Trop Rock'N Duval©, LLC Schedule

Oct 27-Nov 2, 2025

The Full 2025 Schedule Is Now Available!

NOTE: All times and performers listed are still subject to change due to venue and performers changes in schedules. (it happens.) Some times will be added later. Updates occur right up to the event—and even during the event.

**Check the schedule each day to ensure nothing has changed**


To navigate this page, click the buttons below...

Welcome to

Trop Rock'N Duval 2025

Where the heart of Key West beats to the rhythm of Trop Rock music!

Less than 2 weeks to go!

We are thrilled to present an exciting lineup of talented musicians, lively venues, and unforgettable experiences. From laid-back beach vibes to high-energy performances, this event promises to transport you to a tropical paradise.

You'll find the detailed schedule, included below with performance times and locations, so you can plan your days and nights filled with music, fun, and fantastic memories.

There's also a spreadsheet version with many more venues and local talent and some not part of the official Trop Rock'N Duval venues. (we have not yet received the spreadsheet)

Get ready to dive into the ultimate Trop Rock celebration!

It will be here before you know it.

Just ADDED this week - Mac's Place - on N. Roosevelt Blvd at Truman Ave and Eisenhower Ln. A Tiki Bar and Restaurant, Right on the Water. Thurs, Fri and Sat 4-8 PM

recently ADDED - Kaya Island Eats - The Backyard - New times Wed, Thurs, Fri and Sat 1-5 PM. See who's playing there. We still have a couple open spots. But they will be filled very soon.

And also Rockhouse Live, Tues and Wed, We may be adding the upstairs Patio as well. To be decided soon.

Performers 2025

  • Barefoot Reggie Starrett

  • Beth Travers

  • Bob Banerjee

  • Boomer Blake

  • Brian Fields

  • Brian Roberts

  • Dani Hoy

  • Dave Freeman

  • Dave Matchette

  • Dave McKenney

  • Dave Signs

  • Dennis Davis

  • Dennis and Dan McCaughy

    (Tropical Soul)

  • Don Middlebrook

  • Donnie Howard

  • Fred Quistgard

  • Gary Green

  • Harold Boothe

  • Heather Vidal

  • Honey Bee

  • Inna Vision

  • Isabella Stefania

  • Jake Clayton

  • Jason Acy

  • Jax Bowers

  • Jay Yearkes

  • Jeff Dayton

  • Jeff Randall

    2023 TRND Contest Winner

  • Jerry Diaz

  • Jody Bly

  • Joe Holewa (with The Island

  • Castaways Band)

  • John McDonald

  • Jonas Lorence Band

  • Kelly McGuire

  • Key West Chris

  • Klee Liles

  • Kitty Steadman

  • Kristie Bobal

  • Lefty Lucy

  • Mac Martin

  • Margarita Brothers

  • Matt Kelly

  • Mick Fury

  • Mike Mangum

  • Quentin Leverich

  • Paul Kane

  • Paul Mezzanotte

  • Paul Roush

  • Ray Boone (with CBD Band)

  • Rich McGuire

  • Rick Kanut (with the

    Midnight Kahuna Band)

  • Ricky Lamb

  • Roger Bartlett

  • Sara Bug

  • Scott Nickerson

  • Stephanie Biello (with

  • Bahama Mama and the Pain Killers

    2023 and 2024 TRND Contest Winner

  • Steve Hopper

  • Steve Tolliver (with the Trop Rock Junkies)

  • Tall Paul Bobal

  • Theresa Pfeifer

  • Tiki Thom

    2024 TRND Contest Winner

  • Tim Campbell (with the

    Tropical Attitudes Band)

  • Will Kimbrough

  • Zack Reed (with the band Inna Vision)

Passport and T-shirt Pickup Locations

Margaritaville -

  • Wednesday Oct 29 @ 1-5 PM — just to the left of the entrance.
    A window will be open. Please form a line to the left near the building so people can get past.

  • Wednesday Oct 29 @ 5-8 PM — Inside at the Merch Table to the right of the stage near the stairs.

  • Thursday Oct 30 @ 1-5 PM — The window to the left of the entrance

  • Friday Oct 31 @ 1-4 PM — The window to the left of the entrance

Rams Head Southernmost -

  • Saturday Nov 1 - 2-5 PM — At the Merch Table. Hopefully you have already picked them up.

Order your passports now. Click the button below. Support the artists and our charity. And get a discount on food, drinks and Merchandise.

Times and performers may change

Monday, Oct 27

Margaritaville - A BeachFront Radio Supported Event but independent of TRND

  • 8-11 PM: Kitty Steadman

Hogs Breath Saloon (Mon thru Sun) - independent of TRND

  • 12-4 PM: Zack Seemiller

  • 4:30 PM - 8:30 PM: Heather Vidal - Supported by TRND

  • 9:00 PM - 1 AM: Alex Anthony Band

First Flight - Happy Hour - Official TRND Event

  • 4:00 PM - 6:00 PM: John McDonald

    Get an early start for Trop Rock'N Duval and join John for a Happy Hour of fun. A great way to start Trop Rock'N Duval

Rams Head Southernmost - TRND Supported Event

  • 5:00 PM - 8:00 PM: Steve Hopper

Willie T's - TRND Supported Event

  • 11:00 AM - 2:00 PM: The Shanty Hounds (Key West Chris and Dani Hoy)

Times and performers may change

Tuesday, Oct 28

Margaritaville - Official Trop Rock'N Duval, LLC (TRND) Event

  • 11:00 AM - 1:00 PM: Paul Roush

  • 1:00 PM - 3:00 PM: Barefoot Reggie Starrett

  • 3:00 PM - 5:00 PM: John McDonald

  • 5:00 PM - 7:00 PM: Jeff Dayton and Dave Matchette

  • 8:00 PM - 11:00 PM: Kitty Steadman

Surly Siren Saloon - Official TRND Event

The Surly Siren Saloon is Located at 308 Front St

  • 12:00 PM - 2:00 PM: Dave McKenney w/Quentin

  • 2:00 PM - 4:00 PM: Dave Matchette

  • 4:00 PM - 6:00 PM: Boomer Blake w/Quentin

  • 6:00 PM - 8:00 PM: Paul Mezzanotte

  • 9-12 PM: Steve Hopper and The Wolf Island Band

The Alamo - Official TRND Event

The Alamo is Located at 4 Charles St (this is the old Smokin' Tuna location

  • 1:00 PM - 3:00 PM: Beth Travers

  • 3:00 PM - 5:00 PM: Tiki Thom w/Fred Q

  • 5:30 -8:30 PM: The Happy Dog Band (A Grateful Dead tribute band)

