Jake and I did Thailand in December 2019, and I still think of it as one of our best-planned trips ever. Two weeks, five stops: Chiang Mai, Krabi, Koh Samui, and a quick Bangkok finale. (We came via Hong Kong, which gets its own post.) December is the sweet spot โ the heat drops to something manageable, the islands are gorgeous, and the north is cool enough for actual exploring. Here’s how we did it, in order.
Chiang Mai: temples, khao soi, and elephants
We flew Hong Kong to Chiang Mai on HK Express and landed around 6:50 pm โ about a 20-minute drive to the hotel, where we arrived around 8 or 9. First order of business: the Chiang Mai Night Bazaar, about a five-minute walk from Le Mรฉridien. Get your souvenirs here โ it genuinely isn’t a rip-off compared to other parts of Thailand.

Our one full sightseeing day started early, the way travel days should: we were up for the 6:45 sunrise with a plan to catch the 6:30 offering to a monk at Wat Sri Soda, at the base of Wat Phra That. (Worth noting the plan called this “potential negs” โ the very-early wake-up is a real cost, so know yourself.) From 7 to 9 we explored Wat Phra That Doi Suthep and the Bhubing Palace Gardens, then spent the rest of the morning wandering the old city, including the Terracotta Arts Museum.

Then: lunch at Khao Soi Lung Prakit Kaat Gorm, the khao soi spot made famous by Somebody Feed Phil. We got there at 11:30, and the doc’s all-caps warning held โ arrive before 1 or it will be sold out. This is the bowl I still think about: rich coconut curry broth, the crunchy noodle nest on top, lime and pickled mustard greens on the side. Chiang Mai’s signature dish at one of its best counters. Go early. No notes.

That afternoon we took a cooking class at BaanThai Cookery School at 4:30 โ one of those activities that sounds touristy and ends up being a highlight. There’s something about cooking the food yourself after eating it all week that locks it in differently.
Wednesday was animal day: 8:30 to 3:30 at Elephant Nature Park on the half-day tour, then back to the hotel pool for the rest of the afternoon (3:30 to 5:30 or 6), followed by Thai massages and a wander around 7 or 8. Dinner was street food at Chang Phueak Gate, the north gate โ a hard yes from the plan, and the detail I love most: the cowboy lady serving khao kha moo, stewed pork leg. If you see the cowboy lady at Chang Phueak Gate, you order the stewed pork leg. Trust me.

We checked out at 10:15 on Thursday, about 15 minutes from the airport, for Bangkok Airways to Krabi at 11:50, landing 1:45.
Krabi: Railay Beach and a day on the water
Krabi was a split hotel stay: one night at Bhu Nga Thani on Thursday, then Phulay Bay Resort Friday through Sunday. Pickup from the airport got us to the hotel around 3 on Thursday, and we headed straight to Railay Beach โ the kind of place where the limestone cliffs do all the talking.
Dinner Thursday was at The Grotto. The useful intel: they don’t take reservations for non-hotel guests, so you just walk in and wing it. Plan accordingly.
Friday was more Railay, plus Ao Phra Nang Beach & Caves โ “great,” per the itinerary, and I’d agree โ before switching over to Phulay Bay. Saturday was the Koh Hong day trip, one of those island days that’s basically a moving postcard. Sunday we took

it easy, checked out around 11 or 11:30, and caught Bangkok Airways to Koh Samui at 1:45, landing 2:35.
Koh Samui: two resorts, one marine park
Four nights on Koh Samui, split between two resorts: Banyan Tree from Sunday the 8th through Tuesday the 10th, then Vana Belle the 10th through the 12th. The drive from the airport was about 25 minutes; we were checked in by 3 or 3:30 Sunday afternoon.
Monday was the big day trip: Ang Thong National Marine Park, the archipelago off Koh Samui. The itinerary links a guide with the note “(sick)” โ Gen-Z travel-speak for unmissable โ and the viewpoint from the marine park is one of those places that makes you put the camera down for a minute. It’s genuinely one of the best day trips on the island.
Tuesday we switched to Vana Belle and kept it simple: Chaweng Beach and Lamai Beach both looked great, so we did both. Wednesday was our last full beach day โ no agenda, which is exactly how a last beach day should be. Thursday we were up at 6


(beach sunrise, maybe), checked out at 8:20, and flew Bangkok Airways to Bangkok at 10:05, landing 11:20.
Bangkok: 48 hours, five stops, one legend
We stayed at the Grand Hyatt Erawan and landed Thursday around 12:30 or 1 after the 35-minute drive. Thursday afternoon and evening were packed on purpose: the royal barge at 3:30, a sky bar for sunset drinks from 5 to 6:30 (sunset at 5:51), and specifically Red Sky Bar โ the plan says go here on Thursday. Then the main event: Raan Jay Fai at 7:30. Jay Fai โ the goggles, the crab omelette, the Michelin star โ needs no introduction from me, but: this was the dinner I was most excited about on the whole trip. Worth every bit of the hype.
Friday was the classic Bangkok day: the Grand Palace and Wat Pho with the reclining Buddha in the morning, then pool and park time. That evening: drinks with Uncle Tom, Cru Champagne Bar at 5 for sunset drinks (sunset 5:51 again), and

Chinatown for dinner. Saturday we checked out around 8 or 8:30 for the 10:55 flight home via Taipei.
Where I stayed
- Le Mรฉridien Chiang Mai โ well located for the Night Bazaar (five-minute walk), a solid base for the temple-heavy days.
- Bhu Nga Thani โ one night before the switch; convenient Krabi landing pad.
- Phulay Bay Resort โ the Krabi splurge, Friday through Sunday.
- Banyan Tree Koh Samui โ first two nights on the island.
- Vana Belle Koh Samui โ the last two nights; easy beach days.
- Grand Hyatt Erawan Bangkok โ two nights in the heart of it all for the finale.
From Bangkok we flew home via Taipei โ two weeks, five stops, and a bowl of khao soi I’d fly back for tomorrow.
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