From the chaotic streets in large cities to the rustic simplicity in the countryside, Southeast Asia has so much to offer in regards to adventure. However, there are also a few locations that blend local culture with Western comforts and these places tend to be the biggest draw for foreign expats who plan to stay for extended periods of time.
Digital nomads, like ourselves, typically like to find a place for a few months that provides certain qualities that make living in a foreign country as comfortable as possible given the natural challenges.
First, we need good reliable Internet which can be found just about anywhere these days, although costs and speed will vary. Next, we desire a reasonably modern and affordable furnished apartment or condo-hotel. And, although we prefer not to admit it, we like a level of comfort which includes access to good grocery stores with some imported foods, a decent selection of restaurants, and easy transportation.
We prefer to be in a location that is rich with activities without being too crowded or cramped with people. In other words, big cities are fun to visit and explore, but not for 3-6 month stints. We like the medium-to-small cities with plenty to offer, but with a manageable landscape.
Finally, there are language and visa challenges in these countries as well. Some areas, English may be spoken sparsely or have more costly visa requirements to stay for 3 months or longer.
This criteria excludes many travel-worthy locations. One can surely enjoy and work remotely for several months in more rustic locations or large cities in Southeast Asia, but four places really stand out in terms of what they offer digital nomads.
Chiang Mai (Thailand): Chiang Mai is the sixth largest city in Thailand and very popular among expats -- for good reason. The clean city's northern climate is a bit more comfortable than Bangkok and it is easily navigable, even without a car. Services are first world, and accommodations and restaurants are plenty. There is a modern mall with one of the area's large grocery stores. Cultural events and street markets are abundant, and several must-see attractions are close enough for a day trip. Chiang Mai also has a world class zoo. Thailand offers a double-entry visa that cost $60 per person and is good for 4 months (requiring a border run after 2 months). Chiang Mai is an easy over-night train ride from Bangkok, but also has its own international airport. Significantly, Chiang Mai is the least expensive city on this list.
Penang (Malaysia): Dubbed the "Pearl of Asia", the island Penang in Malaysia offers everything a digital nomad could desire. The traditional Asian flare of the busy streets of Georgetown give way to modern apartment buildings, high-end subdivisions, and shopping centers along the well-kept coastal road toward Batu Ferringhi. Penang is more of a melting pot of cultures with Mulsim, Chinese, Indian, and Western influences, distinctive from other areas in Southeast Asia. Incredible authentic restaurants are available in nearly every neighborhood, and the shopping ranges from nightly hawker stalls to palace-like modern malls. Malaysia offers free 90-day visas to most Westerners that can be renewed with a simple border run, making it an excellent place to spend extended periods of time.
Phuket (Thailand): Phuket is the largest beach city in Thailand and one of the most popular tourist areas in the country. It's a gateway city to many exotic and more private resort islands in the area. From the seedy colonial flavor of the old part of the city to the newer developments that span the outskirts, Phuket is a blend of authenticity and modernity. Because of heavy tourism, many terrific restaurants and rental villas can be found. However, as a tourist attraction, prices are higher in Phuket than the two previous towns on this list. Phuket has a modern mall and good grocery stores, as well as first-world Internet and other services. You will also have to get the $60 double-entry visa to Thailand to enjoy an extended trip to Phuket and expect to pay a bit more for attractions, taxis, and accommodations.
Singapore: Singapore is an ultra modern and clean city with all the amenities one can imagine. Okay, this is a big city, but its cleanliness, safety, and comparatively light traffic give it a smaller feel than it actually is. There is high-speed internet everywhere, excellent public transportation, and countless restaurants and grocery markets. The city offers many exciting attractions for occupying your free time, but everything in Singapore comes a high cost. If you're a digital nomad with a healthy income, Singapore is an excellent place to drop anchor for a few months to explore all that the city has to offer. Most Westerners get a free 30-day visa upon entry and you may extend your "social visit" to 90-days for $40 SD.