Southeast Asia Itinerary

Thailand | 60 days

Buddhist temples, exotic wildlife, spectacular islands, fascinating history, unique culture, elephants, and delectable local food.

Bali | 90 days

One of the most popular islands in the world to visit, with roughly 3 million tourists every year. Bali is known for its warm hospitality, monkeys, and ancient culture.

Thailand Overview

Time Limit: 60-90 Days

Opportunity Cost: Relatively Low

Visa Strategy: VOA + Tourist Visa (TR) or just Tourist Visa (TR)

Locations: Chiang Mai (main) → Bangkok (potentially) → Phuket (potentially)

Monthly Cost: $1500-2500/mo

Total Cost (Low): $3000-$4500

Total Cost (High): $5000-7500

Average 90-Day Total Cost: $6000

Pre-trip Planning


  1. Schedule flight | Costs approx. $1,000 one-way
  2. Schedule Accommodation | Airbnb or Hotel
  3. Get essential Thailand apps | Google Maps, Google Translate, etc.

Day 1


  1. Leave plane | Get off airplane
  2. Convert currency | Convert probably 250-500 USD each
  3. SIM Cards | Go with AIS 5G (the green one)
  4. Transportation | Go to scheduled Airbnb/hotel
  5. Get set up | Work, personal, etc.
  6. Find restaurant to eat at | Sustenance

Day 2-7


  1. Scout out city | See what’s nearby
  2. Find gym | (Most important)
  3. Locate local restaurants to eat at consistently | Sustenance

Day 8-30


  1. Work | Don’t get distracted
  2. Go gym | (Most important)
  3. Visit tourist attractions | Temples, markets, etc.
  4. ELEPHANTS | (Tied with gym for most important)
  5. Follow a consistent schedule | Don’t get distracted

Day 31-60


  1. All same objectives at day 8-30 | Follow similar schedule
  2. Figure out if you’re staying for another 30 days | Depends on visa and goals
  3. If only 60 days, get ready for Bali | Get Bali visa and accommodation planned

Day 61-90


  1. Either stay another 30 days in Thailand or head to Bali
  2. If heading to Bali, get on flight | One-way flight costs approx. $300 and takes 10 hrs

Time Limit

60 to 90 days. Two to three months depending on visa strategy, and overall individual product market fit (whether or not the individual enjoys the location).

Opportunity Cost

Rating: Relatively low

Will you be more or less likely to get distracted from the new environment?

The starting point is Chiang Mai, a less hectic and less distraction filled region of Thailand vs Bangkok. Bangkok involves a plethora of shopping and nightlife, both distractions from the main objective (grow the business and make exorbitant amounts of money).

To start, ideally the goal is to stay in Chiang Mai and get a grip of the new environment.

Plan for the first month being a culture shock and a decent amount of wasted time.

But with a less chaotic city, it will ideally be easier to focus on work and business.

While of course still exploring Thailand and all it has to offer.


The goal is to start in Chiang Mai (Northern Thailand) and if it’s not a good fit, work our way down to cities like Bankok or Phuket (Southern Thailand).

This way we start at the top of Thailand and go in one direction, without backtracking and potentially wasting time.

Most likely scenario is staying in Chiang Mai for the majority of the time and taking small trips to other parts of the country as needed.

Chiang Mai is the “headquarters of the remote work movement in Thailand, with dozens of coworking spaces. Chiang Mai has mountain views and a slower pace of life.”

Bangkok is a “vibrant and culturally-rich city with many cafes and coworking spaces. Bangkok is also relatively cheap and has a large community of digital nomads.”

Potential Cons: During certain times of the year (Jan-April), pollution may be at elevated levels. Northern Thailand (Chiang Mai) usually gets more polluted than Southern Thailand due to field burning.

If this were the case and pollution is a serious issue, the plan would be to head south to a city like Phuket where potential pollution would be less of an issue.

Visit the transportation section for the most effective way to travel between cities.

Experiences (To-Do Checklist)

These are not just limited to Chiang Mai, but also include other must-see destinations that could be multi-day trips in Thailand.

Jump to Chiang Mai specific checklist.

Phang Nga

Koh Phi Phi

Khao Sok National Park

Elephant Sanctuaries

Reference Images: Joel Friend YT

Chiang Mai Specific Checklist:

  1. Shop at One Nimbean
  2. Visit the Sunday Night Market
  3. See the Wat Phra Singh
  4. Go to Huag Tueng Tao Lake
  5. Eat local northern Thai food
  6. Eat at a night market (or Gate market)
  7. ELEPHANTS 🐘 (2 hr drive potentially, but worth it)
  8. TEMPLES (in old city)


This is just to show current flight prices from different cities around the world. The best strategy for getting airline tickets is booking directly through the airlines website.


Currency exchange and general banking info.

