This post is a guest contribution from one of our incredible BoldlyGo community members, Gretchen Navy. Gretchen is a mom of three who loves exploring the world as a family, always searching for destinations that strike the perfect balance between adventure, culture, and relaxation. Her recent journey through Singapore and Thailand highlights how meaningful family travel can be, from long-tail boat adventures in Krabi to unforgettable moments with elephants in Chiang Mai. We love showcasing real stories from within our community because some of the best travel inspiration and strategies come from travelers actually out there experiencing it all firsthand. If you’d like to share your own travel story or points-and-miles win with the BoldlyGo community, you can submit your contribution here.

Thailand Family Travel Overview

This trip was always about Thailand. Krabi’s beaches, Koh Samui’s slower pace, and Chiang Mai’s culture were what drew us in. On paper, this itinerary sounds like too much: Raleigh to Seattle, then Singapore, Krabi, Koh Samui, Chiang Mai, back to Singapore, then New York, then home to Raleigh. But getting there with three kids, multiple flights, and a 16-hour journey across the world felt daunting. Instead, it worked because we strategically planned no more than one flight per day and chose a longer stopover in Singapore to allow time to get over the jet lag and ease into our adventure. What we didn’t expect was how smoothly it would all come together and how well each part of the trip balanced the next.

First Stop: Seattle

To position ourselves to the west coast, we started with a five hour flight from Raleigh to Seattle and spent one night at Hotel 1000 LXR Seattle. Through Amex Fine Hotels & Resorts (FHR), the $302 nightly rate dropped to $102 after the $200 FHR credit. The stay also came with a $100 hotel credit, a $60 brunch credit, and two complimentary cocktails. Add all that up and we actually got paid to stay at this hotel!

The room was surprisingly great for a family. It had a queen bed in one section and another room with a king bed and a large bathroom. The kids immediately became obsessed with the bathtub because the water came straight through the ceiling, which they found hilarious.

Upon arrival, we used the hotel credits at the onsite restaurant All Water Seafood & Oyster Bar. The staff kindly let us combine both the $60 breakfast credit and the $100 hotel credit toward a really good lunch.

Later that evening we visited the hotel bar, Rosebay, and used the two cocktail credits there. The atmosphere was cozy and chic with a lodge-like feel, as if you had just stepped in from the ski slopes, and the table games in the lounge ended up being a hit with the kids.

We kept the day in Seattle simple. Then we viewed the Space Needle, spent time at the Pacific Science Center with its interactive exhibits, butterfly sanctuary, and planetarium, and walked through Pike Place Market.

We had hoped to see fish flying through the air like on TV, but because it was January 1, all of the fish markets were closed. We still grabbed a photo at the original Starbucks, then called it a day, knowing the long-haul flight was the next day.

The Flight That Changed Our Lives

Singapore Airlines business class from Seattle to Singapore.

Now let’s talk about this amazing flight. We flew Singapore Airlines from Seattle to Singapore in business class and it was life changing. We redeemed 108,000 miles plus $5.60 per person for seats that were going for about $5,000 each in cash. Yes, that’s an immense amount of points for a family of five, but the redemption was well worth it for the comfort we experienced during the 16-hour flight to Asia.

The seats were incredible! They resembled oversized lazy-boy chairs which folded down into completely lie-flat beds. We had several pillows each, a thick cozy blanket, slippers, headphones, and amenity kits on request. There were several good storage spots for personal items as well as a large in-flight entertainment screen, which were hugely helpful during a flight that long.

The top-notch service was best part. The flight attendants consistently made sure our children were taken care of first. They served them before us, helped cut up their food, and brought them anything they asked for, including Doritos and M&M’s! At one point they even helped our 5-year-old take a few bites of his dinner so we could actually enjoy our own meals.

