Musical Magic to Enliven the Keys Island Chain

FLORIDA KEYS — The laid-back atmosphere of the Florida Keys carries the sound of music across the island chain with live musical performances – both indoor and outdoor – and music festivals across many genres delighting Keys visitors with a variety of options.

While a number of notable musical happenings are listed here, a comprehensive calendar of offerings can be found at fla-keys.com/calendar/arts-culture/florida-keys/current/. 

The Studios of Key West, 533 Eaton St., presents multiple opportunities to enjoy live music. Performances include a rooftop concert by vocalist Libby York, "Spring Has Sprung" March 27; folk music’s “Rustic Renaissance Man” John McCutcheon (April15-16); and worldwide "Bluegrass Ambassadors" the Henhouse Prowlers (April 22-23). Times of shows vary.

Impromptu Classical Concerts of Key West has brought a variety of stellar ensembles playing classical music in all styles to the southernmost island city for over 50 years. The acclaimed organization’s 2025 concerts conclude this season with Duo Beaux Arts, Catherine Lan and Tao Lin, March 23. The performances take place at 4 p.m. at the historic St. Paul’s Episcopal Church at 401 Duval St.

Rams Head Presents Key West brings several big-name acts to two separate venues as part of the Key West Concert Series: 

• The Key West Theater at 512 Eaton St. delights music lovers with a packed season of performances in an intimate setting. Upcoming performances include Awaken: The Music of YES April 6; and Delta blues virtuoso Tab Benoit with Sierra Green and the Giants April 11. 
• At the Coffee Butler Amphitheater, 21 E. Quay Road, music lovers can enjoy top names performing live in an open-air, waterfront setting. Nate Smith with Chase Matthews are set to appear May 1 as part of the annual Key West Songwriters Festival. 

Also in Key West, the Tennessee Williams Theatre, located at 5901 College Road, presents a sparkling lineup of top musical talent including “Joy in the Cabaret” starring Joy Hawkins March 12 and 13; “Free Fallin’ - the Tom Petty Experience” March 29; the “Buckets N Boards” comedy percussion show April 1st; and a trip back in time to the hottest entertainment of Las Vegas with “The Rat Pack - One More Time” on April 5th.

Also at Tennessee William Theatre, the South Florida Symphony Orchestra, launched 27 years ago in Key West under the direction of Maestra Sebrina Maria Alfonso, brings dynamic performances for music lovers in the island city. In the orchestra’s homage to Wolfgang Amadeus Mozart March 15, the symphony performs the hauntingly beautiful “Requiem” with vocal performances by four remarkable soloists and the South Florida Symphony Chorus. 

For an outdoor concert experience, the Florida Keys Community Concert Band hosts the free “Pops in the Park” series. Upcoming performances, each on Saturday afternoons at 4 p.m., include “Twilight Tunes” featuring movie and show tunes on March 29 with special guests Ukulele Joy; and “Conch Classics” featuring international music from throughout time April 19. The  performances are held at Islamorada’s Founders Park amphitheater, mile marker 87 bayside. 

Islamorada Community Entertainment brings quality entertainment and cultural events to the Upper Keys including performances in the Beats on the Bay music series at the amphitheater in Islamorada’s Founders Park, mile marker 87 bayside. The Beats on the Bay series finale, Bay Jam on April 13, takes over the amphitheater from 11 a.m. to 8 p.m. The annual art and music festival features a packed lineup of musicians along with art, craft and food vendors.

The annual Afro Roots Fest returns to the Keys Friday through Sunday, April 4-6, with a weekend of free musical entertainment highlighting Afro-Caribbean vibes in the beer garden at Florida Keys Brewing Company in Islamorada, 81611 Old Highway. Performances are to feature Cortadito playing traditional Cuban folk music of the early 20th century, roots and reggae beats with Philip Montalban, Latin funk and fusion by Electric Piquete and more. 

The Key West Songwriters Festival is to showcase America’s foremost performing songwriters appearing on multiple stages and venues in the island city Wednesday through Sunday, April 30-May 4. The highly acclaimed event typically includes more than 50 shows and over 200 country and pop music hitmakers. Now in its 29th year, the festival has become a tradition for top writers and musicians, while offering an unparalleled experience for music fans.