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  • Cait

STEAL MY VACATION: A Perfect, Two Week Thailand Itinerary

Updated: Nov 11, 2020

2 Week Thailand Itinerary, Cait Without Borders

Thailand has it all—bustling party cities like Bangkok, jungles and elephants in Chiang Mai, and pristine beaches in Phuket. It may seem impossible to “do it all”; but this two week itinerary will help you travel Thailand like a pro.

I am a planner and researcher, so I always have a self-created itinerary for all of my travels. When people come to me with travel-related questions, it is almost always for planning advice, attraction recommendations, or travel tips. And usually, it is with a request for my entire itinerary! So I have started a “steal my vacation” series where I will share my travel itineraries (after they have been tried and tested, of course) with links to all of my official TripAdvisor reviews. I hope you find these tools helpful!


You are all unique, individual snowflakes, so your travel style might be different from mine. Take this into consideration when reading my reviews and suggestions since they are, by their nature, subjective.

My style:

I am an active traveler. I prefer to “go and do” more than “go and see”, so you won’t see many museum visits or pure beach vacations in my itineraries.

I am also independent, so I avoid most guided tours like the plague. Small group tours are necessary from time to time, but I will pay extra money for more exclusive experiences.

While I do enjoy a luxury resort (who doesn’t?), it is not always in my budget. But since I am experience-oriented (and usually pretty busy on my trips), I am comfortable with moderate or even budget accommodations—or sometimes even camping. I am always very open about the quality of lodgings in my official TripAdvisor reviews.

My husband and fellow adventure partner is almost my opposite. We both agree on active experiences (kayaking, hiking, working out); but he also enjoys relaxing on vacation (he loathes the idea of setting an alarm) and comfortable accommodations. He prefers to leave things unplanned and enjoys wandering around cities.

But we both agree that we love to eat and drink on vacation. Definitely.

Between the two of us, we make a very balanced itinerary. You will find plenty of scheduled and researched (aka vetted, quality) activities in addition to scheduled “down time” (where I have researched other potential activities that don’t require pre-planning or reservations—just in case).

DISCLAIMER: Remember, everything is a suggestion. There are thousands of hotels or attractions to choose from, and just because I list it does not mean it is the best option. My TripAdvisor reviews will provide additional details that will hopefully help you determine whether the activity, restaurant, or hotel is right for you.

Ok, now on to our two week Thailand itinerary!

THAILAND—Cities, Jungles, and Beaches


Bangkok is a bustling city with crazy nightlife, beautiful temples, and delicious street food. You may have preconceived notions about Bangkok (I know I did), but it isn’t all like The Hangover III. Since most flights into Thailand arrive in Bangkok, I would suggest spending 2-3 days in this city (which I actually enjoyed more than I thought I would!).



Arrive in Bangkok and check into the Aloft Bangkok Sukhumvit hotel.

(See my Aloft Bangkok TripAdvisor review here).

The hotel is located in the middle of the nightlife hub, with easy access to restaurants, bars, and clubs within walking distance. I chose this hotel because it was moderately priced (and very cheap with Starwood points!) and because of its location. If you are hoping to spend more time at the temples, consider a hotel closer to the Chao Phraya River.

Aloft Hotel Bangkok


Spend the afternoon/evening exploring. We left our fate to chance and picked a restaurant that I hadn’t properly researched and it was just ok, so I won’t recommend it here. But for some suggestions of well-reviewed options that may be a little farther away from Aloft, check out Maya, (Indian food) or La Monita Taqueria (Mexican food).

Sri Cowboy Street, Bangkok

Go Out

Want to head out for the evening? If you are curious, Soi Cowboy or Sukhumvit 11 are infamous for wild Bangkok nightlife, including one “GirlyBoy Show”. This is not recommended for families or the faint of heart. We aren’t big “nightlife” people, so dinner and drinks were ok for us, but it was interesting to see how the “business” was run outside these venues.

Alternate Suggestions



Sleep in if you were out late ;)


Hop on the metro or grab a taxi to the Old City—this took us about an hour in traffic. We started our day at the Tha Maharaj “mall” on the water where we visited Gram for an AMAZING brunch! Immediately afterwards, we indulged in ice-cream at Stickhouse.

Visit the Old City

The two main attractions here are The Grand Palace (which we walked past, but didn’t visit) and Wat Arun.

(See my official TripAdvisor review of Wat Arun here).

Wat Arun at Sunset
Wat Arun details

We spent a majority of the day walking around the market. It is very touristy, but a lot of fun and the street food is amazing! There are a lot of temples and attractions in the area, so the Old City can easily take a full day—or two if you are thorough!

BEWARE OF SCAMS! Sneaky tuk tuk drivers may ask where you are going, and then tell you it is “closed”. They will then offer to take you to other attractions…but you will have to stop at their “sponsors” along the way where you will be pressured to buy items. This happened to my *ahem* friend *cough*.


Visit Wat Arun before closing, then finish your evening with a delicious dinner on the water at Eat Sight Story, where we had perfect sunset views of the temple.

