Ever since our honeymoon in Bali last year, Ally and I had been itching to get back to Southeast Asia—and Ally’s 30th birthday gave us the perfect excuse. Thailand was at the top of our list, and this trip more than delivered. Over the course of two weeks, we explored the bustling energy of Bangkok, the serene mountains and night markets of Chiang Mai, the colorful temples of Chiang Rai, the turquoise waters of Koh Phi Phi, the jungle tranquility of Khao Sok National Park, and the stunning beaches of Railay. We packed our days with massages, cultural experiences, natural beauty, and, of course, incredible food. Here’s a detailed look at our full 14-day Thailand travel itinerary, along with some of the highlights that made the journey so special.
Getting There
Our adventure began with a 15-hour flight from Chicago to Seoul. During our short layover—made slightly longer by a minor delay—we had time to visit a Priority Pass lounge for Korean snacks and drinks. Refueled and refreshed, we then boarded a six-hour flight to Bangkok. We landed just after midnight and quickly called a Grab to take us to our hotel, the Grand Hyatt Erawan Bangkok. We checked in during the early hours of the morning, tired but excited to finally be in Thailand.
Bangkok: Tailors, Temples, and Street Food
Day 1: Temples and Muay Thai
After a much-needed breakfast at the hotel, we dove straight into the city. Our first stop was Peninsula Tailors, where I ordered two custom suits and a cashmere winter coat—an ideal opportunity to take advantage of Thailand’s reputation for high-quality, affordable tailoring. Even more impressive was the speed of the process, with custom pieces often ready for final fittings and pickup in as little as one week.
We spent the afternoon temple-hopping, visiting the Grand Palace and the famous Wat Pho, home of the Reclining Buddha. The intricate architecture, golden spires, and the sheer energy of the temple grounds gave us an immediate glimpse into the heart of Thai culture, and wandering barefoot across the gleaming tile floors in the tropical heat was an experience all its own.
Later that evening, we headed to Rajadamnern Stadium for an unforgettable night of Muay Thai fights. We were treated to nine bouts featuring both local talent and international fighters, including two Americans we had a blast cheering for. We opted for VIP Balcony seats, which came with free-flowing beer and snacks—a fantastic perk—though truly, there wasn’t a bad seat in the house. The event itself felt like a major production, complete with kiss cams, dance cams, and t-shirts being launched into the crowd. The energy and adrenaline were exactly what we needed to power through our jet lag.
Day 2: Markets and a Chef’s Table
We started our second day early with a tour to the famous Maeklong Railway Market and Damnoen Saduak Floating Market. The railway market, where vendors hurriedly pull back their goods as trains pass inches away, felt lively and authentic. The floating market was more tourist-oriented but still a fun experience — plus, we got to enjoy delicious panang curry and mango sticky rice.
Back in Bangkok that evening, we had a bit of a misadventure. Bangkok traffic turned what should have been a 30-minute drive into a 1.5-hour crawl, causing us to miss the first few courses of our much-anticipated dinner at Ōre. Fortunately, the dinner consisted of 30 courses and the staff went out of their way to make sure it was still a special night. Based on the level of service and the courses we did experience, we fully expect to see this restaurant in a future edition of the Michelin guide.
With an early morning flight to Chiang Mai on the horizon, we turned in for the night ready for the next chapter of our journey.
Chiang Mai and Chiang Rai: Temples, Flavors, and Northern Charm
Day 3: Arrival and Exploration in Chiang Mai
On day three, we caught a morning flight to Chiang Mai and checked into the serene The Inside House, where we splurged on the stunning Doi Suthep Pool Suite. The suite featured a large glass-walled private pool, an outdoor soaking tub, and beautiful views overlooking the city. It was the perfect blend of modern luxury and classic Thai design, offering a peaceful retreat after long days of exploring.
