14 Days In Thailand Itinerary

Sawadika! One of the most pampering destinations in the world, you simply cannot go wrong with a trip Thailand. Exotic, diverse and beautifully chaotic – every traveler must make the pilgrimage to Thailand at least once in their lifetime, though there’s a high chance of return visit. Impressive temples and colorful markets await in the mega-city of Bangkok, while on the outer islands, your decisions vary from when to get a massage to when to go for a dip? While mass tourism has stripped a lot of charm, this itinerary for spending up to two weeks in Thailand will help stay in front of the bandwagon.


Thailand is one of the world’s best value-for-money destinations. It’s also one of the prettiest places you’ll ever visit. The problem is that you aren’t the only ones who have figured this out. So, if you’re looking to have the place all to yourself, look elsewhere. Thailand lives and breathes tourism. In fact, tourists are pretty much everywhere you look. Kind of like Bangkok smog. But have no fear – with a little bit of planning, you’ll have a memorable experience.

What’s Included In This Two Weeks In Thailand Itinerary?

Several sections make up this guide:

Chiang Mai: The Missing Piece

This Thailand itinerary focuses on its islands and beaches. Northern Thailand, particularly Chiang Mai certainly deserves a few days. Chiang Mai is a stunning historic city and a culinary hub. Travelers can use the city as a base for exploring parts of Northern Thailand. If you want to include Chiang Mai, skip one of the beach stops mentioned in this Thailand Itinerary. I recommend skipping Railay Beach as it was not as impressive as we had hoped.

Thailand Travel Tips

The first section of this two-week Thailand itinerary highlights general travel tips. Later sections focus on specific regional tips.

Quick Finds

Bangkok’s Airports

You’ll likely enter Thailand via Bangkok, a megacity with two international airports: Suvarnabhumi and Don Mueang. Suvarnabhumi is the ultra-modern airport serving all major airlines, while Don Mueang serves the low-cost airlines. Keep this in mind when booking your international and domestic flights, as airports are far apart and require plenty of travel time in between.

Booking Accommodations

While accommodations in Bangkok are plentiful, the same cannot be said about the popular beach stops. It’s wise to book in advance. Contrary to belief, good hotels in Thailand are not cheap at all. If you want to stay at attractive locations with high standards, book early and budget accordingly.

Local SIM Card

Purchase a local SIM Card at the airport upon arrival. This will extremely come in handy, especially in Bangkok.

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Domestic Flights in Thailand

Domestic flights in Thailand are very cheap, with lots of competition over popular routes. However, safety is always a concern. This is the reason why we chose to fly with Nok Air, a great low-cost airline that Thai Airways partially owns.

Staying Healthy in Thailand

I strongly suggest carrying a first aid kit and a ‘small pharmacy’ that includes pills against a headache, fever, food poisoning, diarrhea, etc. We met a handful of tourists who got sick on the outer islands during the weekend when pharmacies were shut. Moreover, always check Tripadvisor before eating in a restaurant. If somebody recently got sick, there’s a very good chance they posted a review. This trick worked for us, and we managed to avoid a few potential mines. In any case, make sure you have the right travel insurance plan to match your traveling style.

The Royal Family

Do not, I repeat – do not joke or even mention the royal family. Don’t even accidentally step on bills as they carry the portrait of the late King Rama IX. Offending the monarchy can get both locals and tourists into some serious trouble!

What to Pack

The Rough Guide to Thailand 2023

Don’t leave without the Rough Guide to Thailand and the Lonely Planet Pocket Bangkok. Together with this sample itinerary – they will be your best friends on the trip to Thailand. The Rough Guide to Thailand’s Beaches and Islands will do the job if you’re only visiting Bangkok and the beaches.

Pack very light, quick-drying clothes. If you’re visiting the islands and beaches – a backpack is better than a trolly since you’ll need to walk over sand and shallow water to get in or out of your ride. Here’s a list of recommended travel items.

Choosing the Right Thai Island To Visit

If you’re visiting Thailand on a short holiday – choosing the right island or beach destination is a real challenge. You’ll hear conflicting recommendations from friends and might attempt to squeeze in as many stops as you possibly can. Keep in mind that Thailand is huge! Its best islands and beaches are concentrated in the southern Gulf of the Andaman Sea (Railay Beach, Ko Phi Phi, Phuket, Ko Lanta) and in the Bay of Thailand (Ko Tao, Ko Phangan, Ko Samui). The most important factor when choosing your stops is the weather. Here’s a general rule of thumb:

  • May – October: the rainy season, expect frequent rain. It’s not the best time to visit the islands if on a short visit.
  • Nov – Feb: the cool season, ideal for visiting the islands of the southern Andaman Sea
  • Dec – April: the hot season, ideal for visiting the islands of the Bay of Thailand (+ Andaman Sea)

In any case – unless you like package holidays – avoid staying in Phuket, Pattaya, and Krabi. Not that these are not necessarily nice places, but they lack the authenticity that independent travelers usually seek. I also advise spending at least 3-5 nights at each stop. This will not only allow you to unwind and enjoy the beach but also explore the surrounding area on awesome day trips. Also, keep in mind that transfers from one island to another take a few hours, either by land or sea, so it’s best to keep these to a minimum.

Finally – I haven’t been to all of Thailand’s islands and beaches, but here are the best choices:

Which islands to visit in Thailand and when?

Andaman Sea (Nov-Apr)

  • Popular: Ko Phi Phi, Railay Beach
  • Laid back: Ko Lanta, Ko Similan (diving), Ko Yao Noi, Ko Jum, Ko Hai, Ko Lipe

Bay of Thailand (Dec-Apr)

  • Popular: Ko Chang, Ko Samui, Ko Phangan
  • Laid back: Ko Kood, Ko Tao