In my experience Dian is not likely to be super helpful regarding extensions. Some people manage to get 6 months, but if you are looking for a solution so that you can leave your bike for an undefined period of time, I think that the best solution is to cancel the TIP, at aduana and then return with the bike to a secure parking in Ipiales. Technically I believe this is illegal, but it seems that aduana is not very strict or worried about this issue. In order to cancel the TIP you have to park and go inside the office, after finishing with the paperwork, it appears that it is quite easy to return to Ipiales if that is your intention. If you look on iOverlander you can see there is one specific long term parking there that has mostly quite good reviews and has been used by multiple travellers as a way to securely store there vehicle for extended periods. There are also many other private options for long term parking such as hotels, garages, and the like. The idea would be that when you return to continue travelling you drive past the Aduana without stopping, park at immigration and complete your personal exit formalities and then continue to Ecuador to complete that paperwork and enter there. After that you should be able to return to Colombia by passing through Customs and Immigration normally and receiving a fresh TIP. I believe there are several threads on HUBB discussing this process. I also believe this can also be done at the Maicao border with Venezuela. There apparently is a sort of no mans land between the colombian and venezuelan border posts and there are actual shops there, and a lady there has some sort of warehouse where people have stored motorcycles in the past.
If you find another foreigner who is interested in buying your bike and prefer to do that rather than selling it. It would probably be a better solution. Probably the easiest thing to do is create a poder (power of attorney). That gives them the right to drive the motorcycle and people have successfully travelled all over south america (and further) using this method. The wording on the poder can include giving them the right to sell, ship, drive, and use with all the same rights as the legal owner. This needs to be at least notarized, and preferably apostilled. It is easiest to do this while you are still in the country and with the new owner present. If you decide to leave your bike in long term parking in Ipiales and then later find someone who wants to buy your bike, there are some ways to accomplish this, but it will generally be more difficult. One other consideration is to look into the process for transfer of ownership for a Chilean vehicle. I believe this may be possible to do online, and I think it might even be possible to do without you or the bike being physically in Chile, but I dont remember the details. If it is possible then that may save you some hassle. If it is not you should at least know how proper transfer of ownership works so if someone buys yours bike, and intends to drive it back to Chile, they will know whether it is possible to legally transfer it into their own name, as that will make the whole situation better for them, and much easier for them to sell or pass on to another traveller if that is what they decide to do after finishing riding. If the future owner is a Chilean national probably they already know the process. If the future owner is Colombian the vehicle would have to be legally imported in order for them to drive it here, as to the best of my knowledge it is illegal for them to drive a foreign registered vehicle here in colombia.
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