Cuisine: Cuban seafood with Caribbean influence. Begin your journey in a lively space that evokes the golden era of 1950s tropical Havana—where the flavors of the sea meet Cuban tradition, in a setting inspired by Ernest Hemingway’s “The Old Man and the Sea.”

Historic Cultural Landmark. Pause beneath the shade of one of Little Havana’s most enduring cultural landmarks. This historic venue was the first in the United States to screen American films with Spanish subtitles—a quiet revolution that reflected the neighborhood’s emerging identity. As your guide shares its story, you’ll uncover how this theater helped shape Little Havana’s artistic spirit and became a lasting symbol of Cuban-American heritage.

Cuisine: Cuban-style tapas & tropical cocktails. Step into a landmark that has pulsed with music and memory since 1935. Once a jazz-era dance hall that hosted legends like Billie Holiday and Count Basie, this vibrant venue blends vintage charm with the lush ambiance of a tropical courtyard. As the rhythm of Latin jazz fills the air, you’ll savor a bold Cuban bite alongside a handcrafted cocktail—evoking the golden glamour of Havana nightlife.

Cultural Landmark. Between tastings, pause at one of the neighborhood’s most enduring social spaces—a shaded enclave where locals gather for lively games, sharp banter, and decades-old rituals. The soft clack of domino tiles and the occasional burst of banter offer a quiet window into Little Havana’s living heritage.

Cuisine: Traditional Cuban. Along this storied stretch of Calle Ocho, step into a space that channels the warmth and vibrancy of 1950s Havana. Surrounded by vintage photos, retro furnishings, and live Cuban music, you’ll savor a dish rooted in tradition—crafted with simple ingredients, bold flavors, and a sense of history you can taste.

Cuisine: Classic Latin sweets. Delight in a warm, golden treat that’s crisp at the edges, dusted with cinnamon, and served just moments after it’s made. Though its roots trace back to Spain, this beloved indulgence has become a staple across Latin America—and a nostalgic favorite in Cuban street food culture.

Cultural Exhibit. Wander through a curated space where vintage cars, murals, and original artwork come together in a vibrant tribute to Cuban heritage. Tucked within Rooster Alley, this stop also features a recreated guayabera shirt shop—offering a playful yet meaningful glimpse into island tradition and craftsmanship.

Cigar-making demonstration and Cuban coffee. Watch master rollers shape cigars by hand—a craft passed down through generations—while you enjoy a bold, aromatic sip of authentic Cuban coffee. Before you go, you’ll have the chance to bring a taste of the experience home with you.