  • 9:00 PM - 12:00 Mid: Rich McGuire and Friends (lots of friends) - Time to Party

Tiki House - Official TRND Event

  • Hosted by Shore LIfe Radio - Welcome to the Island

  • 12-5 PM - Various artists all day

  • Guest performers - Steve Hopper, Matt Kelly

Salty Frog - Official TRND Event

  • 3-6 PM - Tall Paul and Kristie

Rick's - TRND Supported Event

  • Rick's Downstairs

  • 12:00 - 3:00 PM: The Shanty Hounds

Hogs Breath Saloon - independent of TRND

  • 12-4 PM: Harley Ray

  • 4:30 PM - 8:30 PM: Heather Vidal - Supported by TRND

  • 9:00 PM - 1 AM: Alex Anthony Band

Times and performers may change

Wednesday, Oct 29

Margaritaville - Welcome to Key West

and BeachFront Radio's Trop Rock'N Duval LLC

Welcome Party - Official Trop Rock'N Duval, LLC (TRND) Event

  • 11:00 AM - 1:00 PM: Welcome Party - - - - Opening Show- Jody Bly

A special note: Listed below are some of the musicians that will be performing with artists throughout the happening this week, Dave Matchette, Scott Nickerson, Fred Quistgard, Klee Liles, Gary Green, Jax Bowers, Quentin Leverich, Bob Banerjee, Theresa Pfeifer, and other independent musicians that help make the artists sound great. Please tip them and give them love whenever you see them, they work really hard all week long. Thanks.

  • 1-8 PM. Margaritaville is the official place to pick up your T-Shirts and Passports.

  • 1-5 PM get them outside to the left of the entrance. A window will be open. After that inside near the stage where the merch table will be set up.

  • 1:00 PM: Host BeachFront Radio with BeachBum Andy and Emcee Tiki Thom

  • 1:05 PM: Beth Travers

  • 1:15 PM: Stephanie Biello - The Bahama Mama and her Painkiller

  • 1:25 PM: Paul Mezzanote

  • 1:35 PM: Ray Boone and Jake Clayton

  • 1:45-2:10 PM: Harold Boothe, Jeff Randall and Mick Fury w/Fred Q

  • 2:20 PM: Boomer Blake, Tim Campbell

  • 2:40 PM: Dennis Davis

  • 2:50 PM: Jason Acy

  • 3:00 PM: Jeff Dayton

  • 3:15 PM: Tropical Soul

  • 3:30 PM: Dave McKenney

  • 3:45 PM: Steve Hopper

  • 4:00 PM: Rich McGuire

  • 4:15 PM: Mac Martin

  • 4:30 PM: Barefoot Reggie Starrett

  • 4:45 PM: Paul Roush

  • 5:00 PM: Sara Bug

  • Ends at 5:15 PM

  • 5:30 PM - 8:00 PM: Jeff Dayton, Roger Bartlett and Dave Matchette

  • 9:00 PM - 12:00 Mid: Kitty Steadman

Surly Siren Saloon - Official TRND Event

  • 12-2 PM: Mac Martin

  • 2-4 PM: Bahama Mama and the Painkillers

  • 4-6 PM: Jeff Randall and the Rusty Ole Phlockers

  • 6-8 PM: Tropical Soul

  • 9-12 PM: The Island Castaway Band

The Alamo - Official TRND Event

Bring your Raffle Baskets to the Alamo

  • The Alamo is Located at 4 Charles St, (this is the old Smokin' Tuna location

  • The Raffle will be open starting on Thursday 1-6 PM at The Alamo. Also Friday 1-6 PM and Last Chance Saturday, 11-2 PM. Tickets can be purchased on site. Be sure to put your phone number on the back of the ticket so we can notify you if you are a winner.

  • Raffle baskets can be brought to The Alamo back room, drawings will be held Saturday at 2 PM. Winners can pick up the baskets until 6 PM Saturday.

  • All proceeds will go to both of our causes - Our Charity "The Shriners Hospitals for Children" and to the Songwriters Fund. The same fund that the Passports go to for supporting all the great music and our Charity.

The Alamo - Official TRND Event

  • The Alamo is Located at 4 Charles St, (this is the old Smokin' Tuna location

  • Raffle baskets can be brought to The Alamo back room, drawings will be held Saturday at 2 PM. Winners can pick up the baskets until 6 PM Saturday.

  • 1:00 PM - 3:00 PM: Steve Hopper

  • 3:15 PM - 5:15 PM: Mick Fury

  • 5:30 -8:30 PM: The Happy Dog Band (A Grateful Dead tribute band)

  • 9:00 PM - 12:00 PM: Bahama Mama and the Painkillers - Time to party

First Flight - Happy Hour - Official TRND Event

  • 4:00 PM - 6:00 PM: John McDonald

    Get an early start for Trop Rock'N Duval and join John for a Happy Hour of fun. A great way to start Trop Rock'N Duval

Island Dogs - Official TRND Event

  • 10 AM-12:50 PM Barefoot Reggie Starrett

  • 1-3:50 PM Klee Liles

  • 4-6:50 PM Dennis Davis

  • 7:00 PM - 10:00 PM: John McDonald

Rams Head Southernmost - Official TRND Event

  • 12:00 PM - 2:00 PM: Dave Freeman (will need system) a system will be provided

  • 2:30 - 4:30 PM: Paul Mezzanote (will need system)

  • 4:45 PM - 6:15 PM: Jerry Diaz (will need own system)

  • 6:30 PM - 8:00 PM: Jason Acy (will need system)

Kaya Island Eats - The Backyard - Official TRND Event

  • Located 618 Duval St.

  • 1:00 - 3:00 PM: Rich McGuire

  • 3:00 - 5:00 PM: Boomer Blake

Andy's Cabana - Official OOTSK Event -Welcome Party

  • - - Supported by TRND

  • 5-8 PM - Featuring Dave McKenney and the Hungry Hardluck Heroes Band

  • and many special guests.

  • More details to come

Rockhouse Live Grill - Official TRND Event

  • NOTE: New Location 404 Southard - The old location is now closed. . . .

