Before we dive in and lay out the best 2-week Thailand itinerary, lemme start by saying…I FREAKING LOVE THAILAND. It’s a beautiful country with loving, hospitable people, mouth-watering food, and some of the most breathtaking landscapes you will ever see. It’s no surprise it’s called the “land of smiles”. There wasn’t a single Thai we met who wasn’t absolutely gracious and welcoming. If you have the chance to spend time getting to know some locals, definitely do so. 

Thailand isn’t a small country. There is SO much to see. While you could easily spend 6 months exploring, most of us don’t have that flexibility (or vacation time). Two weeks in Thailand is a great way to see some of the country’s highlights while maximizing your vacation time. In two short weeks we completely fell in love with Thailand and will 100% go back. 

You don’t wanna be THAT tourist, so let’s first chat real quick about some do’s and don’ts in Thai culture:

• DO learn a few sayings in Thai. If you only learn two things in thai, learn hello and thank you. Learning how to say just these two things is a super easy way to show Thai’s that you respect their culture. Note, there is no exact way to transliterate the Thai language to written English, so you are likely to see the same thing spelled multiple different ways (this can get confusing when you look up places in Google). Thai’s differentiate between if the speaker is a male or female. If you are a female, you add “ka” to the end, if you are a male, you add “krab” to the end
  • Hello – sawasdee ka/krab pronounced “sah-wah-dee”
  • Thank You – khob khun ka/krab pronounced as it looks
• DO smile! It’s a great way to show locals how happy you are to be visiting their country, and may even open up the possibility for a conversation. Thailand is not one of the country’s where you should avoid making eye contact with people.
• DO dress appropriately. Thai culture is more conservative than us westerners are probably used to, so please don’t walk around in short shorts and tank tops. It’s fairly easy to dress appropriately. I wore loose flowing pants and skirts and short sleeved shirts. Austin wore shorts and short sleeved shirts (aka just his normal clothes). Note that some temples will require men to have long pants, so it’s worth carrying a pair of loose pants around with you in case you need them. 

• Do practice appropriate temple etiquette. A proper visit to Thailand wouldn’t be complete without visiting at least a few wats. Just make sure you are doing so in a way that is respectful to these religious sites. For more in-depth temple etiquette read this article.
• DON’T touch Thai people’s heads. The feet are considered the dirtiest part of the body, while the head is the cleanest and holiest. I’m not sure WHY you would ever touch someone else’s head that you don’t know, but just be aware of it and make sure not to.
• DON’T touch monks. Interacting with the monks at Thai temples is a super unique way to learn about monkhood and Thai culture. If you have a chance to engage with a monk, please note monks are not allowed to touch women during their monkhood (including their family members). If you are a woman and need to hand anything to a monk, like a pen or money, use your right hand to set it down where they can pick it up.
• DON’T point at things with your feet. In the same vein as the head being sacred, your feet are deemed unclean. Don’t point to things on shelves etc. using your feet. It’s considered disrespectful.
• DON’T talk negatively about the monarchy. It’s against the law to disrespect the royal family, so keep any negative thoughts about the monarchy to yourself. Personally, I just avoided the topic altogether. We actually had a Grab driver talk about how corrupt he thought the monarchy was & I was so uncomfortable I just sat there and nodded along because I was so unsure how to act.

Now that we know how to respect Thai culture and not piss anyone off, let’s get to your 2-Week Thailand Itinerary!!

2-Week Thailand Itinerary

Likelihood is your 2-week Thailand itinerary will begin and end with flights in and out of Bangkok, the country’s capital city, so you might as well spend a few days thriving in the chaos. The differences between the more historic and more modern parts are so drastic that I seriously had to keep reminding myself we were still in the same city. For this reason, we chose to bookend the beginning and end of our trip with Bangkok.

Below is our recommended 2 week Thailand itinerary. This can easily be adjusted if you have more or less time available! Below is a general timeline, then we will delve deeper into the highlights and tips of each spot. So let’s do it!

