Asia Trip Planner: Japan or Southeast Asia, a 14-Day Route and When to Go

Six guides across two very different Asias: Japan's trains, temples and precision, and Southeast Asia's beaches, street food and low prices. Here is how to pick, how to link them, and a two-week route to start from.

How to plan a Asia trip

The six Asian guides on this site split into two trips that rarely belong in the same two weeks. Japan (Tokyo and Kyoto) is a cool-climate country of punctual trains, temples, ramen counters and hotel rooms that cost as much as Europe's. Southeast Asia (Bangkok, Phuket, Singapore and Bali) is tropical, cheap outside Singapore, slower, and organised around beaches, night markets and a scooter or a driver rather than a rail pass. The flight between the two, Tokyo or Osaka to Bangkok or Singapore, is six to seven hours, so combining them is a fourteen-day undertaking with a long travel day in the middle, not a weekend add-on.

The first-trip decision is therefore simple. Ten days: pick one. Japan alone is Tokyo plus Kyoto with the Shinkansen between them and day trips from each. Southeast Asia alone is a capital plus a beach: Bangkok and Phuket, or Singapore and Bali. Fourteen days or more: Japan for the first nine, then fly south for the beach finale, which is the route on this page. Whatever you choose, fly open-jaw (into one city, home from another) and count the time zones: Tokyo is thirteen to fourteen hours ahead of New York, and the first day is mostly lost to jet lag.

Which cities for a first trip

  • First time in Japan: Tokyo and Kyoto

    Tokyo for the scale, the food and the neighbourhoods (Shibuya, Shinjuku, Asakusa, Harajuku), Kyoto for the temples, gardens and geisha districts that Tokyo lost to war and growth. Five nights in Tokyo with a Nikko or Kamakura day trip, four in Kyoto with Nara and Osaka within an hour, and the Shinkansen between them in two and a quarter hours. Fly into Tokyo Haneda or Narita and home from Osaka Kansai.

  • First time in Southeast Asia: Bangkok and Phuket

    Bangkok is the region's great capital: temples, canals, the best street food on earth and rooms from $30. Phuket is a 90-minute flight away with the Andaman's islands (Phi Phi, Similan, Phang Nga Bay) on day trips from its west-coast beaches. Three nights in the city and five or six on the coast is the shape; November to April is the season for both.

  • Easiest, cleanest, most expensive: Singapore and Bali

    Singapore is Asia with the difficulty dialled down: English everywhere, a metro that reaches everything, hawker centres where a $4 plate is Michelin-listed, and Changi, the world's best-connected airport. Two or three nights is enough. Bali is a two-and-a-half-hour flight on and rewards seven or more: Ubud's rice terraces and temples, then Uluwatu, Canggu or Seminyak for the surf and sunset beaches.

  • Food above all: Tokyo, Bangkok and Singapore

    Three of the world's five great eating cities in one line: Tokyo's sushi counters, ramen and depachika food halls, Bangkok's boat-noodle alleys, Chinatown and Michelin street stalls, Singapore's hawker centres and Peranakan kitchens. The flights link them in six and a half and two and a half hours. Skip the beach entirely and give each four nights.

  • Temples and tradition: Kyoto and Bangkok

    Kyoto has 1,600 Buddhist temples and 400 Shinto shrines, the Fushimi Inari gates and the Arashiyama bamboo grove; Bangkok has Wat Pho's reclining Buddha, Wat Arun at sunset and the Grand Palace. Six hours' flying apart, and the contrast between Zen restraint and Thai gold is the point. Add Kyoto's Nara and Bangkok's Ayutthaya as the day trips.

  • Surf, yoga and long stays: Bali

    Bali on its own for two or three weeks is the classic slow trip: a villa in Ubud with a pool for $60 to $150 a night, beginner surf at Kuta and Canggu, reef breaks at Uluwatu, sunrise on Mount Batur, and cafés built for laptops. Fly in through Singapore, Kuala Lumpur, Doha or Taipei; Denpasar has no nonstops from North America or Europe.

14 days, three cities: Tokyo, Kyoto and Bangkok

Five nights in Tokyo, four in Kyoto and four in Bangkok, with the Shinkansen in the middle of Japan and one long flight south. Fly into Tokyo and home from Bangkok. Each city's guide has the full three-day itinerary; the Plan-this-trip buttons open the planner prefilled with the city.