While we waited for our room to be ready, we walked to Wat Phra Singh, a beautiful temple near our hotel. We then made a lunch stop at Khao Soi Lung Prakit Kad Kom, a Michelin-recommended restaurant famous for serving khao soi, Chiang Mai’s most iconic dish. Ally was especially excited to try this restaurant because it had been featured on her favorite show, Somebody Feed Phil. The khao soi was absolutely delicious, and our meal cost us less than $2 USD — a testament to the incredible value of dining in Thailand.
We spent the rest of the afternoon relaxing with a beautiful tea service at the hotel and treating ourselves to massages at the on-site spa. We grabbed dinner at Tikky Café, which offered delicious fruit smoothies alongside an extensive menu of Thai dishes. It was the perfect casual spot after a busy day of exploring Chiang Mai. Later that evening, we ventured out to explore the bustling Kalare Night Bazaar and surrounding markets, where we enjoyed live music, cold drinks, and tried our hand at shooting pellet guns at stuffed figurines.
Day 4: A Day in Chiang Rai
On day four, we took a full-day trip to Chiang Rai, starting with visits to the surreal Blue Temple and the thought-provoking Black House. The Blue Temple, known for its vibrant sapphire interior and intricate murals, felt both modern and mystical. In contrast, the Black House presented a darker, more avant-garde experience with its collection of haunting artworks and animal remains.
After the morning’s sightseeing, we stopped at Cafe Lista for a much-needed coffee and Thai iced tea break. Refreshed, we continued to the iconic White Temple, a dazzling work of contemporary art filled with gleaming white facades and mirrored accents. The White Temple was easily one of the most impressive stops of the day, blending traditional Buddhist elements with imaginative modern symbolism. After spending a few hours at the temple, we headed back to Chiang Mai, arriving just in time for dinner at The Inside House’s restaurant, GHIN.
Day 5: Cooking, Massages, and Mango Sticky Rice
On day five, we spent the morning learning to make some of Thailand’s most famous dishes at Zabb E Lee cooking school, located in the heart of Chiang Mai. After a colorful market tour where we picked out fresh herbs and vegetables, we got hands-on in the kitchen, cooking (and devouring) spring rolls, pad thai, tom yum kung, panang curry, and mango sticky rice. Each dish was explained step-by-step, and the small group size meant we had plenty of personal guidance and tips from our cheerful instructor.
After another elegant afternoon tea at the hotel, we indulged in massages at Makkha Spa, a tranquil retreat tucked down a quiet lane in the old city. The treatments were luxurious and deeply relaxing, incorporating traditional Thai techniques that left us feeling renewed. Capped off with yet another serving of mango sticky rice as a post-massage treat, we returned to our hotel full and blissfully relaxed, finishing the night with room service and a peaceful dip in our private pool.
Koh Phi Phi: Island Adventures
Day 6: Traveling to Koh Phi Phi
The next morning, we caught an early flight to Krabi, followed by a transfer to Klong Jilad Pier and a ferry ride to Koh Phi Phi. The boat ride offered our first glimpse of the island’s stunning turquoise waters and distinctive cliffs rising straight from the sea. Upon arrival, we checked into Panmanee Hotel, a clean, recently renovated spot tucked on a quieter street just a short walk from the heart of town.
After settling in, we spent the afternoon wandering the island’s narrow, winding lanes, browsing souvenir shops, and enjoying a beachside drink with our toes in the sand. As the sun began to dip toward the horizon, we found a quiet stretch of beach to sit and watch the sky erupt into brilliant shades of orange and pink. That evening, we grabbed dinner at a cozy Italian restaurant before turning in early in preparation for the next morning’s sunrise adventure.