  • 2:00 PM - 5:00 PM: Shanty Hounds - to be confirmed (TBC)

Salty Frog - Official TRND Event

  • 3-6 PM: Tall Paul and Kristie

Schooner Wharf - Supported by TRND

  • 12-6:00 PM Ricky Lamb's Hump Day On The Island Artists Showcase

  • 12:00-12:30 Ricky Lamb

  • 12:30-1:00 - Jerry Diaz

  • 1:00-1:30 - Boomer Blake

  • 1:30-2:00 - John McDonald

  • 2:00-2:30 - Dennis Davis

  • 2:30-3:00 - Reggie Starrett

  • 3:00-3:30 - Isabella Stefania

  • 3:30-4:00 - Harold Boothe

  • 4:00-4:30 - Beth Travers

  • 4:30-5:00 - Bob Banerjee

  • 5:00-5:30 - Bahama Mama and Her Painkiller

  • 5:30-6:00 - Steve Hopper

  • 7:00-11:00 Ricky Lamb and No bad Days Band w/Quentin

Hogs Breath Saloon - independent of TRND

  • 12-4 PM: Andy Maurmen

  • 4:30 PM - 8:30 PM: Heather Vidal - Supported by TRND

  • 9:00 PM - 1 AM: Alex Anthony Band

Sloppy Joe's Bar - independent of TRND

  • 12:00 PM - 5:00 PM: Brian Roberts - TBC

Times and performers may change

Thursday, Oct 30

Margaritaville - Official Trop Rock'N Duval, LLC (TRND) Event

  • 11:00 AM - 12:50 PM: Harold Boothe w/Fred Q, Bob Banerjee

  • 1-5 PM. Margaritaville is the official place to pick up your T-Shirts and Passports.

  • 1-5 PM get them outside to the left of the entrance. A window will be open.

  • 1:00 PM - 2:50 PM: Ray Boone and Jake Clayton

  • 3:00 PM - 5:00 PM: Boomer Blake, w/Quentin

  • 5:30 PM - 8:00 PM: Tim Campbell and the Tropical Attitudes

  • 9:00 PM - 12:00 Mid: Kitty Steadman

The Blood Drive - Official TRND Event

Near Margaritaville on Fleming Street - They are now ready to take reservations -

  • 9:00 AM - 3 PM - Go to the Special Events Page and click on Blood Drive icon for details on how to sign up.

Surly Siren Saloon - Official TRND Event

The Surly Siren Saloon is Located at 308 Front St

Songwriters Showcase with Jody Bly

  • 12:00 PM: BFR Showcase host Jody Bly

  • 12-1 PM: Jody Bly + Steve Hopper + John McDonald

  • 1-2 PM: Theresa Pfeifer + Mick Fury + Beth Travers

  • 2-3 PM: Jeff Randall + Jax Bowers + Jason Acy

  • 3-4 PM: Harold Boothe + Sara Bug + Rich McGuire

  • 4-5 PM: Jody Bly + Mac Martin + Paul Roush

  • 5-6:30 PM: Dave Signs and Jax Bowers

  • 7:00 PM - 10:00 PM: BeachFront Radio at the Surly Siren Presents

  • "The Ladies of Trop Rock'N Duval©"

  • Featuring - Stephanie Biello (Bahama Mama), Beth Travers and Dani Hoy

  • Guest performers: Isabella Stefania, Sara Bug, Theresa Pfeifer,

  • Heather Vidal, Honey Bee, Lefty Lucy

  • Backup musicians: Quentin Leverich

  • 10-12 Mid: Mick Fury w/Quentin

The Alamo - Official TRND Event

Raffle Baskets open to purchase tickets

  • The Alamo is Located at 4 Charles St, (this is the old Smokin' Tuna location

  • 1-5 PM: Raffle will be open to Purchase Tickets. Be sure to put your phone number on the back of the ticket so we can notify you if you are a winner.

  • The Raffle will be open starting on Thursday 1-5 PM at The Alamo. Also Friday 1-5 PM and Last Chance Saturday, 11-2 PM. Tickets can be purchased on site. Be sure to put your phone number on the back of the ticket so we can notify you if you are a winner.

  • Raffle baskets can be brought to The Alamo back room, drawings will be held Saturday at 2 PM. Winners can pick up the baskets until 6 PM Saturday.

  • All proceeds will go to both of our causes - Our Charity "The Shriners Hospitals for Children" and to the Songwriters Fund. The same fund that the Passports go to for supporting all the great music and our Charity.

The Alamo - Official TRND Event

  • The Alamo is Located at 4 Charles St, (this is the old Smokin' Tuna location

  • Raffle baskets can be brought to The Alamo back room, drawings will be held Saturday at 2 PM. Winners can pick up the baskets until 6 PM Saturday.

  • 1:00 PM - 5:30 PM: Jeff Dayton - songwriters showcase, w/Dave Matchette

  • 1-2 PM: Jeff Dayton + Isabella Stefania + Mac Martin

  • 2-3 PM: Paul Kane + Joe Holewa + John McDonald w/Fred Q

  • 3-4 PM: Jeff Dayton + Barefoot Reggie + Steve Hopper

  • 4-5 PM: Roger Bartlett + Ray Boone + Jake Clayton

  • 5-5:30 PM: Jeff Dayton wrap up. Special guest maybe

  • 6:00 PM - 8:50 PM: Jeff Randall and the Rusty Ole Flockers

  • 9 PM - 12 Mid: - The Island Castaways Band - Time to Party

Viva Argentinian Steakhouse - Official TRND Event

  • Viva Argentinian Steakhouse is Located at 903 Duval St, - they are partners with The Alamo - This is as great dinner location for listening to some great music while you dine.

  • 1-3 PM: Honey Bee with Roger B ( a system is needed here, one will be made available)

  • 3:30-5:30 PM: Jason Acy

  • 6-9 PM: Harold Boothe w/Fred Q

Island Dogs - Official TRND Event

  • 10 AM-12:50 PM Paul Roush

  • 1-3:50 PM Jerry Diaz

  • 4-6:30 PM Tropical Soul

  • 7-10 PM CBD Band

Mac's Place - Official TRND Event

  • Located at 1605 N Roosevelt Blvd

  • Corner of Truman Ave and Eisenhower Ln, right on the water

  • 4:00 - 6:00 PM: Donnie Howard

  • 6:00 - 8:00 PM: Dave Freeman

Rams Head Southernmost - Official TRND Event

This is the BeachFront Radio - - - Tropical Mall

  • 12-5 PM - This year we will have our very first Official BeachFront Radio Tropical Mall at Rams Heads so you can shop for some great tropical merchandise while you listen to Kelly and other great performers. . The vendors will be there Thurs, Fri and Sat 12-5 PM.