  1. Days 1–5, Tokyo: Land at Haneda (closer) or Narita (the Narita Express is an hour to Tokyo Station). Base in Shinjuku, Shibuya or Asakusa. Day one is jet lag and a neighbourhood walk; then Senso-ji and Asakusa, the Meiji Shrine and Harajuku, Tsukiji's outer market and Ginza, teamLab and Odaiba, Shibuya Crossing at dusk, and a day trip to Nikko or Kamakura. A Suica card on your phone pays for every train and convenience store.
  2. Day 6, Tokyo to Kyoto by Shinkansen: The Nozomi runs Tokyo to Kyoto in about two hours and fifteen minutes, every ten minutes, for around ¥14,000 unreserved; the Hikari takes two hours forty. Reserve a window seat on the right (D or E) for Mount Fuji an hour out. Send big suitcases ahead with a takkyubin luggage service from your hotel for about ¥2,500 and carry a day bag; the trains have little luggage space.
  3. Days 6–9, Kyoto: Four nights: Fushimi Inari at 7am before the crowds, then Gion and Kiyomizu-dera; Arashiyama's bamboo grove and Tenryu-ji the next morning with the Kinkaku-ji golden pavilion after lunch; a day in Nara with the deer and the Great Buddha (45 minutes by train); and an evening in Osaka's Dotonbori (15 minutes by Shinkansen or 30 by local train). Book Kyoto hotels months ahead in cherry-blossom and autumn-colour weeks.
  4. Day 10, Osaka to Bangkok by air: Nonstop flights from Kansai (KIX) to Bangkok Suvarnabhumi take about six hours and cost $200 to $500 on Thai, Peach or ANA-partner services; Tokyo Haneda has more choice if you prefer to return north. Leave Kyoto after breakfast (the Haruka train to Kansai is 75 minutes), land in Bangkok mid-evening, and take the Airport Rail Link or a metered taxi (about ฿400 plus tolls) into town.
  5. Days 10–14, Bangkok: Four nights: the Grand Palace, Wat Pho and Wat Arun by river boat the first morning; Chatuchak weekend market or the Jim Thompson House and a rooftop bar the second; a day trip to Ayutthaya's ruins or the Maeklong railway market and Damnoen Saduak floating market the third; Chinatown's Yaowarat Road for the last dinner. Fly home from Suvarnabhumi, or add a Phuket week if the calendar allows.

Plan this trip: Tokyo · Plan this trip: Kyoto · Plan this trip: Bangkok

Trains, flights and the JR Pass question

Japan by rail

The Shinkansen network is the fastest way between Japanese cities: Tokyo to Kyoto 2h15, Kyoto to Osaka 15 minutes, Kyoto to Hiroshima 1h40, Tokyo to Kanazawa 2h30. The nationwide Japan Rail Pass rose steeply in price and now rarely pays for itself on a simple Tokyo–Kyoto–Osaka trip; buy point-to-point tickets at the station or through the official SmartEX app instead, and consider a regional pass only if you loop back. Inside the cities, an IC card (Suica or ICOCA, added to an iPhone or Android wallet) covers every subway, bus and most vending machines.

Southeast Asia by air and road

Distances are flights: Bangkok to Phuket 1h25 ($30 to $80 on AirAsia, Nok, Thai Vietjet or Thai Airways), Bangkok to Singapore 2h30, Singapore to Bali 2h40, Bangkok to Bali 4h20. Overnight trains run Bangkok to Surat Thani for the Gulf islands, and Grab (the regional ride-hailing app) is the honest way to get around Bangkok, Phuket and Bali; agree nothing with a taxi driver that Grab has not priced first. Bali has no trains and no real buses; hire a driver for about $50 to $60 a day for the temple and rice-terrace circuits.

Linking the two Asias

Tokyo or Osaka to Bangkok takes six to seven hours nonstop, Tokyo to Singapore about seven, Tokyo to Bali seven and a half (Garuda or via Singapore). Fares are lowest booked two to four months out and outside Japan's Golden Week (late April to early May), Obon (mid-August) and the New Year, when Japanese travellers fill every southbound seat. Fly Japan first: you arrive rested into the cool, then unwind on the beach at the end rather than flying home from the heat into a Tokyo winter.

When to go: cherry blossoms, monsoons and heat

Japan's two peaks (Late March to early April, and mid-November)

Cherry-blossom season (sakura) reaches Tokyo and Kyoto in late March or the first days of April, and autumn colour peaks in Kyoto in the second half of November. Both are spectacular and both double hotel prices; book six months ahead. May, early June and October are the comfortable, cheaper alternatives. Mid-June to mid-July is the rainy season, July and August are 30 to 35°C and humid, and September carries the typhoon risk.

Thailand's seasons (November to February cool and dry; May to October monsoon on the Andaman coast)

Bangkok's best months are November to February, when the sky is clear and the evenings are 22 to 25°C; March to May is brutally hot, and June to October brings daily afternoon downpours that pass in an hour. Phuket's west coast is calm and clear from November to April and closed to many boat trips from May to October, when the Andaman swell arrives; the Gulf islands (Koh Samui) run the opposite pattern. Songkran, the water-festival New Year in mid-April, shuts much of the country for three days.

Bali and Singapore (Bali dry April to October; Singapore year-round)

Bali's dry season runs April to October, with July and August the busiest and most expensive weeks (Australian school holidays) and May, June and September the sweet spot. The wet season, November to March, still has sunny mornings and rain that arrives in the afternoon, and prices drop by a third outside Christmas. Singapore sits a degree north of the equator at 25 to 33°C every month; the northeast monsoon from November to January is the wetter stretch, but there is no bad time.

