Welcome to Jerry Pellegrino's Website

Jerry Pellegrino is a singer/songwriter/entertainer who lives in Naples, Florida. He was born in New York City and lived in the White Mountains of New Hampshire for 20 years (performing as part of the duo "Lang & Pellegrino") before moving to the sunshine state in 1996. He is a full time musician and plays at various hotels, clubs, “tiki” bars and private/corporate events in Southwest Florida.

With over 700 songs (see full song list), Jerry can please any audience. He covers most musical styles: 50’s, 60’s, 70’s, 80’s, 90’s and current songs of today; Tropical/Island/Reggae; Oldies; Motown; Classic Rock; Country & Country rock; Singer/Songwriter; Easy Listening; Blues, Irish and, of course, originals from his album, “The Tropical Cowboy”, which includes his infamous “How Can I Miss You, If You Won’t Go Away” song.

Jerry caters to the crowd, never playing the same songs in the same order – ever!  He takes requests, plays longer sets than Bruce Springsteen (“honey, does this guy ever take a break?”) and tries to create a “fun” atmosphere. A good time is had by all!


Jerry is playing at the Island Gypsy on the Isle Of Capri every Sunday  from 3-6 PM. 

He will be at Cafe Luna on 5th Avenue in Naples on Wednesdays, December 17 and on Mondays, Dec. 22 & 29 from 7-10.   He will be at Cafe Luna East on Friday, Dec. 26 from 6-9 PM.  In January, Jerry will be at Cafe Luna on 5th Avenue on Tuesdays, Jan. 6 & 13 and Wednesdays, Jan. 7, 21, 28 from 7-10 PM.

Come on down and join the fun!


Where Jerry has performed in southwest Florida:
  • Naples Beach Hotel
  • Wine Loft  of Naples (Mercado)
  • "Quinn's On The Beach" Marco Marriott Hotel (7 years)
  • McCabe's Irish Pub, Naples (5 years)
  • Ritz Carlton Hotel pool side, Naples
  • Handsome Harry's Third Street Bistro, Naples
  • Island Gypsy, Isle of Capri
  • Dolphin Tiki Bar, Marco island   
  • Cafe Luna East, Naples
  • Cafe Luna, 5th Avenue, Naples
  • Erin's Isle Restaurant & Irish Pub, Naples
  • South Street Grill,Naples
  • Lely Resort Players Club, Naples
  • Village Pub in Venetian Village, Naples
  • Old Naples Pub, 3rd Street, Naples
  • Snook Inn, Marco Island
  • Virgina's Restaurant, Naples
  • Fitzgerald's Irish Pub
  • La Playa Hotel, Naples 
  • Sandy Parrot Tiki Bar & Grill, S. Ft Myers
  • Sydney's Pub, Tiberon Resort, Naples
  • Chapel Grill, Naples
  • Evenings On 5th, Naples
  • Evenings On 3rd,Naples
  • Little Bar, Goodlette
  • Old Marco Lodge, Goodlette
  • Edgewater Beach Hotel, Naples
  • La Casita, Marco Island
  • Pelican Marsh Golf Club, Naples
  • Bay Colony, Naples
  • Registry Hotel,Naples
  • Backwater Jack's, Bonita
  • Island Country Club, Naples
  • Kensington CC, Naples
  • Collier Reserve, Naples     
  • Commons Club,Naples
  • Marco Beach Ocean Resort
  • Naples Bath & Tennis
  • Miramar Lakes Beach Grill
  • Estuary, Naples
  • Chrissy's Tavern & Bistro, Naples
  • Bill's Steak & Seafood, Naples
  • Treviso Bay, Naples
  • Bonita Bay Club, Bonita Springs



Website Builder