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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!