  • Last year we had a couple of vendors there offering Custom made Jewelry and one of our Sponsors "Travel by Georgia" were there offering you great travel opportunities including the Parrot Head Cruises.

  • This year we will have many more great Tropical Jewelry and Crafts booths set up and many other cool tropical merchandise.

Rams Head Southernmost - Official TRND Event and Hosted by Songwriters Island Radio

  • 11:30 AM - 1:30 PM: Rich McGuire ( a system is needed here, one will be made available)

  • 2:00 PM - 5:00 PM: Kelly McGuire - Lighthouse Songwriters Showcase with Songwriters Island Radio

- - - - VIP-KF tickets (ie, VIP-Kelly Fans) - All VIP-KF persons will be seated at a table near Kelly. All seats without tables are FREE, no tickets needed. There will be a limited number of tables in the back of the courtyard as well. Food and Drinks available to all for purchase. But chair seating is FREE and first come first to sit.

- - - - Kelly's Guest performers - - -

Time schedule

  • 2:00 - Steve Hopper

  • 2:20 - Beth Travers

  • 2:40 - Kelly McGuire

  • 3:00 - Dave McKenney

  • 3:20 - Jeff Randall

  • 3:40 - Kelly McGuire

  • 4:00 - Lefty Lucy

  • 4:20 - Mick Fury

  • 4:40-5:30 - Kelly McGuire

  • 6:00 PM - 8:00 PM: Mick Fury - at the side bar

Kaya Island Eats - The Backyard - Official TRND Event

  • Located 618 Duval St.

  • 1:00 - 3:00: Tiki Thom songwriters Showcase

  • 1:00-1:40 - Donnie Howard, Barefoot Reggie, Sara Bug

  • 1:40-2:10 - Sara Bug, Tiki Thom

  • 2:10-3:00 - Lefty Lucy, Dave Freeman

  • 3:00 - 5:00: Dennis Davis

HERE IT IS - - - THIS IS THE VERY SPECIAL

PUB CRAWL ANNOUNCEMENT

YOU'VE BEEN WAITING FOR !!!

  •  This Pub Crawl is organized by Cathy Polcari to honor and celebrate the life of her dear husband Dave Polcari. From Cathy "To me: the only mandatory place and time is Sunset Pier.  Dave loved it here and it’s our toast to him.  (pssst…hey Dave; a green spark would be amazing.  See what you can do about that.)"

  • The Pub Crawl is open to anyone that wants to have a good time. You didn't have to know Dave but after this Pub Crawl is over you will feel as if you've known him forever.

  • This is the schedule: All times are intended to let you know where and when you can hook back up with us, should you get distracted by something sparkly.

  • Full Schedule

  • 12:30 – 2:00       Willie T’s             525 Duval St       tank top pick-up and donation drop    

  •  2:00 – 3:00          Margaritaville     500 Duval St       Get your passport if you didn’t already

  • 3:00 – 3:30          Fat Tuesday        305 Duval St       grab your frozen concoction for the road

  • 3:30 – 4:30          The Alamo          4 Charles St        This is the Old Smokin’ Tuna

  • 4:30 – 5:30          Cap’t Tonys         428 Greene St    don’t forget the coin for his fish

  • 6:00 - ?                Sunset Pier          0 Duval St            Sunset is at 6:48 group toast to Our Dave

  • 8:00                      Tiki House           203 Duval St       Grand Finale: lots of music and shenanigans

    We will be joined by our very own traveling minstrel: Paul Mezzanotte (singer/songwriter, retired Airforce, and all around good guy). Paul will be serenading you along the way, even hooking up to the mic for a couple of songs and a toast at a some of the stops along the way. Feel Free to join in the Pub Crawl. After the last toast to Dave (Yes there will be many toasts along the way) then everyone will make their way over to the TIki House upstairs for a WHOLE LOTTA PHUN and as Cathy says lots of shenanigans.

  • Just below is a QR code where you can donate directly to the TRMA Artists Relief Fund.

  • Dave's favorite charity of choice. Or click the blue "Click Here" button.

Tiki House - Official TRND Event

  • - - - BeachFront Radio event

  • The Pub Crawl Continues - its an After Crawl Party !!!

  • 8 PM - 12 Mid - This is where the PUB CRAWL Party begins. A very special surprise band will entertain you the rest of the evening. This is a party not to be missed. And Here is the announcement - - - -

  • Get ready to escape to paradise with a one-of-a-kind band the Margarita Brothers, the band that brings the ultimate tropical rock experience directly to you! Imagine the sun on your face, sand between your toes, and a cool drink in your hand – that's the vibe these seasoned musicians deliver with every performance. Blending the laid-back rhythms of reggae, the soulful sway of calypso, a bunch of Jimmy Buffett, lots of Beach Boys and the undeniable energy of classic rock, the Margarita Brothers craft a sound that's both refreshingly unique and instantly familiar. Their infectious melodies and high-energy stage presence guarantee a good time, transporting audiences to an island getaway no matter where they play. Check out their video on the BFR TV channels. . . . Or Click the button below.

Official OOTSK Event

Order of the Sleepless Knights Sunset Cruise

  • - - supported by TRND

  • 5:00-7:30 PM Featuring Dave McKenney and the Hungry Hardluck Heroies Band with special guests Roger Bartlett and Honey Bee.

  • They will be performing the entire set list from the show at Mallory Square on January 9, 1976.

Salty Frog - Official TRND Event

  • 3-6 PM: Tall Paul and Kristie

Roofttop Island - A Sunset Concert with John McDonald and Friends at the Studios of Key West on the Rooftop

- Official TRND Event

  • 5-7:00 PM - click Here for more details

    EXPERIENCE SUNSET IN KEY WEST IN A FUN, NEW WAY - FROM A DRAMATIC, ROOFTOP PANORAMA!!!