We also used Singapore Airlines’ “Book the Cook” option and selected meals a few weeks before departure. My husband, 11 year old, and I dined on lobster Thermidor, braised duck, beef tenderloin, salmon, ramen, short ribs, salad salmon salad. For the younger two kids, we were able to select kids meals like chicken tenders, pasta, and Singapore chicken and rice. For dessert, we indulged in chocolate truffles, raspberry cheesecake, chocolate mousse, and Oreos and Häagen-Dazs ice cream. They also served a fruit and cheese platter with the dessert course. All of our meals felt like a high-quality, fine-dining experience, and the drinks were fantastic as well.

Passing time on the long flight wasn’t too difficult. The 8- and 5-year-old cozied up together to watch a movie, while our 11-year-old documented everything to show his friends back home and eventually built himself a pretty serious pillow-and-blanket fort when it was time for bed. It honestly did not feel like a 16-hour flight, and after hearing horror stories about doing this route in economy, I was incredibly grateful we got to experience it this way.

Singapore: The Perfect First Stop in Southeast Asia

We arrived in Singapore around 5pm feeling pretty well rested. The airport was easy to navigate and passport control was a breeze. From the airport, we booked a car via the Grab app which took us to the Holiday Inn Orchard City Centre where we stayed for four nights. The stay cost 93,000 IHG points, compared with a cash price of around $1,300, and we were upgraded to a king suite which gave us a lot more space plus an extra half bathroom. The hotel’s location in Orchard City made it easy to navigate around Singapore.

Four nights in Singapore turned out to be exactly the right amount of time to get through the jet lag. We were up well before sunrise the first three mornings and chose to wander Orchard Road while the malls were still empty and the streets were quiet. On one of those walks, the kids spotted a smoothie vending machine, which became our stopgap breakfast until restaurants opened. The smoothies were such a hit that we went back two more times. On our last morning in Singapore, my husband did a long uphill walk to Fort Canning, a former military base that now offers an amazing view of the city.

Singapore also made getting around incredibly easy. We used public transit throughout the stay, easily bouncing between trains and buses. The kids especially loved the double-decker buses and the city is so walkable that we ended up getting a lot of steps in every day. While it was definitely hot in Singapore, but coming from North Carolina, the heat and humidity really didn’t faze us.

What We Did in Singapore

On our first day in Singapore, we headed out to Marina Bay Sands, which is a 57 story resort consisting of a hotel, casino, entertainment space, restaurants, a shopping mall, and an art museum. The complex is comprised of 3 towers and spanning across the towers is the Sands SkyPark rooftop containing an observation deck, gardens, and a 150 meter infinity pool. It’s one of those must-see places, even if you don’t spend much time or money there. They have a Spectra light and water show daily at 8:00 and 9:00 p.m. We tried on our last two nights in Singapore to make it to this but, unfortunately, jet lag won both nights.

After visiting Marina Bay Sands, we walked over to Gardens by the Bay, a park right on the water known for its 16-story tall Supertree Grove. There is a large children’s area here with lots to explore. We walked through the outdoor gardens and then over to the Far East Organization Children’s Garden, which has a water play area and tree houses to climb and explore. The kids spent a few hours there before we wandered to the hawker-style café for lunch.

The waterfall inside the Cloud Forest.

After lunch, we ventured to the Cloud Forest, which is a glass conservatory that greets you with a huge indoor waterfall the moment you walk in. During our visit it had a Jurassic World theme with animatronic dinosaurs, which made it even more fun for the kids. We spent about an hour and a half there, walking the aerial paths through the treetops and viewing the waterfall from all different angles. Tickets were about $20 per adult and $17 per child.

Right next to the Cloud Forest is the world’s largest glass greenhouse called the Flower Dome, which we did not visit. And there’s also a musical light show among the Supertrees at night, which we unfortunately missed as well.

On our second day in Singapore, we ventured over to Sentosa Island via monorail without much of a plan and stumbled upon several cool things. First was Palawan Beach, which was in a little cove so the water was nice and calm. The kids spent some time swimming. And right there on the beach was a WWII-era pillbox, which my history loving husband thought was super cool. Then we walked down the beach and found a suspension bridge which took us to a sign that said “Southernmost Point of Continental Asia.” Across the water from there you can see Indonesia.

