Sentence 1: Madeira's hotels, many of them traditional, older style accommodations, have long have been clustered in the hotel and tourist zones hugging Funchal's western coast.

Sentence 2: Madeira does not have any hotels in Funchal.
Is this second sentence entailed by the first?

Answer: no

Sentence 1: Somehow, he knew I'd understand.

Sentence 2: He was intelligent and knew me well.
Is this second sentence entailed by the first?

Answer: it is not possible to tell

Sentence 1: and uh it's usually not a very smooth smooth thing we were uh lucky i was lucky too that i only have my one brother

Sentence 2: It's usually very easy, but I had a hard time.
Is this second sentence entailed by the first?

Answer:
no