Two Weeks in Thailand: Ultimate Bucket List Itinerary
Creating the ultimate itinerary for two weeks in Thailand was not easy, but so worth it. I have always wanted to go to Thailand. Elephants? Check. Jungles? Check. Beaches? Check. Pad Thai? Check.
For those reasons and more, Thailand has consistently held a solid position at the very top of my bucket list.
Not wanting to delay my dream any further, I sacrificed opportunities to take shorter domestic trips and actively saved up my precious American vacation time (and money) to finally venture off to Asia. Regardless of many internet recommendations to spend at least a month in Thailand, I was determined to create an itinerary that would make the most of my non-negotiable two weeks.
CREATING AN Itinerary FOR TWO WEEKS IN THAILAND
I spent countless hours and late nights researching and creating a Thailand itinerary that would maximize every single moment of my two weeks. After I got back from Thailand, so many of my friends and family members wanted to know how my trip went (I said the word “amazing” a lot during this period of my life). Moreover, they wanted to know: how did I plan it? The truth is, as much as I love planning and curating unique trips, Thailand was pretty difficult to plan.
Planning an itinerary for two weeks in Thailand, a continent I had never touched, was hard. I didn’t have the luxury of multiple weeks of vacation time, nor the luxury of knowing I would have a lot of time left in my future to make a return trip. The whole “going blind thing” really adds extra weight as I am frequently stressed out about potentially missing out on something I would have wanted to see.
Accordingly, I was on the hunt for experienced, honest bloggers who could tell me how I should best utilize my two weeks in Thailand and create the perfect itinerary for a first-time visitor. As fun as that hunt sounds, the problem with so many blogs is they definitely have great content, but it is seriously time-consuming to weed through everything.
BEST BUCKET LIST ITINERARY FOR TWO WEEKS IN THAILAND
In knowing there are others out there dreaming of checking Thailand off their bucket list, but facing the same “it’s so hard to plan” predicament, I want to share my straight-to-the-point two-week Thailand itinerary in the hopes of making your life a little easier. Without hesitation, I can honestly say this itinerary is awesome AND it is ideal for first-time visitors. You will experience so many bucket list adventures!
TWO WEEKS IN THAILAND: ITINERARY WEEK 1
Also, you’ll notice the total days add up to more than 14, but that’s because I include travel/transportation days since those always count in my mind! Week 1/Day #1 for this itinerary starts on a Friday.
DAY #1 & #2 • depart FOR THAILAND!
Flight: Depart Boston (BOS) @ 5:40pm, Arrive Los Angeles (LAX) @ 9:06p
I always include travel days in my itineraries. After all, a long layover might provide the opportunity to add in some fun activities. In this case, though, my layover consisted of lots of waiting around in LAX until my next flight.
Depending on where you are flying from, the goal is to book a flight journey that will have you landing in your final destination (Bangkok) at an ideal hour. For me, this meant departing from Boston and connecting in Los Angeles and Beijing. Boston has direct flights to China but my budget didn’t allow for that luxury.
Flight: Depart Los Angeles (LAX) @ 1:40am, Arrive Beijing (PEK) @ +5:20am
I left Los Angeles early Saturday morning to embark across the Pacific. At 13 hours long, the flight from LAX to PEK was the longest flight I’ve ever taken! It was a weird sensation being on an airplane for so long. After a while, I just stopped looking at the time and faded in and out of sleep.
Sleep: Airplane
DAY #3 • ACTUAL START OF TWO WEEKS IN THAILAND
Flight: Depart Beijing (PEK) @ 8:15am, Arrive Bangkok (BKK) @ 12:30pm
Disoriented from a 13 hour plane ride and facing a wild shift in time zones, the Beijing airport was certainly a unique experience. I was mostly fascinated by China’s intense security, requiring transit passengers to go through customs/border control twice. Additionally, no cell phones were allowed to be used, even on airplane mode, for the entire duration of my final 5-hour flight (I was so bored).
Finally Land in Bangkok!!
Woo – made it to Thailand! This is where the two weeks in Thailand itinerary really begins. Once you land and pass through customs in Bangkok (much easier than in China), take the SRTET City Line from the airport to Phaya Thai (~26 min, 7 stops). You could take a taxi from the airport to the city but the train gives you the chance the dive straight into the full Bangkok experience.
Once you arrive at the Phaya Thai stop, use the app ‘Grab’ to order a taxi to take you to Loogchoob Homestay.
Photo Credit: Loogchoob Homestay 
Photo Credit: Loogchoob Homestay
You will be exhausted from flights and time changes so I recommend spending the afternoon walking in the vicinity of the hotel, experiencing culture shock, and eating street food.
Sleep: Loogchoob Homestay (Bangkok)
DAY #4 • EXPLORE BANGKOK
First stop = coffee. After careful research (decent coffee is essential for my functioning), I found Snooze Coffee House Restaurant. If you are looking for a great coffee shop in Bangkok, look no further. Then, from the coffee shop, walk about 5 minutes to take the Chao Phraya Express Boat from the Rama 8 Bridge stop.