Bangkok – 3 Nights

Ayutthaya – Day Trip

Chiang Mai – 3 Nights

Koh Lanta – 3 Nights

Khao Sok Lake – 2 Nights

Bangkok – 2 Nights

Bangkok – 3 Nights

Bangkok’s a city with unparalleled character and truly feels so woven into the fabric of Thai culture that I really don’t think you can skip it. The second you walk out of that airport, you’ll know you’re in Bangkok. Immediately the air hits you in the face filled with humidity and hints of gasoline and spices. There’s so much you can see or do in Bangkok, but don’t get overwhelmed by it! The chaos is all part of the experience – just try not to get run over by the mopeds. 

For the first stop in Bangkok I recommend staying in the Riverside Area and focusing on historical and cultural sights. We stayed in Riva Arun, directly on the Chao Phraya River. It was conveniently located within walking distance of major cultural sites and we had great views of Wat Arun directly from our balcony.  Below are some quick ideas of things to do in Bangkok, for a more in-depth look at what’s worth your time and what isn’t, check out the Best and Worst Bangkok Tourist Spots in 2020. In the historic areas it’s pretty easy to walk around, but once your feet are exhausted either call a Grab (Thailand’s Uber) or a hail down a tuk-tuk. 

Things to do in Bangkok

• Wat Pho – home of the famous Reclining Buddha. Make sure to get there pretty early in the morning, we went at 8 am and beat most of the crowds. I’d recommend heading to see the Reclining Buddha first, but don’t rush out after that, there are tons of beautiful things to see at Wat Pho. It is also considered the spiritual home of Thai massages, and you can still pay to get one on your visit.

• Wat Arun – Known as the “Temple of the Dawn” for the way it glows in the (you guessed it) dawn, it’s one of Bangkok’s most iconic landmarks. Personally I preferred Wat Pho, but Wat Arun is definitely worth heading over to, even if just for the ferry ride across the Chao Phraya River. Again, this is a popular spot that gets crowded quickly, so either go early in the morning or just before sunset.
• Drinks on a rooftop bar overlooking the Chao Phraya River – There are lots of bars and hotels offering views of the river. We just got drinks on the rooftop of our hotel (Riva Arun – LINK) where the drinks were really overpriced, but we were so jetlagged we didn’t care, and it ended up being a spectacular place to watch the sunset behind Wat Arun.
• Chatuchak Weekend Market – Only open on the weekends. One of my biggest regrets in our 2-Week Thailand Itinerary was not making it to the Weekend Market. The only day we could go I was so jet-lagged I didn’t have the energy, but I wish I’d pushed through!

Ayutthaya – Day Trip from Bangkok

A day trip to Ayutthaya in your 2-week Thailand itinerary is absolutely worth it. It’s only about an hour and a half drive from Bangkok. The best way is to hire a driver for the day who can drive you to Ayutthaya, take you from site to site, and get you back to Bangkok before dinner. Ayutthaya is the old capital of historic Thailand, back when it was the Kingdom of Siam. The city was destroyed by the Burmese army in 1767 and the ruins of the old city are an UNESCO World Heritage Site.

A common mistake is thinking the ruins are at one location, in a centralized area. On the contrary, the ruins are sprawling all throughout the city. It feels like around every corner is a ruin with a plaque in Thai describing the significance (too bad I can’t read Thai). I’d highly recommend hiring a tour guide. We didn’t do this and really regret it. The ruins are beautiful and impactful, but it’s hard to get a full appreciation for everything when you don’t really know what it all means.

Must See Ruins in Ayutthaya

• Wat Yai Chai Mongkhon – I’d start with this one as it gets pretty crowded so it’s best first thing in the morning.

• Wat Phra Sri Sanphet – the largest ruin site we walked around. We spent around an hour exploring the grounds. It was the holiest temple of the Royal Palace and is a definite must-see.
• Wat Chaiwatthanaram – one of Ayutthaya’s better known ruins. It’s beautiful even to this day. Seeing the de-headed Buddas and burn marks reallys helps grasp the gravity of what happened to this ancient city.

Chiang Mai- 3 Nights

After spending just a few days in Chiang Mai in our 2-week Thailand itinerary, I decided I could live here (no seriously, I asked Austin if we should go home, get our dog, and move to Thailand). Unlike Bangkok, Chiang Mai has a much more relaxed atmosphere. It’s a city offering local markets, trendy cafes, beautiful scenery, boutique shopping, and so much more. The older parts of the city are surrounded by an 800 year old wall and moat. How cool right?? A real moat. I don’t think there are any alligators unfortunately though. Outside the ancient walls lies Nimmanhaemin Road. A trendy district with artisy shops and modern malls that’s definitely worth a stroll..