There’s a free shuttle that takes you to several stops throughout Sentosa Island, so we hopped on it and rode it down to the cable car. The cable car ride over the island had incredible views of the harbor and skyline. On the way back to our hotel, we stopped to eat at a hawker-style food center in VivoCity Mall. A Singapore hawker center is an open-air complex full of food stalls that sell affordable, diverse dishes. Basically like a food hall. Prices typically range from $5-$10. Universal Studios Singapore is also out on Sentosa Island, however, we did not get a chance to check it out.

One of our favorite Singapore days was also one of the simplest: East Coast Park, Singapore’s largest coastal park which spans about 9 miles right along the water. We spent the day along the coast, playground hopping, exploring the walking paths and beaches, and stopping by casual restaurants. After some bigger sightseeing days, it was nice to take this day at a slower pace.

By the time we left Singapore, we felt adjusted, settled, and ready for what came next. It was time to head to Thailand, the part of the trip we’d been building toward all along.

Thailand: The Heart of the Trip

From Singapore, we flew Scoot Airlines to Krabi, Thailand and officially shifted from reset mode into adventure mode. We used Andaman Islands Tour and Travel for all of our excursions in Thailand as well as some airport and ferry transfers. They were also a great resource throughout the trip.

Krabi

We spent five nights in Krabi at Ananta Burin Resort, booking two connecting rooms through Capital One Travel. The cash price was $1,328 and after using the $300 Venture X travel credit, we paid $1,028. The hotel was a very easy family fit thanks to the fun waterslides and it was only a seven minute walk to both the beach and the night market.

Hong Islands Tour

Hong Islands Long Tail Boat

Our biggest Krabi highlight was the Hong Islands private tour. We were picked up from the hotel at 6:30 a.m. and taken to our own long tail boat. The tour guide was very specific about timing and efficiency so we could be the first boat to a couple of the islands and that made all the difference. We were able to explore quiet beaches with just the five of us before the other boats started arriving. The tour began at sunrise and took us to La Ding, Pak Bia, Hong Lagoon, and Hong Island Bay. The cliffs rising straight out of the ocean were some of the most breathtaking and dramatic scenery we’d ever seen. Even though it was an early start, it was well worth it for the peaceful, crowd-free time in a place that otherwise fills up quickly.

Hong Islands Tour Pricing

Krabi Discovery Tour

Wat Tham Suea – Tiger Temple

We also did the Krabi Discovery Tour, which was another full-day private outing that mixed natural stops with temples and city sights. We visited the hot springs, which were a relaxing break with different pools to lounge in, then the Emerald Pool with its crystal-clear water, and the Blue Lagoon. Once again, the guides were so good at timing that we were among the first guests to arrive. The day also included Wat Tham Suea, also known as Tiger Cave Temple, Wat Kaew Korawaram temple, the Ao Nang Mountain Buddha temple, and the crab statue. Lunch was served on a private floating dock and somewhere in the middle of all that they surprised my husband with a birthday cake and sang to him.

Krabi Discovery Tour Pricing

Living The Krabi Life

When we weren’t on tours, Krabi was easy to enjoy. One day we took a Tuk Tuk to Ao Nang Beach, where the kids loved the cute swings, the long tail boats lined up along the shore, and the cafés scattered around town. Landmark Ao Nang Night Market became one of our favorite evening stops because it offered tons of vendors with unique food options, live music and performers on stage, and bounce houses and trampolines for the kids. The low prices made it easy to try a lot of different foods.

Krabi also had that very convenient Thailand rhythm of daily life—massage and nail salons everywhere, 7-Elevens on seemingly every corner, laundromats, pharmacies, tourist stands, and restaurants. We found a great little restaurant just a few hundred yards from our hotel called Banh Thai and ate there several times for lunch, dinner, and even breakfast. Everything we ate there was delicious and the staff was exceptionally kind.

