Live at Moe's
Blush Salon grand opening. Photo by Brianna Martins, BoHo Creative
Blush Salon grand opening. Photo by Brianna Martins, BoHo Creative
Playing for the Naples Oxygen grand opening.
Playing for the Naples Oxygen grand opening.
Playing for the Naples Oxygen grand opening.
Appearing weekly at Moes
Playing a private party in Naples.
Playing a private party in Naples.
Wedding at Cheeca Lodge, FL Keys
Let me entertain your guests with an eclectic mix of songs ranging from timeless blues standards all the way up to current hits. I can provide a variety of genres tailored to your audience, including: ambience/dinner music, classic rock & blues to rock the place, bluegrass/country, even Irish music! More than "just a guy with a guitar singing". I keep it interesting with songs on mandolin and dobro as well as spicing it up with percussion, added harmonies and harmonica. I don't use backing tracks. It's all me (with the exception of the harmonies from my harmonizer pedal.)
Need a full band? I also play in a classic rock/blues band when you really want to rock! DJ capability also!
22 reviews
Brandon M.
May 23, 2026I hired Kelly play the guitar and sing on the beach while I proposed to my girlfriend. There was a very time sensitive aspect of it, and everything had to go just right. Kelly arrived even earlier than I would’ve expected, and due to his careful planning, everything went perfect. As a musician myself, Kelly played the guitar beautifully and had an amazing voice. I would without a doubt hire him again!
Hired as: Singing Guitarist
Matt V.
March 19, 2021I hired Kelly to play our St. Patrick’s Day Party. Kelly was absolutely fantastic! Arrived and was setup ready to go as guests arrived. Extremely friendly, communicated top notch with me before the event. My friends had such a great time! His Irish music is awesome, as well as his other party jams! He accommodated everything we asked for. He mixes up guitar, mandolin, harmonica! I already booked him for next year! Highly recommended!
Hired as: Classic Rock Band, Guitarist, Irish / Scottish Entertainment, Mandolin Player, Multi-Instrumentalist, One Man Band, Singing Guitarist
Kelly Winfield
Matt,
Thank you so much! You guys were a great crowd. Looking forward to next year! Slainte!
Anita G.
February 8, 2020Kelli was amazing! He was able to choose songs just by reading the crowd and everyone loved what he sang! He even controlled the volume during dinner so folks could enjoy their table conversations and music!! Thanks Kelli for making our even fun!!!
Hired as: One Man Band, Singing Guitarist
Kelly Winfield
Anita,
Thanks again for the booking! I appreciate your kind words and your generous tip! See you next time...
Dustin M.
May 21, 2019Kelly responded quick and played the specific song I wanted. He followed all instructions surprising my girlfriend on the beach as I proposed and performed perfectly ! Would recommend to anyone !!!
Hired as: Guitarist
Kelly Winfield
Dustin,
Thanks for continuing my 5-star rating! Congratulations on your engagement! Keep me in mind for future events!
Travis H.
November 26, 2017I hired kelly for my proposal and he was amazing!! First off he was easy to contact and very responsive. I requested some songs that he did not know but he learned them in 2 days and absolutely crushed them. Lastly he was very accommodating for some special requests that really made the night extra special. Highly recommended!!
Hired as: Singing Guitarist
Price range: Contact for rates
Languages: English
Gig length: 60 - 240 minutes
Insurance: $1,000,000 - General liability
Your audience will be delighted with an eclectic song list insterspersed with humorous banter and interesting anecdotes sure to keep listeners engaged.
Kelly Winfield started his love of music at the age of 8 singing in church choirs, then later in high school and college. He received formal voice training in college and performed in an internationally broadcast program. Recently he sang the national anthem acapella in front of Florida Governor Rick Scott and other dignitaries. Kelly's real love, though is 70's influenced classic folk and rock. He has a 4-octave range which allows him to sing high and clear like John Denver or growl the blues like Muddy Waters! He has been performing in front of audiences large and small most of his life. Not only has he has performed all around America but also in Australia and Mexico.
Kelly is a self-taught multi-instrumentalist. Inspired by his father's harmonica playing, he took up the "harp" in his teens and perfected his technique on lonely road sides hitch-hiking around the South. His first guitar was a used Teisco Del-ray Strat copy he bought for $15 when he was 16. He finally managed to get a real Stratocaster at age 18, after a guy in a Lincoln with lots of insurance crunched his primer brown 1965 VW micro-bus. Kelly continues to expand his horizons by taking up mandolin, dobro and banjo. Kelly has been playing in duos, solo and in bands around Southwest FL for the past twenty-five years.
I can supply everything but the stage!