One of the most unique things about Chiang Mai is how you get around.  In contrast with Bangkok, metered taxis are hard to find. Instead they have a collection of red pickup trucks called songthaews (pronounced song-tao). Note, there are other colors of songthaews, but the red ones are the ones that stay around Chiang Mai, other colors drive to outside areas. Songthaew literally means two-rows, which makes sense because the back of the trucks have 2 rows of benches accommodating around 10 passengers max. They’re super easy to use once you get the hang of it. Unlike regular taxis, you don’t just hop in and tell them where you’re going. The songthaews are comparable to a city bus. They go in one direction, and you hop on and off as you please. If you try to get one to stop and they wave you away, they aren’t being rude, they’re probably full or they’ve been hired for a private ride (more on that later). Once you get on, enjoy the ride, and press the buttons on the wall to ding the driver, letting them know you’re ready to hop off. Easy! The rides usually cost 20-100 baht per person depending on how far you’re going. Definitely the cheapest way to get around Chiang Mai, and IMO the most fun.

Things to do in Chiang Mai

• Blind Massage at Thai Massage Conservation Club – HANDS DOWN one of my favorite experiences in Thailand, and honestly maybe my whole life. If there’s only one things from this 2 week Thailand itinerary that you choose to do, this should be it. Thai’s have realized blind massage therapists are the best at providing massages because due to their loss of one sense, they have increased their sensitivity of another sense, touch. After spending 2 hours with a blind masseuse, I have to say they are 100% correct. This massage was nothing like the typical relaxing massages we have in the States. Far from it. Everyone is in the same room with massage tables spread out every 3 feet or so. No music. No oils. If I reached out I could have touched the tables on either side of me. We originally booked two 1-hour massages. About 12 minutes in I asked to extend both our massages to 2 hours. SO WORTH IT. Go, and get a 2 hour massage. Don’t even think of going for less than 2 hours. You’ll just end up extending it. 
  • 99 Ratchamanka Rd, Tambon Phra Sing, Mueang Chiang Mai District, Chiang Mai 50200, Thailand

• Doi Suthep Temple – Doi Suthep is the famous mountain temple about 45 minutes outside of Chiang Mai. The easiest way to get there is to take a songthaew. You can either hop in one that drives up and down all day or you can hire a driver to take you up, wait for you, and drive you back down. We paid a songthaew 300 baht each way to drive us up and wait for us. Either way, my recommendation is to go as early as possible. We went around 11am and it was already way too crowded to get any good photos of those beautiful dragon steps or enjoy the temple without being shoulder to shoulder with all the other tourists.
• Warorot Market – Skip the Chiang Mai Night Bazaar which is full of tourists, and head over to the Warorot Market for an authentic night market experience. The best meal we had in Thailand was from a vendor at the Warorot Market. It was a spicy noodle dish that cost around 30 baht (~ $1) and while it didn’t look like much, it was UNREAL. We ate it in the middle of the street while mopeds zipped by, really topping off the whole experience.

Koh Lanta – 3 Nights

Are you wat’d out yet?? Now that you’ve had your fill of Thai city life, it’s time to slow down and experience some of the most beautiful landscapes you’ve ever seen. If there’s one thing Thailand isn’t lacking, it’s gorgeous islands. If you’re anything like us, picking which island to visit can be a tough decision to make. We knew we didn’t want to go to Phuket because we were looking for a more authentic experience. After narrowing it down to Koh Samui and Koh Lanta, we made the BEST decision (IMO) and spent 3 nights in Koh Lanta. .

Once you’ve decided you agree with me, grab a flight from Chiang Mai to Krabi. We stayed at the Twin Lotus Resort & Spa and were able to utilize their airport shuttle service for the 2 hour drive and ferry to the island from the Krabi airport. Koh Lanta has a little bit of everything. There’s a small shopping district on the north side of the island, local markets on the weekends, and breathtaking beaches stretching up and down the island. One of the main reasons we picked Koh Lanta was its proximity to Koh Haa. Koh Haa is a small collection of 5 islands (Haa is five in Thai) known for their incredible snorkeling and diving. 10/10 would recommend. 

