How to get from Dili, Timor Leste to Kupang, Indonesia overland

En route to Kupang. 

En route to Kupang. 

Country number three on my itinerary is the sprawling archipelago of Indonesia. 

I was traveling from Dili, the capital of Timor Leste, into the Indonesia’s West Timor, before flying from Kupang city to Flores to continue inching west over the several thousand kilometres to Jakarta.  

For those traveling around Indonesia for a few months at a time, crossing the border into Timor Leste is a common way to get out of Indonesian territory to renew the ridiculously short 30-day visas. In fact, it seems the only tourists I met in Timor Leste were there for that exact purpose. 

Most will then fly back to Bali - a quick and easy way to get back to the more comfortable parts of Indonesia. 

But for those wanting to explore West Timor, Flores, the Alora Islands or Rote, the best place to begin is Kupang - the largest city in West Timor and a regional hub for East Nusa Tenggara. 

There is so much misinformation about the Dili to Kupang overland route. I spent hours reading horror stories of border crossings gone wrong; of travellers having to navigate through complicated Indonesian bureaucracy to be allowed to cross the border; of people simply giving up and catching the newly opened air route between the two Timorese capitals. 

But in reality, this is an extremely easy, cheap border crossing. You can easily get a Visa-On-Arrival at the Indonesian border (for free) and its best option if you want to get a sense of the differences between East and West Timor. 


Catching Local Buses

It is possible to get local buses from Dili to Batugade - the small village the hugs the Timor Leste-Indonesian border. With a little bit of tetun, and a lot of patience, its possible to flag down the larger inter-city buses that frequently pass along Avenue President Nicolau Lobato - the main road that runs through the heart of Dili. 

The buses slowly amble along the coastal road - which is in surprisingly good condition for Timor Leste standards - ending at the border, about a 4 hour drive from Dili. 

From the Indonesian side of the border, there are dozens of minibuses waiting to transport those willing to pay, as well as taxis and private cars. Expect to pay much less than on the Timor Leste side. 

Atambua is only a 20 minute drive from the border, and is West Timor’s second city. From there, there are frequent local buses to Kupang. 

Note - I did not take this option, because there is an even easier, more comfortable way between Dili and Kupang:


Catching the Paradise Travel Bus

For those willing to splurge the $22 for the 12 hour trip, Paradise Travel - a small company operating bus services on both sides of Timor - is the best option. 

Paradise Travel is located on the side of a strip mall on Avenue President Nicolau Lobato -  directly opposite the F-FDTL headquarters in central Dili. 

It’s advised you go there the day before you leave to secure a seat on the 12 seaters buses. They run a service every day, departing Dili at 8am. 


Crossing the Border

The Paradise bus left at 8am sharp, and after only two and half hours, made it to the border by Batugade. 

From there, be prepared: you’ll be kicked out of the bus with all your gear, have to navigate exiting Timor Leste, and then walk the 200 meters through no-man’s land to the Indonesian border. 

Contrary to what may have been the case in the past, crossing the Indonesian border is a breeze - if you don’t make my mistake.

I naively didn’t have my onward flight out of Indonesia booked. As my VISA was being issued, I was asked in detail about my itinerary, and asked to show confirmation of my flight out of Indonesia, which I didn’t have. 

Quickly, I was whisked into a back room and face to face with Indonesian authorities, who bluntly told me I simply couldn’t enter Indonesia. I was facing at least one night in Batugade, a tiny border village in the middle of nowhere. 

I had to think on my feet, assure them of my intentions to leave within 30 days, and actually use my phone to book a cheap flight from Surabaya to Singapore (which I had no intention of taking) - all the while maintaining the friendliest, most respectful disposition I could muster. 

As I was entering my card details to pay for the flight, the guard seemed to lose patience, and just let me go. I didn’t end up buying the US$50 flight, but learnt my lesson. 

While the border guards were quite friendly, this mistake ensured that they interrogated me at length about my plans in Indonesia. I had to list all the towns I planned on visiting, how I was getting there, where I was staying, and why. After about 15 minutes, I was free to go - my free Visa-On-Arrival was issued, and I was in Indonesia. 


From the Border, Sit Back and Enjoy The View

The drive from the border to Kupang is one of the more memorable road trips in all my travels. You first pass through Atambua for a delicious local lunch, and continue on through leafy hill-side villages all the way to Kupang. Much of West Timor - like East Timor - is blanketed by deep valleys and soaring mountains. 

Make sure when booking your Paradise Travel bus, you ask for a window seat (I didn’t and was wedged in a middle seat for 12 uncomfortable hours). 

Expect to arrive in Kupang at about 7pm local time. The bus will drop you at your nominated hostel (I stayed at Lavalon Seaview, a nondescript but extremely affordable option in the centre of town). 

Dinner at Kupang's outdoor seafood court, near Lavalon Hostel. 

Dinner at Kupang's outdoor seafood court, near Lavalon Hostel. 



Bus - US$22

Lunch - ~US$3

Edward Cavanoughtimorleste