About Us

InsightCuba has sent nearly 20,000 travelers to Cuba since its inception in 2000, making us the most experienced provider of licensed people-to-people Cuba travel in the industry.

The Leader in People-to-People Cuba Travel

InsightCuba is a single destination tour operator specializing solely in legal people-to-people travel to Cuba for Americans. As pioneers in people-to-people travel to Cuba since 2000, we've brought nearly 20,000 Americans to this fascinating island country - making us the most experienced provider of licensed people-to-people 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 17 years of detailed research, extensive exploration, and our long-established relationships on the island, resulting in lifelong memories for our guests. With six Signature Cuba tours, a handful of Specialty Cuba tours, three Small Ship Cuba Cruises, and numerous Private Cuba tours offered across more than 250 departure dates spanning the entire country, insightCuba offers the broadest selection of Cuba tours 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. Additionally, insightCuba’s long-time president, Tom Popper has been a contributor on CNN, ABC, NBC, and National Public Radio.

For two consecutive years beginning in 2015, we won the Conde Nast Traveler World's Top Cuba Travel Specialist Award and in 2015 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 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 and our people-to-people tours are authorized by the U.S. Department of the Treasury's, Office of Foreign Asset Control (OFAC), allowing any American who books a Cuba tour with insightCuba to travel to Cuba legally.

As a registered guest on one of our people-to-people tours, you are permitted to travel to Cuba and re-enter the U.S. legally. InsightCuba handles all the paperwork and requirements for your trip. Simply register for one of our Cuba tours and leave the rest to us.