San Juan & El Yunque Trip Leader

Love to have fun and do good? Want to share epic travel experiences? We have just the job for you.

Have Fun Do Good Logo
Have Fun Do Good Logo

Contract Seasonal Trip Leader

At Have Fun Do Good, we value diversity of thought, experience, and background. We are committed to providing a supportive and inclusive work environment that encourages growth and development for all of our employees, regardless of their background or level of experience. We understand that not every candidate may meet all of the qualifications listed in our job postings, but we encourage anyone who is interested in our company and passionate about our mission to apply. We believe that a candidate’s potential and eagerness to learn are just as important as their previous experience.

We celebrate diversity and are proud to be an equal opportunity employer. We do not discriminate based on race, color, religion, national origin, sex, gender identity or expression, sexual orientation, age, marital status, veteran status, or disability status. We welcome and encourage candidates of all backgrounds and identities to apply for our job openings.

Company Overview + Mission

Hey there, we’re Have Fun Do Good. We specialize in group travel that gives back. We plan unforgettable experiences that leave our travelers feeling good long after they’ve landed. We create opportunities for people to make a difference in the communities they visit, and our ultimate goal is to promote responsible tourism that benefits both our travelers and the places they visit!

Job Summary

We’re seeking seasonal contract Trip Leaders to join our team! If you’re a passionate explorer looking for the opportunity to lead travelers to the best sites and attractions in your region, Have Fun Do Good is the place for you.

As a Trip Leader, you’ll be responsible for helping our travelers experience the destination like a local, guiding our travelers on hikes and around their destination, while providing historical and cultural context about the destination. You’ll ensure their safety and foster a sense of community throughout the trip. Trip Leaders should possess excellent communication skills, a love of travel, and extensive knowledge of your region.


Job Title

San Juan & El Yunque Trip Leader 

Job Location

Trip will start in San Juan and then go to El Yunque National Forest (Naguabo), PR

Trip Leaders should be located within 50 miles of the job location.


$300 per night plus any gratuities from travelers.

Accommodation and all meals for the duration of trip dates will be included.

Trip Dates

February 15 – 19, 2024

December 5 – 9, 2024

Virtual Training Dates

Will take place via Google Meet. Dates to be determined.


  • Lead guided trips for travelers, showcasing the best sites and attractions according to predetermined trip itinerary 
  • Provide travelers with historical, cultural, and general context and information about the destination 
  • Communicate effectively with travelers before, during, and after the trip to ensure their satisfaction and address any concerns they may have 
  • Manage any unforeseen issues that may arise during the trip, such as inclement weather, transportation delays, or changes in itinerary 
  • Ensure the safety and well-being of travelers during the trip, following all safety protocols and guidelines
  • Liaise with other members of the Have Fun Do Good team to execute successful trips by sharing direct insight and feedback from each trip 


  • Passion for travel, social impact + community engagement
  • Wilderness First Responder (WFR) or Wilderness Advanced First Aid (WAFA) or similar certification
  • Cardiopulmonary resuscitation (CPR) and automated external defibrillator (AED) certifications or similar certification
  • National Tour Association (NTA) Certified Tour Professional or similar certification
  • Certified Interpretive Guide (CIG) or similar certification
  • Valid Commercial Driver’s License and ability to drive a 12-15 passenger van
  • Local expert in the trip location and ability to pivot trip plans in case of inclement weather or other unforeseen disruption
  • Bachelor’s degree in hospitality, tourism, or a related field
  • At least 2-3 years of experience in the travel industry, preferably in tour guiding
  • Strong interpersonal skills, ability to communicate effectively and respectfully with people from diverse backgrounds and cultures
  • Strong organizational, time, people, and crisis management skills, with the ability to manage group interpersonal dynamics
  • Strong problem solving skills with the ability to generate creative solutions quickly
  • Flexibility to work weekends and four-night/five-day trips at a time

If you are passionate about travel, have excellent communication + organizational skills, and want to help others experience the joy of travel, we encourage you to apply to be a Trip Leader for Have Fun Do Good!

How to Apply

If you’re excited about the opportunity to join the Have Fun Do Good team as a Trip Leader, we can’t wait to hear from you! To apply, simply send your resume and a brief cover letter to

At Have Fun Do Good, the safety and well-being of our team and travelers is of utmost importance. As part of our unwavering commitment to maintaining a secure and positive environment for everyone involved in our trips, we conduct comprehensive state and federal background checks and drug tests via for all our team members. In addition to these checks, we also conduct thorough reference checks to ensure that we hire individuals with the right skills, experience, and attitude to help us fulfill our mission of providing travelers with meaningful and fun experiences that have a positive impact within the United States.

We want potential team members to be aware that these checks are a standard part of our hiring process. We strongly believe that conducting these checks is a crucial step in creating an enjoyable and secure environment for our team members and travelers. We appreciate your understanding and cooperation as we strive to build a community that prioritizes the safety and well-being of everyone involved.

Have Fun Do Good Logo
Have Fun Do Good Logo