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When should I apply for ESTA?

You can apply for ESTA any time you like - but the U.S. government generally recommends people to apply for ESTA 72 hours before their trip. Even though an ESTA can take minutes or even seconds to be approved, there are some applications that can take the full 72 hours to process through. These tend to be applications where the information is unclear or containing mistakes, so make sure to be clear and accurate when filling out yours!
Since it is valid for 2 years, you could always apply for your ESTA permit when purchasing your tickets. It’s always better to complete the application early, in case there are any mistakes or issues that result in you having to reapply, or in case your denied and need to reapply. Click here for more information on why your application could be denied.
If you think that any of the criteria for inadmissibility contained within the Immigration and Nationality Act apply to you, then you should apply for a B1 or B2 visa instead. However, it must be noted that obtaining a visa is generally a much more lengthier process than the ESTA, if you want to know more about the differences between an ESTA and a visa then have a look at the relevant page here.
If you’re coming to the U.S. by land either via Canada or Mexico, then you do not need an ESTA permit. The permit is only needed for air or sea travel. However, if you are coming to the U.S. using a personal yacht or personal boat, then you will need a B1 or B2 Visa. On the other hand, if you’re going to the U.S. on a cruise, then you can enter the U.S. using your ESTA.
Something to bear in mind is that an ESTA does not guarantee entry to the U.S. That decision is dependent on Customs and Border Protection (CBP). The CBP can deny or cancel an ESTA at any point during or before travel.