Anna Chittenden
Conversations with friendsWhat makes Asia special to them: adventures and tips from interesting people with ties to the region
Anna Chittenden is the founder of Lost Guides, a series of books that provide a trustworthy source of curated places, eliminating the tedious research process.
Anna Chittenden brings a rare perspective to Thailand — shaped by twelve years of living in Singapore and exploring Southeast Asia. Rather than sharing typical travel stories, she focuses on genuine experiences, like discovering a Chinese opera tucked away in the backstreets of Bangkok or biking through the serene landscapes of Koh Yao Noi. Her travel style is all about balancing planning with an open heart. She encourages talking to local chefs, wandering aimlessly, and letting locals introduce you to the area's hidden gems.
For families and couples, Anna emphasizes a laid-back approach to travel, prioritizing destinations that are welcoming, meaningful, and harmoniously aligned with the local way of life. It's all about immersing yourself in nature and embracing the slow pace of life, creating lasting memories along the way.
Sophia first met Anna Chittenden in 2017 while living in Singapore. She had been using Anna’s Singapore, Bali, and Japan guidebooks and loved the way Anna uncovered small, thoughtful places — the kind you’d never find without someone with her eye. She reached out to tell Anna how much her work meant to her, and Anna 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 distinctive lens that defined Lost Guides, she now designs custom trips through Alchemist Travel.
Anna and Sophia recently reconnected to talk about Thailand — a country Anna knows deeply — and the mix of familiar favorites, hidden corners, and meaningful moments that keep travelers returning. Whether you’re planning a family trip or hoping to wander a little off the beaten path, Anna’s perspective offers a refreshing way to experience Thailand with intention and ease.
Q&A with ANNA chittenden
Q: You’re known for finding great, under-the-radar places. How do you usually discover those hidden spots when you travel?
A: 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 neighborhood and then just wandering around and seeing what looks interesting.
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Q: Has living in Singapore changed what you look for when you travel? For example, do you seek more nature, culture, or slower places?
A: 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.
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Q: 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?
A: As I mentioned before, we always speak to people when we arrive, such as chefs or people working at the hotels. Recently, while staying at Six Senses Samui, we asked one of the staff members for their favorite local dishes and whether they could make them. Sometimes the food on hotel menus can be quite limited, but they are normally happy to let you order off the menu.
Q: 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?
A: 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 neighborhoods where locals and expats live, instead of hitting the tourist spots.
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Q: 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?
A: I know that Bangkok is pretty famous, but I love finding the neighborhoods 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 back street. 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 minimal 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.
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Q: For families, what Thai destinations feel both welcoming and easy, yet still offer something different from the usual spots?
A: 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.
Q: 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?
A: 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.
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Q: For families or couples wanting to slow down and travel more meaningfully in Thailand, what practical tips would you give them
A: 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.
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Q: What does your ideal trip to Thailand include?
A: Thailand offers so much, I think going to a city is as fun as the islands. Bangkok is a must. Chinatown, Jim Thompson’s house, the 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!