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How to Plan a Trip to Singapore and Thailand 2024/2025

By RitaUpdated Jan. 10, 2024

Singapore and Thailand are popular for a quick taste of Southeast Asia, especially when a couple or a family has limited time. You could quickly enjoy the best of both countries: cityscapes, immersive cultural experiences, leisurely beach time, and food adventures.

In this article, you can get some tips on time allocations, hand-picked itineraries, and the best times to visit Singapore and Thailand.

How Long to Spend in Singapore and Thailand

When planning your first trip to Singapore and Thailand, you should allocate at least 10 days to discover all their major highlights.

More often, our clients prefer 2 weeks or more for a comfortable pace and in-depth exploration. You could spend 3–4 days in Singapore and 10+ days in Thailand.

In Singapore, 3 days are enough to discover the city highlights. For families with teenagers, you could extend your trip by one more day to go to theme parks, such as Universal Studios.

Thailand has more to offer and its top destinations are Bangkok, Chiang Mai, and the tropical islands (mainly Phuket or Koh Samui). To explore it better, you could travel to Chiang Rai for a tranquil and romantic vibe, and have some adventures in Khao Sok National Park.

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Itinerary Suggestions for Singapore and Thailand

We have carefully selected two hand-picked itineraries for your reference: our 10-day itinerary for the best of Singapore and Thailand and our 2-week tour. Specializing in customizing private tours, we're happy to tailor-make your itinerary to suit your interests.

A Typical10-Day Singapore and Thailand Tour

This 10-day itinerary seamlessly blends the modern allure of Singapore with the cultural richness of Thailand. From exploring the iconic Merlion Park in Singapore to immersing in the historic grandeur of Bangkok's Grand Palace and the serene landscapes of Chiang Mai, the journey concludes with a tranquil escape to the pristine shores of Phuket or Koh Samui. 

Phuket is recommended for its abundant water activities and easy access while Koh Samui embraces a more romantic vibe.

  • Days 1–2: Singapore (Merlion Park, Singapore Botanic Gardens, National Orchid Garden)
  • Day 3: Singapore to Bangkok, Thailand
  • Days 4–5: Bangkok  (the Grand Palace, renowned temples, railway market, longtail boat ride, foodie tour)
  • Days 6-7 Chiang Mai (elephant sanctuary, morning almsgiving, flower market visit, Doi Suthep walking tour)
  • Days 8-10: Phuket 

This itinerary can be tailor-made according to your interests and requirements

A Classic 2-Week Itinerary for Singapore and Thailand

If you prefer a more relaxed tour pace with more eye-opening destinations, this itinerary is an ideal option.

In addition to typical 10-day travel activities, you could discover tranquil Chiang Rai and lesser-known Ayutthaya as well as spend more time on the beach.

Thailand's immersive cultural activities deserve a try, such as Muay Thai, morning almsgiving, and traditional Thai massages. 

You could check out the following carefully crafted itinerary for inspiration or click Create My Trip to customize your ideal trip based on your preferences.

  • Days 1–2: Singapore (multicultural city sightseeing, awesome skylines, food hunting tour, night safari) 
  • Day 3: Singapore - Bangkok
  • Day 4: Bangkok Highlights (Grand Palace, Wat Arun, Long-Tail Cruise)
  • Day 5: Bangkok - Ayutthaya - Bangkok - Chiang Rai
  • Day 6: Chiang Rai White Temple
  • Day 7: Chiang Rai - Chiang Mai
  • Day 8: Chiang Mai Elephant
  • Day 9: Chiang Mai - Phuket or Koh Samui
  • Day 10-13: Beach leisure time
  • Day 14: Departure. 

Want more itinerary ideas about a 2-week Southeast Asia trip? See our 2-Week Southeast Asia Itineraries for Couples, Families, and More>>>

Costs for a Private Trip to Singapore and Thailand

Traveling in Singapore and Thailand, a customized private tour would create an exclusive and stress-free experience for your trip as a family or couple.

Usually, you would need about US$200–250 per day per person for quality 4/5-star hotels, nice meals, convenient transport, and private, tailored touring.

Apart from the international flights from/to your country, you would need to spend about US$9,500–12,000 on a 2-week private trip for a family with 2 adults and 2 kids, while a couple can expect to spend about US$5,600–7,000.

To save costs, you could take your trip during Thailand's low season (May to October). While you may encounter daily afternoon downpours that last for 1–2 hours, you can still enjoy the trip with a well-organized private tour with a flexible schedule and wet weather options.

Best Times for a Singapore and Thailand Trip

Singapore and Thailand have different weather patterns. Singapore offers dry and sunny weather most of the time between February and October while Thailand experiences its dry season from November to April. Therefore, February to April is the best time to enjoy rain-free days in both countries.

If your priority is spending more time on a beach vacation and cultural adventures in Thailand, you could just consider the best time in Thailand (December to March). After all, Singapore offers abundant indoor activities, which are less affected by rainfall.

If you're planning a summer family trip to Singapore and Thailand, you could take advantage of the best weather in Singapore and the lowest prices during Thailand's rainy season (May to October). Although you're likely to experience daily rainfall, most of the showers last for 1–2 hours in the afternoon or throughout the night so travel is still possible.

With late rains, the island of Koh Samui is a perfect destination for enjoying some dry beach time during a summer trip (Samui's rainfall is only moderate from May to September).

Which Country to Enter First

Both Singapore and Thailand are popular air hubs in Asia, so no matter which country you arrive in first, you could easily get the best value flights from/to your home country.

Based on our experience, starting from Singapore then traveling to Thailand is highly welcomed for its energetic-to-relaxing tour format, especially by retired couples. They love to add a Singapore–Thailand trip to their international cruise journeys, which stop in Singapore.

Upon arrival in Singapore or Thailand, direct flights that last for 2–3 hours are the easiest and most convenient way to travel between the two destinations.

Personalizing Your Southeast Asia Trips With Us

At Asia Highlights, we have created over 10,000+ big trips for insightful travelers, mostly for families and couples. We truly understand that every single big trip planned for our clients is not just for good holiday memories but also for joyful celebrations of life's milestones.

You are warmly welcomed to have us customize your own trip based on your group size, interests, and other needs. Sit back and use our Create My Trip service.

In addition to the above itineraries, we also have other itineraries you may be interested in:

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Get Inspired with Some Popular Itineraries

At Asia Highlights, we create your kind of journey — your dates, your destinations, at your pace. You can have any trip tailor made for your travel.

More Travel Ideas and Inspiration

Start planning your tailor-made tour with 1-1 help from our travel advisors. Create My Trip
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