Day 7: Maya Bay and Return to Krabi
We started day seven early with a sunrise tour to Maya Bay, arriving just as the first light began to glow over the famous white sands. The bay, made iconic by the movie The Beach, was breathtaking in the early morning calm, with crystal-clear waters and towering limestone cliffs creating a scene straight out of a dream. Due to ongoing conservation efforts, tourists are no longer allowed to swim at Maya Bay—but that didn’t detract from the experience. In fact, we spotted several baby sharks darting around in the shallows, a sign of the bay’s recovering marine ecosystem. Having the beach mostly to ourselves was a magical experience and made the early wake-up call completely worth it.
Our tour also included a stop at Pileh Lagoon, where we swam in the warm, emerald-green water surrounded by dramatic rock faces that felt like the walls of a secret paradise. Next, we passed by Viking Cave, an important cultural site known for its ancient wall paintings and as a home to highly prized bird nests used in traditional Chinese delicacies. At Loh Samah Bay, we took a peaceful snorkeling break, marveling at the vibrant coral and tropical fish in the sheltered, calm waters. Finally, we stopped at Monkey Bay, where playful monkeys scrambled across the rocks and low-hanging trees, eyeing the visitors with mischievous curiosity.
After a magical morning on the water, we caught the afternoon ferry back to Krabi and checked into Centara Ao Nang Beach Resort & Spa, where the laid-back beach vibe was a welcome change of pace. We wrapped up the day with a beachfront dinner at REEVE Beach Club, enjoying cold drinks, fresh seafood, live music, and a lively fire show that lit up the night sky.
Khao Sok National Park: Jungle Escapes and Floating Camps
Day 8: Elephant Hills Jungle Camp
After breakfast, we were picked up by Elephant Hills and transferred to their Jungle Camp in Khao Sok National Park, set deep within the lush rainforest. Upon arrival, we settled into our luxurious tented accommodations, which blended the adventure of camping with the comfort of a boutique hotel.
That afternoon, we had the incredible experience of feeding and interacting with rescued elephants. We learned about each elephant’s unique rescue story and the extensive conservation efforts that Elephant Hills supports. The guides taught us how to prepare the elephants’ medicine balls—a sweet and healthy treat packed with nutrients—and we got to feed them to the elephants alongside fresh fruits and sugar cane. Observing these gentle giants up close, as they happily munched on their treats and bathed in the mud, was truly one of the most memorable moments of the trip.
Later, we set out for a peaceful canoe ride down the Sok River. Gliding along the calm water, we were surrounded by towering limestone cliffs and dense, vibrant jungle, while monkeys rustled in the trees overhead. The scenery felt almost otherworldly, as if we had been teleported to Pandora. As night fell, we gathered under the stars for a delicious dinner, accompanied by a lively cultural show performed by local schoolchildren.
Day 9: Floating Lake Camp Adventure
After breakfast, we boarded a longtail boat and journeyed across the serene waters of Cheow Lan Lake to Elephant Hills’ Lake Camp. Our accommodations for the night were floating luxury tents, each perched atop the emerald waters with breathtaking views of the national park. The tents were simple yet elegant, offering comfortable beds, running water, and private decks where we could step directly into the lake for a refreshing swim. It was the perfect blend of rustic adventure and modern convenience, allowing us to fully immerse ourselves in the natural beauty of Khao Sok while still enjoying a few welcome comforts.
The day was packed with activities: we spent time swimming off our decks, kayaking through hidden lagoons and narrow jungle channels, and venturing on a guided jungle trek to a remote bat cave. The cave, tucked deep within the cliffs, was filled with stalactites, stalagmites, and the eerie flutter of bat wings overhead. As evening approached, we returned to camp just in time to watch the sun set, casting a golden glow across the lake. After sunset, we enjoyed another hearty and satisfying dinner at the floating camp restaurant, surrounded by the sounds of the jungle at night.
Day 10: Lake Kayaking and Return to Ao Nang
The next morning, we set out for one final adventure on Cheow Lan Lake, joining a guided kayaking tour through the still waters and hidden jungle inlets. Paddling quietly along the shoreline, we spotted a family of otters, monkeys swinging from branch to branch, hornbills flying above the trees, and heard the calls of gibbons echoing across the lake. The tranquility and raw beauty of the scenery made for a perfect farewell to Elephant Hills.
