Tantra + Guests

The Playlist

A brand new concert series at The Studios (click here to view the full lineup →)
Graphic poster reading “Live Hip-Hop Show” with a gold vintage microphone illustration and splashes of pink and yellow. Text lists performers DJ Maya, Tantra, Luffkid, 3 Spliffs & Pastor Pat, JMAC, and Voice of the Streets Little P, with a note honoring a fallen hip-hop poet.

Saturday, March 28, 7pm

Hugh’s View

$30

sponsored by The Artist House

Due to the overwhelming response to the first concert, we’re thrilled to announce a repeat performance! As a female emcee with over 20 years in the hip-hop industry, Tantra understands the power of lifting up personal, intricate stories that exist outside commercial norms. For this event, she elevates a genre that doesn’t often have a platform on our little island. Performing songs from her upcoming third album, Initiation, Tantra will be joined by a lineup of local conscious rappers, poets, and hip-hop artists—continuing the spirit of collaboration, storytelling, and community that made the first night such a success.

Tantra + Guests

The Playlist

A brand new concert series at The Studios (click here to view the full lineup →)
Colorful graffiti-style event poster reading ‘Where Art Meets Intelligent Rhymes,’ featuring the artist Tantra, DJ Maya, Luffkid, 3 Spliffs, Bria Ansara, and a illustrated boombox.

Saturday, January 24, 6pm

Hugh’s View

$30

sponsored by The Artist House

As a female emcee, who’s spent 20 years in the hip-hop industry, Tantra understands the importance of lifting up the personal and intricate stories that differ from the commercial norms. For this event, Tantra elevates a genre that doesn’t typically have a big voice on our little island. Performing songs from her upcoming third album, Initiation, she will also be joined by several other local conscious rappers, poets and hip-hop artists.

The Key Rhyme Collective opens for Tantra, featuring 3 Spliffs, LuFFKid, Bria Ansara and DJ Maya, plus poets Ginny and Arida Davis

Wintergreen Oil Transfers

Angelica Clyman (PEAR)

A layered print featuring architectural shapes such as arches and windows in muted pastel colors—pink, blue, and yellow. Ghostlike figures and palm tree textures blend into the scene, giving the composition a dreamy, historic, washed-out effect.

Saturday, May 16, 10:30am – 12pm

Hugh’s View

$85

Discover the magic of wintergreen oil as a tool to transfer toner images onto various surfaces. After learning the transfer process, embellish your piece with mixed media to explore personal history, memory, and storytelling through visual layering.

More details

Instruction Style: Hands-on | Exploratory | Mixed Media

Skill Level: All Levels

Classical Crossover

Irie Monte, Michelle Sanchez & Zach Brown

The Playlist

A brand new concert series at The Studios (click here to view the full lineup →)
Three musicians pictured side by side: violinist Irie Monte smiling and holding her violin, violist Michelle Sanchez holding a viola, and cellist Zach Brown playing the cello.

Monday, February 9, 6pm

Hugh’s View

$50

sponsored by Key West Historic Inns

Bartók to the Blue Ridge Mountains: Folk Roots to Fiddle Strings traces a vibrant musical journey from Eastern European folk traditions to American fiddle and Americana styles. From the rhythmic drive of Bartók’s Romanian Folk Dances to beloved melodies by Dvořák, and John Hartford, this program celebrates how folk music continues to inspire composers across oceans and generations. Please welcome Irie Monte (violin), Michelle Sanchez (viola), and Zachary Brown (cello) to the stage for a very special evening of string trio music, where classical elegance meets the raw, joyful spirit of fiddle traditions.

Souvenirs: Zoë Lewis

The Playlist

A brand new concert series at The Studios (click here to view the full lineup →)
A performer wearing a tropical-print shirt and black beret sings and plays the piano on stage with arms outstretched in front of a red curtain.

