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Cy Winstanley

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Music genres

Responds in about 56 min


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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 8 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, responsiveness, and work quality.

Exceptional 5.0

15 reviews

5

100%

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0%

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pro avatar
Emily W.

Aug 11, 2025

Cy was great from beginning to end! He was so easy to communicate with. I work at a large company and we have a lot of accounting hoops our vendors must go through. Cy was so professional and was able to complete all our paperwork with a great attitude.
Cy Winstanley's reply
Thanks for the shining review Emily - really fun event and solid crew!
pro avatar
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
Colleen B.

May 16, 2023

Hired on Thumbtack

We couldn’t have found a better performer!! When we looked up each performer and listened to their style of music, it was very easy to choose Cy Winstanley to play for our wedding! Cy Winstanley is a very talented singer! He even took the time to learn our first song. I was so blown away at his talent! He made our day absolutely magical!! Everything went very smooth and he played while people mingled. I never had to ask him to do anything; he had a plan for everything. He was completely prepared! He even set up in multiple areas and had no problem when having to move into the dance floor area after playing music for the meal. He was ready to go with the flow with whatever happened throughout the day. My whole family Enjoyed his singing! Everyone loved him, it felt as if he was just part of the family! I can assure you this is the musician you want for any event! He is absolutely wonderful!!! Thank you Cy Winstanley for all your hard work!! We will have more photos soon. Hope to keep in touch and have you back for any event we have in the future!

Details: Wedding reception • 26 - 50 guests • 31 - 50 years old • 51 or older • Vocals • Guitar • No preference • Variety • Outdoors

Music Entertainment
pro avatar
Rebecca w.

Oct 31, 2022

Hired on Thumbtack

Cy was a hit at my husband's work promotion! He was very accommodating to all our needs and played great music that we all love!!! I would highly recommend!!!!! Thank you again Cy!!! RTW

Details: General event / party • 26 - 50 guests • 31 - 50 years old • Guitar • Variety • Pop / top 40 • Other

Cy Winstanley's reply
Thank you kindly Rebecca! Enjoyed playing for you all v much.
Music Entertainment
pro avatar
Dave W.

Nov 12, 2015

Hired on Thumbtack

Cy is simply an excellent teacher. He prioritizes teaching with music you like, emphasizing songs that will improve your whatever elements of your technique need work -- in my case it is all elements. As a result of Cy's intructuon I've gotten better in all phases of playing: rhythm, lead, and most importantly everything in between. He's also friendly and flexible, and a great musician with great taste.
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Cy Winstanley

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