Thailand might just be my all-time favorite destination in Southeast Asia. During my 2024 sabbatical, I devoted three weeks to uncovering the magic of the country, spending time in the bustling cityscape of Bangkok, the historical ruins of Sukhothai, the artsy heart of Chiang Mai, and the otherworldly temples of Chiang Rai. This article is a quick overview of my trip. You can click each location for a more in depth review, and also find my top tour recommendations here.
Snapshot of Thailand: Culture, Regions, and Vibe
Thailand is a blend of tradition and excitement, split into unique regions each with its own charm. In the central region, Bangkok thrives with neon lights, street food heaven, and history. The north is filled with lush mountains, sacred temples, and artsy towns like Chiang Mai and Chiang Rai. And let’s not forget southern Thailand—the ultimate beach paradise. While I skipped the southern beaches this trip, the central and northern regions offered a rich mix of cultural, culinary, and artistic gems and perfect for a 2-3 week itinerary.
In the heart of the country lies the bustling metropolis of Bangkok, the capital city that pulsates with energy and excitement. As the central hub of Thailand, Bangkok is a melting pot of cultures, where towering skyscrapers stand alongside ornate temples, and traditional markets coexist with modern shopping malls. The city’s streets are alive with the sights and sounds of street vendors, offering a tantalizing array of culinary delights, from spicy curries to sweet treats. Bangkok’s nightlife is equally vibrant, with neon lights illuminating the city’s bars and clubs, where visitors can dance the night away.
Venturing north, travelers will find themselves immersed in a world of natural beauty and spiritual tranquility. The northern region of Thailand is characterized by its lush mountains, cascading waterfalls, and ancient temples. The cities of Chiang Mai and Chiang Rai are popular destinations for those seeking a more relaxed and cultural experience. Chiang Mai, with its charming old town and numerous temples, is a haven for art lovers and spiritual seekers. Chiang Rai, known for its unique White Temple and Black House, is a must-visit for those interested in contemporary art and architecture.
My Itinerary
I took about 3 weeks to travel through Thailand, which was a perfect amount for me. With this itinerary, you’ll get a taste of Thailand’s history, culture, and local life in just the right mix of adventure and relaxation. Each stop has its own charm and something unforgettable to offer, so feel free to use this as your guide or reach out to design the perfect Thailand itinerary just for you! You could easily cut some time in Bangkok and Chiang Mai to see the Southern beaches as well.
Days 1–8: Bangkok – Settle in, explore temples, vibrant neighborhoods, and street food. Add on a few day trips like Ayutthaya.
Days 9–10: Sukhothai – Discover ancient ruins of the old kingdom
Days 11–17: Chiang Mai – Dive into art, nature, and the northern cuisine. Day trips to parks are a great addition as well.
Days 18–20: Chiang Rai – Visit unique temples and enjoy Thawan Duchanee’s Black House
Day 21: Cross to Laos – Start a river cruise from the Thai border to Luang Prabang
Interested in traveling yourself but need to adjust this itinerary to better suit your needs? Book a Trip Proposal Package with me and we’ll work together to create your perfect vacation, complete with an easy guide to follow with bookable links.
Booking Smart and Traveling Well
When planning my 10-week adventure through Asia, I knew I wanted Thailand as the starting point. Between the relaxed vibe, incredibly welcoming people, and the endless array of temples and vibrant cities, it felt like the perfect introduction to Southeast Asia. It was a great choice—Thailand’s culture is warm and friendly, and it’s easy to settle in quickly.
After a New Year’s celebration in Honolulu, I booked an economy-plus seat to Seoul during Capital One’s annual travel sale. Sales like these offer a ton of incredible deals and promotions and this one timed perfectly with my sabbatical plans, so I jumped on the opportunity to redeem a direct flight to Seoul on Hawaiian Airlines. I lucked out and got a two seat row to myself for the flight!
This particular sale was accessible to Capital One cardholders. I highly recommend signing up for their Venture X card as a great introduction to the world of points and miles. It’s honestly my favorite card overall for beginners and simple setups, and you can get a great sign up bonus of 75,000 miles through my link here!
Because I booked my flights separately over two days, I chose to stay inside Seoul Airport’s transit hotel once I arrived. My flight to Bangkok was the next morning, and this gave me a chance to adjust to the jet lag with a full night of sleep in an actual bed. After a quick workout in the morning, I left my room and walked straight to my gate for my flight to Bangkok on AirAsia, also booked through the Capital One sale. I arrived in Bangkok well rested and ready for adventure, even with a long haul economy flight thanks to how I spaced this travel out.