Monday, March 23, 7pm

Helmerich Theater

$50

sponsored by Strunk Ace Hardware

Storyteller, songwriter, and globetrotter Zoë Lewis presents a whimsical musical memoir spanning childhood in England to adventures around the world. With songs, stories, and multimedia magic, Lewis blends humor, heart, and high energy into a joyful reflection on memory, belonging, and the art of living fully.

Cortadito

The Playlist

A brand new concert series at The Studios (click here to view the full lineup →)
ive members of the band Cortadito stand outdoors in suits by the water at sunset, posing together with historic stone architecture behind them.

Friday, March 6, 7pm

Helmerich Theater

$85 front row, $50

Hailing from Miami, Cortadito revives the soulful rhythms of Son Cubano—the sound that inspired the Buena Vista Social Club. Blending guitar, trumpet, and percussion, this acclaimed ensemble channels the joy and nostalgia of Cuba’s golden era, transporting audiences through melody, movement, and irresistible island swing.

Riff on RoxFilm

Logo graphic reading “Riff on RoxFilm – Roxbury International Film Festival” in bold black and red text.

The Roxbury International Film Festival is the largest New England festival dedicated to celebrating films by, for and about people of color around the world. Originally introduced to The Studios by our good friend Ed DeMore, the fest offers an exclusive chance to see two beautiful films, plus a series of curated shorts, all in one place. The two day festival includes a kick off rooftop reception, talkbacks, and meet-and-greets with directors, plus a special closing reception honoring the life, legacy and passion of our dear friend Ed.

supported in part by the Community Foundation of the Florida Keys

Fri Feb 6

Friday Evening Premiere: Paradise Reflected

Blue-toned title card reading ‘Paradise Reflected’ over a calm ocean horizon with the text mirrored in the water.

Opening night kicks off by grounding RoxFilm’s global storytelling in the lived experience of Key West: a local filmmaker presents a premiere of his new film, plus a visiting artist gives a talk about his exhibit rooted in Bahama Village.

Sat Feb 7

Saturday Matinee Shorts

2 kids on bikes

A powerful selection of short films curated by RoxFilm—intimate, urgent stories that cross borders, generations, and lived experiences. Together, they highlight how personal stories can illuminate larger social truths.

Sat Feb 7

Saturday Evening: Waiting for Superman

A woman sits at a table with a young boy, watching as he works with crayons and paper in a classroom or home setting.

We close the weekend with a message about taking action today to strengthen our community of tomorrow, seen through the eyes of five students making their way through the American education system.

Flamy Grant

The Playlist

A brand new concert series at The Studios (click here to view the full lineup →)
A drag performer with voluminous pink curls and bold makeup plays a turquoise acoustic guitar outdoors, wearing a green ruffled robe over a hot pink outfit and smiling brightly.

Sorry, Wednesday’s rooftop show has been canceled 

Tuesday, January 6, 7pm

Helmerich Theater

$85 front row, $50

Award-winning and Billboard-charting artist Flamy Grant is a shame-slaying, hip-swaying, singing-songwriting drag queen from Asheville, North Carolina. Her 2022 debut record, Bible Belt Baby, reached the #1 spot on the iTunes Christian Chart (the first drag performer to achieve this feat). She is also a finalist for the 2025 International Folk Music Awards Artist of the Year and has been featured in Rolling Stone, Billboard, Entertainment Weekly, People, and more. Her music has over 1.5 million streams on Spotify, Apple, and Amazon music. A powerhouse vocalist and intrepid songwriter who blends folk, gospel, and roots, Flamy drags audiences into a therapeutic, theatrical mix of storytelling and song. Armed with a bold lip and a blistering voice, Flamy is brilliant, resilient proof that nothing is sacred (but everything is holy) and shame belongs in the closet.

sponsored by Harrison Gallery

Ricky Skaggs and Sharon White

Old Town New Folk

Concert series sponsored by Blue Heaven (click here to view the full lineup →)
Ricky Skaggs and Sharon White smile warmly outdoors, each holding their instruments — Skaggs with his mandolin, White with her guitar. Sunlight filters through the trees behind them, capturing the warmth, harmony, and enduring partnership that define their decades-long musical and personal journey.

