We booked a sunset sail for a family of four and really enjoyed it. After a hectic day sightseeing and shopping this was a perfect tonic. We boarded the Shearwater which I think is the smaller boat but there seemed to be room for all. We basically picked a spot and laid down and relaxed. New York is beautiful at night and we really appreciated that the captain did not play any music so we could relax and soak in the sights and sounds of Manhattan at night. Unlike some other "sailing tours" we have been on they actually put up the sails and shut off the motor which was great. Definitely would recommend .