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We (German passports) are currently planning a trip based around Miami in February. We also want to visit the Bahamas for a few days and move on towards Cuba.

Question 1: What is the current status regarding flights between the US and Cuba? From what I can see there are no direct flights from Nassau to Santiago, so we will have to travel via Miami or Havana when leaving the Bahamas. I have found flights from Miami to Santiago but was wondering whether or not these are really available to the public?

Question 2: Is there any potential issue with traveling through Miami multiple times in terms of customs and immigration? Our Flight back home would also have to connect through Miami, simply because this is our cheapest option at the time. In this case our trip would be: home->Miami->Nassau->Miami->Santiago->Miami->home, which seems rather weird.

We are cleared to enter each of the countries individually, but would this sequence really work?

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Question 1: There are only charter flights between Miami and Santiago. However, Aerogaviota and Bahamasair fly directly from Nassau to Havana. As for Miami-Havana flights, American, Delta and Frontier airlines are launching regular nonstop services now in December

Question 2: Sure, if the CBP asks you about the reason for the amount of entries, just explain it to them. I don't see why it should be an issue - you're not overstaying in the WHTI area after all, nor are you violating the Terms of the VWP.

Nowadays when using APC kiosks, they reportedly ask you far fewer questions in most cases anyway.

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