Colombia to Venezuela (Cucuta)
This one was nice and chill, if a bit bewildering. You should try to give yourself a full day, as there's a bit of running around to do, and places close for a bit midday.
You can't cross at Puente Internacional Simon Bolivar (the main crossing) as they don't have the ability to close your TIP, so instead go to Puente Internacional Atancio Girardot, about 15 minutes north. It also has the advantage of being a much less chaotic border. Ride ahead through the row of kiosks and pull up at the building on your right with a green sign saying 'sellos pasaportes'. Inside there is a little office where you will get the exit stamp for your passport. Ride ahead and do a u-turn to your left (ignore the no u-turn sign) and pass through the kiosks for entry into Colombia. Just explain that you need to cancel your vehicle permissions and exit Colombia and they will wave you through. Park in the car park for the immigration office into Colombia - on the opposite side of the car park is a little building for DIAN. You'll need to show them the email you received when you first got the TIP - it should have a green 'autorizada' line in it. Also hand over passport & registration (originals - they just need to write down the details).
They will fill out a copy of your DIAN that they already have on file and you will both sign it. You will get an email confirmation that your TIP is closed, but take a picture of the completed form just in case anything goes wrong.
From there you have to ride back towards Colombia, do a u-turn at the roundabout and ride back through the kiosks you started at. This time you can carry on across the bridge to Venezuela. If you have a camera with you, there's a cool photo op of the Venezuela border gate with the mountains in the background
At the kiosk you hand over your passport & answer some questions (occupation, plans for your time there etc) and give a phone number. They will run off and take a copy of your passport. I asked for the maximum stay and they told me it would be 90 days. Interestingly the stamp doesn't actually specify how long you've got. It is free.
After that you are through the border, and you need to get your insurance & TIP in town. Start by following the road ahead and to the right, following signs for San Antonio. About 1km further on you will come to a little town with some hotels. Look for a sign saying 'Todos Seguros' directing you up a side road to your left. 50 meters up the road you'll come to a house with a sign outside for 'seguros'. Here you can buy 1 year insurance for 50,000COP and your 5 year 'fit to drive' certificate for another 50,000COP. Liliana, the very nice woman who gets these documents ready for you will probably invite you into the house to help her find your plate number & vin on the documents. It all seems very unofficial, but it's legit.
Now drive back to the main road, continue on and take a right at the roundabout. You are now driving back towards Puente Internacional Simon Bolivar, but on the Venezuelan side. Just before you get to the checkpoint, turn left and go through the big red gates into the Seniat car park. You'll be directed where to park up, and which door to go through. Hand over your passport, license, registration, and insurance (all originals). They will do all the paperwork while you wait and bring you the completed forms to sign for 90 days TIP - also free.
A few kilometers up the road there is inexplicably another checkpoint where they may ask for your passport and TIP to ensure everything is in order. Otherwise you're done.
Venezuela to Colombia(San Antonio)
Ride up to the border, pass through the kiosk area and park up on the right next to the sidewalk. Behind you to the right is the queue for passport exit stamp, under the curved canopy. Exit stamp is free.
Ride ahead to the roundabout, go all the way around and back the way you came, back past the kiosks, then turn right through the red gates into the SENIAT car park. Park up at the back next to all the bikes, and walk through the red door, hand over your passport & TIP and wait a few minutes, they will keep the TIP & stamp the page in your passport with your bike exit. Free.
Back through the kiosk area, this time straight ahead at the roundabout, over the bridge, past the kiosks & park at the little layby on your right. Then walk to the big white colonial building behind you, it was on your right side as you rode up. Wait in line & get your 90 day entry stamp for Colombia. Free.
You can't get your DIAN temporary vehicle import at this border, you need to ride into Colombia & north to the other border at Puenta Internacional Atanasio Girardot (unfortunately you can't cancel your Venezuelan TIP at this border, so you need to start at the other one). We were stopped at a police checkpoint on the way out & they tried to fine us for not having insurance. We just kept explaining we can't get insurance till we have a TIP & we need to ride to the other border for that. After a 15 minute standoff they let us go.
At the new border, ride ahead to the kiosk & explain you are ENTERING Colombia. They will send you ahead, you do a u-turn to your left at the no u-turn sign, explain again at the next kiosk, then drive ahead to the car park & park up next to the DIAN kiosk.
Ideally you will still have data and a bit of cell signal as you will now need to take a PDF of your passport, exit stamp, vehicle reg, & Vin number (you can't really do this in advance as you need the exit stamp first, but they will help you as best they can). You need to log in to the Dian.gov.co website, fill in a bunch of info & upload the PDFs.
Once that goes through you'll get email confirmation, then inside the kiosk they will fill out your TIP, get you to sign, and send you another email confirmation.
