Expert-Guided Cuba Tours 2026 & 2027

Escape the ordinary with Insight Cuba Tours—your trusted Cuba travel specialist since 2000. As a single-destination tour operator, we focus exclusively on authentic, expert-guided Cuba tour packages, offering immersive experiences under the "Support for the Cuban People" travel license. With over 20,000 Americans guided through Cuba, our tours are highly rated and travel advisor approved.

What sets us apart? Our exclusive access to Cuba’s most iconic cultural events, including the Havana Jazz Festival, vibrant jazz scene tours, and the thrilling Havana full & half marathons. These bucket-list experiences are not offered by any other operator—reserve your adventure now while space lasts!

Featured in The New Yorker, Fodor's, Frommer's, USA Today, CNN, and more, Insight Cuba Tours is a return guest favorite and a leader in stress-free, culturally rich travel. Plan your getaway for 2026 or 2027—contact us today to check availability and customize your trip.