Using the boat to get around, spend the day exploring the major sights of Bangkok, including the Temple of Emerald Buddha, Wat Pho, and Wat Arun. Walk the city streets extensively, perhaps pausing for a dessert break at the beautiful riverfront Mandarin Oriental hotel. Finish the day by checking out a staple of the modern city, a massive mall called Siam Discovery.
Sleep: Loogchoob Homestay (Bangkok)
DAY #5 • Bangkok to Chiang Mai
Waking up early (still not sure what time my body thinks it is), I took a pre-scheduled taxi, which was coordinated with the Loogchoob Homestay host night before, to the Bangkok DMK airport. DMK is quicker to get to than BKK and offers a number of flights with low-cost airlines.
Flight: Depart Bangkok (DKK) @ 10:30am, Arrive Chiang Mai (CNX) @ 12:40pm
Upon landing in Chiang Mai, practice your negotiation skills to get an airport taxi to Chiang Mai’s Old City. Check into the Thailand Guest House, then walk straight to Sense Massage & Spa. There are a lot of spas in Chiang Mai, but Sense Massage & Spa was conveniently recommended by my dental hygienist who honeymooned in Thailand. Enjoy a 2-hour luxurious spa treatment for the amazing price of $40 USD.
After the spa, casually walk around the Old City of Chiang Mai, taking in the sights that differ quite a bit from Bangkok. Chiang Mai feels much calmer and more manageable than Bangkok.
While walking around, there are many fish spas offering people the chance to let fish nibble dead skin from their feet. I initially heard of this spa treatment from the Kardashians (naturally), so I had to try out this bizarre experience. I ended up stopping in Beary Bear Fish Spa; it seemed well-run. There really is nothing quite like the sensation of fish nibbling on your feet… but I still recommend It.
Sleep: Thailand Guest House (Chiang Mai – Old City)
DAY #6 • EXPLORE CHIANG MAI
My Chiang Mai coffee recommendation is Coffee Lovers. On this day, I walked a ton, embracing Chiang Mai’s laid back vibe and visiting the Wat Chedi Luang Temple.
At the Temple, I stumbled upon an outdoor classroom set up under a tent. Buddhist monks were sharing intimate conversations with the public about their experience in the monastery. I chatted for a bit with a monk my brother’s age (20), it was an absolutely fascinating conversation as he was quite open to answering my endless list of questions.
In the evening, I took a negotiated taxi to Doi Suthep, a mountaintop temple. After climbing the many steps to the top, I explored the temple and watched the sunset over the city.
Sleep: Thailand Guest House (Chiang Mai – Old City)
DAY #7 • VISIT ELEPHANT NATURE PARK
An itinerary for two weeks in Thailand would not be complete without seeing elephants! I booked the Elephant Nature Park experience well in advance, prior to having any sort of plan in place for my trip. Elephant Nature Park is one of the very few ethical sanctuaries in Thailand and overnight stays book out remarkably fast (understandably).
Meeting at the Elephant Nature Park office in Chiang Mai, head out on a group bus to spend the day and night at the sanctuary.
Sleep: Overnight Elephant Nature Park Package (Elephant Nature Park)
DAY #8 • CHIANG MAI Lantern Festival (CAREFULLY TIME YOUR TWO WEEKS IN THAILAND*)
After saying goodbye to the elephants, return to Chiang Mai via the Elephant Nature Park tour bus. Entirely coincidental, I was in Chiang Mai during the world-famous Thailand festival known as Loi Krathong. Loi Krathong celebrations occur throughout the country and in Chiang Mai, specifically, there is the lantern festival called Yi Peng.
*If you schedule your trip to Thailand during the full moon of the 12th Thai Month, you can partake in the annual festival celebrations of Loi Krathong. If you arrange to be in Chiang Mai, specifically, you can witness Loi Krathong overlap with the lantern festival, Yi Peng.
TRAVEL TIP
I got extremely lucky and just by chanced booked my two weeks in Thailand and Chiang Mai visit during this exact time! Make sure to book accommodation that allows easy access to ideal lantern release and viewing locations.
Sleep: Baan Songum (Chiang Mai)
DAY #9 • EXPLORE CHIANG MAI
My Chiang Mai coffee recommendation: MAR Marocchino
In a new area of the city, spend day #9 walking around and getting to know more of Chiang Mai.
Sleep: Baan Songum (Chiang Mai)
TWO WEEKS IN THAILAND: ITINERARY WEEK 2
Day #10 started on a Sunday so I’m considering this the start of itinerary week two in Thailand!
DAY #10 • TRAVEL TO KHAO SOK NATIONAL PARK
Flight: Depart Chiang Mai (CNX) @ 7:10am, Arrive Surat Thani (URT) @ 9:05am
Getting to Khao Sok National Park, specifically from Surat Thani airport, was the trickiest part of the trip so I dedicated a separate blog post to explain how I made it work.