  • With guest appearance by Jerry Diaz

    The view from this Rooftop vantage point is amazing. You can see the island in a way you've never seen it before. Plus what a way to enjoy some great music from one of the original performers in Trop Rock and an award winning TRMA artist as well.

Hogs Breath Saloon - independent of TRND

  • 12-4 PM: Dan Harvey

  • 4:30 PM - 8:30 PM: Heather Vidal - Supported by TRND

  • 9:00 PM - 1 AM: Alex Anthony Band

Two Friends - TRND Supported Event

  • 1 - 4 PM: The Shanty Hounds

Durty Harry's - Tiki Man Radio Event - Key West Bound

independent of TRND

  • All times and Performers are TBD

  • 11-12 PM: The Shanty Hounds

Times and performers may change

Friday, Oct 31

Margaritaville - All Songs Jim Morris

- Official Trop Rock'N Duval, LLC (TRND) Event

  • 1-4 PM. Margaritaville is the official place to pick up your T-Shirts and Passports.

  • 1-4 PM get them outside to the left of the entrance. A window will be open.

  • Saturday 2-5 PM at Rams Head Southernmost to Pick up your t-shirts and passports

  • 11:00 - 12:00 PM: The Island Castaways Band, all original music and some covers

  • The All Songs Jim Morris Day, or songs written about him or a tribute to him.

  • 12:00 PM - 4:00 PM: Host Beach Bum Andy

  • 12:00 PM: Ray Boone and Jake Clayton

  • 12:15-45 PM: Island Castaways Band

  • 12:55 PM: Beth Travers

  • 1:10 PM: Barefoot Reggie

  • 1:25 PM: Paul Roush

  • 1:40 PM: Jody Bly

  • 1:55 PM: Steve Hopper

  • 2:10 PM: Mac Martin

  • 2:25 PM: Dennis Davis

  • 2:40 PM: John McDonald

  • 3:00 PM: Jerry Diaz

  • 3:15 PM: Tim Campbell

  • 3:45 PM: Last song with all Musicians - Sangria Wine - toast by BeachBum Andy

  • Back to the Regularly Scheduled performers

  • 4:30 PM - 6:30 PM: Roger Bartlett and Honey Bee

  • 6:30 PM - 8:30 PM: Margarita Brothers

  • 9:00 PM - 12:00 Mid: Kitty Steadman

The Blood Drive - Official TRND Event

Near Margaritaville on Fleming Street - they are now ready to take reservations -

  • 9:00 AM - 3 PM - Go to the Special Events Page and click on Blood Drive icon for details on how to sign up.

Surly Siren Saloon - Official TRND Event

The Surly Siren Saloon is Located at 308 Front St

  • 12:00 PM - 1:50 PM: Boomer Blake

  • 2:00 PM - 3:50 PM: Jason Acy

  • 4:00 PM - 6:00 PM: Mick Fury

  • 6:15 PM - 8:15 PM: Midnight Kahuna

  • 9:00 PM - 12 Mid: The Island Castaways Band

The Alamo - Official TRND Event

Raffle Baskets open to purchase tickets

  • The Alamo is Located at 4 Charles St

  • 1-5 PM: Raffle is OPEN to purchase tickets. Be sure to put your phone number on the back of the ticket so we can notify you if you are a winner.

  • The Raffle will be open starting on Thursday 1-5 PM at The Alamo. Also Friday 1-5 PM and Last Chance Saturday, 11-2 PM. Tickets can be purchased on site. Be sure to put your phone number on the back of the ticket so we can notify you if you are a winner.

  • Raffle baskets can be brought to The Alamo back room, drawings will be held Saturday at 2 PM. Winners can pick up the baskets until 6 PM Saturday.

  • All proceeds will go to both of our causes - Our Charity "The Shriners Hospitals for Children" and to the Songwriters Fund. The same fund that the Passports go to for supporting all the great music and our Charity.

The Alamo - Official TRND Event

  • The Alamo is Located at 4 Charles St

  • Raffle baskets can be brought to The Alamo back room, drawings will be held Saturday at 2 PM. Winners can pick up the baskets until 6 PM Saturday.

  • 1:00 PM - 2:50 PM: Rich McGuire

  • 3:00 PM - 5:00 PM: Tropical Soul

  • 5:30-8:30 PM: Jess & Jill and Friends (A Grateful Dead Tribute band)

  • 9:00 PM - 12:00 Mid: John McDonald w/Quentin and Dave Freeman - Time to Party

Viva Argentinian Steakhouse - Official TRND Event

Viva Argentinian Steakhouse is Located at 903 Duval St, Key West, FL 33040-6615 - they are partners with The Alamo - This is as great dinner location for listening to some great music while you dine.

  • 1-3 PM: Ray Boone and Jake Clayton ( a system is needed here, one will be made available)

  • 3:30-5:30 PM: Sara Bug

  • 6:00-9 PM: Bahama Mama and her Pain Killer w/Isabella Stefania

Official OOTSK Event

The Conch Train - Order of the Sleepless Knights Tour

  • - - Supported by TRND.

  • - - hurry only 2 seats remaining.

  • 2 PM - 3 PM - Take a tour of the Buffett Hot Spots . . . . The Tour takes you to all the places Jimmy hung out wrote songs about and other facts about the time he spent in Key West. The tour ends at the Knight's gathering at the Chicken Preserve. The Chicken Preserve features Artwork by David Wegman, T-shirts and lots of Island History. David Wegman was a long time friend of Jimmy Buffett and his stories will keep you entertained for hours.

Pool Party !!! Key West Historic Inns

  • These five lively hotels, known as the Key West Historic Inns, are located up and down Duval Street. And a couple of them will be hosting Pool Parties for some of our fun-loving Trop Rock fans with some of your favorite artists providing the entertainment. . . . NOTE: Special room rates apply when staying at the hotel as a Trop Rock'N Duval fan. See our Lodging page.

  • Pool Party at The Winslows Bungalows is located at 725 Truman Ave.

  • 2-5 PM: Bahama Mama and the Painkillers

  • Bathing suits optional, but clothing of some kind is required, and having a lot of Fun is Mandatory.

  • Join us at the Bungalow Bar at Winslow’s Bungalows for a lively day with Bahama Mama and the Painkillers, a crowd-favorite band serving up beachy vibes inspired by Sublime, Jimmy Buffett, and Jack Johnson. Take in vocals by Stephanie Biello, live guitar, keyboard and keytar tunes while you sip drink specials poolside or hang out at the bar and grab a burger or hot dog and everyone who comes with their Festival Passport gets one on us! It’s all good vibes, great music, and tropical fun.

