Beer Drinkers and Sail Raisers, Hanna's Reef
Life on a Boat by Gene Mitchell
French Kissing Life, by Kenny Chesney
The first two are a little on the corny side, but I love the lyrics. The third one is one of my alltime favorite songs to listen to on the water. With one of the alltime great sailing lyrics "french kissing life square in the mouth sailing out on the sea". There are about 4 or 5 songs (including Magic, Soul of a Sailor, Somewhere in the Sun) that are sailing specific on Chesney's "Be As you Are" album.
Other favorite sailing songs:
Into the Mystic, Van Morrison
Sailing Away from the Madness, Kelly Mcguire
Sloop John B, Beach Boys
Ride Captain Ride, Blues Image
The Sun and the Wind, Gene Mitchell
Local Knowledge, Hanna's Reef
Out on the Ocean by Rick Steffen (Not sailing specific but a great on the water song)
Doesn't matter the era or genre or even if you like them, I will sort them out. Beaches, oceans, and particularly stinkpots don't count. The song needs to be about sailing or sailors, but it doesn't have to be in the title.
Shrimpboats by Jo Stafford, 1951. There is an oddity here: I was 5 in Savannah, Ga when this song came out. She mentions sails in the song but upon researching shrimp boats, the 1950 era boats didn't seem to have any sails, they looked to be just smaller versions of today's boats. I'm hoping the author was older and reminiscing about HIS childhood. I found some 1910 boats with sails but these were very different boats.
Geez, after 12 pages of responses I can't believe you guys left out this classic historical song! Back in my big band days, we would always always include this in the set list for any waterfront venues, including Schaffer's Canal House (recently reopened, by the way), St. Michaels, Rehoboth Beach, etc. As a general rule, the drunker we were, the better