The Perfect Two Week Itinerary in Thailand

This blog originally grew from my experiences in long term travel and usually focuses on advice for gap years and career breaks, but I’m going to do something different today. I’m going to represent my part-time adventurer brethren out there.

Because that’s where I’m at right now. I’m meant to be a grown-up these days and attempt to keep up a 9-5 (or a 8-6 like most of us actually end up with), with rent to pay and shit to do. But don’t worry, I’m never giving up on the adventures. They just tend to be compacted into shorter and more intense trips where I try to see as much and do as much as I possibly can.

And I know sooo many people in this camp, backpacking the world in stages, in 2 week trips at a time. So today I’m going to show you how you can travel Thailand and get as much of your bucket list ticked off as possible, in just two weeks. It’s a hard task but that’s what us in the rat race massive are faced with. Let’s do this.


Flying into Bangkok will usually get you much cheaper flights than anywhere else in Thailand, so is the ideal place to start your Thai adventure. You’re likely going to be jet lagged so I wouldn’t aim to do anything particularly cultural or noteworthy on this day. Just rock up to Khao San Road and explore the backpacking mecca that is this road. Eat Pad Thai from a street vendor, try your first Chang beer at the bars that line the street and if you really fancy it, eat a fried cricket.

HOSTEL RECOMMENDATION: Sawasdee House, Rambuttri

Tuk tuk, Thailand

Bangkok buckets on Khao San Road


Today is the day to see the best that Bangkok has to offer. Start early to fit in as much as you can! Head for a river tour first thing, your hostel should be able to book one for you. They have awesome ones that give you a lovely ride down the river, seeing the riverside houses and randomly feeding catfish with bread (it’s horrifying), then moving onto Wat Arun and Wat Po. Wat Arun is a gorgeous temple with steep steps and cool views from the top, and Wat Po is the one you’ve probs seen on Insta of the giant golden buddha. Both are super cool. Get a tuk-tuk back to Rambuttri and spend the afternoon wandering the stalls full of pretty trinkets and treasures. Grab a massage from the spas, eat Thai Green or Massaman Curry (both are so good) and spend the evening partying at one of the nearby rooftop bars.

HOSTEL RECOMMENDATION: Sawasdee House, Rambuttri

Wat Arun

Bangkok, Thailand


This morning your choice is either to visit the Grand Palace or the floating markets. Both are what they say on the tin. It’s an early start if you want to go to the floating markets, and remember to cover your shoulders and knees if you want to go to the Grand Palace. You could definitely do both if you want but timing is pretty tight. Because tonight you need to get the overnight train to the islands! Get snacks from the train station for the evening and bring a book, it’s not the most exciting journey. It’s an experience though as you begin seated in armchairs until the train staff come through and turn them into bunk beds.

Grand Palace, Bangkok


The train arrives at Surat Thani where you alight to a bus to the port, then a boat to Koh Phangan. It’s quite a journey but that’s what backpacking in Thailand is all about! Arriving at lunchtime, grab something to eat in the town area of Haad Rin, I recommend Lazy House for comfy sofas and free wifi after your long journey. Explore the island this afternoon or lay by the pool if you feel like relaxing. Tonight you will experience one of Haad Rin’s legendary beach parties! There are loads of  restaurants for dinner and loads of bars for pre-drinks, just make sure you get down to the beach for fire performers, buckets of sangsom and dancing on tables.

HOSTEL RECOMMENDATION: Friendly Resort, Haad Rin

Beach Party, Koh Phangan



Today, after you nurse your hangover with a full English, it’s your day to go on a day trip in Koh Phangan. There are a lot of options here from going on an elephant trek (although there’s always a bit of controversy over animal welfare so make sure you do your research) or a boat ride around the island, stopping for snorkelling and visiting other beaches on the island. Both are a lot of fun so depends whats on your bucket list! Koh Phangan is the party island so this evening will be yours to visit some other bars or go to infamous backpacker pool parties on the island. I would just go back to the Haad Rin beach party because it’s a lot of fun.

HOSTEL RECOMMENDATION: Friendly Resort, Haad Rin

Boat ride, Thailand


Leave early from Koh Phangan and catch the morning ferry to the island of Koh Tao. Once you’ve dropped off your luggage at your hostel, explore the area at your leisure and chill out at the beach-facing restaurants. If you want to go diving you may want to spend more time here getting your PADI qualification or taking in the marine life, but I’m not much of a diver so I’ll go with my itinerary. In the evening, grad some dinner at Fizz and spend the night sitting out on the colourful beanbags that line Sairee Beach with pretty lanterns nearby and yet more fire performers. It’s a really nice place for a chilled evening.


