When you go sailing in DST, the only time you get the awesome sailing track is when the player is "working," such as reeling an anchor or raising/lowering a sail. Unfortunately, the music only plays for a short duration and may not play again (it depends if you do enough "working"). It also only plays for the player doing the working action, not for your friends that are onboard, who will say "what music are you talking about?" when you hear the awesome track.
My suggestion is that if the boat is in motion, the sailing track should play for all players onboard. I got this idea from playing SW recently, where simply getting on a boat will constantly play the sailing music in SW. It made sailing in SW more lively since I just get sad when the sailing music inevitably stops playing when you sail in DST.