(See my official TripAdvisor review of Eat Sight Story here).

Nighttime dinner setting in Thailand
Wat Arun at sunset in Bangkok

Chiang Mai

Chiang Mai is the second biggest city in Thailand, located in the northernmost part of the country. It is a tourist destination, but not as crowded as other parts of Thailand. If you have time, Chiang Rai and Pai are within a few hours of Chiang Mai and also worth a visit!



I am a huge fan of Airbnb, especially in foreign cities. They feel more authentic than bland, carbon-copy hotel chains and have the added benefit of blending into the local neighborhoods. Plus, they are usually less expensive.

We stayed in a traditional Thai teak house right next to the historic Old City Square. We had the entire house to ourselves (for $66USD/night!) in a perfect location. It was a bit rustic (no A/C as of this writing, but they are working on it), but we loved it! Plus, we were just around the corner from the epic Baan Bakery, where we enjoyed freshly baked pastries every. Single. Morning.

(Check out our Airbnb).


Chiang Mai’s Old City is contained within a huge square bordered by a moat and bits of crumbling leftover walls. There are temples dotted throughout, but this area is mostly restaurants, bars, and great night market shopping—including some of the best street food I have ever had!

Chiang Mai Night Bazaar

Visit the Night Market

You can visit the Chiang Mai Night Bazaar at the end of Chang Khlan road by the river. We would finish most days here for shopping or eating delicious street food.

Alternate Suggestions

  • There are plenty of culinary bike tour operators if you would like to explore the city street food by bike!

  • There are a number of other night markets you can explore.


Motorbike to Doi Suthep

For about 250 Baht/day (about $8), you can rent a motorbike at rental locations throughout the city. Andrew and I doubled up on one and my brother and his girlfriend shared another. This was an amazing way to see Chiang Mai! The traffic can be a little hairy until you get out on the mountain road, where you will enjoy a winding journey and gorgeous views.

WARNING: Apparently, you now need an “international driving license” to drive motorbikes (but not to rent them—which is interesting). We were both pulled over by the Thai police (my brother and his girlfriend actually went to a police station full of other foreign drivers) and paid a fine of 200 Baht for failure to produce a license. Our “ticket/receipt” allowed us to drive for three days. Each time we were pulled over, we just had to show our piece of paper and we were allowed to continue riding.

Doi Suthep National Park is a gorgeous national park with plenty of hiking trails, waterfalls, and temples. We opted to cruise around on our motorbikes all day and take small stops for sightseeing.

Alternate Suggestion:

  • If don’t fancy driving a motorbike, there are plenty of songthaews (red taxis) that will take you to Doi Suthep from the city. You can hike instead!


Since we had the benefit of staying in our own house, we usually came back in the evenings to shower and have a few drinks on our outdoor patio before heading into the city. If we didn’t eat excellent street food at the night market, we would find a restaurant as we walked.

An expat recommended our favorite restaurant, and we loved it so much we went twice. Definitely visit Dash early during your stay—in case you have to go back for more!

(See my official TripAdvisor review of Dash here).


Ride the Samoeng Loop

Hop on your motorbike (you’ll be a pro at driving one by day two) and follow this 80km drive past beautiful fields and mountains right outside Chiang Mai.

Full disclosure: we intended to take this ride, but became helplessly lost and never found our way. We went back up to Doi Suthep for a bit and then back to our house. My brother eventually found it and confirmed it really was a beautiful drive. Just get directions before you go.

Alternate Suggestions:

  • Take a day trip to Chiang Rai to see the famous White Temple. Check out the Blue Temple as well. It’s about 3 hours of travel each way, but there are plenty of tour groups that provide mini-bus transportation. I would have loved to see it (for photographic purposes), but no one in my group was keen enough on temples (or photography) to make the journey.

Get a Thai Massage

There are dozens and dozens of massage facilities in Chiang Mai. If you walk a block, you will see at least a handful. Most of them will cost about 200-300 Baht for an hour massage (less than $10USD). But, of course, I did some research to find a good location.

Try Fah Lanna Spa. You can go to the retreat (which is more expensive—but still cheap by American standards, though I did not experience it firsthand) or go to the night market location.

(See my official TripAdvisor review of Fah Lanna Spa here).


Take a Thai Cooking Class

Start your day off with a light breakfast, because a Thai Cooking Class will keep you fed the rest of the day! There are plenty to choose from, but we loved the Thai Farm Cooking School! The staff picked us up in the morning and we returned to the city around 5pm.

(See my official TripAdvisor review of the Thai Farm Cooking School here).

Thai Cooking Class at Thai Farm Cooking School, Chiang Mai


Spend Quality Time with Elephants

IMPORTANT NOTE: There are a lot of elephant experiences advertised around Chiang Mai. Please be diligent when researching elephant care facilities, as many elephants are mistreated. Any facilities that encourage elephant riding or “acts” like painting pictures are not animal-friendly. Check out this BBC article for more information.

