Singapore and Thailand are popular destinations for a short taste of Southeast Asia, especially for couples or families with limited time. Here you can enjoy the best of both countries in a short period: vibrant cities, immersive cultural experiences, relaxing beach days, and culinary adventures.

This article provides tips on time management, hand-picked travel itineraries, and the best times to travel to Singapore and Thailand.

  • Which country should you enter first?

    • How long should one spend in Singapore and Thailand?

    When planning your first trip to Singapore and Thailand, you should allow at least 10 days to discover all the major sights.

    Our clients typically prefer two weeks or more to explore the trip at their leisure and in detail. For example, they might spend three to four days in Singapore and ten or more days in Thailand.

    Three days are enough to discover Singapore's main attractions. Families with teenagers can extend their stay by a day to visit theme parks like Universal Studios.

    Thailand has so much more to offer, and some of the most popular destinations include Bangkok, Chiang Mai, and the tropical islands (especially Phuket and Koh Samui). To get a better feel for the country, a visit to Chiang Rai is highly recommended, where you can enjoy a tranquil and romantic atmosphere, while Khao Sok National Park offers more adventurous experiences.

    Travel suggestions for Singapore and Thailand

    We have carefully selected two itineraries for you: our 10-day tour of the highlights of Singapore and Thailand, and our 2-week tour. As we specialize in tailoring private tours, we would be happy to create a customized itinerary to perfectly suit your needs.

    A typical 10-day tour of Singapore and Thailand

    This 10-day trip harmoniously blends the modern charm of Singapore with the cultural richness of Thailand. From exploring Singapore's famous Merlion Park and immersing yourself in the historical splendor of Bangkok's Grand Palace to the idyllic landscapes of Chiang Mai, the journey concludes with a relaxing stay on the pristine beaches of Phuket or Koh Samui.

    Phuket is recommended due to its numerous water sports opportunities and good accessibility, while Koh Samui offers a more romantic atmosphere.

  • Days 1-2: Singapore (Merlion Park, Singapore Botanic Gardens, National Orchid Garden)
  • Day 3: From Singapore to Bangkok, Thailand
  • Days 4-5: Bangkok (Grand Palace, famous temples, railway market, longtail boat ride, culinary tour)
  • Days 6-7 Chiang Mai (elephant sanctuary, morning alms giving, visit to the flower market, walk through Doi Suthep)

    • This itinerary can be individually tailored to your interests and wishes.

    A classic 2-week itinerary for Singapore and Thailand

    If you prefer a more relaxed tour with more exciting destinations, this itinerary is the ideal choice.

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

    Thailand's authentic cultural experiences, such as Muay Thai, morning alms-giving, and traditional Thai massages, are worth trying.

    You can view the following carefully compiled itinerary for inspiration or click on "Create my trip" to customize your ideal trip to your liking.

  • Days 1-2: Singapore (city tour through the multicultural city, impressive skyline, culinary discovery tour, night safari)
  • Day 3: Singapore - Bangkok
  • Day 4: Bangkok Highlights (Grand Palace, Wat Arun, Longtail 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
  • Days 10-13: Leisure time at the beach

    • Looking for more travel suggestions for a 2-week Southeast Asia trip? Discover our 2-week Southeast Asia tours for couples, families, and more >>>

    Costs for a private trip to Singapore and Thailand

    When traveling to Singapore and Thailand, a customized private tour offers you an exclusive and stress-free experience for your trip as a family or couple.

    Normally, you need about 200–250 US dollars per person per day for high-quality 4- or 5-star hotels, good meals, comfortable transportation, and private, individually designed excursions.

    Aside from international flights to/from your country, you should budget approximately US$9,500 to US$12,000 for a two-week private trip for a family of two adults and two children, while a couple can expect to pay approximately US$5,600 to US$7,000.

    To save money, traveling during Thailand's off-season (May to October) is recommended. While there can be one- to two-hour rain showers every afternoon, a well-organized private tour with flexible schedules and alternative plans in case of rain ensures an enjoyable trip.

    Best time to travel to Singapore and Thailand

    Singapore and Thailand have different weather patterns. Singapore generally experiences dry and sunny weather between February and October, while Thailand's dry season lasts from November to April. Therefore, the period from February to April is the best time to travel to both countries for rain-free days.

    If your main goal in Thailand is to spend time on the beach and enjoy cultural experiences, you should consider the best time to travel to Thailand (December to March). Finally, Singapore offers numerous indoor activities that are less affected by rain.

    If you're planning a summer family trip to Singapore and Thailand, you can take advantage of the best weather in Singapore and the lowest prices during Thailand's rainy season (May to October). While it's likely to rain daily, the showers usually only last one or two hours in the afternoon or at night, so travel is still possible.

    Thanks to the late rainfall, the island of Koh Samui is a perfect destination to enjoy a few dry beach days during a summer trip (it only rains moderately on Samui from May to September).

    Both Singapore and Thailand are popular air travel hubs in Asia. No matter which country you arrive in first, you can easily find the cheapest flights to/from your home country.

    Our experience shows that combining Singapore as a starting point with a trip to Thailand is very popular, especially among retired couples, due to its diverse travel format – from active to relaxing. They often combine their international cruises, which stop in Singapore, with a side trip from Singapore to Thailand.

    Upon arrival in Singapore or Thailand, direct flights with a flight time of 2-3 hours are the easiest and most convenient way to travel between the two destinations.

    Design your Southeast Asia trips with us to be completely individual

    At Thailand Highlights, we have already organized over 10,000 unforgettable trips for discerning travelers, primarily families and couples. We know that every single trip we plan for our clients not only creates wonderful holiday memories but also celebrates life's joyful milestones.

    We would be happy to put together a customized trip tailored to your wishes – based on group size, interests, and other needs. Sit back and take advantage of our "Plan Your Trip" service.

    In addition to the above-mentioned itineraries, we also have other itineraries that might interest you:

  • 15-day round trip through the best of Thailand, Cambodia and Vietnam
  • 19-day highlights of Thailand, Cambodia and Vietnam
  • More Southeast Asia trips