Chad Olin


Travel + Leisure A List Travel Agent Chad Olin
Photo: Courtesy of the agent

Olin builds Cuba trips that explore the rich creative legacy of the island. One weeklong itinerary included salsa dancing at Havana nightclubs and a visit to Finca Vigía, the home where Ernest Hemingway lived for 20 years. Olin has also arranged jam sessions with Latin Grammy–nominated jazz musician Roberto Carlos Rodríguez Valdés and a visit with a local tile maker. He is also keen to get clients outside of Havana by including cities like Viñales, Cienfuegos, and Trinidad into his itineraries.

Concerned about the country's visa application and other logistics? Olin is up-to-speed on the latest developments and is praised by his clients for making their travels as seamless as possible. He also favors smaller hotel options. :Paseo 206, La Reserva and Loma del Angel are some of my favorite luxury proprties, which are owned and operated privately and can booked by Americans in compliance with the 'support for the Cuban people' travel category," Olin notes.


Languages Spoken: English and Spanish

Minimum Daily Spend: From $400 per day

Trip Planning Fees: None

Contact Info

chad@cuba​ | (305) 930-5194 | Miami


"We traveled with Cuba Candela in 2019 and hope to go back with Chad and his team as soon as possible. My husband and I travel regularly, much of it internationally, and our first trip to Cuba was one of our most memorable and favorite travel destinations we have ever visited. We don't typically travel with a host, instead we like to discover on our own and at our own pace, however I couldn't and wouldn't travel Cuba without Chad and his team. He curates unique, meaningful experiences that are thoughtful and incredibly well-run. Cuba would not be easy to navigate on your own, especially as you might in other countries with Yelp references, recommendations from friends or even social media highlights, and we definitely felt like we got to visit all the places we had dreamed of and also discovered many more that we would not have been able to find or even hear of on our own. I can not recommend Chad and his team enough!" Jamie C.

Was this page helpful?
Related Articles