We visited the Elephant Nature Park for a truly magical experience. The elephants have been rescued from the logging and entertainment industries, but can no longer be released into the wild. The park is well respected and even earned a nod from National Geographic.

(See my official TripAdvisor review of the Elephant Nature Park here).

Elephant Nature Park, Walking with elephants in Chiang Mai, Thailand
Elephant Nature Park, Walking with elephants in Chiang Mai, Thailand


Free Day!

Consider relaxing, getting another massage, taking an overnight trip to Pai or Chiang Rai, or spending a night in a luxury jungle retreat.

You could also get a jumpstart on the next leg of the itinerary if you are pressed for time!

Krabi Beach

Most people include a beach stay on their Thailand itinerary, but those people head to Phuket. Just a few hours south is a slightly lesser known slice of paradise called Krabi Beach.

We Love Krabi Beach sign



We checked into our little terrace we booked through Airbnb. We were located away from the touristy bustle of the town in Ao Nang, but it may have been a little too far, in my opinion. It took us about 30 minutes to drive to town by motorbike.

(Check out my official TripAdvisor review of Khaothong Terrace Resort here).

Day at leisure

DAY 10

Longtail Boat Island Hopping

There are plenty of island tours you can book anywhere in town. But I do not like large guided group tours (have I said that before?)—and being stuffed on a boat with 30 other people to be herded like cattle from island to island did not sound like a good time to me.

Instead, we booked a private longtail for just 3,500 Baht (just a little over $100USD). It included water, lunch, and fresh fruit provided by the resort.

Not sure what a longtail boat is? You have probably seen them all over Instagram and Pinterest. They run by motor and look great in photos, but don’t expect anything fancy on the inside. Seating is just a basic, wooden bench. But our longtail boat had a small mat and two large pillows for reclining (fancy!).

Long tail boats at Phi Phi Island, Thailand

I couldn’t even tell you where we went on this day. We told the resort staff member what types of places we wanted to visit ahead of time and they relayed the information to the driver. In short: we wanted to visit beautiful, uncrowded islands. We got our wish! We enjoyed beautiful stretches of beach all to ourselves—and if another boat pulled up, we just hopped back on ours and sailed off to the next bit of paradise!

TIP: If you want islands to yourself, get out of Krabi town and charter a boat from another location. Most resorts outside of the town proper can rustle up drivers for you and take you to less touristy islands. As I mentioned, our resort had better prices and it is located less than 30 minutes from town (by motorbike).

DAY 11

Relaxation and a Thai Massage

When in Thailand, get lots of Thai massages, right? We ordered an hour massage in our terrace.

Explore Krabi Town

Krabi Town is similar to any beachside town in the US—except for the monkeys and multitude of karst islands just off the shore. Explore the shops and restaurants or enjoy an outdoor massage by the ocean.

A Fancy Dinner

This is one experience I regret that we didn’t do. The Grotto is a beautiful dining location at an exclusive resort. The tables are right on the water under towering limestone cliffs. Our resort had a difficult time securing a reservation, and it costs about $200USD per person. However, if you can swing it, this seems like the place to go!

DAY 12

Longtail Boat Island Hopping—Phi Phi Island

The private charter in Ao Nang to Phi Phi Island was much more expensive than our first. We paid about 7,500 Baht (but probably should have negotiated) for the day. The ride to Phi Phi Islands by longtail boat takes about 2 hours and the islands experience a lot more tourist traffic—including hoards of people being shuttled on packed boats. However, Phi Phi Island is pretty unique. There is an entire town on the island with restaurants, shopping, and some resorts. If you have the opportunity, it might be fun to spend a night.

Phi Phi Don

Take a walk through the tourist town on Phi Phi Don and keep walking up into the residential section. If you hike for about an hour and a half, you will reach the Phi Phi View Point. This is a beautiful place to see both sides of Phi Phi Island. An enterprising family built a ticket booth at the entrance of the lookout---so be sure to have 30 Baht per person on hand for the entrance fee.

Maya Bay

This is a popular location, but since we went after our hike, most tour boats were getting ready to leave. The sun was also sinking behind the cliffs, leaving most of the bay in shadow, but it was still beautiful. We had purchased floatation devices and enjoyed the water after our steep, hot hike.

DAY 13

Free Day Suggestions:

  • Visit Railay Beach

  • More island hopping—Tup Island, Chicken Island, Bond Island, etc

  • Take a Thai Cooking Class if you didn’t in Chiang Mai

  • Kayaking (we had intended to do this, but ran out of time!)

  • Visit Bioluminescent Caves

  • Eat all the pad thai you can handle

  • Relax!

DAY 14

Travel Home

And cry about how much you are going to miss Thailand. And drink three margaritas because you are in denial about leaving. Not that I did any of those things.

DAY 15

Start dreaming of your next adventure!

Did you find this helpful? I would love your feedback for my next itinerary. Where are you dreaming of going next? Send me an email in the form below!

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