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Cy Winstanley

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Scheduling
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Music genres

Responds in about 4 hours


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About
// Solo Guitar & Voice // Hey there! I'm Cy Winstanley, a singer-guitarist in Nashville, TN. Born and raised in New Zealand, I've been working in the music industry for more than 20 years and have performed and toured all around the world. I play frequently around Nashville as a solo performer at weddings and corporate functions, I also work as a live and session guitarist for numerous recording artists and write and record songs myself. I know over 300 songs from new to old. I'm very comfy in the folk/Americana vibe, but also play a bunch of soul, country and lots of classic rock. // Jazz Trio // I also have a jazz trio that performs classic standards + blues and groove tunes. Instrumentation is commonly guitar/voice, piano, upright bass, but can be reduced or expanded to accommodate size and budget. Unless specified, all quotes include a sound system and all that's needed for me to perform.
Overview

Hired 11 times

Serves Nashville, TN

Background checked

1 employee

16 years in business

Business hours

Sun9:00 am - 8:00 pmMon9:00 am - 11:59 pm

Payment methods

This pro accepts payments via Apple Pay, Cash, Check, Square cash app, Venmo, and Zelle.

Social media

Facebook, Instagram

Services offered
Music types
Event type

Wedding reception

Wedding ceremony

Birthday party

Cocktail hour

Music genres

Pop / top 40

Rock / classic rock

Jazz / Blues

Covers

Projects and media
Projects and media
Reviews

Customers rated this pro highly for professionalism, work quality, and responsiveness.

Exceptional 5.0

18 reviews

5

100%

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0%

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pro avatar
Dan M.

Mar 10, 2026

Hired on Thumbtack

Cy was absolutely fantastic and elevated our event to an entirely new level. His music is so great, and his easy style was a hit with everyone at the event. He is incredibly talented and I would hire him again without hesitation. He was super easy to communicate with prior to the event, and everything was smooth & seamless from start to finish. It was an absolute pleasure working with him!!

Details: Cocktail hour • 26 - 50 guests • 31 - 50 years old • 18 - 30 years old • 51 or older • Vocals • Guitar • Variety • Jazz / Blues • Covers • Banquet hall / ballroom

Music Entertainment
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PJ D.

Apr 5, 2026

Hired on Thumbtack

I hired Cy to play a party at my house. From start to finish he was responsive and open to my thoughts about the event. My group lives to sign karaoke and Cy went above and beyond allowing us to join him for a number of songs throughout the party. He took our list of songs learning some new ones just to make the experience amazing. I would 100% recommend CY for anyone looking for a musician for their event.

Details: Birthday party • 26 - 50 guests • 31 - 50 years old • Vocals • Guitar • Rock / classic rock • Covers • Variety • Country / bluegrass • Other

Music Entertainment
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Michael K.

May 28, 2026

Hired on Thumbtack

Cy was incredible playing for our wedding ceremony. He was extremely responsive and very adaptable to late changes. He worked with us to create the best ceremony possible for us. Very grateful and highly recommend him!

Details: Wedding ceremony • 51 - 75 guests • 18 - 30 years old • 51 or older • 31 - 50 years old • Guitar • Vocals • Other strings • Covers • Outdoors

Music Entertainment
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Whitney S.

Aug 11, 2025

Cy played our office summer event and really made the experience feel like a celebration! He had an incredible attitude with it being VERY hot that day as well. We would certainly have Cy play for us again.
Cy Winstanley's reply
Legend, thanks Whitney. It was hot for sure, but a good sweat is good for the soul...or something like that. Thanks!
pro avatar
Maria C.

Aug 26, 2024

Hired on Thumbtack

Cy performed at my sisters rehearsal dinner and wedding and was absolutely incredible! The guests and my family cannot say enough good things about Cy! He was incredibly kind, is a great performer, and is extremely easy to communicate with. We hope to see Cy perform again the future! Thank you so much!

Details: Cocktail hour • 76 - 100 guests • 18 - 30 years old • 31 - 50 years old • 51 or older • Vocals • Guitar • No preference • Pop / top 40 • Rock / classic rock • Covers • Country / bluegrass • Oldies • Outdoors

Cy Winstanley's reply
Dawww thanks Maria! Really honored that you had me at both events. Y’all are awesome :)
Music Entertainment
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Cy Winstanley

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