Ok guys! We have done it! My husband is here post closing the visa office in Havana!! I will write how we did it. I had to learn things the hard way (costly way).
1. There was no way a passport would be going into Cuban mail. Not an option.
2. After thinking about me flying down and getting his passport, and sending it to Mexico, we decided that he would go to Trinidad and Tobago. I don't have a lot of vacation time at work and me flying down and back and then down and back, would time consuming.
3. A plane ticket to Trinidad and Tobago. They will not let a Cuban get on the plane without a return ticket to Havana. At first, I had bought a plane ticket from Havana to POS, then POS to Canada. About 20 minutes before boarding, I received a call saying I had to buy him a plane ticket back to Havana otherwise, they wouldn't let him on the plane. Bought plane ticket last minute. He flew with Caribbean Airlines.
4. When they land in POS, they are given a tourist card with their plane ticket exit date as an "expiry" of sorts. Make sure you buy a plane ticket at least two weeks....because if you don't, and you haven't gotten the"come and get your passport" request, you will have to change the ticket and they will have to go to T&T Immigration to get an extension.
5. $1000 USD (although he was not asked to prove he had the money).
6. We always get travel insurance (again, he was asked for no proof).
7. Airbnb reservation or hotel accommodation of proof that they have a place to stay.
Prior to going to the VAC office, you have to fill out a VAC consent form (TT Services Consent Form)(
https://www.vfsglobal.ca/Canada/Trinidad-and-Tobago/pdf/Consent-Form-Revised-Deliverable-VFS.pdf) and bring 2 copies. This gives them the authority to handle your file. Then, you need to pay the VAC a $12 "Package Transmission Fee" (
https://www.vfsglobal.ca/Canada/Trinidad-and-Tobago/pdf/Consent-Form-Revised-Deliverable-VFS.pdf) The "Package Transmission" fee is the DHL cost to send your documents to the High Commission. I ended up doing a bank transfer from my account to the DHL Scotiabank account. It wouldn't allow me online to pay because the applicant's name is different than the credit card name (at least that is the only thing I could think of as to why my credit card wouldn't work). The VAC needed that receipt before they would send the package. You can pay at the VAC office, but you need a credit card or debit card.
I was told the process would take 2 -30 days and after a week, I sent an email asking if they could give me a timeline due to increasing costs. They were really amazing, because I got an email saying that they would process everything and send it to the VAC office the next day.
We also had an Airbnb that was within walking distance to the VAC office - Mamelan Bed & Breakfast. We wanted a place where he didn't have to taxi everywhere. It was one of the most affordable places.
And now, he's here!! I ended up cancelling the return flight to Havana, then using those credits to fly him to Toronto. Cancelled the Westjet flight from POS to Calgary and then used those credits to fly him from Toronto to Calgary. Time in Immigration in Toronto - 15 minutes. It was incredibly easy!
It has been a process and we are finally done!