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What makes Asia special to them: adventures and tips from interesting people with ties to the region
Anna Chittenden, founder of Lost Guides on Thailand
I first met Anna Chittenden back in 2017, while living in Singapore. I used her Singapore, Bali and Japan guide books and loved the way she uncovered small, thoughtful places — the kind you’d never find unless someone with her eye pointed them out. I reached out to tell her how much her work resonated with me, and she kindly agreed to meet for coffee at Tiong Bahru Bakery (a must visit in Singapore). Since then, Anna has continued to shape the way people experience travel. Through the same unique lens as Lost Guides, she now designs custom trips through Alchemist Travel, planning journeys with the same curious, creative lens that made her guides so beloved. Anna and I reconnected to talk about Thailand, a country she’s explored in depth, and the mix of familiar favorites, hidden gems, and meaningful moments that keep travelers returning again and again. Whether you’re planning a family trip or looking to wander a little off the beaten path, Anna’s insights offer a refreshing way to experience Thailand with intention and ease.
You’ve explored so much of Southeast Asia while living in Singapore, how has being based there shaped the way you see and experience the region?
That’s such a great question and I feel like living somewhere long term (I’ve lived in Singapore for 12 years) helps me to see the region from a viewpoint of both a local and an outsider. Spending so much time here I am really able to dig deep beneath the surface and see the region not as a tourist destination but a place where people live and work. For me that’s always finding the right neighbourhoods where locals and expats live, instead of hitting the tourists spots.
When you think about Thailand beyond the famous islands and cities, which places have surprised you the most during your travels? Any small towns or little pockets of culture that felt especially memorable?
I know that Bangkok is pretty famous but I love finding the neighbourhoods that resonate with me, such as Chinatown. I have this wonderful memory of walking through the back alleys one evening and coming across a Chinese opera performance in a backstreet. One of the islands I love the most is Koh Ya Noi. It’s really easy to get to as you fly into Phuket and take a 30 min boat, but it’s the total opposite of Phuket. It’s a tiny traditional island with a low level of tourist development. Six Senses Ya Noi is heaven on earth. We love the bicycle rides you can do around the islands too. I haven’t done this for years but I love taking the train in Thailand. The overnight train from Bangkok to Surat Thani in a sleeper cabin is so comfortable and such a fun experience, to get to the islands Koh Phangan, Koh Tao and Koh Samui.
For families, what Thai destinations feel both welcoming and easy, yet still offer something different from the usual spots? We always take the children to Koh Samui. One of the things that’s important for us when travelling with kids is not only the destination but the journey to get there. The flight is 2 hours from Singapore to Koh Samui and then the hotels can be reached in around 15 mins so it feels like such an easy journey and we can make the most of the day being there, not all day travelling.
You’re known for finding great, under-the-radar places. How do you usually discover those hidden spots when you travel? I think it’s mixture of doing a little pre-planning but also just walking around and keeping your eyes open. I like to not be fixed on an itinerary but to speak to people when we get there. For example, when we went for dinner at Gaa Bangkok, the chef Garima Arora told us about a restaurant we should try called Khua Kling Pak Sod in Ari which we absolutely love (home-style Southern Thai food.) If you’re too fixed on your itinerary before you go you’ll miss out on the hidden gems. I like picking out a neighbourhood and then just wondering around and seeing what looks interesting.
Has living in Singapore changed what you look for when you travel? For example, do you seek more nature, culture, or slower places? Yes definitely, living in a city that, although has some nature, is mainly quite developed, we do mainly look for places immersed in nature when travelling.
What are some Thai dishes or food experiences you always recommend to people, especially those who’ve already been to the typical restaurants or night markets? As I mentioned before we always speak to people when we arrive such a chefs or people working at the hotels. Recently when we were staying at Six Senses Samui we asked one of the staff for their favourite local dishes and then asked if they were able to make them. Sometimes the food on the menus in hotels can be quite limited but they are normally quite happy to let you order off menu.
Can you share a moment from your time in Thailand that has stayed with you a person, a landscape, or a story that left a mark? The views from Ya Noi island are out of this world. They look over an incredible vista of limestone karsts. There’s something in the light that feels so heavenly. When you arrive you feel transported to another world.
For families or couples wanting to slow down and travel more meaningfully in Thailand, what practical tips would you give them? Taking the train if you have time! Also heading a bit further on from the main tourist spots like Phuket. Or even heading to the smaller islands if you have the time.
What does your ideal trip to Thailand include? Thailand offers so much, I think going to a city is as fun as the islands. Bangkok is a must. Chinatown, Jim Thompsons house, floating market, great restaurants and bars. With the children Six Senses on Koh Samui is perfect for us
Food wise I love a crab curry!
