Travel + Leisure A List Travel Agent Chad Olin

Chad Olin


His specialty is curating itineraries centered on cultural programming, like jam sessions with Latin Grammy–nominated jazz musician Roberto Carlos Rodríguez Valdés, performances by some of Cuba’s top salsa dancers, and tours of must-see art venues like Havana’s factory turned creative hub Fabrica de Arte Cubano. “We appeal to culturally curious experience-seekers who value authenticity and connection above all,” he says. Thanks to his contacts on the ground, Olin can make the impossible happen — like reuniting emigrants with long-lost family members. (A different but no less challenging undertaking was developing an itinerary that met the intellectual requirements of a 16-year-old debate champion.) For alternatives to large high-end resorts like the Gran Hotel Manzana Kempinski, ask Olin to recommend smaller gems like Paseo 26 and Lomo del Angel. Have questions about the country’s travel rules and restrictions? Olin is up-to-speed on the latest developments (he even published a 2020 guide detailing the country’s visa application and other logistics) and is praised by his clients for making their travels as seamless as possible.


Languages Spoken: English and Spanish 

Minimum Daily Spend: From $400 per day

Trip Planning Fees: None

Contact Info

chad@cuba​ | 443-834-3186 | Miami


“Chad set up a very thorough weeklong trip to Havana, during which we toured the city’s top historic and cultural attractions and explored surrounding towns and areas, like the fishing village of Cojimar and the old city of Trinidad. His expertise was evident every step of the way, from the information he provided us pre-trip to the selection of our hotels and guides. We cannot say enough about how thoughtful and attentive Chad and his Cuba Candela staff were.” — John and Tanya Filla