta for two weeks and Bangkok for a week is a well-worn pattern, and monthly rooms cost less than a third of nightly rates. The DTV visa covers stays up to 180 days.
• Budget: take the 13:45 day train to Ayutthaya and the second-class fan sleeper (around 600 THB) instead of air-con, use government buses rather than flights for Chiang Mai to Chiang Rai and Krabi to Trang, and sleep on Railay East, Ko Lanta’s Khlong Dao or Phi Phi’s Long Beach rather than the headline beaches. The 14-day loop can be done for 25,000 THB ($750).
• Culture over beaches: replace the island days with Isaan: night train to Khon Kaen or Udon Thani, the Khmer sanctuary at Phanom Rung near Buriram, the Mekong at Nong Khai and Nakhon Phanom, and som tam at every market. Almost no other tourists, and the cheapest region in the country.
• Entry rules: since 15 September 2026 most Western passports get 30 days visa-free, extendable once by 30 days for 1,900 THB, and everyone must file the free Thailand Digital Arrival Card online within three days of arrival. The 14-day loop fits; a month-long version needs the extension or an e-visa.

Thailand rewards booking the fixed points early and leaving the rest loose. Reserve the sleeper train (SRT D-Ticket, 90 days out), the one domestic flight between north and south, and any room between 20 December and 10 January, when island resorts impose three-to-five-night minimums and gala dinner surcharges. Everything else, including ferries, minivans and most guesthouses, can be bought a day or two ahead on 12Go or at the pier, and walk-in rates on the islands often beat online prices outside peak weeks.

Allow buffers: a morning ferry plus an afternoon flight is fine; a lunchtime ferry plus an evening international departure is not, since Andaman boats run late and Bangkok traffic can turn a 45-minute airport run into two hours. Suvarnabhumi and Don Mueang are 50 km apart with no direct train, so check which Bangkok airport your domestic flight uses before you book a connection. Songkran (13-15 April) empties Bangkok and fills every train and bus for the days either side, and Loy Krathong (24 November 2026) does the same to Chiang Mai and Sukhothai, so book those weeks a month or more ahead.