Ride into Cucuta to buy mandatory SOAT Insurance. AFAIK the only place that can insure foreign vehicles is Da Seguros on the corner of Calle 14 and Avenida 4. It is a little door around the corner from the main office, and is only open Monday to Friday, and closes for lunch. You'll need Passport, original vehicle reg, license (the system wont accept your passport number in place of cedula but license number seems to work) and copy of passport & vehicle reg, and you can email them your DIAN if you haven't printed a copy. You also need an address (hotel address is fine) phone number and email. You can pay by card in the office, or for cash you need to go to the nearby bank to pay & get a receipt. For our motorbikes it was 175k COP per bike for 3 months. You'll get an email with PDF proof of your SOAT and they'll also print a copy for you if you ask.
Colombia to Ecuador (Ipiales)
You'll need data on your phone for this process, and there are no ATMs at the border so bring some cash in case you have a long wait. There is no charge for the entry/exit process.
Follow the line of traffic down the hill and curve around the the right, park up by the roadside or in the little carpark on the right. Inside the brown brick building you close your TIP (you'll need the email you got when you opened it, with the authorization number). Free. Walk to the building south of you - the line for getting your passport exit stamp is on the south side of the building. Free
Ride across the bridge, head right and pull up outside the blue and white migracion building in the car park. Walk through the courtyard to the glass doors at the back, and get your 90 day passport entry stamp. Free.
Walk back towards the car park. At the line of windows facing the car park, next to the bank, hand your bike registration in at the window furthest to the right. Your reg will be put in a stack, and depending on how many other people have handed in their reg before you, it can take anything from 15 minutes to 3 hours. They will give you a rough idea of your wait time.
Once its your turn, they will photograph your license plate & VIN, and will ask you for a phone number and email. You will get an email with a code, which you give them, then they print two copies of the TIP - one for you to sign & hand over, and one for you to keep. Check the VIN & Licence plate is correct. Free
As far as I was told, you do not need to buy insurance - the Ecuadorean system has compulsory insurance tied to yearly vehicle tax for residents, and foreigners are covered by that system.
As you are leaving the car park (if you're on a bike), avoid the left lane and pull right across to the right lane. The left lane has pressure activated fumigation so you'll get sprayed with disinfectant.
Ecuador to Peru (La Balsa)
I highly recommend this border crossing - it's super quiet & chill, very quick and easy. The views on the way there are great too, though the road surface is a little tedious if it's raining.
Follow the road down to the river and stop outside the aduana and migracion buildings on your left. TIP gets handed over with no receipt, and your passport gets stamped next door. Takes about 10 minutes for both together and is free.
You can change any dollars for soles at the restaurant across the street for a surprisingly good rate.
Ride ahead, under the black and yellow barrier (for some reason they've bent it into a curve you can drive under instead of leaving it open) and across the bridge. You have to leave your vehicle on the bridge in front of the Peruvian Barrier, and walk to the cluster of buildings on your left. You have to walk past the aduana building to get to the migracion building, but its easy to find.
Hand over passport, email address, phone number, get fingerprinted, answer some questions. 90 days no problem, free. Takes about 10 minutes.
Walk back to aduana, hand over passport, license, vehicle reg. If you have a car or van you can (maybe) buy insurance online in advance. We had motorbikes so couldn't. The aduana officer originally said we needed it, but when we explained we couldn't buy it in advance he gave us the TIP, and asked that we whatsapp him proof once we'd bought insurance later that day. Free, 10 minutes.
The nearest place we found we could buy insurance was in Jaen - about 3 hours ride from the border, so give yourself enough time to get there before close of office. Also, you are not allowed to bring fruit or veg across the border, though in my experience they were pretty laid back about this rule.
Peru to Bolivia (Kasani)
Fill out your Sivetur online in advance here
http://anbsw01.aduana.gob.bo:7401/sivetur/Parametro.jsp
You'll get a reference number when you submit, you'll need it at the border.
As you approach the cluster of buildings on the Peru side, the building to get your exit stamp is not the building labelled migracions, its the white two storey building on your right. Stamp will take minutes, and is free. Ride up to the barrier, aduana is on your right. They will take your passport & TIP, look at the bike for a bit, maybe ask you some questions. Once they have stamped your TIP closed you can ask for a photo. Free.
Ride across the bridge, and park up at the closed barrier. Migracion building is on your left, down the embankment. Standard is 30 days, they'll give you 90 if you ask for it, but it won't show up in your passport, so you have to take their word for it. Free (unless you are from USA apparently - check online for visa costs).
Next door to the left is the aduana office. You'll need to login to the free wifi, scan the QR code on the wall & complete the tourist entry form. You'll get a confirmation code to show the officer. Also show the Sivetur code number you got in advance, and your passport & vehicle reg. Explain that you need 90days to match your passport. If they ask why, just say you are planning to explore remote areas and it won't be easy to renew every 30 days. They shouldn't give you any trouble. Free. The officer will come with you to check your vehicle vin, and open the barrier. Whole process took less than an hour.
No insurance available at the border or in Copacabana. Nearest I could find was in La Paz.