About Us

InsightCuba has sent tens of thousands of travelers to Cuba since its inception in 2000, making us the most experienced provider of legal Cuba travel in the industry.

The Leader in legal Cuba Travel

InsightCuba is a single destination tour operator specializing solely in legal travel to Cuba for Americans. Since 2000, we've brought tens of thousands of Americans to this fascinating island country—making us one of the most experienced providers of legal Cuba travel in the industry. Learn more about our history of legal travel to Cuba.

Our in-country knowledge and expertise is unmatched in the industry, allowing us to provide travelers with unique access to people and places the average person rarely sees. Simply said, we do Cuba better than anyone else.

Our success is built on nearly 20 years of detailed research, extensive exploration, and our long-established relationships on the island, resulting in lifelong memories for our guests. With an array of Small Group Cuba tours and Specialty Cuba tours, along with Private Departure and Custom-Made tours, insightCuba offers the broadest selection of trips to Cuba available.


InsightCuba has been featured and talked about in hundreds of publications and major media outlets across the country including the New York Times, Washington Post, the Miami Herald, and The New Yorker, to mention a few.

In 2020 and for our sixth consecutive year, insightCuba won the Conde Nast Traveler World's Top Cuba Travel Specialist Award. We also won the Conde Nast Travel Editor's Pick for our Legendary Cuba tour.

Our Staff, Your Partner in Travel

We wouldn't be where we are today if it weren't for our staff, the folks responsible for meticulously crafting every aspect of our tours. All of us here at insightCuba are as passionate about travel as you are—in fact, our wanderlust has led us collectively to well over 100 countries. Some of our Travel Specialists spend on average two weeks annually on the ground in Cuba, joining tours and exploring the island's every nook and cranny to ensure that we offer the most meaningful and memorable experiences our guests could ask for.

Legal Travel to Cuba

InsightCuba is authorized by the U.S. Department of the Treasury's, Office of Foreign Asset Control (OFAC), under a general license that allows Americans to travel to Cuba. As a registered guest on one of our tours, you are permitted to travel to Cuba and re-enter the U.S. legally. We handle all the paperwork and requirements for your trip. Simply register for one of our Cuba tours and leave the rest to us.