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Sizemore

Sizemore is musical duo Jack Sizemore and his wife, Amy Dalley- Sizemore. Jack Sizemore and his wife Amy began playing music together 15 years ago.

They met while writing songs at the same publishing company in Nashville. At the time, Amy (Amy Dalley) was in the midst of a record deal and was headed out on a national tour as the opening act for Toby Keith and Rascal Flatts. She asked Jack to get a band together and told him they would be doing shows in arenas. He didn't exactly believe her at first. He assumed she was just inflating the deta

ils to get him to agree to put a band together. After all, he was already an artist in his own right. He had a Pop/Rock deal on RCA records in New York and had toured the world. But Amy wasn’t inflating the details. They went on tour with a great band and had a blast. They became close friends sharing the stage not only on that tour, but on many radio tours in promotion for Amy’s singles. Somewhere a long the way they fell in love and married in 2005. Since 2010, Jack has been on the road, playing guitar and singing backgrounds with country superstar, Jason Aldean. “I’ve gotten to do a lot of really cool things with this band. We’ve played all the late night talk shows, sold out stadiums and been all over the world with these guys. We are definetly a band of brothers. I’m excited to see what else we will get into. ”

Though Amy continued to write songs, she came off the road to be able to stay at home with their two children. But she missed playing live music. So, Sizemore, was born. Sizemore is an acoustic duo with an eclectic mix of songs that spans every genre. “I think it’s fun to be driving down the road, flipping through the stations and think, oh I wanna sing that! We will work it up and put it into the Sizemore rotation. I am a total sucker for teen pop songs! Jack would play all James Taylor If I let him! But, we like to mix in some Destiny’s Child, Kenny Chesney and The Allmand Brothers too. We like to keep it fresh, so we are working up new tunes all the time.” Amy said. Jack adds, “My favorite configuration of Sizemore is when I’m playing acoustic and she’s singing. After 15 + years of playing together, we kinda have a thing.”

Though their musical roads have taken them each to extraordinary places, they feel lucky that they are still able to share the stage together. “I feel like it is a really special thing to be married to someone you admire musically. I’m glad he is willing to play for 20,000 people one night and play for 100 the next night with me. But when we are playing together in these smaller venues it doesn’t feel small or insignificant. It feels special. At least it does to me.” Amy said. Recently the Sizemore’s moved to beautiful Saint Augustine, Florida. They are very excited to be in such a music rich town. “ We have been coming here for several years not only to play music, but also to go out and listen to other artists play. We were chomping at the bit to move here. Its my favorite place on the planet! “ Amy said. They have taken a few months to get settled in, but are excited about their residency at The Tropical Tradewinds Lounge ( 124 Charlotte street, Saint Augustine, Fl) Every Thursday from 5-8pm beginning November 2nd.

05/23/2026

Can’t wait to see y’all tomorrow at Tradewinds to celebrate Memorial Day weekend ! Only a few shows left before Jack hits the road so come on out and giggle a little 💃🕺🎤👯🎸

05/10/2026

Happy Mother’s Day !! We will be doing our thing at Tradewinds today at 5:30 and I can’t wait to see your smiling faces 😄😄 come let loose , sing along ( but not too loud 🤣) and have a great time ! We are playing all your favorites today ! Well ok … we are playing all MY favorites today ! Come see us! 🎸🎤💃🕺👯

04/12/2026

Where ya at Tradewinds lovers ?!?? We will be doing our thing tomorrow for SUNDAY FUNDAY !! 5:30-8:30 This will be our last show in April ! We will be back in May … so come on in and have a good time . 🤪

04/05/2026

Can’t wait to see y’all ! We will be jamming the jams on Easter Sunday - 5:30-8:30 and we are pumped 💪💪 Tradewinds Tropical Longe in beautiful Saint Augustine!! Yall come 🎸🎤💃🕺

03/22/2026

We can’t wait to see your smiling faces at Tradewinds!! We will be singin and stompin starting at 5:30 💃🕺yall get ready 🤘🤘

03/15/2026

We can’t wait to see you Tradewinds at 5:30 today !!! It’s gonna be fun !!

03/07/2026

See y’all at Tradewinds!!

🎶 GUESS WHO’S BACK AT TRADE WINDS??????🎶

Two familiar faces are coming back to bring that Trade Winds Happy Hour magic. 🍹🎤

The songs you know.
The harmonies you love.
The kind of music that makes the whole room sing along and sway.

Yep… Sizemore Duo is back!

If you’ve seen them before, you already know what kind of happy hour this is going to be… 😎

Happy Hour + Great Music = Trade Winds at its best.

02/14/2026

Love is in the air and warmer temps are headed this way !! Also … add these to your calendar ! I’m excited 🎸🎉❤️

TRADEWINDS TROPICAL LOUNGE
March 8,15, and 22
April 5, and 12
May 3,10,24,31
June 7

SUNDAYS @5:30 BOUT TO BE LIT 🔥

12/21/2025

We are gonna have fun whether you like it or not !! So COME ON!!! We will be singing and stomping at the Tradewinds Tropical Lounge at 5:30 tonight in gorgeous St Augustine . It is such a blessing to get to sing songs with the person I love most in this life . And such a blessing to be able to do it in a place I love the most . This is our last show of 2025 and we are PUMPED ( ok, it’s me …I am . I AM PUMPED 🤪🤪) But we can’t wait to see your smiling faces !! Let’s goooooo!!!!

12/12/2025

2 shows left for 2025 !! We will not be back to our regularly scheduled shenanigans till … March ish …. So YALL COME ON OUT!! Tradewinds Tropical Lounge Sunday Dec 14 5:30 AND
Sunday Dec 21 at 5:30 💪🎄❤️🎉

11/30/2025

Yall know !!! Yall KNOW what today is !!! SUNDAY FUNDAY!! Jack and I will be strummin and stompin and singin at Trade Winds Tropical Lounge starting at 5:30 today ! We cannot wait to see your smiling faces singing all your faves right back to us under the glow of those Christmas lights 🎄🎅🧑‍🎄🎸🎤 let’s do this 🔥🔥🔥

Address

124 Charlotte St
Saint Augustine, FL
32084

Website

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