Things to do in Koh Lanta

• Snorkel or dive tour to Koh Haa – we booked ours through Hidden Depths tours. They are absolutely amazing and I couldn’t recommend them enough. The tour picks you up from your resort and brings you to the pier where you’ll meet up with the rest of the group. We loved that they only take 15 or so guests at a time so it’s a great way to meet other travellers as well.
• Self-guided moped tour – I was originally super against renting a moped in Thailand because we’ve all heard horror stories about tourists in foreign countries ending up in horrible motorbike accidents. After being in Bangkok and Chiang Mai I knew there was no way we could survive those roads, but thankfully Koh Lanta isn’t anything like that. The roads are large, uncongested, and easy to navigate. Hands down, our overall favorite day in Thailand was the day we rented a moped and drove up and down the west side of Koh Lanta. A 24-hour rental should cost no more than 200-300 baht making it by far the cheapest and easiest way to see all Koh Lanta has to offer. Spending a day stopping at any scenic viewpoint, restaurant, bar, or beach you see is absolutely the best way to experience Koh Lanta. Hit some of these highlights on your self-guided moped tour:

• Diamond Cliff Restaurant for the views and a smoothie

• Ploy Pai Lin Restaurant enjoy THE BEST LUNCH VIEWS of all time.

• Hike to Khlong Chak Waterfall & Bat Cave

• Walk out to the southern tip of the island at Mu Ko Lanta National Park (watch out for the monkeys, they will take your shit)

• Why Not Bar for an evening drink on the beach

• Freedom Bar to watch the sunset

Khao Sok National Park – 2 Nights.

Are you prepared for the most serene experience of your 2 week Thailand itinerary, and possibly your whole life?? Awesome. You’re ready to cut off from society for a few days on Cheow Lan Lake. We booked our 2 night stay with Khao Sok Lake Tours in a Modern Comforts room, but I would recommend you book the next level up if you can. Our room was doable, but I would’ve preferred something a tad nicer that maybe didn’t come with a 5 inch spider in our bathroom (I used the community bathrooms the whole time we were there because of our unwanted guest). Beyond our spider intruder, everything about our Khao Sok experience was amazing. For a reasonable fee, they can transport you from the airport, or an alternate location within a few hours drive. They picked us up directly at our hotel in Koh Lanta, had us swap vans after the ferry, and then drove us all the way to the main office of Khao Sok Lake tours where we met up with our guides.

Book through the same company we did and make sure you ask for Kim as your guide. For 3 days and 2 nights it was just Austin and I, our guide Kim, and our thai longtail boat driver, Sun. We learned so much from Kim about the history of the lake on our safari boat tours and even more about the jungle and it’s inhabitants on our jungle walks. Kim has such an immense love for the jungle, and it really shows. We had the unparalleled opportunity to appreciate the lake and animals through his eyes. But the true highlight of our time in Khao Sok was Kim himself..

If you aren’t impressed by him, I don’t know what could ever impress you. For a few years, he had predominantly German guests after a German couple did a tour and wrote a travel guide about it, so he knows like 4 languages fluently even though he hasn’t been to school since he was a child. He can tear off a piece of grass while walking and turn it into a beautiful braided ring, custom fit to your hand. And his laugh will make anyone light up. .

If Kim isn’t enough to convince you to spend a few nights sleeping in a floating bungalow, the views outta be. Being on Cheow Lan Lake is one of those experiences where it’s hard for your brain to even grasp how breathtaking the views around you are. The cliffs towering over you as you fly by on a traditional thai longtail boat feels like a scene out of a movie. Go to Khao Sok, you won’t be disappointed.

Bangkok – 2 Nights

Unfortunately, it’s time to head back to Bangkok to soak up the last bit of Thai culture before you gotta leave. But this time, stay in the modern side of Bangkok. It’ll be hard to tell you’re even in the same city as last time. We stayed at Hotel Muse. It’s a bit pricey, but the location is phenomenal and we fully enjoyed the luxury after spending 3 days on a lake. How you spend your last few days in Bangkok depends on what you’re feeling up to. We chose to spend our days wandering the streets drinking Thai iced coffee, shopping for last minute souvenirs, getting foot massages before those long-haul flights home, and eating all the street food we could get our hands on. 

