HarborFest is a weekend filled with many things maritime, but few are as able to get us in a celebratory mood as the music wafting through Sag Harbor. Getting ready to hear songs of the sea got us thinking about the top ship/sailing/boat songs of all time, and we couldn’t keep our favorites to ourselves. Take a look, and a listen. And don’t be afraid to sing along!
10) “Sloop John B” by The Beach Boys
This many years later and it still makes us want to raise a sail (but we’d be remiss not to also mention the Jerry Jeff Walker cover of this one is worth a listen).
9) “I’m Shipping Up to Boston” by Dropkick Murphys
Sailors losing legs is a common if somewhat unpleasant bit of seafaring lore that gives this song a boost onto our list. Besides, if it can provide inspiration for UFC fighters and Martin Scorsese alike, it must have something going for it.
8) “Day-O (The Banana Boat Song)” by Harry Belafonte
Still a gem, even with the Beetlejuice flashbacks.
7) “The Castaway Song—Led Zeppelin Meets Gilligan” by Orange Hat
With all due respect (and it is due) to “Stairway to Gilligan’s Island” this mashing of Led Zeppelin and the castaway classic raises pop-culture parady to another lever.
6) “Brady” by Looking Glass
How many sailors from days of yore would have sympathized with the line “But my life, my lover, my lady is the sea”?
5) “Wreck of Edmund Fitzgerald” by Gordon Lightfoot
A history lesson and haunting tune in one.
4) “Son of a Son of a Sailor” by Jimmy Buffett
No list would be complete without a boat ballad from Mr. Buffett.
3) “Southern Cross” by Crosby Stills and Nash
How many tunes do you know that can reference the Marquesas, Papeete and lost love?
2) “If I Had a Boat” by Lyle Lovett
When it comes right down to it, maybe all you really need in life is a boat and a pony.
1) “The Downeaster Alexa” by Billy Joel
If you listen to this ode to Long Island’s fishermen and don’t get a rush of chills, have to fight back tears and uncover a range of emotions you weren’t sure you had…listen again.
The eclectic mix of “Ships, Sails and a Sag-Inspired Singalong” is brought to you by Flying Point Surf Shop in Sag Harbor. Stop by during HarborFest or visit them online at flyingpointsurf.com.