50 Best Country Songs About Sailing

Best Country Sailing Songs to Play on the Water

There’s a strange rhythm that comes with being on the water. It’s part calm, part restless, the way waves can look steady one second and wild the next. Country songs that fit sailing often lean into that split feeling, even if they were never written with boats in mind. You’ll find verses that sound like wide open seas, or choruses that feel like the horizon stretching farther than you meant to chase. The connection is loose but strong enough to carry.

Sailing stories in music have always drifted between literal and metaphorical. Some tracks picture salt air and ropes on deck, while others swap the sails for memories, heartbreak, or escape. Listeners tie them back to the water anyway because the themes cross over so easily. Even when the lyrics could fit pop, rock, country, and R&B songs, the sound of steel strings or fiddle gives it a pull that feels like drifting past the shoreline. It’s less about getting the details right and more about catching that restless motion.

The fun part is that not every track needs to be anchored in sailing to hit that mood. A few lean more into freedom, some wander into nostalgia, and others capture that lonely space you feel when the shoreline fades behind you. They all still ride the same current, pushing forward into the kind of open space only water can give. Here are the best country sailing songs that capture that drift.

1. 'Boats' by Kenny Chesney

2. 'Where the Boat Leaves From' by Zac Brown Band

3. 'Knee Deep' by Zac Brown Band featuring Jimmy Buffett

4. 'Buy Me a Boat' by Chris Janson

5. 'Pontoon' by Little Big Town

6. 'The Seashores of Old Mexico' by George Strait

7. 'Redneck Yacht Club' by Craig Morgan

8. 'Sailin' the Wind' by Loggins & Messina

9. 'No Shoes, No Shirt, No Problems' by Kenny Chesney

10. 'Changes in Latitudes, Changes in Attitudes' by Jimmy Buffett

11. 'I Was on a Boat That Day' by Old Dominion

12. 'Margaritaville' by Jimmy Buffett

13. 'A Pirate Looks at Forty' by Jimmy Buffett

14. 'Toes' by Zac Brown Band

15. 'One Margarita' by Luke Bryan

16. 'Soul of a Sailor' by Kenny Chesney

17. 'Beer in Mexico' by Kenny Chesney

18. 'On the Boat Again' by Jake Owen

19. 'Southern Cross' by Crosby, Stills & Nash

20. 'The River' by Garth Brooks

21. 'Sail Away' by David Gray

22. 'Son of a Son of a Sailor' by Jimmy Buffett

23. 'The Wreck of the Edmund Fitzgerald' by Gordon Lightfoot

24. 'Sail On Sailor' by The Beach Boys

25. 'Come Sail Away' by Styx

26. 'Sailing' by Christopher Cross

27. 'Brandy (You're a Fine Girl)' by Looking Glass

28. 'A Sailboat in the Moonlight' by Billie Holiday

29. 'Into the Mystic' by Van Morrison

30. 'Boats to Build' by Jimmy Buffett

31. 'It's Five O'Clock Somewhere' by Alan Jackson and Jimmy Buffett

32. 'Somewhere on a Beach' by Dierks Bentley

33. 'I Need a Boat' by The Mavericks

34. 'Coastal Confessions' by Alan Jackson

35. 'The Mermaid' by Great Big Sea

36. 'Barefoot Blue Jean Night' by Jake Owen

37. 'Pirate Flag' by Kenny Chesney

38. 'Something 'Bout a Boat' by The Swon Brothers

39. 'Fisherman's Blues' by The Waterboys

40. 'Sloop John B' by The Beach Boys

41. 'Sailing to the Shore' by James Taylor

42. 'Castaway' by Zac Brown Band

43. 'Day Drinking' by Little Big Town

44. 'Sunshine and Summertime' by Faith Hill

45. 'All the Way to the Ocean' by Jack Johnson and Ben Harper

46. 'Blue Water' by Brad Paisley

47. 'Island Song' by Zac Brown Band

48. 'Drift Away' by Dobie Gray

49. 'Boats, Beaches, and Beer' by Kenny Chesney

50. 'Summertime' by Kenny Chesney