Oz to USA via Cuba

The Visa Waiver Program is primarily designed for short tourist visits. The B-2 is the standard visa for visitors who travel frequently to the US for business or pleasure. It is a multiple entry visa that is valid for ten (10) years and allows a visitor to stay for up to 6 months at a time.

The Visa Waiver Program allows visa-less entry for up to ninety (90) days for nationals from certain countries--UK included. The regulations do not specifiy how often the VWP can be used, but someone who uses it 3-4 times a year will probably come under scrutiny eventually. Now that there is pre-clearance application (ESTA) that may not be as much of a consideration. But VWP is not designed for the frequent traveller to the US. If it hasn't been a problem for you up to this point, it probably won't be in the future. Overuse could raise questions though.

The application for the B-2 is usually submitted to the US Embassy or designated consulates in the applicant's home country. It involves a face to face interview. The application though can be submitted at any Embassy so you could apply at the US Interests Section in Havana.

I am not worried about questions now that my son and his mother have legal residency in the US, but I prefer not to force that face-to-face interview unless I have to ! (Though I guess then, I might be able to fly direct.)

Thanks

I was not putting a Cuba factor into the VWP equation. Repeated use of the VWP could give rise to suspicion that the entrant might be residing and/or working in the US in violation of the immigration laws. An explanation of the situtation would probably suffice, but some people don't like to reveal personal information to a government official.

I know someone---Euro national residing in Mexico---who was told last time he used the VWP that he needed to get a B-2 if he planned to continue travelling frequently to the US. Perhaps the principal disadvantage of the VWP is that in exchange for the US government's waiver of the visa requirement, the visitor waives all right to contest a decision of CBP officer to deny entry. A B-2 visa holder has some limited recourse when entry is denied.