TOLEDO, Spain — Flamenco is as diverse as Andalucía. Across Spain’s southernmost region, local aficionados brag that only their native performers express the true soulfulness of the music, a fusion of Gypsy, Muslim, Jewish, and Spanish elements that began developing there more than 200 years ago. But for the greatest talents, such as the brilliant guitarist Tomatito and the dazzling quintet Son de la Frontera (“Sound of the Frontier”), they put aside their differences to celebrate artists who transcend local boundaries.

This year, those boundaries will stretch to include New York. The World Music Institute and Flamenco Festival Inc. will present Tomatito at Town Hall this coming Saturday and Son de la Frontera at the Skirball Center on February 23 and 24.

“These musicians give a good idea of how flamenco is evolving,” Miguel Marin, the director of Flamenco Festival Inc., said recently. “Tomatito is more associated with traditional flamenco and Son de la Frontera with experimentation. But in fact, both remain true to flamenco’s roots. At the same time, in their own ways, they experiment. Not in order to be avant garde nor in attempts to be trendy, but instead by finding in other music — maybe jazz or tango or Cuban melodies — rhythms and instrumentation that enrich what already exists in flamenco.”

Before a private concert at a country estate here in November, the 50-year-old Tomatito, a tall, handsome man who wears his dark, curly hair to his shoulders, spoke passionately of his feelings for flamenco. “I love my instrument. I love music. It keeps me vibrant, my mind alive,” he said. “I’m constantly toying with ideas and keeping my eye on new things that come out. But our musical culture is cast in stone from an early age. I’m never going to learn to play another style. I played flamenco since I was a child and I still don’t know how. I’m always searching for more, pushing further and further.”

Tomatito (né José Fernández Torres) earned his distinguished reputation through touring and popular recordings. But he remains closely tied to his Andalucian Gypsy roots, and between engagements returns to his hometown of Almeria, where he lives with his wife and children.

“I can’t tell you what is important about flamenco,” he said, “because I was born into it. All my family was in flamenco. I knew nothing else from the time I was a baby. But I can tell you that it is deeply sustaining. It goes into the soul, where it touches all your sentiments.”

Comparing flamenco with jazz and the blues as art forms rooted in social strife and community, Tomatito explained that flamenco grew out of the persecution of the Gypsies, Muslims, and Jews during the Inquisition in the 15th century. “It’s in our blood,” he said. “It must come from the heart or it sounds fake. It’s music born of the soul’s anguish. I plan very little that I play — maybe just the opening and close. I am spontaneous, of the moment. My music reflects my mood, whether I am happy or sad. There’s nothing I can do about that. I am always exposed.” Winner of a 2005 Latin Grammy Award for his fifth album, “Aguadulce,” Tomatito imbues his songs with a particularly robust Gypsy flavor, a result not only of his heritage but of his 20-year collaboration with the legendary Gypsy singer Camaron de la Isla, who died in 1992.

His choice of collaborators provides a window to his wide-ranging curiosity. They include the jazz pianist Michel Camilo and the guitarists George Benson and Luis Salinas. Tomatito also experiments with Afro-Cuban and Brazilian music. In 2006, he recorded an impressive album with Mr. Camilo called “Spain Again” that uses music to connect the Spanish-speaking cultures of Europe, Latin America, and the Caribbean. It is an artistically rich connection also explored by Son de la Frontera, which takes the soulful music of the late guitarist Diego del Gastor as its inspiration. The quintet’s concept is one of a pop and rock band deeply rooted in flamenco. Pioneers in the introduction of the Cuban tres (a guitar-lute hybrid with three sets of double metal strings) to flamenco, Son de la Frontera creatively reinterprets the playing, dancing, and singing of Morón de la Frontera, near Seville.

Every player in the quintet is in some way related to del Gastor or Morón. They include the leader, Raul Rodriguez, who plays the percussive, rapid-firing tres; the singer, Moi de Moron; the dancer Manuel Flores, and two great-nephews of del Gastor, the guitarists Paco de Amparo and Pepe Torres. Nominated for the 2008 BBC Radio 3 Awards for World Music, the quintet employs the rhythms of North India, Afghanistan, and North Africa — the Gypsies who settled in Andalusia in the 11th century originated in North India and traveled to Spain by way of the Near East and South America — and especially those of Cuba.

“It’s understandable,” Mr. Rodriguez said. “The place where the boats moored before embarking on their journeys to Cuba was in Cadiz. When they got to the other side of the Atlantic, the first port of call was Havana. I think it’s essential and really important to look back, listen to the old-timers, and learn. Without using its past, flamenco has no future. It’s the only possible option. You have to look back to bring information to the present and focus it with great care and respect toward the future.”

Son de la Frontera and Tomatito often receive rock-star welcomes when they perform. But at Tomatito’s recent private concert here, the guests were thrilled to have him and his group perform for them alone. Wearing an elegant black jacket and jeans, the guitarist opened with simple chords before a second guitarist joined in and a singer and a dancer clapped their hands. Accelerating the tempo, Tomatito shifted the harmonies, changing the mood. With his head bowed over his guitar, he produced spiraling arpeggios, wisps of sound that abruptly changed into bursts of strumming.

For one guest, he wasn’t loud or fast enough.

“Maestro, let’s warm up,” the gentleman rudely yelled out.

“You know, sir,” Tomatito responded patiently, his fingers gentle on the strings, “it’s always little by little in flamenco. We build slowly.”