Tuesday, March 24, 7pm

Helmerich Theater

$125 front row, $85 general admission

Wednesday, March 25, 7pm

Hugh’s View

$125 front row, $95 general admission

This season of Old Town New Folk closes with an evening of bluegrass brilliance and pure harmony, as two of country music’s most celebrated voices share the stage.

Ricky Skaggs and Sharon White are a musical partnership woven from love, legacy, and more than six decades of song. Earning 12 #1 hit singles, 15 GRAMMY® Awards, 13 IBMA Awards, nine ACM Awards, eight CMA Awards (including Entertainer of the Year), along with inductions into the Bluegrass Music and Country Music Hall of Fame, Ricky Skaggs is truly a pioneer of Bluegrass and Country music. Since his beginnings in music over 60 years ago, the Grand Ole Opry member has released more than 30 albums and performed thousands of live shows with his ace backing band, Kentucky Thunder. He started his own record label, Skaggs Family Records, in 1997, releasing 12 consecutive GRAMMY®-nominated albums and has published his autobiography, “Kentucky Traveler.”

Sharon White is a member of beloved Country-Gospel family band, The Whites, and has been making music alongside her father Buck and sister Cheryl for more than five decades. They originally began as a Bluegrass group, but the family trio became well known for their string of Country hits in the 1980s, including “Hangin’ Around,” “Give Me Back That Old Familiar Feeling,” and “Pins and Needles.” The Whites are Grand Ole Opry members and were involved in the 2001 hit movie and soundtrack, O Brother, Where Art Thou? They have gone on to win GRAMMY®, CMA and Dove Awards, among others.

Joining the evening is Mike Rogers, celebrated vocalist and founding member of the acclaimed harmony group Brothers of the Heart. Formerly the lead singer of the chart-topping band BlackHawk, Rogers brings deep roots in classic country and bluegrass, adding another layer of harmony to this unforgettable night.

Old Town New Folk is underwritten by Nick and Lorie Howley, with additional support from Doug and Sherri Montgomery, John and Marilyn Rintamaki, Nell Smets, and Michael Blades and Kathy Kilroy. 

Jake Shimabukuro

Old Town New Folk

Concert series sponsored by Blue Heaven (click here to view the full lineup →)
Ukulele virtuoso Jake Shimabukuro stands against a vivid red wall, strumming his instrument with a relaxed smile. Dressed in a black leather jacket and dark shirt, he radiates calm confidence and creative energy, embodying the boundary-breaking spirit that has made him one of the world’s most celebrated ukulele players.

Tuesday, March 10, 7pm

Helmerich Theater

$125 front row, $85 general admission

Wednesday, March 11, 7pm

Hugh’s View

$125 front row, $95 general admission

Hailed as the “Jimi Hendrix of the ukulele,” Jake Shimabukuro has taken the four-string instrument to breathtaking new heights. Since first gaining worldwide fame with his viral rendition of George Harrison’s “While My Guitar Gently Weeps,” Shimabukuro has toured the globe—from the Hollywood Bowl to the Sydney Opera House—mesmerizing audiences with his lightning-fast technique and genre-defying sound.

Over the course of more than a dozen albums, the Hawaii-born musician has collaborated with an astonishing roster that includes Yo-Yo Ma, Jimmy Buffett, Bela Fleck, Bette Midler, and Willie Nelson. His most recent project, Blues Experience, finds him joining forces with Fleetwood Mac co-founder Mick Fleetwood for an exhilarating take on blues classics, reimagined through ukulele and percussion.

A passionate collaborator and storyteller, Shimabukuro channels joy, innovation, and pure musical spirit in every note. His concerts are dazzling celebrations of connection—proof that even the smallest instrument can carry the biggest sound.

Old Town New Folk is underwritten by Nick and Lorie Howley, with additional support from Doug and Sherri Montgomery, John and Marilyn Rintamaki, Nell Smets, and Michael Blades and Kathy Kilroy.