After returning to camp, we enjoyed a final lunch overlooking the lake before boarding a boat back to the mainland. From there, we made our way back to Ao Nang and checked once again into Centara Ao Nang Beach Resort & Spa, grateful for a peaceful night of rest after our unforgettable jungle adventure.
Railay Beach: Secluded Luxury and Stunning Cliffs
Day 11: Railay Beach Retreat
On day eleven, we caught a morning transfer to Railay Beach, arriving by boat to the stunning shoreline where dramatic limestone cliffs meet soft white sand. We checked into the luxurious Rayavadee Resort, a hidden gem tucked into lush tropical gardens. Our villa felt like a private sanctuary, blending seamlessly into the natural surroundings with elegant Thai decor and thoughtful touches.
We kicked off our stay with a leisurely lunch by the pool, where we shared a “Thai pizza” topped with rich panang curry—a creative and delicious twist on a classic dish—alongside refreshing cocktails under the swaying palms. Afterward, we treated ourselves to a relaxing afternoon massage at the resort’s spa, set in a peaceful pavilion surrounded by lush jungle greenery.
That evening, we enjoyed a magical twilight dinner at The Grotto, the resort’s famous cave restaurant. Nestled under a natural cliff right at the beach, The Grotto offered an unforgettable setting. We dined on steak and fresh seafood as the sun dipped below the horizon, casting a soft golden glow across the cliffs and creating a dreamlike atmosphere that made the evening feel truly special.
Day 12: Relaxation at Rayavadee
On day twelve, we spent the day lounging by the pool, swimming in the warm, clear waters, and wandering along Railay’s stunning beaches. The dramatic cliffs towering over the shoreline created a breathtaking backdrop everywhere we went, and we enjoyed watching adventurous rock climbers scale the limestone walls as we relaxed on the beach. The relaxed, car-free atmosphere of Railay beach felt like a hidden slice of paradise.
That evening, we dined at one of the resort’s restaurants, where I decided to challenge the kitchen to serve my crab curry “ped mak mak” (“very, very spicy”). The chefs delivered with enthusiasm, preparing a dish so spicy it left me sweating and laughing between bites. Staff members kept peeking out from the kitchen to see how I was handling the heat, and we all shared a few laughs over the fiery experience.
Bangkok: Final Flavors and Farewell
Day 13: Return to Bangkok
In the morning, we departed Rayavadee to begin our journey back to Bangkok. Because it was low tide, we boarded an inventive tractor-drawn dock that carried us out into deeper water, where a boat was waiting to pick us up for our transfer to Krabi Airport. We caught a short domestic flight to Bangkok, where we checked into one of the best hotels in Bangkok, the Kimpton Maa-Lai Bangkok, known for its contemporary design and vibrant atmosphere. After settling into our room, we visited Peninsula Tailors for my final fittings, where the tailor made a few last tweaks to ensure a perfect fit.
That evening, we dove into Bangkok’s culinary scene with a “Bangkok Backstreets” food tour through Chinatown. We were lucky to have Annie as our guide—she was funny, insightful, and made the night feel extra special. We enjoyed learning about the mixture of Thai and Chinese influences in the food—or as Annie playfully called it, “Thainese.” Highlights included tender chicken satay, rolled noodle soup, Chinese chive dumplings, and soy sauce flavored ice cream. We sampled a seemingly endless number of dishes while weaving our way through the maze of vibrant street stalls and hidden alleys, each corner revealing something new and delicious. Near the end of the tour, Annie had one last surprise for us, leading the group in singing happy birthday to Ally (a few weeks early) and giving her cake to take home!
