Thanks for all the great suggestions!

Would anyone recommend any particular cruise lines for a sunset cruise? Do these need to be booked in advance?

I am definitely looking forward to a mix of relaxing by the pool/beach and seeing the sights of the town. Does anyone know if Key West is like New Orleans in the sense that you can walk around outdoors while drinking alcoholic beverages? :)

Any other must-sees or must-dos?

Thanks again!