Things to do in modern Bangkok

• Get a Rooftop Drink in the City – I don’t know about you but I’m a sucker for a good rooftop bar. We chose to go for the well known Lebua Tower, made famous from The Hangover Part II. It’s on the 63rd floor and super touristy, but it definitely provides some breathtaking views of the City. If you go, get in line before they open at 6pm to avoid the crowds, and stay until after the sun sets. While there’s no entrance fee they make up for it with insanely expensive drinks (I’m talking $25+ cocktail’s), but it’s totally worth it.  They have a fairly strict dress code, no sandals for men, no hats, no graphic tees, etc. Not too hard to abide by but you will need to plan ahead. We also got drinks on the rooftop of our hotel, Hotel Muse. The views weren’t nearly as impressive, but it was a great atmosphere and a lot more relaxed than Lebua. If you grab a drink at Hotel Muse, you HAVE to get the spicy cocktail, it’s seriously the best cocktail I’ve ever had.
• Visit a Mall – I usually hate malls, but we walked through the MBK Shopping Center and it is NOTHING like American malls. It’s like a street market with hundreds of vendors, but crammed into a modern building. I wouldn’t say it’s a must do experience, but it’s a really cool way to spend a few hours. We opted for a few slices of the famous Coconut Custard Toast at Mont Nom Sod, highly recommend. Also a good place to grab a few souvenirs for family and friends back home.
• Drink the best Orange Juice of your life at Thip Samai – Thip Samai is famous for having the world’s best Pad Thai. People line up hours before they open for the chance to get a plate of Pad Thai wrapped in an egg (honestly, it’s amazing how they do this, I had to see it to understand it). We waited for about an hour and a half and ordered 2 plates of Pad Thai, and 2 large bottles of the famous fresh squeezed orange juice. The bottles of OJ will set you back 3 times as much as the Pad Thai will, and IT’S SO WORTH IT. If you want to wait in line to try the Pad Thai, I won’t stop you, but the OJ is easily the best part (TBH I wasn’t all that impressed with the Pad Thai anyways).

Are you planning a trip to Thailand? Ask me anything! I’d love to help. 

Additional Travel Tips

• Eat so much street food – Street food is what makes Bangkok, well, Bangkok. It’s everywhere you go, at every hour of the day. The quality of food you can eat at a “pop-up” restaurant on the sidewalk is unreal. Don’t be afraid of eating street food. There are a few easy rules to follow to make sure you’re safe eating at a vendor:
  • If the food is already made and just sitting there, don’t get it, make sure they are actively cooking your food
  • Don’t get drinks with chipped ice, only the long tubular ice
  • If there’s a line of people waiting, 100% go there. Doesn’t matter what it is, it’ll be good.
• Walk 5-8 minutes off the beaten path – Here’s a tip to make the absolute best of your 2-week Thailand itinerary: After hitting up a popular attraction or tourist spot, walk 5-8 minutes away from the action. The shops, bars, restaurants, and crowds around high traffic tourist spots are usually overpriced and unauthentic. But, you can typically find more authentic and local food carts and shops just a few blocks away from the major attractions. Some of the best ways to experience a city is to wander around aimlessly and enjoy it without an itinerary. We’ve found some of our favorite souvenirs, meals, and experiences this way!

• Travel sustainably – Let’s be real, everyone cares (at least on some level I hope) about the environment. No one who travels WANTS to be an irresponsible tourist, but that being said, we don’t always realize the negative effects we’re having on a community (guilty as charged). Therefore, knowing is half the battle. When you travel, you’re taking action with your money, voting with your choices, and impacting local communities with your wallet. The focus of responsible travel is to make conscious travel decisions that protect and respect the communities you’re visiting. Read this article for tips on how to be a responsible tourist.
• Ask a friend – Chances are you probably know someone who has been to Bangkok! Ask them their favorite part, the most delicious dish they tried, and what they wished they would’ve done differently. Asking for help is almost always a good idea, especially when it comes to travel recommendations!