Island Dogs - Official TRND Event

  • 10 AM-1 PM: Steve Hopper

  • 1-4 PM Songwriters Showcase - Host Jeff Randall

  • - - - 1-2 PM Jeff Randall

  • - - - 2-2:30 Jerry Diaz

  • - - - 2:30-3 Beth Travers

  • - - - 3-3:30 Mick Fury

  • - - - 3:30-3:50 Jeff Randall

  • 4-5:50 PM: Paul Roush

  • 6-9 PM Jeff Dayton and Dave Matchette

Hanks Hair of the Dog - Official TRND Event

  • 12:00 PM - 2:00 PM: Don Middlebrook

  • 2:15 PM - 4:15 PM: Tiki Thom

Mac's Place - Official TRND Event

  • Located at 1605 N Roosevelt Blvd

  • Corner of Truman Ave and Eisenhower Ln, right on the water

  • 4:00 - 6:00 PM: Mac Martin

  • 6:00 - 8:00 PM: Jake Clayton

Rams Head Southernmost - Official TRND Event

This is the BeachFront Radio - - - Tropical Mall

  • 12-5 PM - This year we will have our very first Official BeachFront Radio Tropical Mall at Rams Heads so you can shop for some great tropical merchandise while you listen to Kelly and other great performers. . The vendors will be there Thurs, Fri and Sat 12-5 PM.

  • Last year we had a couple of vendors there offering Custom made Jewelry and one of our Sponsors "Travel by Georgia" were there offering you great travel opportunities including the Parrot Head Cruises.

  • This year we will have many more great Tropical Jewelry and Crafts booths set up and many other cool tropical merchandise.

Rams Head Southernmost - Official TRND Event and Hosted by Songwriters Island Radio

  • 11:30 AM - 1:30 PM: Dennis Davis ( a system is needed here, one will be made available)

  • 2:00 PM - 5:00 PM: Kelly McGuire - Lighthouse Songwriters Showcase with Songwriters Island Radio

- - - - VIP-KF tickets (ie, VIP-Kelly Fans) - All VIP-KF persons will be seated at a table near Kelly. All seats without tables are FREE , no tickets needed. There will be a limited number of tables in the back of the courtyard as well. Food and Drinks available to all for purchase.

But chair seating is FREE and first come first to sit.

- - - - Kelly's Guest performers - - -

Time schedule

  • 2:00 - Heather Vidal

  • 2:20 - Sara Bug

  • 2:40 - Kelly McGuire

  • 3:00 - Jeff Dayton

  • 3:20 - Donnie Howard

  • 3:40 - Kelly McGuire

  • 4:00 - Isabella Stefania

  • 4:20 - Jason Acy

  • 4:40 - Kelly McGuire

  • 5:00 - Harold Booth

  • 5:20 - Kelly McGuire

  • 6:00 PM - 8:00 PM: on the BIG stage in the back Courtyard -

  • Jeff Randall and the Rusty Ole Flockers

Kaya Island Eats - The Backyard - Official TRND Event

  • Located 618 Duval St.

  • 1:00 - 3:00: Isabelle Stefania

  • 3:00 - 5:00: Lefty Lucy

  • 5-8 pm; independent of TRND

  • 8-12 Mid: Inna Vision - A Hawaiian Reggae Band

The Key West Theater - Will Kimbrough and Friends with special guest - Tall Paul

- Official TRND Event - Sponsored by BeachFront Radio

  • *** This show still has seats available. Don't miss out, order now.

  • 5-6:30 PM: Concert Performance by Will Kimbrough and Friends with special guest Tall Paul

  • - Tickets to both shows sold separately - go to the Special Events Page to get tickets or

The Key West Theater - Buffett Thru the Years Tribute Show

- Official TRND Event - Sponsored by BeachFront Radio

This show is SOLD OUT!

  • *** This show is Totally Sold Out. Email us to be put on the waiting list.

  • Email Andy at - troprocksongs@yahoo.com

  • Buffett through the Years Tribute Show

  • 512 Eaton St, Doors open at 7:00 PM.

  • Show Times - 8-10:30 PM: Buffett through the Years with Dave McKenney, Tim Campbell and the Tropical Attitudes Band, w/ Roger Bartlett, Will Kimbrough, Boomer Blake, and possibly a couple others joining in on the fun to be announced at a later date.

Schooner Wharf - Supported by TRND

  • Friday Halloween Show Schooners Wharf

  • 7:00-11:30 - Jonas Lorence Band

Tipsy Rooster - Supported by TRND

  • 9:00-12:00 - Steve Hopper

Sunset Cruise - Sebago Watersports with Jerry Diaz

- - - - Supported by TRND

  • 5-7 PM Jerry Diaz, with special guests including Barefoot Reggie Starrett and others

Hogs Breath Saloon - independent of TRND

  • 12-4 PM: Dan Harvey

  • 4:30 PM - 8:30 PM: Heather Vidal - Supported by TRND

  • 9:00 PM - 1 AM: Alex Anthony Band

Durty Harry's - Tiki Man Radio Event - Key West Bound

independent of TRND

  • All Times and performers are TBD

Times and performers may change

Saturday, Nov 1

Margaritaville - Official Trop Rock'N Duval, LLC (TRND) Event

  • 12- 1:20 PM: Jerry Diaz

  • 1:30- 3:20 PM: Dan McCaughey

  • 3:30- 4:50 PM: Boomer Blake, w/Quentin

  • 5:00 PM - 6:45 PM: Don Middlebrook

  • 7:00 PM - 8:30 PM: Tim Cambell and the Tropical Attitudes

  • 9:00 PM - 12:00 Mid: Kitty Steadman

The Blood Drive - Official TRND Event

Near Margaritaville on Fleming Street - they are now ready to take reservations -

  • 9:00 AM - 3 PM - Go to the Special Events Page and click on Blood Drive icon for details on how to sign up.