Afterward, we hopped into a tuk-tuk for an exhilarating ride back to the hotel, weaving through traffic and watching the city lights blur by. We capped off the night with cocktails at the Kimpton’s rooftop bar, where a live DJ set the mood with vibrant beats as we enjoyed panoramic views of the glittering Bangkok skyline under the warm evening air.
Day 14: Final Day and Departure
Our final day in Bangkok was spent shopping for snacks, souvenirs, and gifts (including a new suitcase to carry everything home). We wandered through bustling malls and local markets, picking up dried mango, Thai inhalers, hand-crafted ceramics made by local artisans, and other small treasures to remember the trip by. After picking up my finished suits from the tailor, which turned out beautifully, we returned to the hotel for a few farewell drinks in the cozy lobby bar. Relaxing over our final cocktails, we reflected on the highlights of our adventure before heading to the airport for our flight home.
Know Before You Go: Tips for Visiting Thailand
Best Time to Visit
The best time to visit Thailand is during the cool, dry season from November to early April. Temperatures are more manageable, and there’s less rain—perfect for beach days and sightseeing. If you’re planning to visit multiple regions, keep in mind that weather can vary between the north (Chiang Mai) and the islands in the south. Also note that northern Thailand experiences “burning season” between February and April, when farmers burn fields and air quality can become very poor—something to consider if you plan to spend time in Chiang Mai or the surrounding areas during these months.
What to Pack
Thailand is hot and humid year-round, so lightweight, breathable clothing is a must. Bring modest outfits that cover your shoulders and knees for visiting temples, along with comfortable walking shoes for all the exploring you’ll do. Swimwear is essential for beach days and hotel pools, and don’t forget bug spray and sunscreen—the tropical sun and mosquitoes are no joke. A portable charger will come in handy for long days out, and a light rain jacket or umbrella is smart if you’re traveling during the shoulder seasons. Everything from clothing to toiletries is incredibly affordable in Thailand, so it’s easy (and even fun) to under-pack and simply pick up anything you need at local markets once you arrive.
Cultural Etiquette
Respect plays a big role in Thai culture, and it often starts with the small things. Always remove your shoes before entering a temple or someone’s home, as a sign of cleanliness and respect. When visiting religious sites, be sure to dress modestly—clothing should cover your shoulders and knees. A respectful “wai” (palms pressed together with a slight bow) is a common greeting and is appreciated, especially when meeting elders or monks. Additionally, avoid touching anyone’s head, even playfully, as it is considered the most sacred part of the body in Thai culture.
Other Helpful Tips
Cash is king at markets and smaller shops, so it’s always smart to carry small denominations with you. When it comes to getting around, the Grab app is the easiest and most reliable option in cities—often cheaper and less confusing than taxis. Staying hydrated is important in Thailand’s tropical climate; bottled water is cheap and widely available almost everywhere. And don’t shy away from the street food scene—as long as you stick to busy, popular stalls, you’ll find some of the most delicious and authentic meals Thailand has to offer.
With a little preparation, traveling in Thailand is incredibly rewarding — and once you’re there, the warmth of the people and the beauty of the country will leave a lasting impression.
Final Thoughts on Our Two Weeks in Thailand
Our two weeks in Thailand were filled with unforgettable experiences, from the energy of Bangkok’s bustling streets to the serenity of Cheow Lan Lake in Khao Sok. We marveled at golden temples, haggled at colorful markets, feasted on incredible cuisine, and found peace floating on emerald-green lakes. Each destination offered something unique, yet everywhere we went, we were met with kindness, beauty, and a spirit of adventure.
If you’re planning a trip to Thailand, our advice is simple: dive in. Embrace the unexpected, try everything (especially the street food!), and leave plenty of space in your bag—and your heart—for the memories you’ll make along the way.
If you need help planning your own Thailand adventure, we’d love to help! As travel specialists, we can create a personalized itinerary tailored to your interests, style, and budget—so you can spend less time stressing and more time exploring. Reach out to start planning your dream trip today!
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