By Fiona Brander, Compass travel columnist

Let’s discuss the current hot topic: ESTAs and Cuba.
Since 2021, individuals who have been in Cuba are no longer eligible for an ESTA and must apply for a full B1/B2 visa. You are not banned from the US, you simply cannot use the ESTA anymore. The Cayman Compass has reported recently that a number of travellers who have visited Cuba since 2021, despite not having a Cuban stamp in their passports, have had their ESTAs revoked.
There is also a new question on the ESTA form which asks if you have been in Cuba since 12 Jan. 2021. Answering ‘yes’ to this question will result in a denial of the ESTA application.
Answering ‘no’, despite being in Cuba since 2021, would mean providing false information on the ESTA application and could have serious consequences; it may adversely affect future travel to the United States.
Also note, besides Cuba, travelling to Iraq, North Korea, Syria, Iran, Sudan, Libya, Somalia or Yemen since 1 March 2011 can also disqualify you from obtaining an ESTA.
There has been some confusion around whether 2011 was being used as the cut-off date for Cuba travel, but we have confirmed this is not the case.
What’s worrying some folks is that when you fill out the ESTA form, the crucial question 9 simply asks if you have been to any of those named countries – including Cuba – since 2011.
However, if you click yes, that’s not an automatic denial; you will be asked to provide additional information and routed to an advice page which essentially says that if you’ve been to Cuba after 2011 but before 2021, you will not be denied an ESTA.
For some reassurance, a client who had been in Cuba in 2019, completed the form on Wednesday and had the ESTA approved within an hour. Clients who visited after 2021, however, are seeing their applications rejected.
So what happens next?
What happens if you have been to Cuba since 2021 and normally use an ESTA to enter the US? What happens if you wish to go to Cuba in the future? Should you cancel your trip to Cuba? These are some of the questions travellers are asking this week.
If you normally use an ESTA and you wish to fly to or via the US this year, then yes, maybe you should cancel your Cuba trip. The first appointment at the moment for a US visa in Jamaica is mid-November.
The main thing to know is if you have visited Cuba since 12 January 2021 or plan to visit in the future, you are not banned from the US but you cannot use an ESTA anymore. You are allowed to apply for a US visa. So let’s talk more about your options.

For those without a US passport, residency, or a Canadian passport, obtaining a visa, or a visa waiver, is necessary to enter the United States. Among the options available are the ESTA, B1/B2 visa, and US waiver. Each serves a specific purpose, so let’s explore the differences between them.
ESTA
The ESTA is a visa waiver programme and not an actual US visa. It stands for ‘Electronic System for Travel Authorisation’ and is also known as VWP (Visa Waiver Programme).
To obtain approval, you need to apply online through the US Department of Homeland Security. It can take up to 72 hours to be approved or denied, and it costs US$21 per person.
Your passport will be checked for a valid ESTA both at the airline check-in desk and US immigration. The ESTA is electronically linked to your passport number.
The ESTA is available to citizens of 40 countries, including the UK, EU countries, Australia and New Zealand, among others.
However, an actual Cayman passport is not eligible for an ESTA, requiring a US visa or a waiver from Cayman immigration.
Once approved, the ESTA is valid for two years or until your passport expires, whichever comes first. It allows up to 90 days in the US per visit, with reasonable intervals between visits to avoid raising suspicion of attempting to live in the US.
Full US visa (B1/B2 non-immigrant visa)
For most tourists or workers visiting the US, the B1/B2 non-immigrant visa is suitable. It costs US$185 and remains valid for 10 years. The visa is even valid in expired passports, with the condition that you carry both the new passport and the old passport with the valid visa.
Once you possess a US visa, you no longer need an ESTA, and it’s generally not possible to have both simultaneously.
The B1/B2 visa permits stays of up to 180 days per visit and allows multiple visits for temporary occasional business, tourism or medical treatment purposes. Unlike the ESTA, you can fly on a private charter into the US with a full visa, which can be crucial for urgent medical situations, especially when you live on an island.
However, obtaining a US visa can be challenging – especially for residents of Cayman – without a US embassy on island. Appointments with the embassy in Kingston often take a long time to schedule, and the entire process can last several weeks.
Notably, visiting Cuba since 12 Jan. 2021 does not affect eligibility for the B1/B2 visas.
Challenges in obtaining a US visa
The process of securing an appointment can be time-consuming and, as of mid-July, appointments are scheduled months in advance, with the next available one currently mid-November in Kingston, Jamaica.
Once the appointment is confirmed, travellers need to make additional arrangements, including booking flights and accommodation, which incur added expenses. Typically, travellers need to spend at least one night in Kingston to complete the first step of the visa process.
During the appointment, travellers hope for a smooth process and approval from the US Embassy for their visa. However, the process does not conclude at the appointment itself.
Upon returning to Cayman, the visa applicant must send their passport back to Jamaica using a courier service, like DHL, and then patiently await the return of their passport with the US visa attached. This final step can take anywhere from two to three weeks or even longer.
Considering the time-consuming visa application process, travellers fortunate enough to secure an appointment in mid-November may only be able to fly to or via the US in December or possibly January.
There are many fabulous hotels including the beautiful Strawberry Hills hotel located just 30 minutes from Kingston in the stunning Blue Mountains, so a trip to get a US visa doesn’t have to be a chore.
US waiver for Caymanian passport holders
The US waiver is exclusively for Caymanian passport holders. It is a one-time waiver for entering the US and is meant only for visiting purposes.
Caymanian passport holders can obtain the waiver from Cayman immigration at a cost of CI$25. It is valid for a flight from Cayman to the US only. Notably, visiting Cuba since 12 Jan. 2021 does not affect eligibility for the US waiver.
Cayman passports are not eligible for an ESTA. You would need to apply for the British Overseas passport which allows a ESTA subject to the Cuba restriction advised above.
Further questions on the USA waiver for Caymanian passport holders need to be referred to Cayman Immigration.
In conclusion, understanding the differences between the ESTA, B1/B2 visa, and US waiver is essential for smooth travel to the United States. Each option has its pros and cons, depending on your circumstances and travel needs.
- Travel Pros’ Fiona Brander has launched a new monthly column in the Cayman Compass answering your travel queries and untangling some of the complexities of modern-day travel. She starts this week with the latest on the US clampdown on visitors who have been to Cuba. If you’ve got a question or idea for her next column, email [email protected].
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