Tour Leader



We are seeking a dynamic, enthusiastic, self-starter who has experience in the Cuba travel industry to help provide outstanding travel programs to Cuba for our guests.
InsightCuba, a leading provider of licensed travel to Cuba for U.S. citizens is accepting applications for the position of tour leader and guide.  
As an insightCuba tour leader and guide, you will work with a dedicated team focused on providing incredible travel experiences, exciting tours, and outstanding customer service. The tour leader is responsible for accompanying the guests throughout Cuba to ensure that each tour meets or exceeds the guest’s expectations. A comprehensive training program will be provided.


  • Travel to Cuba with small groups of people 
  • Maintain control and oversee the well-being of guests and programming
  • Maintain integrity of insightCuba and people-to-people programming
  • Confirm hotels, scheduled activities to institutions, restaurants, and special events
  • Group orientation based on insightCuba Orientation Manual
  • Ensure all guests are aware of and adhere to U.S. regulations regarding legal travel to Cuba
  • Guide guests on the tour and in daily activities
  • Maintain relationship with Cuban drivers and community organizations
  • Proactively anticipate and resolve any potential issues for the group or individuals
  • Report emergency issues and maintain detailed notes of emergency procedure
  • Submit reports and receipts in a timely manner
  • Provide program updates, itineraries, and summaries while on the ground


  • Must have 5+ years working as a tour guide for Havantur, San Cristobal, Amistur, Gaviota or similar. 
  • Must be adept at dealing with constantly changing situations
  • Must  have full knowledge of the areas where the group will travel
  • Fluent in English and Spanish
  • Excellent leadership skills
  • Must be confident speaking in front of a group and possess extensive experience working with American groups in Cuba
  • Excellent interpersonal and management skills
  • Must be flexible and able to work independently
  • Must be willing to work shifts that vary from day to night and operate seven days a week
  • Possess a high energy level, a get it done attitude, and an affinity for adventure and challenge
  • First Aid certified 


This is a contracted position.

How to Apply:

For consideration, please submit a cover letter outlining the top three skills that will help you excel in this role, as well as your resume, and salary requirements. Please email this to
For more information about insightCuba please visit us at
InsightCuba is an equal opportunity employer and always employs qualified individuals based on job-related qualifications regardless of race, religion, color, gender, sexual orientation, marital status, national origin, age, disability, or any other classification protected under applicable federal, state, or local law.