Surly Siren Saloon - Official TRND Event

The Surly Siren Saloon is Located at 308 Front St, 2nd Floor

  • 12:00 PM - 2:00 PM: Harold Boothe w/Fred Q

  • 2:30 PM - 5:00 PM: CBD Band

  • 5:15 PM - 8:15 PM: Jeff Dayton and Dave Matchette

  • 9:00 PM - 12 Mid: Bahama Mama and the Pain Killers

The Alamo - Official TRND Event

Raffle Baskets open to purchase tickets

  • The Alamo is Located at 4 Charles St (this is the old Smokin' Tuna location

  • 11-2 PM: Last Chance to purchase Raffle tickets. Be sure to put your phone number on the back of the ticket so we can notify you if you are a winner.

  • 1 PM: Drawings to be held.

  • The Raffle will be open starting on Thursday 12-6 PM at The Alamo. Also Friday 12-6 PM and Last Chance Saturday, 11-2 PM. Tickets can be purchased on site. Be sure to put your phone number on the back of the ticket so we can notify you if you are a winner.

  • 2 PM: Drawings will be held Saturday at 2 PM.

  • 2-6 PM: Winners may pick up their baskets.

  • All proceeds will go to both of our causes - Our Charity "The Shriners Hospitals for Children" and to the Songwriters Fund. The same fund that the Passports go to for supporting all the great music and our Charity.

The Alamo - Official TRND Event

  • The Alamo is Located at 4 Charles St, Key West, FL 33040-6615 (this is the old Smokin' Tuna location

  • Raffle baskets can be brought to The Alamo back room, drawings will be held Saturday at 2 PM. Winners can pick up the baskets until 6 PM Saturday.

  • 11:00 - 1:00 PM: The Shanty Hounds

  • 12:00 PM approx. until 3 or 4 . . . I heard the Key West Parrothead Club may be showing up for a Club Social Party.

  • 1:00 - 2:50 PM: Mick Fury

  • 3:00 - 5:00 PM: Midnight Kahuna

  • 5:30 -8:30 PM: The Happy Dog Band (A Grateful Dead tribute band)

  • 9:00 PM - 12 Mid: The Island Castaways Band

Viva Argentinian Steakhouse - Official TRND Event

Viva Argentinian Steakhouse is Located at 903 Duval St - they are partners with The Alamo - This is as great dinner location for listening to some great music while you dine.

  • 1-3:00 PM: - Jody Bly ( a system is needed here, one will be made available)

  • 3:30-6:00 PM: Roger Bartlett and Honey Bee

  • 6:30-9 PM: Paul Roush

Island Dogs - Official TRND Event

  • 10 AM-11:30 AM Theresa Pfeifer w/Quentin

  • 12:00 PM - 2 PM Beth Travers

  • 1-4 PM - FSU Fooball Game - or it could be 4-7 or 7-11. check the schedule for any changes once the game time has been announced.

  • 4:15-7:15 PM: Tropical Soul

  • 8-11 PM: Boomers Basement - with Jerry Diaz and the Shanty Hounds (Key West Chris and Dani Hoy)

Tiki House - Official TRND Event

  • Hosted by Shore Life Radio

  • 12-5 PM - All times and performers at TBD

  • Guest performers - Barefoot Reggie, Steve Hopper, Donnie Howard

Official OOTSK Event

The Conch Train - Order of the Sleepless Knights Tour

  • - - Supported by TRND.

This Train is SOLD OUT. Seats still left on the Friday train.

  • 10:45 AM - 11:45 PM - The Tour takes you to all the places Jimmy hung out wrote songs about and other facts about the time he spent in Key West. The tour ends at Hanks Hair of the Dog where you can enjoy the sounds of Dave McKenney and the Hungry Hardluck Heroes Band 12-2 PM.

Hanks Hair of the Dog - Official TRND Event

  • 12:00 PM - 2:00 PM: Dave McKenney and the Hungry Hardluck Heroes Band w/Theresa and Quentin, last stop on the Conch Train Tour

  • 2:15 PM - 4:15 PM: Sara Bug

Mac's Place - Official TRND Event

  • Located at 1605 N Roosevelt Blvd

  • Corner of Truman Ave and Eisenhower Ln, right on the water

  • 4:00 - 6:00 PM: Tiki Thom

  • 6:00 - 8:00 PM: Lefty Lucy

Kaya Island Eats - The Backyard - Official TRND Event

  • Located 618 Duval St.

  • 1:00 - 3:00: Donnie Howard

  • 3:00 - 5:00: Bob Banerjee, Jeff Randal, and Harold Boothe w/Fred Q

  • 5-8 pm; independent of TRND

  • 8-12 Mid: Inna Vision - A Hawaiian Reggae Band

Pool Party !!! Key West Historic Inns

  • These five lively hotels, known as the Key West Historic Inns, are located up and down Duval Street. And a couple of them will be hosting Pool Parties for some of our fun-loving Trop Rock fans with some of your favorite artists providing the entertainment. . . . NOTE: Special room rates apply when staying at the hotel as a Trop Rock'N Duval fan. See our Lodging page.

  • Pool Party at The Lighthouse Hotel is located at 902 Whitehead St.

  • 4-7 PM: Dave Freeman and Friends. Let's party !!!

  • Again, Bathing suits optional, but clothing of some kind is required, and having a lot of Fun is Mandatory.

  • Kick back at Isabel’s Bar at the Lighthouse Hotel for an evening of island rhythm and laid-back fun with Trop Rock’N Duval legend Dave Freeman and his band. Whether you're soaking up the scene poolside or sipping cocktails at the bar, enjoy smooth keyboard grooves, standout vocals, and tropical drink specials. Plus, we’re firing up the grill and serving burgers and hot dogs and everyone who comes with their Festival Passport gets one on us! It’s your perfect Key West escape—live music, good feels, and chill vibes.

First Flight - Happy Hour - Official TRND Event

  • 4:00 PM - 6:00 PM: John McDonald and Mango Man Jay Yerkes

    Keep things going and join John for a Happy Hour of fun. A great way to have fun on Saturday evening for Trop Rock'N Duval

Rams Head Southernmost - Official TRND Event

This is the BeachFront Radio - - - Tropical Mall

  • 12-5 PM - This year we will have our very first Official BeachFront Radio Tropical Mall at Rams Heads so you can shop for some great tropical merchandise while you listen to Kelly and other great performers. . The vendors will be there Thurs, Fri and Sat 12-5 PM.

  • Last year we had a couple of vendors there offering Custom made Jewelry and one of our Sponsors "Travel by Georgia" were there offering you great travel opportunities including the Parrot Head Cruises.

