Parrot Heads Afloat: Fins Up Rocks the Nautical Mile

Sailing Into Margaritaville: A Dinner Cruise with Fins Up

Fins To The Left, Sunsets To The Right

This weekend we got to see something truly special — my brother Paul’s first gig with his new band, Fins Up, a Jimmy Buffett tribute band that brought the tropical island spirit right to Long Island. Paul plays bass guitar, anchoring the rhythm for an ensemble packed with talent. Their ensemble was something you don’t hear every day — ukulele players strumming out that breezy island rhythm, a fabulous lead singer who had the crowd hooked from the first note, a harmonica player adding soulful flair, a violin weaving unexpected magic into the mix, and more talented musicians rounding out the sound.

The Nautical Mile Vibe

The performance was part of an all-day Jimmy Buffett celebration along Freeport’s famous Nautical Mile — a lively waterfront strip lined with seafood restaurants, bars, and shops. After an afternoon of music and festivities, the evening’s highlight was our sunset dinner cruise aboard the Sapphire Princess. The yacht was decked out in full tropical theme, complete with palm tree décor, colorful banners, and an open bar serving up fruity frozen concoctions and rum punch. Passengers leaned into the theme, wearing tropical prints, leis, and playful parrot hats. Many were longtime Jimmy Buffett fans — or “Parrot Heads” — who knew every lyric and swayed with the music.

Smooth Sailing at Sunset

The weather couldn’t have been more perfect — warm but not too hot, a gentle breeze dancing off the bay, and a sky slowly melting into shades of orange and pink as we cruised along the calm canal and bay waters. Fins Up delivered a fantastic setlist filled with Buffett favorites: Margaritaville, It’s Five O’Clock Somewhere, Volcano, Son of a Son of a Sailor, Boat Drinks, Cheeseburger in Paradise, and of course, the party anthem Fins. The crowd sang along, cheered, and even got up to dance, turning the yacht into a floating dance floor.

Surprise Covers and Island Grooves

The band also surprised us with a few crowd-pleasing covers — Bob Marley’s Stir It Up, Blondie’s The Tide is High, The Rolling Stones’ Dead Flowers, and the smooth Latin groove of Oye Como Va. Every tune was delivered with skill, warmth, and just the right amount of playfulness

  Proud Moments and Happy Memories

Watching Paul perform was a proud moment — he looked completely in his element, playing alongside such talented musicians. The guests onboard clearly felt the same joy, smiling and dancing as the sun dipped below the horizon.

A Sunset to Remember

As we returned to the dock, the Nautical Mile still buzzed with life — music drifting from bars, laughter spilling into the street, and that unmistakable seaside energy in the air. It was the perfect ending to Freeport’s Jimmy Buffett Day — a celebration of music, good company, and the promise that there’s always a little paradise to be found. 

Follow The Band

If you want to keep the island vibes going, follow Fins Up on Instagram at @finsup_longislandmusic.