Friday
Surprise
5:30pm - 6:00pm
•
Marco Island, FL
Friday
Grandeza CC
6:00pm - 9:00pm
Wednesday
St. Patrick’s Day party
All-day event
Saturday
Wedding Ceremony
5:00pm - 6:00pm
•
Naples, FL
Friday
Dinner Party
7:00pm - 10:00pm
•
Naples, FL
Saturday
Restaurant/Bar Event
5:00pm - 8:00pm
•
Fort Myers Beach, FL
Monday
Freedom Boat Club social
5:30pm - 7:30pm
Monday
Corporate Event
7:00pm - 9:30pm
•
Bonita Springs, FL
Saturday
Graduation
5:00pm - 9:00pm
•
North Fort Myers, FL
Saturday
Holiday Party (Christmas)
7:30pm - 10:30pm
•
Cape Coral, FL
Friday
Cultural Event
6:00pm - 9:00pm
•
Fort Myers, FL
Saturday
Birthday (Adult)
5:00pm - 9:00pm
•
Cape Coral, FL
Saturday
Birthday (Adult)
6:00pm - 10:00pm
•
Cape Coral, FL
Saturday
Birthday (Adult)
2:00pm - 6:00pm
•
Naples, FL
Friday
Cocktail Party
6:00pm - 8:00pm
•
Naples, FL
Saturday
Wedding Ceremony
6:00pm - 7:00pm
•
Fort Myers, FL
Saturday
Holiday Party (Other)
6:00pm - 12:00am (Sun)
•
Naples, FL
Saturday
House Party
7:00pm - 11:00pm
•
Fort Myers, FL
Saturday
Birthday (Adult)
5:30pm - 9:00pm
•
Naples, FL
Saturday
Birthday Party
7:00pm - 8:30pm
•
Naples, FL
Saturday
Private Party
7:30pm - 9:30pm
•
Fort Myers, FL
Saturday
Private Party
7:00pm - 10:00pm
•
Fort Myers, FL
Saturday
Birthday Party
4:00pm - 8:30pm
•
Naples, FL
Saturday
Birthday Party
5:00pm - 8:00pm
•
Naples, FL
Saturday
Other
6:30pm - 9:00pm
•
Fort Myers, FL
Thursday
Wedding Ceremony
6:30pm - 7:30pm
•
Naples, FL
Thursday
Private Party
5:00pm - 7:00pm
•
Estero, FL
Wednesday
Club/Nightclub
6:00pm - 9:00pm
•
Bonita Springs, FL
Thursday
Wedding Ceremony
6:00pm - 10:30pm
•
Naples, FL
Friday
Birthday Party
6:00pm - 8:00pm
•
Naples, FL
Saturday
Birthday Party
7:30pm - 8:00pm
•
Sanibel, FL
Monday
Birthday Party
7:00pm - 9:00pm
•
Fort Myers, FL
Thursday
Grand Opening
5:00pm - 8:00pm
•
Naples, FL
Below is a partial list of songs. Set lists can be custom-tailored for your particular venue. I take requests! If you'd like a particular song, I can usually learn it and perform it for you. If I don't already know it--I know a LOT of songs.
MARGARITAVILLE Jimmy Buffett
SHE TALKS TO ANGELS Black Crowes
'OL RED. Blake Shelton
Folsom Prison Blues. Johnny Cash
Blue on Black. Kenny Wayne Shepherd
EVERY ROSE HAS ITS’ THORN Poison
COPPERHEAD ROAD Steve Earle
LOSING MY RELIGION R.E.M.