After five lovely days in Krabi, it was time to make our to the island of Koh Samui. To get there, we took a three-hour van transfer from Krabi to Donsak Pier and then took the Seatran ferry to Nathon Pier in Koh Samui. The ferry itself was about 45 minutes and cost $5.50 per adult and $2.75 per child.

Koh Samui: Easy, Fun, and Family Friendly

We spent five nights in Koh Samui at the Holiday Inn Samui Bophut, using 164,000 IHG points. The cash price of the stay was around $2,400. The hotel is especially kid-friendly thanks to its large kids club with daily activities and splash pad/pool area with waterslides that kept our kids entertained for hours. The kids club had a large indoor area with a climbing structure my kids returned to again and again. Typically, my 11 year old feels too old for kids clubs, but he actually enjoyed the one at this hotel.

The guest rooms are family-oriented and the hotel has direct access to the beach. The location was one of the best parts. It sat right next to Fisherman’s Village, just steps away from restaurants, beach walks, and evening entertainment.

Koh Madsum & Koh Tan Island Tour

Koh Madsum, Pig Island

We took another private long tail boat trip to Koh Madsum, better known as Pig Island, and Koh Tan. This excursion was absolutely for the kids and it was exceptional. We started early again and were the first ones on the island to meet the pigs. There were so many of them and they were friendly and not shy at all. At one point we tried to pick up a little baby pig, which squealed loudly to make it clear that was not happening! After a few hours playing with the pigs, we boarded the boat for Koh Tan and went snorkeling. The snorkeling was great, although honestly, the kids may have enjoyed jumping off the top deck of the boat even more!

Koh Madsum & Koh Tan Tour Pricing

Fisherman’s Village

Night Market, Fisherman’s Village

Some of our favorite Samui moments happened off-tour. One of the best meals of the trip came from The Hut Café, located right at the beginning of Fisherman’s Village. The kids also loved circus night at the hotel.

In the evenings, Coco Tam’s was the easy choice. It sits directly across from the hotel and hosts nightly fire shows at 7:30 and 9:00 p.m that we watched from the beach. The nightly market in Fisherman’s Village was livelier than the one in Krabi with street vendors offering everything from fresh seafood and Thai street food to souvenirs and live music, making it an easy and fun place to grab dinner and soak in the local atmosphere with the kids.

Koh Samui offered the perfect balance of relaxation and fun, giving us time to recharge before the next leg. Next up was Chiang Mai, where the focus shifted to more meaningful, hands-on experiences.

Chiang Mai: The Most Meaningful Stop

Our final stop in Thailand was Chiang Mai. From Koh Samui we flew Bangkok Airways to Chiang Mai and checked into At Chiang Mai Hotel. At $462 for four nights including breakfast, it was one of the best-value stays of the trip and also the most unique. The hotel had a boutique feel, was beautifully decorated with vintage Thai décor, and our room was spacious enough to comfortably fit all five of us. Being in the heart of the Old City made it incredibly easy to walk to temples, markets, and parks.

Elephant Sanctuary

Kanta Elephant Sanctuary

The Kanta Elephant Sanctuary ended up being the most meaningful experience of the entire trip. From the moment we arrived, the focus was on education as much as interaction. Our guide walked us through the history of each elephant, explaining how many had been rescued from the logging industry or circuses and what daily care now looks like for them in a protected environment.

The experience itself was very hands-on. We started by changing into matching outfits, referred to as traditional mahout clothing. Wearing matching outfits helps the elephants recognize visitors as friendly, safe caretakers. We met each of the six elephants and they graciously let us pet them and feed them sugarcane and corn stalks. Then we prepared food for them called “vitamin balls” which contained tamarind, sticky rice, bananas, and salt. We rolled them into balls and fed them directly to the elephants. Being that close to animals of that size was both surreal and surprisingly calm.

The highlight for the kids was the bathing portion. We walked with the elephants into the water and helped scrub them down, which turned into a mix of laughter and splashing. We even got sprayed by an elephant! It was neat to be able to participate in their daily routine rather than observing from a distance. The entire experience was exceptional and it checked every box: engaging for the kids, educational for all of us, and something we’ll all remember long after the trip.