Learning the points and miles world, as well as how to navigate booking in general, made this trip financially possible and comfortable. I saved over $8,000 through smart redemption opportunities and taking advantage of sales for my flights and hotels during my sabbatical. If this sounds like a dream, don’t miss out on learning more with my Rewards 101 Coaching—where I can guide you to get these same travel wins! If you’re ready to book but not quite sure how to best use your points and miles, you can also book my Redemption Coaching Package, where we’ll work together until you find your perfect redemption opportunity.
Bangkok: A Beautiful Chaos
Bangkok hit me with full sensory overload in the best possible way—an explosion of smells, sounds, and lights that felt like the pulse of Thailand itself. With its endless alleys, quirky cafes, and a mix of temples and towering skyscrapers, Bangkok’s energy is electrifying. I stayed eight days here and packed in a mix of city exploration, from the local gay scene to the vibrant street art and architecture.
One unforgettable highlight was a bicycle food tour that guided me through Bangkok’s lesser-known food havens, tasting everything from spicy street noodles to Thai iced coffee. If you want to dive into Bangkok’s cuisine and culture like a local, don’t miss this bicycle food tour on my Viator recommendations!
Art Tip: Bangkok’s Museum of Contemporary Art houses masterpieces by Thawan Duchanee, whose art speaks to Thai culture in a bold, almost surreal way.
Sukhothai: Ruins and History
Next up was Sukhothai, reached by Bangkok Airways. This town may be small, but it’s home to one of Thailand’s most significant historical parks. Sukhothai is perfect for a peaceful yet inspiring journey into Thailand’s past, and the guided bicycle tour of the ruins will leave you awestruck.
I lucked out with my timing—there was a festival in town celebrating one of Sukhothai’s ancient kings with night markets, local food stalls, and even an festival show telling the story of the king, featuring elephants and a mock battle from local student performers! It was a beautiful two days exploring ancient Thai history amongst the incredible ruins.
Planning Tip: The ruins of Sukhothai are incredible and well worth a visit, however there’s not much to do in the surrounding area and town. Two days was the perfect amount of time, giving you a full day for the ruins and a travel day on either side.
Chiang Mai: A Blend of Old, New, and Flavorful
After a four-hour bus ride (just $15!) from Sukhothai, I arrived in Chiang Mai. Known for its rich culture, beautiful temples, and nearby incredible parks like Doi Inthanon, Chiang Mai is like stepping into an ancient postcard, with the old town’s moat and surrounding temples as the centerpiece. Definitely invest some time to explore the local temples, they are simply breathtaking in the backdrop of such a beautiful and historic city.
One of my top experiences here was a street food tour, where I tasted the city’s best treats and learned the stories behind each dish—like the perfect Khao Soi and crispy roti. Chiang Mai is a foodie paradise, and this street food tour is a must for anyone looking to explore beyond northern cuisine.
Activity Tip: If you love drag shows, be sure to check out the 6ixcret Show which puts on an incredible event every night. One of the queens lit the bar on fire the night I went! (In a safe and controlled way hehe)
Chiang Rai: Temples That Take Your Breath Away
Last stop: Chiang Rai, a city where temples double as works of art. I traveled here specifically to see Thawan Duchanee’s “Black House” and the fantastical White Temple—both dreamlike, both unforgettable. I even managed to catch the Thailand Biennale, which added an extra layer of magic interweaving modern art exhibits with serene temples and historical landmarks.
For anyone who loves art, culture, and a touch of the surreal, Chiang Rai’s temples are a can’t-miss.
Art Tip: Make sure to plan plenty of time for the Black House. I left my full day tour early and skipped the Golden Triangle portion so I could spend the whole afternoon here exploring Duchanee’s brilliance and oddities.
Saying Goodbye… Until Next Time
From Chiang Rai, I traveled to the border with Laos for my next adventure, taking a serene river cruise to the old capital, Luang Prabang. Parting from Thailand was bittersweet, but this journey opened up a world of experiences I can’t wait to revisit.
Interested in creating a trip like this? Book my Full Service Travel Design and we’ll work together to create your perfect itinerary. I can take care of all the logistics and booking for you for a stress free experience. You can also explore the sub-posts for each city to get a detailed rundown of each destination. Until then, check out my curated Viator tours to start planning your own Thai adventure!