As of 9/4/2023:

1 USD = 35.29 Thai Baht

100 USD = 3529 Thai Baht

1000 USD = 35290 Thai Baht

Currency Exchange

Reference Images: Retired Working For You

Transaction fee is a FLAT FEE. Don’t take out small amounts from the ATM or it will add up.

Thailand ATM fees: typically around 220 baht

How to Avoid Fee: Go to Bank and Withdraw

ATM Tips: The card comes out of AFTER you take the cash. First take the cash, then second, REMEMBER the card.

Banking Checklist

  1. Tell your bank you are traveling internationally so you don’t get ATM locked via fraud protection
  2. Use transfer wise (Wise) for cost effective currency conversion


Thailand has three main provider options.

Dtac 5G – the blue one

true 5G – the red one

AIS 5G – the green one (preferred choice for no reason at all)

Walk up to the counter (at the airport when arriving in Thailand) and ask them for a SIM card for travel.

They will show packages for certain periods of time.

  • 8-day, 15-day, and 30-day packages

Since time spent in Thailand will be more than 30-days. All you need to do is top up by dialing in. See graphic below:

Reference Images: Retired Working For You

They offer 4G and 5G options. The 30-day prices as of June 2023 are:

4G Price: 999 baht (29 USD)

5G Price: 1699 baht (39 USD)

Essential Thailand Apps

  1. Google Maps
  2. Google Translate (point at sign and translate Thai letters)
  3. teenee (Yelp of Thailand)
  4. Grab and Bolt (Uber of Thailand)
  5. Line (WhatsApp of Thailand)


  1. To Leave Airport

Potentially get a taxi. Be careful of taxis that don’t use meters. This usually is not a problem when leaving the airport. It is usually a problem anywhere else in the cities.

If they ask “highway” say yes and give the driver money to pay for tolls (they will ask). This is most likely not a scam.

  1. To Travel Between Cities

Use tour agencies. Very easy and simple to navigate.

Cheap flights in between cities in Thailand are the fastest option. If you wanted to save even more money, 12Go aggregates trains, buses, and ferries for affordable travel.

Health Insurance

  1. Safety Wing

This is a popular choice by YouTubers who get sponsored by SafteyWing or have an affiliate link.

  1. Other Options

Other options include Allianz, which may cost a bit more but may have better reviews and testimonials from travelers.

Gym (Most Important)

Chiang Mai, Thailand bodybuilding gym options:

  1. T.M. Muscle Gym
  2. GOGYM Chiangmai
  3. Gold Hillside Gym and Fitness

Bangkok, Thailand bodybuilding gym options:

  1. Muscle Factory
  2. The Track Bangkok
  3. Muscle Lab Gym

Phuket, Thailand bodybuilding gym options:

  1. Primal Fitness
  2. Titan Fitness Camp
  3. Unit 27 Total Conditioning (not really bodybuilding gym)


Bangkok Belly (food poisoning), happens when locals wash vegetables in local water and ice in drinks.

Tip: Bring related medication


Originally the strategy will be renting an Airbnb (or hotel for shorter stays).

Airbnb is the better option originally because you don’t have to deal with deposits and it’s completely legal since it’s 2-3 months or less.

Also Airbnb is more familiar to westerners. It will be marginally more expensive though.

Airbnb lists Chiang Mai monthly rentals (with 2+ rooms) at about 800-1900/mo.

So most likely costs could be anywhere from $500-1000 per month on rent if split by two people.

Keep in mind, Airbnb is the more expensive option for renting too.


  1. Thailand King


You can apparently be put in jail for some reason.

  1. 7-11s

There’s one everywhere and they have lots of variety for foods, drinks, coffee, etc.

Bali General Overview

Best Time to Visit Bali: April – October

Busiest time in Bali: June-July

Time limit: 90+ days (subject to change)

Important Items to bring to Bali

  • Clothes for humidity/breezy clothes
  • Shorts
  • Tee-shirts
  • Hiking shoes for volcanoes
  • Rain coat
  • Hat
  • Reef-safe sunscreen (hard to find in Bali so get beforehand)
  • Diarrhea Medication (Bali Belly: from eating local food)

Apps Needed In Bali

  1. WhatsApp
  2. Facebook
  3. Grab (Uber)
  4. Gojek (Cheaper Indonesian version of Grab, Can order meds via app)
  5. Google Maps (Apple maps doesn’t work)

Trip Length

Best time to visit Thailand: November to April

Best time to visit Bali: April to October

Potential months to visit include:

January: 31 days

February: 28 days

March: 31 days

April: 30 days

May: 31 days

June: 30 days

July: 31 days

August: 1-31 days

September: 0-1 days

Total: 6-8 Months

This is the basic overview of Thailand and Bali.

If all goes well. It could be longer if visiting nearby countries like Singapore or Malaysia.

This post may contain affiliate links. For more information, see our disclosure policy.

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