Special Events

Thursday Oct 30, 2025 8-10 PM. At the Key West Theater. . . 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 them out at Margaritabrothers.com or click the Learn More button below

also check their Facebook page - a link is right on their Home page.

Thursday, Oct 30; 4:30-7:00 PM

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

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.

THIS EVENT IS TOTALLY SOLD OUT !!!.

Get ready to be transported to the sunny shores of Key West as BeachFront Radio proudly presents “Buffett Through the Years Tribute Show”—an unforgettable musical journey celebrating the legendary Jimmy Buffett! This is not just a concert; it’s an immersive experience that takes you through the rich tapestry of Buffett’s storied career, right here in Key West. And this year it will be at The Key West Theatre. Special Guests include Roger Bartlett and Honey Bee, . . .

. . . . . and just added WIll Kimbrough.

Dates and times for 2025 are still TBD. Last year was a BIG hit and we even had to add Saturday there was so many that wanted to participate.

Thursday, October 30th from 9 AM to 4 PM, and Friday, the 31st from 9 AM to 2 PM and most likely Saturday Nov 1st.

Join us for the Trop Rock'N Duval Blood Drive and help us "Keep the Party Going" by supporting cancer patients in need of blood donations! In partnership with Margaritaville and OneBlood, we're bringing back the largest blood drive in the Florida Keys. Be part of this lifesaving effort and score an exclusive shirt for donors! Sign up now by emailing TRDBloodDrive@aol.com with your preferred date, time, and shirt size. Let’s show the world that we’re still number one and make a real difference together!

Thursday, Oct 30; Friday, Oct 31; Saturday, Nov 1 - all days 2-5 PM

Join us for an unforgettable musical experience at Kelly McGuire's Lighthouse Songwriters Showcase, hosted by Songwriters Island Radio and broadcast live! Enjoy an intimate setting with Kelly McGuire and other talented songwriters in the beautiful back courtyard of Rams Head Southernmost. Regular seating is FREE, first come first seated. . . .But wait there's more . . . And this year we will have our Tropical Mall at Rams Heads so you can shop for some great tropical merchandise while you listen to Kelly and other great performers. . . . And wait there's still more. on Friday and Saturday evening we will have parties in the back area with bands performing on the big stage with dancing, fun, and great music from 6-8 PM. The evening fun is all FREE. And be sure to have your Passports with you for discounts on food and drinks, but no discounts on fun, you can have all the fun you want for no extra charge.