Koh Tao

Ko Tao Soiree Beach


If you can manage it, wake up early for morning yoga on the beach. Then get a taxi boat over to the gorgeous collection of islands just off the shore called Koh Nang Yuan. They’re ridiculously idyllic and a must-see when you’re in Ko Tao. Spend the day hiking up to the view point and relaxing on the beach. Once you’re back on the main island, spend the evening at the infamous Ladyboy Cabaret, it’s really entertaining I promise.


Koh Tao, Thailand


Ok, this is a long day of travelling but it’s worth it. I would advise leaving Ko Tao early to make the most of the day as your journey will involve a ferry to the mainland, a bus to the other side and another ferry out to the West islands. It’s hardcore but then you’ll be in Ko Phi Phi! Spend the day settling in and try out one of the novelty restaurants for dinner. There’s everything from a Pirate-themed eatery to a American Diner. Enjoy!

Koh Phi Phi in the rain


As yesterday was pretty hectic, this is a great chance to just relax. Spend the day at the beach and exploring the island. There’s a great hike through the jungle to Long Beach and lots of boutiques to shop in. In the evening head to the beach for, yes that’s right, another beach party! Hey, it’s Thailand, it’s what you do here. If you’re into it, there’s also a Thai Boxing ring you can go to, to watch a fight and even take part! I’ll pass on that one…

Long Beach, Koh Phi Phi


Today it’s time for a day trip to Maya Bay, the little cove we all know and love from the film, The Beach, The day trip usually involves stopping at a spot to go snorkelling on the way there, some time to enjoy the stunning Maya Bay, then a stop at Monkey Beach on the way back. Yep a beach full monkeys. Why not? Spend another night soaking up the nightlife in Koh Phi Phi.

Maya Bay, Thailand


Today’s travelling is a ferry to Phuket. After all of the sights you’ve seen in Thailand so far, Phuket is going to be a shock. It’s very commercial and full of Starbucks and McDonalds. It’s weird. But it’s got a good beach so if you’re not beached out by now, get your tan on. In the evening, go check out the ‘red light strip’ in Patong. It’s sooo seedy but it’s something to see to believe. I had an early night in Phuket after the Koh Phi Phi fun. Phuket isn’t my scene but it’s got an airport. Which you’ll need tomorrow.

Patong, Phuket

Patong, Phuket


Fly to Chiang Mai today, flights are fairly cheap so it won’t blow the budget but it does cut out a lot of travelling across Thailand, with just a 2 hour flight. Spend the afternoon exploring the city of Chiang Mai, seeing more awesome temples and make sure you get an amazing slice of cake from Art Cafe. Spend the night with a Chang in your hand, browsing the Ladies Night Market. It’s full of cushion covers and handmade jewellery and basically all the best things. And it’s much cheaper than the other places you’ve visited so far.


Chiang Mai, Thailand


Today’s the day to tick off your Chiang Mai bucket list item. This could be a hike in the mountains, a day with an elephant mahout, or my personal favourite, a Thai cooking course! Chiang Mai is very chilled so instead of partying it’ll be a laid back beer in a bar, taking it all in and reflecting over your two week adventure!


Baan Thai Cook Course, Chiang Mai

Thai Snacks


Today is home time! Fly home from Chiang Mai or via Bangkok.


That concludes my two week itinerary in Thailand! Full of cultural sights, fun activities, quality beach time and sufficient partying. What more could you want? Ok I know it’s really full-on and involves a lot of travelling, and let’s face it you’ll need another holiday to recover. But if you’re on the career ladder like me, it’s what we gotta do to see the world. It’s a hard life I know.

What did you think of the two week itinerary in Thailand? Let me know in the comments below or tweet me @HeelsInBackpack!

2 thoughts on “The Perfect Two Week Itinerary in Thailand

  • 21st February 2017 at 11:09 pm

    Great itinerary! When did you visit Thailand? I’m considering going in early September.

    • Kara // Heels In My Backpack
      22nd February 2017 at 10:31 am

      Thanks! I actually visited a few different times of year – January, March and April. Varied weather for all of it to be honest so I don’t think it matters too much when you go in the year!


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