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If you hire this pro, you’re covered by a money-back guarantee. Learn more
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 12 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.
Customers rated this pro highly for professionalism, work quality, and responsiveness.
Exceptional 5.0
19 reviews
5
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Read reviews that mention:
PJ D.
Apr 5, 2026
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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
Dan M.
Mar 10, 2026
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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
Michael K.
May 28, 2026
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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
Michelle C.
2 weeks ago
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Hired on Thumbtack
Cy performed nicely at our home for my 60th birthday party. Everyone enjoyed the evening.
Music Entertainment
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!
Credentials
Background Check
Cy Winstanley
FAQs
What should the customer know about your pricing (e.g., discounts, fees)?
Standard pricing covers 3 sets of music over 3-4 hours, but can do different lengths or intervals if needed. For weddings, available for an extra charge is ceremony performance and the learning of a special song. This is typically a shorter set that covers the aisle entry/exit, signing of the register and 15 minutes of background music as guests are mingling prior to the ceremony.
What is your typical process for working with a new customer?
I like to have a chat or exchange emails about musical tastes the client has, how many guests, and any specific programming events that need to be worked about during the performance.
What education and/or training do you have that relates to your work?
I've been playing for many years in all manner of styles. I studied jazz at college early on in my career and have a very comfortable grasp on technical, and theoretical aspects of music. I play in many different kinds of bands in a variety of genres, some of which is improvised music. All in all it mean that I can happily read a room and adapt!