TAKE IT EASY Eagles
SOUTHERN CROSS Crosby, Stills & Nash
LET HER CRY Hootie & the Blowfish
GOT MY MOJO WORKIN’ Muddy Waters
GOOD RIDDANCE (TIME OF YOUR LIFE) Green Day
SUMMERTIME BLUES The Who (Eddie Cochran)
HEY, BARTENDER! Johnny Lee
Turn the Page. Bob Seger
MOVE IT ON OVER George Thorogood
KEEP YOUR HANDS TO YOURSELF Georgia Satellites
MELISSA Allman Brothers
SHE HATES ME Puddle of Mud
3 A.M. Matchbox 20
Heart of Gold. Neil Young
DEAD OR ALIVE. Bon Jovi
TAMPICO TRAUMA Jimmy Buffet
SATURDAY NIGHT Eagles
SEAGULL Bad Company
FEELIN’ ALRIGHT Dave Mason
DEAD FLOWERS The Rolling Stones LIVINGSTON’S GONE TO TEXAS Jimmy Buffet
DEAR ABBEY John Prine
NEEDLE AND THE DAMAGE DONE Neil Young
THE WEIGHT The Band
THESE DAYS Dan Fogelberg
AS THE RAVEN FLIES Dan Fogelberg
BRING IT ON HOME Dave Mason (Sam Cooke)
ROCKY MOUNTAIN HIGH John Denver
SHANTY Jonathan Edwards
SPANISH PIPED DREAM John Prine
THESE DAYS Jackson Browne
COUNTRY ROADS John Denver
LADY IN BLACK Uriah Heep
BEFORE YOU ACCUSE ME Eric Clapton
NOBODY KNOWS YOU WHEN YOU’RE DOWN AND OUT Eric Clapton
WHIPPIN’ POST Allman Brothers
PEACEFUL, EASY FEELING Eagles
GIMME 3 STEPS Lynyrd Skynyrd
SIMPLE MAN Lynyrd Skynyrd
ROCKIN’ IN THE FREE WORLD Neil Young
BLUES BEFORE SUNRISE Eric Clapton
BONEY FINGERS Hoyt Axton
WILLING Little Feat
COWS WITH GUNS Dana Lyons
LITTLE MARTHA Allman Brothers
MAINSTREET Bob Seger
GALWAY GIRL Steve Earle
SIGNS Tesla (5 Man Electrical Band)
7 BRIDGES ROAD Eagles
NIGHT MOVES Bob Seger
LIFE BY THE DROP Stevie Ray Vaughn
THE A@#HOLE SONG David Allen Coe
ICE CREAM MAN Van Halen
REMEMBER SONG Tom Rush
IF MY NOSE WAS RUNNIN’ MONEY Aaron Wilbern
WISH YOU WERE HERE Pink Floyd
THE WIZARD Uriah Heep
DREAMS (I’LL NEVER SEE) Allman Brothers
JESUS JUST LEFT CHICAGO ZZ Top
MADAME BLUE Styx
THE CAPTAIN AND THE KID Jimmy Buffet
BELL BOTTOM BLUES Eric Clapton
PLEASE, DON’T BURY ME John Prine
4 & 20 Crosby, Stills & Nash
THE BALLAD OF SPIDER JOHN Jimmy Buffett
YOUNGBLOOD Bad Company (The Coasters)
MIDNIGHT RIDER Allman Brothers
CROSSROADS Eric Clapton (Robert Johnson)
SHAKE YOUR MONEYMAKER Elmore James
I HEAR YOU KNOCKIN' Dave Edmunds
KNOCKIN' ON HEAVEN'S DOOR Bob Dylan
CAN'T YOU SEE Marshall Tucker Band
SEARCHIN' FOR A RAINBOW Marshall Tucker Band
HONKY-TONK WOMEN The Rolling Stones
APE-MAN The Kinks
LAWYERS, GUNS & MONEY Warren Zevon
DOWN BY THE RIVER Neil Young
ROCKY RACCOON Beatles
MOUNTAIN DEW Charlie Daniels
LONG-HAIRED COUNTRY BOY Charlie Daniels
TOES Zac Browne
ANOTHER BEER IN MEXICO Kenney Chesney
WAY OUT HERE Josh Thompson
IN COLOR. Jamey Johnson
SOME BEACH Blake Shelton
ALL SUMMER LONG. Kid Rock
WHISKEY BENT & HELLBOUND Hank Williams Jr.
SMALL-TOWN USA. Justin Moore
RIGHT WHERE I NEED TO BE Gary Allan
ARE YOU SURE HANK DONE IT THIS WAY? Waylon Jennings
BIG GREEN TRACTOR Jason Aldean
TEQUILA MAKES HER CLOTHES FALL OFF Joe Nichols
PEOPLE ARE CRAZY. Billy Currington
BILOXI Jimmy Buffett/Jesse Winchester
THE WINO AND I KNOW Jimmy Buffett
CHANGES IN LATTITUDES, CHANGES IN ATTITUDES Jimmy Buffet
IRISH MUSIC
DIRTY OLD TOWN The Pogues
IRISH ROVER The Pogues
THE FIELDS OF ATHENRY Traditional Irish folksong
MOLLY MALONE Traditional Irish folksong
SEVEN DRUNKEN NIGHTS The Dubliners
THE WILD ROVER The Dubliners
DANNY BOY Traditional Irish folksong
BOTANY BAY Traditional Irish folksong
WHISKEY IN THE JAR Belle & Sebastian (Thin Lizzy, etc.)
...Plus a hundred more--too many to list!
Eagles, Jackson Browne, Dan Fogelberg, John Denver, John Prine, CS&N, Blues, Southern Rock, Bluegrass.
110V electrical outlet
APPLAUSE!
Multi-Instrumentalist