I’ll be honest: Before I went to Thailand, I just kind of imagined it as one big beach. The reality is that Thailand is just about as diverse as a country can get. The beaches have very little in common with the big cities and likewise, the rural towns also feel like a completely different world entirely. This first-time itinerary begins in Bangkok and moves more-or-less south to Railay. From there, you can likely fly out of the airports in either Krabi or Phuket, or easily grab a cheap flight or bus back to Bangkok.
Bangkok: 2 days
For most travelers, Bangkok is the wild, brash, out-my-god-I’m-can’t-believe-I’m-in-Thailand introduction to the country. It’s dirty and gritty around some corners, and extremely modern and sophisticated around others. There are plenty of temples and other attractions to see in Bangkok, but I’ve always preferred to just wander around and eat street food. Particularly when you first arrive, there’s no better way to get acclimatized to Thailand.
Ayutthaya: 1 day
It’s easy to visit Ayutthaya as a day-trip from Bangkok or, of course, you can stay overnight too. The city was an ancient Thai capital between the 14th and 18th centuries, and its Phra Nakhon Si Ayutthaya Historical Park is a UNESCO World Heritage Site. Personally, I’m more enthralled with historic religious monuments than modern ones, so Ayutthaya was the perfect place for me to experience the more cultural side of Thailand. For a few dollars, you can rent a bike and then ride around and explore the ruins at your own pace.
Kanchanaburi: 3 days
Kanchanaburi is a chilled-out little riverside town, probably best known for its association with the book and movie the Bridge Over the River Kwai. The town is home to a number of memorials and attractions, including the infamous bridge, connected to the dark events that took place here during WWII. On a lighter note, the surrounding province (also called Kanchanburi) has over seven national parks, so the city is a great base for trekking to jungles, rivers, waterfalls, and lakes. Although Kanchanaburi is not exactly off-the-beaten track, it does give you a small taste of what Thailand looks like outside the big cities and beach resorts.
Koh Chang: 3 days
Koh Chang is one of my favorite Thai islands. The colors of the water and sand aren’t as dramatic as you’ll see on the islands further south, but the beaches are still beautiful nonetheless. There’s no denying that development is happening quickly here – I saw construction almost everywhere I went and new hotels seem to be opening every day – but it’s still much more relaxed than tourist-tired islands like Phuket and Koh Samui. On the east coast of the island, you can still find traditional fishing villages where locals continue on with their way of life in spite of the backpackers drinking Chang beers on the beaches nearby. Plus, the interior of this large island is still mostly dense rainforest, so you can mix a few hikes in with your beachside time.
Koh Phangan: 3 days
Koh Phangan is most often associated with the Full Moon Party, but there’s a lot more to this island than buckets and body paint. Of course, that’s not to say you shouldn’t go to the legendary party – I definitely needed to experience it just once – but it’s definitely worth hanging around the island for a few days before or after to see Koh Phangan in its less-frenzied form. There are more than a dozen beaches scattered around the island, many of which live up to all those tropical beach fantasies of pearly white sands and turquoise waters. The island is relatively small and the roads are decent, so you can base yourself on one beach, and then rent a bike or motorbike to explore the rest of the island. Another option is to split your time between here and Koh Tao, which is only a short boat ride away.
Railay: 2 days
Railay feels like an island, but it’s actually just separated from the Krabi mainland by a stretch of massive limestone cliffs. If you’ve ever spent time day-dreaming over Google images of Thailand, you’ve probably seen Railay’s iconic Phra Nang Bay. Aside from being really darn pretty, Railay is one of the world’s top rock climbing destinations and, in the evening, you can watch groups of wild monkeys descend from the trees and make their way down to the beach. It’s as good a place as any to finish a trip; or, if you have more time, you can reach a number of islands within a few hours by boat from here, including Ko Phi Phi, Ko Lanta and Phuket.