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/. 

Florida Keys Concert Association presents extraordinary performances in both Marathon and Islamorada through February. Audiences can enjoy the energy of the lively Trio Zimbalist Monday and Tuesday, Feb. 10 and 11; the artistic and technical prowess of rising stars Stella Chen on violin and George Li on piano Feb. 17 and 18; and the prize-winning Esme String Quartet, Feb. 24 and 25. Monday concerts take place at the Marathon High School Performing Arts Center at 350 Sombrero Beach Road, while Tuesday concerts at the Coral Shores High School Performing Arts Center at 89901 Old Highway. Shows start at 7:30 p.m.

The Studios of Key West, 533 Eaton St., presents multiple opportunities to enjoy live music. Performances include rooftop concerts by vocalist Libby York — Full Moon Love Stories on Feb. 12, and Spring Has Sprung March 27; the musical “confessional masterpieces” and timeless vocals by husband-and-wife duo Over the Rhine on March 4 and 5); 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 continue that tradition with the Dover Quartet, named one of the greatest string quartets of the last 100 years, Feb. 9; this season’s rising star, pianist Avery Gagliano, Feb. 23; the pioneering oboe, bassoon and piano ensemble, Poulenc Trio, March 9; and Duo Beaux Arts, Catherine Lan and Tao Lin, March 23. 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 the “greatest front porch blues band in the world,” The Reverend Payton’s Big Damn Band Feb. 5; The Steel Wheels Feb. 13; Western swing virtuosos Asleep at the Wheel Feb. 28; 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. Upcoming concerts include the legendary Gipsy Kings featuring Nicholas Reyes on Feb. 8; The Beach Boys Feb. 28; multi-platinum selling country star Brett Young March 8; and Nate Smith with Chase Matthews appearing 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 the star of TV’s Will & Grace in “Eric McCormick in Concert” Feb. 8th; a celebration of the iconic music of Broadway with “The Four Phantoms” Feb. 12th; A String Quartet Plays Feb. 21; Bobby Nesbit starring in “The Cabaret with Bobby in the Lobby” Feb. 23 and 24; Neil Berg’s ultimate rock concert and history lesson, “50 Years of Rock 'n’ Roll” Feb. 29th; singer-songwriter Sam Carlos on March 5th; Spanish guitarist Martina Bevis March 7; “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. The orchestra’s Valentine’s Day performance on Feb. 14 is to focus on compositions that celebrate love, headlined by the swashbuckling “Don Juan,” a musical tale of the fictional Spanish rogue, by Richard Strauss. In its 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 “Kokomo Key” featuring Florida songs and tropical music Feb. 22 with special guests Mangrove Swamp Band; “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 February performance is to be held at Murray Nelson Government Center’s Peace Park, mile marker 102 bayside, with the remainder 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. Dark Side of the Sol recreates the sounds of Pink Floyd on Feb. 14, and The Freebirds pay tribute March 7 to the music of Lynyrd Skynyrd. Performances begin at 6:30 p.m. Admission is free but there is a $10 fee for parking. 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.