Factor30, I don't have the number of letters. I think that it may be a song with lyrics something like "Everybody's talking" or similar and have a connection to transatlantic ship journeys. Sorry.
Sailing was on an album called Atlantic Crossing so it could be the answer to 2, but i don't think sailing is a common topic.
I still think the answers could be almost anything.
Have you got an example please of one that has been solved?
Some answered questions.
1.What is spoken here? Love.
2. Where does someone wait for me? Somewhere along the road.
3. What does the fair senorita not care for? The song in the air.
4. What has me shakin' like a flivver? Fascinating rhythm.
5. When was it all I hoped it would be? Monday morning.
Hope these might lead you to the answer, factor30, and Mark Rae.