Podcast conversation with David Lee.

Music pouring into the streets, spontaneous salsa dancing, talks with a former political attaché, dropping by a local boxing club, seeing a professional baseball game, and playing catch with local children. You must be in Cuba.

David painted us a rich picture of what a visit to Cuba is like. We had so much to cover, we didn’t even have time to talk about the fishing and scuba diving!

Creating personal connections is at the core of what the trips we plan to Cuba entail. Through Support for the Cuban People, we take you to places like Old Havana Head Start Pre-School to interact with curious and welcoming children in their school environment. Also Habana Compás dance to see an in-studio performance, whose members are classically trained dancers and powerful percussionists.

Your trip to Cuba will give you so many authentic moments to experience and learn about their culture. Here are a few examples:

  • Driving around in a fun, antique convertible cars
  • Tasting coffee
  • Music – from street musicians to professional
  • Cigars – learning about the process from seed to stem
  • Photo safaris
  • Art – galleries, private studios, street art
  • Architecture of Old Havana
  • Finca Vigia, the estate of Ernest Hemingway, where he wrote much The Old Man and the Sea in 1951
  • Visit DADOR, a boutique shop in Old Havana that functions as a design and art collective run by a group of talented women
  • Ballet – in one of most beautiful buildings
  • Old Havana boxing gym
  • Las Terrazas – UNESCO – day trip


  • What is a paladar? (see the video)
  • Rum tasting
  • EL FLORIDITA – home of the daiquiri and Hemingway hangout with live music
  • Stop in at the birthplace of the mojito, the famous Bodeguita del Medio
  • Fabrica de Art – Havana’s hottest night-spot! A multi-faceted venue, built into a former cooking oil factory, features art installations, live music, pop-up fashion stalls, performance art, Indy cinema. Young eclectic crowd of Cubans and foreigners.
  • Enjoy a cocktail in the iconic Hotel Nacional de Cuba


  • Salsa lessons
  • Biking/ebiking in Hanava
  • Walking the Malecon
  • Outside Trinidad – hiking to waterfalls and to admire the incredible fauna and birds
  • Veradero golf course
  • Play baseball with a local team


  • Trinidad – 4 hour drive from Havana. Worth a 2 night stay.
  • Fishing – go out on a liveaboard for an incredible experience. 7 nights.
  • Scuba diving – day trip or liveaboard


  • Dinner with a political sciences professor and former diplomat
  • Havana – Visit studios and galleries of top emerging artists
  • Architects
  • Artists
  • Entrepreneurs
  • Local chefs and cooks

Insider Access

  • Private concert performance on the Guardia’s rooftop with an award winning jazz trio


  • Small boutique hotels
  • 5*

Takeaway tips/info

There is cell service and wifi in many places. The way we plan trips is inclusive of expenses, generally excluding meals. No ATMs or credit card usage. You may use US dollars in most paladars and bars.

Videos from David:

If you enjoy this webcast, and love knowing about hidden gems, authentic restaurants, travel updates, and our favorite insights… Every Wednesday. Every week. Sign up for our VIP email HERE.


Extraordinary Experiences for
Adventurous Families

Join our mailing list to be in the know about our favorite new travel finds and the latest travel updates. 

Thanks for signing up! You should receive an email from us shortly (if you don't see it, check your spam).