Costa Rica first for 10 days and then Jamaica. I would fly back to the US via Jamaica and then catch my flight 4 hours later to the UK.

https://uk.usembassy.gov/visas/non-immigrant-visa-faqs/visa-waiver-program-and-esta/

If I enter the United States visa free under the Visa Waiver Program, can I then travel to Canada/Mexico/ Bermuda or the islands in the Caribbean?

Yes, provided you have a return or onward ticket. If your return journey will take you back through the United States, even if only in transit, the total trip, including both periods of time spent in the United States/Canada/Mexico Bermuda, or the islands in the Caribbean cannot exceed 90 days. If it does, you will require a visa.

It is my understanding, but I have not checked the official wording of the regs recently but nor do I believe they have changed - but the link is in post 3, that as you are headed to Costa Rica, the fact that your return flight has a stopover in the USA will be OK.

Had you been travelling to Jamaica alone, then you would have been considered as overstaying the 90 day ESTA single trip limit.

SWT

Thanks for the reply.

Just clarifying so I’m completely sure but leaving the US and qualifying countries ie Mexico and the Caribbean means that I’m leaving the US completely and that on my return I am entering on a new visa, so the limit is not overstated?

Yes, you’d get a new VWP entry when you fly back to the US.

As well as Canada and Mexico, the rest of the list is:

The definition of adjacent islands is in INA, Section 101(b)(5):

Saint Pierre

Miquelon

The Dominican Republic

Haiti

Bermuda

The Bahamas

Barbados

Jamaica

The Windward and Leeward Islands

Trinidad

Martinique

Other British, French, and Netherlands territory or possessions in or bordering on the Caribbean Sea

Make sure you have evidence you were in Costa Rica.

It's not a new visa.

It's a new entry on the ESTA VWP, albeit for a few hours rather than your previous 80 days.

In simple terms, ESTAs allow for any number of multiple entries to the USA within the 2 year validity period (or less if your passport runs out before the date it was granted), but the max duration of each entry or visit is 90 days including time spent in the countries it also applies to.

It's a bummer for folk who leave the USA for an extended period of time but have flights that connect in the USA as there are so many more fight options via US airports, and do not check. Credit to you that you did.

V - I challenge you to find any Caribbean island that list does not cover, and Bermuda, which strictly is not a Caribbean island, is also on the list. Actually given the US approach to the ESTA jurisdiction, I'm surprised it doesn't stretch to the Panama canal!

Yes, horribly complicated.

SWT

PS: Hotel confirmation or credit card receipts or bus tickets for CR should do. And keep them until you're back in Blighty.

The problem is most likely not the second entry to the US but the first entry. You need to have a confirmed ticket out of the area within 90 days. Most European and other ESTA visitors have round-trip tickets which are included in the API airlines sent to USCBP before they arrive at the port of entry. So the OP would need a FLIGHT from the US to beyond Mexico to Costa Rica within 90 days of first arrival.

Walking/driving to Mexico does not produce a US exit record, but flying does. If the OP flies from US to Mexico, USCBP may not know if they exited Mexico. But if it's a nonstop flight from US to CR, then there will be an exit record that resets the ESTA clock, so when flying in from Jamaica, it won't be a problem.

"Other British, French, and Netherlands territory or possessions in or bordering on the Caribbean Sea"

Guyana, French Guiana and Suriname but not Guatemala, Belize, Honduras, El Salvador, Nicaragua, Costa Rica, Panama, Colombia and Venezuela.

Guess someone failed Geography 101 when producing the ESTA list