Kanta Elephant Sanctuary Pricing

Cooking Class

Smile Organic Farm cooking class

Our last excursion of the trip was a cooking class at Smile Organic Farm. It ended up being one of the most fun and interactive days of the entire trip. We started with a visit to a local market, where we walked through stalls packed with fresh herbs, spices, and produce while learning what actually goes into Thai cooking. I must say was wild to see how many ingredients actually go into just one Thai dish!

From there, we headed just outside the city to the farm which was open, relaxed, and surrounded by greenery. My husband, our oldest, and I each took on the role of “head chef,” while our two younger kids were sous chefs, helping prep ingredients and staying involved in the whole process. Instead of everyone cooking the same thing, we chose different dishes to cook and ended up with a full spread of spring rolls, pad Thai, multiple curries and soups, and khao soi, giving us the chance to try a little bit of everything.

Thankfully the food we cooked exceeded our expectations! Our instructor even provided us with a 48 page cookbook with the recipes we cooked as well as many more traditional Thai dishes to cook at home. We were thrilled with how fun and educational the cooking class turned out to be.

Thai Cooking Class Pricing

Chiang Mai and Beyond

Beyond the booked activities, Chiang Mai was easy to explore. The sheer number of temples in the Old City was impressive. We visited Wat Phra Singh, Wat Chedi Luang, Wat Muen Tum, and Wat Phan On. We also visited the Chiang Mai Night Bazaar, which is only open on Sundays. It was huge! So big that after about two hours of walking, shopping, and eating, we still had not seen the whole thing. The only downside was how crowded it was, but that probably came with it being open just one day a week.

For a slower afternoon, we went to Nong Buak Haad Public Park in the southeast corner of the Old City. It had a playground, fountains, flowers, a running track, and a lot of green space. There was even a yoga class in session during our visit. As a bonus, my 11-year-old and I got foot massages right there in the park overlooking the landscape, which was a great impromptu Thailand moment we got to enjoy together..

On our last day, we went just outside the Old City to Central Chiang Mai mall, where the kids loved Bouncetopia, a giant indoor bounce house that gave them a break from the more outdoors-focused activities.

We loved our time in Chiang Mai as it brought a deeper layer to the trip, combining culture and some of our most memorable experiences in one place. It also offered great food and flexible downtime that we all appreciated.

Thailand Travel Tips for Families

• Limited ourselves to one flight per day
• Used points and miles for premium cabins and hotels
• Relied on laundry services instead of overpacking
• Used Grab and Bolt apps for transportation
• Mixed busy sightseeing days with slower beach and park days
• Booked private tours early in the morning to avoid crowds

The Little Things That Made Thailand Work

Thailand changed how we traveled almost immediately. Instead of packing for every scenario, we brought four carry-on suitcases for the entire trip and relied on laundry service as we moved from city to city. In each of the three Thailand stops, we dropped off clothes at a local laundromat and picked them up washed, dried, and folded for somewhere between $8 and $15. It made the whole trip feel lighter and more manageable.

Transportation was also easier than expected. Grab and Bolt are basically the Uber equivalents in Southeast Asia. We used Grab a few times in Singapore, Krabi, and Koh Samui, and in Chiang Mai we used Bolt. Between those apps, tuk tuks, ferry transfers, and short walks, getting around never became a stress point.

I also fully leaned into one of Thailand’s best-value luxuries: massage. Over the course of the trip I got eight full-body Thai massages and two foot massages. Thai massages are different from what I’m used to in the U.S.—the therapist gets on the table with you, and there is a lot more stretching built into the treatment—but I ended up loving that part of it. At $10 to $15 for a one-hour full-body massage, there was no reason not to. The fact that massage parlors were everywhere and generally took walk-ins meant I never had to schedule anything in advance. I also got a gel manicure for $15 and a pedicure for $10.