  • This year we will have many more great Tropical Jewelry and Crafts booths set up and many other cool tropical merchandise.

Rams Head Southernmost - Official TRND Event and Hosted by Songwriters Island Radio

  • 11 AM-1:30 PM Isabella Stefania at the Bar stage ( a system is needed here, one will be made available)

  • 2-5 PM is the Official location to pickup your T-shirts and Passports. Sunday will be the Surly Siren from 12-5 PM.

  • 2:00 PM - 5:00 PM: Kelly McGuire - Lighthouse Songwriters Showcase with Songwriters Island Radio

- - - - VIP-KF tickets (ie, VIP-Kelly Fans) will be available for purchase at $20 per person, All VIP-KF persons will be seated at a table near Kelly. All seats without tables are FREE, no tickets needed. There will be a limited number of tables in the back of the courtyard as well. Food and Drinks available to all for purchase. Click HERE for VIP-KF tickets.

And chair seating is FREE and first come first to sit.

- - - - Kelly's Guest performers - - -

Time schedule

  • 2:00 - Kitty Steadman

  • 2:20 - John McDonald

  • 2:40 - Kelly McGuire

  • 3:00 - Will KImbrough

  • 3:40 - Tim Campbell

  • 4:00 - Tall Paul & Kristie

  • 4:20 - Bahama Mama (Stephania Biello)

  • 4:40-5:30 - Kelly McGuire

  • 6:00 PM - 8:30 PM: on the Big Stage in the back courtyard

  • - - - - Tall Paul and his All Star Friends

Tipsy Rooster - Supported by TRND

  • 9:00-12:00    Steve Hopper

Schooner Wharf - Independent of TRND

  • 7:00-11:00    Trop Rock Junkies

Sunset Cruise - Sebago Watersports with Jerry Diaz

- - - - Supported by TRND

  • 5-7 PM Jerry Diaz, guests To be named later. Click below for tickets.

Hogs Breath Saloon - independent of TRND

  • 12-4 PM: Cliff Cody

  • 4:30 PM - 8:30 PM: Heather Vidal - Supported by TRND

  • 9:00 PM - 1 AM: Alex Anthony Band

Durty Harry's - Tiki Man Radio Event - Key West Bound

independent of TRND

all times and performers are TBD

Times and performers may change

Sunday, Nov 2

Margaritaville - Official Trop Rock'N Duval. LLC (TRND) Event

  • 11 AM - 12:50 PM: Sara Bug

  • 1 - 2:50 PM: Jim Asbell

  • 3 - 5 PM: Bahama Mama and her Painkiller w/Isabella Stefania

  • 5:15 - 7:15 PM: Jeff Randall w/Theresa Pfeifer

  • 8-11 PM: Kitty Steadman

Surly Siren Saloon - All Star Sunday - Official BeachFront Radio and TRND Event

"It's the BeachFront Radio Surly Hot Trop Rock All Star Show Sunday at the Siren !!!"

  • The Surly Siren Saloon is Located at 308 Front St, 2nd Floor

  • 12-5 PM This is the last chance to pickup your T-Shirts if you haven't already.

  • 12-3 PM: BFR Trop Rock All Star Show - Opening acts hosted by BeachBum Andy

  • 12-12:50 PM: Bahama Mama and the Pain Killers

  • 1- 1:40 PM: CBD Band

  • 1:50-2:10 PM:Mac Martin

  • 2:10- 2:50 PM: Don Middlebrook

  • 3-8 PM: BeachFront Radio Presents The Surly Hot Trop Rock All Star Show Sunday at the Siren with special emcees, Tim Campbell and Boomer Blake

  • 3:00 PM: Heather Vidal

  • 3:15 PM: Boomer Blake

  • 3:30-4 PM: Roger Bartlett and Honey Bee

  • 4:00 PM: Theresa Pfeifer

  • 4:15 PM: Jeff Randall

  • 4:30 PM: Dave Matchette

  • 4:45-5:10 PM: Don Middlebrook

  • 5:15 PM: Sara Bug

  • 5:30 pm: Jody Bly

  • 5:40 PM: Winners of the Trop Rock'N Duval songwriting contest

  • 6:00 PM: Special Appearance - Lefty Lucy

  • 6:15 PM: Donnie Howard

  • 6:30 PM: Dennis Davis

  • 6:45 PM: John McDonald

  • 7:00 PM: Ricky Lamb

  • 7:15 PM: Tim Campbell and the Tropical Attitudes Band

  • 8:00 PM: Finale - All musicians sing on the last song

  • 8:15 PM: Official End of TRND 2025

  • BUT NOT THE END OF THE PARTY - stick around for a wild time with ====>>

  • 9-12 Mid: Bob Banerjee and All his crazy Friends

First Flight - Happy Hour - Official TRND Event

  • 4:00 PM - 6:00 PM: John McDonald and Mango Man Jay Yerkes

    Join John and Jay for one last Happy Hour of fun during Trop Rock'N Duval. Then make your way over to the Trop Rock All Star Show at the Surly Siren and watch John there at 6:45 and the Grand Finale of the All Star Show after that.

The Alamo - Official TRND Event

  • 12-2:30 PM: Dennis Davis

Two friends - Supported by TRND

  • 5-9 PM: The Shanty Hounds

Official OOTSK Event

Andy's Cabana - Cheeseburger in Paradise Pirate's Ball

  • - - Supported by TRND

  • Cheeseburger in Paradise Pirate's Ball

  • 1-4 PM ish - A Chicken Preserve Benefit.

  • Exact times and Artists are still TBD

Official OOTSK Event

Hemingway Rum Distillary - Jimmy Buffett Key West Years

  • - - Supported by TRND

  • Jimmy Buffett the Key West Years - This is a ticketed event.

  • A special show that will feature deep cuts from the 70s.

  • 5:30 PM Doors open to VIP - 6:00 PM General Admission

  • The Hungry Hardluck Heroes Band with Roger Bartlett and Honey Bee and special guest Cayman Smith-Martin.

  • Get Tickets (TBD)

Hogs Breath Saloon - independent of TRND

  • 12-4 PM: TBA

  • 4:30 PM - 8:30 PM: Heather Vidal - Supported by TRND

  • 9:00 PM - 1 AM: Alex Anthony Band


Trop Rock'N Duval, LLC is an

Official BeachFront Radio sponsored Event


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