Crowd calendars worth knowing (Golden Week, Chinese New Year and the Bali holidays)

Japan's Golden Week (late April to early May), Obon (mid-August) and the New Year (late December to early January) fill trains and hotels with domestic travellers; avoid them or book far ahead. Chinese New Year (January or February) lifts fares to Singapore, Bangkok and Bali. Bali's Nyepi (a March day of silence) closes the airport for 24 hours and confines everyone indoors; plan around it rather than through it.

What a day costs

Per person, per day, excluding intercontinental flights, with two people sharing a room. Japan and Singapore cost roughly double Thailand and Bali at every band.

  • Shoestring ($40–$90)

    In Bangkok, Phuket and Bali this is a fan-cooled guesthouse or a hostel dorm, street food and warungs for every meal, a scooter or Grab rides, and one paid temple or boat trip a day; the guides' own low ends are $35 to $40. In Japan the same money covers a capsule hotel or hostel, convenience-store breakfasts, ramen and gyudon counters and walking, but not much else.

  • Mid-range ($100–$200)

    Southeast Asia at this level is a pool villa or a four-star hotel, restaurant dinners, day trips with a driver and a massage every afternoon. In Tokyo and Kyoto it is a business hotel or a modest ryokan, a set lunch and an izakaya dinner, Shinkansen tickets and temple entries: the guides put Tokyo at $80 to $150 and Kyoto at $80 to $160. Singapore sits at $80 to $180.

  • Comfortable ($250–$500+)

    Five-star hotels in Bangkok and Bali cost less than three-star ones in Europe, so this band buys beach resorts, private boats and spa days in Southeast Asia. In Japan it buys a ryokan night with kaiseki dinner (often $300 to $600 a person), sushi counters and Green Car seats. Singapore's Marina Bay hotels and Bali's clifftop resorts in high season reach the top of the range.

Visas and arrival cards, stated generally

Entry rules

Japan and Singapore admit US, Canadian, UK, EU and Australian passports without a visa for short tourist stays; Thailand grants a visa exemption on arrival to those and many other nationalities; Indonesia (Bali) sells a visa on arrival, paid at the airport or online beforehand, and Bali adds a small tourist levy on top. Exemption lengths, fees and the online arrival cards that several of these countries now ask for change more often than guidebooks do, so check each country's official immigration site in the month before you fly. Passports need six months' validity in every one of them.

Money

Japan is more cash-friendly than its reputation: cards work in cities, but small restaurants, temples and rural stations still want yen, which 7-Eleven ATMs dispense from foreign cards without drama. Thailand and Bali are cash economies for street food, markets and drivers, with ATMs that charge ฿220 or IDR 50,000 a withdrawal, so take out larger sums less often. Singapore is contactless everywhere. Tipping is not expected in Japan and modest elsewhere.

Health and connectivity

Ask a travel clinic about hepatitis A and typhoid for Thailand and Bali, and carry rehydration salts; the tap water in Bangkok and Bali is not for drinking, in Japan and Singapore it is. An eSIM bought before departure covers all four countries for less than roaming. Japan's etiquette (no eating while walking, shoes off, quiet trains) is easy once seen; in Thai and Balinese temples, cover shoulders and knees and remove shoes where the locals do.

Asia trip planning FAQ

Should a first trip to Asia be Japan or Southeast Asia?

Japan if you want cities, trains, temples and food in a cool climate and can spend $150 a day; Southeast Asia if you want beaches, heat and low prices with a capital thrown in. With fourteen days, do Tokyo and Kyoto first, then fly six hours south to Bangkok or Bali for the beach finale.

Is the Japan Rail Pass worth buying?

Rarely for a Tokyo and Kyoto trip since its large price increase: a Tokyo–Kyoto–Osaka run on point-to-point Shinkansen tickets costs far less than the seven-day pass. It pays only if you ride the bullet train most days, for example Tokyo to Hiroshima and back with Kyoto in between. Buy individual tickets through the official SmartEX app or at the station.

How many days do I need for Tokyo and Kyoto?

Five nights in Tokyo and four in Kyoto, with a day trip from each (Nikko or Kamakura; Nara or Osaka), is a full first trip. Seven days total works with four and three, but the first Tokyo day is usually lost to jet lag, so count it as arrival rather than sightseeing.

When is the best time to visit Asia?

There is no single answer because the seasons oppose each other: Japan is best in late March to May and October to November, Thailand and Phuket from November to April, Bali from May to September, and Singapore all year. A combined Japan-plus-beach trip works best in November, when Kyoto's autumn colour and Thailand's dry season overlap.

Do I need a visa for Japan, Thailand, Singapore or Bali?

For short tourist stays, US, Canadian, UK, EU and Australian passports enter Japan, Singapore and Thailand without a visa and buy a visa on arrival for Indonesia (Bali), which also charges a small tourist levy. Several of these countries now ask for an online arrival card before landing; check each official immigration site the month before you fly, since the rules change.

The six Asia guides

Things to do, where to stay, what to eat, when to go and a three-day sample itinerary for each city.