Gary Winter brings timeless charm, professionalism, and exceptional musical talent to every event he performs at. Whether you’re hosting a sophisticated wedding, a stylish corporate gathering, or an elegant private party, Gary ensures your entertainment is seamless and memorable. Known for his smooth vocals and commanding stage presence, Gary Winter tailors each performance to match the tone and atmosphere of your celebration.
Working alongside Connections Entertainment, Gary offers flexible performance options — from an intimate solo jazz singer experience to the dynamic sound of a full Jazz Swing and Blues Octet. No matter your event size, expect top-tier entertainment without compromise.
Gary’s extensive repertoire spans jazz standards, swing classics, and blues favourites, captivating audiences with songs from legends like Frank Sinatra, Michael Bublé, and Ray Charles. This range ensures your guests will be tapping their feet and creating lasting memories.
For clients interested in more details, check out our Live Jazz Wedding Entertainment page to explore how Gary Winter can transform your special day.
The full ensemble are more like an event orchestra than merely a function band.
Their attention to detail from the initial enquiry to the final show is very professional and nothing is ever too much trouble. Gary’s energy and stage presence ensures our guests always have an amazing time, gauging the right level no matter what the event. Highly recommended.
Tony Murdock
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Booking Gary Winter means choosing a versatile, highly skilled performer who adapts his music to suit your event’s mood. Whether it’s an elegant corporate function, cocktail hour, or lively party, Gary offers:
Vocal & Piano Duo: Perfect for cocktail receptions and intimate settings. Smooth vocals with piano accompaniment set a sophisticated, relaxing mood.
Jazz Trio: Piano, bass, and drums provide warm background music for dinners or mingling. Available with or without vocals for laid-back elegance.
Jazz & Swing Quintet: Adds saxophone and guitar for a fuller, swing sound—ideal for impressing guests with classic jazz and upbeat tunes.
Jazz, Swing & Blues Octet: A full horn section delivers big band energy, perfect for dance floors and larger celebrations.
All packages are customisable, backed by Gary’s professionalism and passion. He ensures a smooth, memorable experience from start to finish.
additional set time
additional 45 min set play timeBand -Quintet
The big band playing 2 X 1-hour setsDuo Act
Gary Winter with piano accompaniment.Quintet Pluss
5pc live band but with EXTRA PUNCH - 5 live instruments including piano, bass, drums, guitar and sax, 2 vocalistsGary Winter Big Band
A total of 11 musicians and three vocalistsHe has always been extremely professional in everything he does. His performances on stage along with his band are simply amazing and it is testament to him that audiences come back time and time again to see and take part in his amazing shows. I can not fault his approach and work ethic and I do so hope we can enjoy many more years of working together and entertaining audiences, which is a job he does so well. Rachel Buxton, Proprietor - Hoveton Hall Estate
The full ensemble are more like an event orchestra than merely a function band. Their attention to detail from the initial enquiry to the final show is very professional and nothing is ever too much trouble. Gary's energy and stage presence ensures our guests always have an amazing time, gauging the right level no matter what the event. Highly recommended. Tony Murdock
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He has always been extremely professional in everything he does. His performances on stage along with his band are simply amazing and it is testament to him that audiences come back time and time again to see and take part in his amazing shows.
I can not fault his approach and work ethic and I do so hope we can enjoy many more years of working together and entertaining audiences, which is a job he does so well.
Rachel Buxton,
Proprietor – Hoveton Hall Estate