Sleep: Khao Sok Silver Cliff Resort (Khao Sok National Park)
DAY #11 • KHAO SOK NATIONAL PARK
Rather than attempt to book a tour online in advance, I booked my Khao Sok National Park tour once I arrived at the Khao Sok Silver Cliff Resort. The owner, a super sweet woman from Scotland, had a booklet with her favorite, affordably priced tours. I ultimately went with a day tour that included exploring Cheow Larn Lake by boat, lunch, and a jungle hike. The hike had the option of going into underwater caves, but while the group headed into the dark abyss, I relaxed outside the cave to avoid my worst nightmare.
When hiking, consider wearing leggings (or long pants if you are a guy!). Leeches are plentiful and will not hesitate to find their way to your skin as you walk through the wet rainforest.
TRAVEL TIP
Sleep: Khao Sok Silver Cliff Resort (Khao Sok National Park)
DAY #12 • TRAVEL TO Railay Beach
With the help of Khao Sok Silver Cliff Resort, I arranged to join a minibus to get from Khao Sok National Park to Ao Nang Beach. The trip took approximately 2.5 hours. Once at Ao Nang Beach, I took a commuter boat to Railay Beach.
The boats run all day from Ao Nang Beach to Railay Beach and take ~15 minutes and cost $60 THB. I then spent the evening wandering the sandy paths of Railay Beach.
I decided to stay in Railay Beach as it seemed like a more beautiful, less touristy option than some of the other areas, like Krabi. With limestone cliffs isolating Railay Beach from the mainland, and the only access via boat, I was excited to venture to a unique “island.” The beauty of Railay Beach certainly exceeded my expectations!
Sleep: Avatar Railay (Railay Beach)
DAY #13 • RELAX AT Railay Beach
After my jungle experience in Khao Sok National Park and traveling to Railay Beach, I spent most of the day relaxing. Phra Nang Beach and Pranang Cave are two highlights of Railay Beach, as well as the East and West sides of Railay Beach.
There are monkeys everywhere in Railay Beach. Do not feed them or make any eye contact as they will take your things or bite you.
TRAVEL TIP
Where to Eat in Railay Beach: Kohinoor Indian Restaurant & Pizza
Sleep: Avatar Railay (Railay Beach)
DAY #14 • TRAVEL TO Ko Lanta
Leaving Railay Beach, I took an early boat back to Ao Nang Beach. There, I negotiated a taxi from Ao Nang Beach to Krabi Airport in order to meet the driver of Pimalai Resort & Spa. I had pre-booked this arrangement and it was included with my Pimalai hotel reservation.
The driver took me to a dock where I boarded the hotel’s private boat to Ko Lanta. Spend the afternoon and evening relaxing at the resort.
Sleep: Pimalai Resort & Spa (Ko Lanta)
DAY #15 • EXPLORE Ko Lanta & VISIT LANTA ANIMAL WELFARE
I promised myself I would spend the entire day relaxing at Pimalai Resort, but the adventurer in me couldn’t sit still…
If you are anything like me, visit Lanta Animal Welfare, a shelter on Ko Lanta dedicated to improving the lives of all animals. I took a guided tour and was so touched by the incredible work of this organization. I highly recommend visiting if you have time!
Post-Shelter Ko Lanta Coffee Recommendation: Peak Café
Later, take a Sunset Snorkel Tour, booked through the Pimalai Resort. I splurged on this tour, but it was worth it!
Sleep: Pimalai Resort & Spa (Ko Lanta)
DAY #16 & #17 & #18 • FLY TO BANGKOK, DEPART THAILAND, ARRIVE HOME
Spend the morning relaxing at the Pimalai Resort and/or walk down the beach to explore nearby shops. Later, take a pre-arranged, reservation-included boat ride and private car to Krabi Airport.
#1 Flight: Depart Krabi (KBV) @ 7:40pm, Arrive Bangkok (BKK) @ 9:05pm
#2 Flight: Depart Bangkok @ 1:05am, Arrive Beijing (PEK) @ +6:30am
#3 Flight: Depart Beijing (BKK) @ 12:00pm, Arrive LAX @ 8:00am (it’s still Sunday, yay time difference!)
#4 Flight: Depart LAX @ 11:26pm, Arrive BOS +7:45am
Arrive at Boston Logan Airport @ 7:45 am on a Monday, then head straight to work as I did. Gotta love limited U.S. vacation days!
TWO WEEKS IN THAILAND: FINAL ITINERARY THOUGHTS
Thailand is one of my favorite places I have visited so far. Do I wish I had more than two weeks? Absolutely. Nevertheless, I truly feel that this bucket list Thailand itinerary allowed me the opportunity to experience so many unique parts of such a beautiful country, all within two weeks’ time. I kept my Thailand itinerary straight-to-the-point, as promised, but comment below if you have any specific questions about my two weeks and I will try my best to answer!
TWO WEEKS IN THAILAND: Where to stay (RECAP)
WHERE to stay in bangkok
WHERE TO STAY IN CHIANG MAI
HOW TO BOOK A STAY AT ELEPHANT NATURE PARK
WHERE TO STAY IN KHAO SOK NATIONAL PARK
WHERE TO STAY IN RAILAY BEACH
WHERE TO STAY IN KO LANTA
Disclosure: I may receive a small commission should you decide to book directly through my accommodation links. Every dollar goes directly back to support Wanderlight Moments & Usher syndrome awareness.