Food was just as approachable. The kids had their own highlights: our 5-year-old loved Thai omelets, our 8-year-old became obsessed with Singapore-style chicken and rice (which we easily found in Thailand) and our 11-year-old was the most adventurous with noodles and curries, especially khao soi. All three of them loved the fresh fruit smoothies. Night markets were probably the biggest food highlight overall because you could get pad Thai, curries, Tom Yum soup, mango sticky rice, grilled meats and seafoods, etc all for the affordable price of 50-200 Baht ($1.50-$6 USD). We fell in love with so many Thai dishes that as soon as we got home, we ordered Thai ingredients and started recreating our favorites like pad Thai, green curry, panang curry, massaman curry, and khao soi in our own kitchen.

Laundry was easy, food was cheap and genuinely good, transportation was simple, and small treats like massages or nail services were extremely affordable. The whole country made it feel possible to travel well and comfortably.

One Final Stop

Jewel Waterfall Changi Airport

We returned to Singapore to position ourselves for our flight home. After flying Scoot Airlines from Chiang Mai, we stopped at the Jewel waterfall upon arrival, which was spectacular! The pictures don’t do it justice.

For our final night, we checked into W Singapore Sentosa Cove using a Marriott free night award. The cash price was around $490, and thanks to our Marriott status we were upgraded to a beautiful corner suite overlooking the marina. The kids immediately loved the huge swimming pool and waterslide, while I made a point to use the hotel’s state-of-the-art fitness center. The only downside was that we were only there for roughly 14 hours, which was nowhere near enough time to really enjoy the beautiful property.

Before our flight the next day, we visited the high-end Singapore Airlines SilverKris Business Class lounge at Changi Airport. The lounge was spacious with plenty of seating zones, along with showers, workspaces, nap areas, and even a room for kids with some games and a television. The food and drinks were top notch with plenty of local and international options to choose from. It was the perfect spot to relax before boarding our 16 hour flight back to the United States.

We again flew Singapore Airlines business class, but this time flew from Singapore to New York (JFK). We used 106,000 miles plus $66.40 per person for seats that were selling for about $4,500 each. One of the coolest things about this flight was we flew right over top of the arctic circle. It was neat to see that on the in-flight screen.

Upon arrival in JFK, we had the opportunity to visit the new Capital One Lounge for the first time and it sure lives up to the hype. With a full bar, made to order dishes, a cheese monger and wine tasting station, coffee bar, plus showers and private rooms, it truly makes for a luxurious experience before flying. I almost didn’t want to get on our flight home!

From JFK, we had a quick one and a half hour flight to Raleigh. Home at last!

Reflecting on the Trip

Looking back, what stands out most isn’t just one destination, it’s the mix of everything. Early mornings on quiet streets in Singapore, long tail boats weaving through limestone cliffs in Krabi, pigs roaming the beach in Koh Samui, and hands-on moments with elephants and cooking in Chiang Mai. The trip had a rhythm to it, we had many active days that were balanced with time to slow down, whether that meant a beach afternoon, a night market, or a last swim before heading home.

We were also fortunate that everything went smoothly, no major flight delays, no illnesses, no unexpected disruptions. It was surreal to see all the time and effort we put into planning this trip come together so seamlessly. As our biggest trip to date, it left us feeling confident about taking on even bigger adventures in the future.

Final Thoughts

Thailand with kids ended up being far easier than we expected. Between the affordability, family-friendly hotels, easy transportation, incredible food, and unforgettable experiences, this trip completely changed how we think about long-haul family travel. From Singapore Airlines business class to island hopping in Krabi and elephant encounters in Chiang Mai, every stop added something unique to the adventure.

Related posts:

What to do in Singapore in 4 Days: A Perfect Blend of Culture, Luxury, and Adventure Marina Bay Sands Review: What $1000 a Night Gets You in Singapore’s Most Iconic Hotel JFK to Singapore Business Class Review on Points Singapore Airlines Changi Airport SilverKris Lounge Bottom Line Review (Terminal 3, SIN)