Living Your Legacy – Adventure Travel Entrepreneur on Designing Bucket-List Trips With Cultural Depth
Podcast: Living Your Legacy
Host: Ray Gutierrez
Guest: Shayla Paz, Founder of Shayla Adventure Travel
Date: March 13, 2026
Episode Overview
This episode spotlights Shayla Paz, a Cuban-American entrepreneur and the creative force behind Shayla Adventure Travel. Shayla shares her journey of using travel to connect people with meaningful cultural experiences, rooted in her personal history of family separation and resilience. She discusses her unique approach to immersive, transformative travel, how she creates “three trips in one” for her clients, and the business philosophies that underpin her growing legacy.
Key Topics & Insights
Shayla’s “Why”: Family, Heritage, and Connection
-
Motivation Rooted in Family: Shayla’s primary "why" is her family, dispersed internationally, and the lifelong effort of bridging those divides.
- Quote (Shayla, 02:51): “You are broken into so many pieces when you are torn apart from your family...I'm always trying to figure out how to bring us together. And that's always like their mission impossible, you know?”
-
Cultural Influence: Shayla’s adventures and business are shaped by growing up in Cuba, navigating constant change, and helping clients understand what adventure and discovery truly mean.
The Philosophy of Immersive Adventure Travel
-
Defining Authentic Adventure: Not just about sightseeing—it's about deep immersion into local culture, history, and people.
- Quote (Shayla, 03:35): “Life in general is an adventure...my whole life has been one adventure after the other one.”
-
Memorable First Journey: Shayla’s first flight, taken alone for surgery, underscored the kindness of strangers and the Cuban spirit—shaping her belief in the transformative power of travel.
- Quote (Shayla, 04:04): “A stranger on the plane, Cuban, helped me...He took me to his house, and the next day, he helped me find a distant cousin’s house.”
“Three Trips in One” Experience
- The Three-Part Travel Philosophy (05:51):
- Anticipation & Dreaming: Planning stage, envisioning goals and matching them to the right destination.
- Living the Experience: The actual journey, turning dreams into reality.
- Reflection & Reliving: Revisiting memories and stories after returning home.
- Quote (Shayla, 05:51): “You experience the destination three times...before you travel...when you are on the trip...and when you come back, every time you look at your memories...So you travel three times.”
Designing Bucket-List Experiences with Depth
-
Understanding Clients’ Dreams: Shayla engages deeply with clients, asking about the motivation behind their bucket-list items to craft truly meaningful trips.
-
Mythbusting Cuba Travel: Dispels misconceptions about travel restrictions to Cuba and explains the step-by-step legal process for Americans.
- Quote (Shayla, 07:59): “You can fly from Miami, you can fly from Tampa, you can fly from New York, you can fly from Atlanta.”
- Full-Service Planning (08:21): “I take care of your visa, your itinerary...I plan everything by the hour, pretty much.”
-
Setting Expectations & Discussing Reality: Encourages open-mindedness due to cultural and economic differences with destinations like Cuba.
- Quote (Shayla, 09:17): “Don't go on this on a trip with expectations...If you're going to immerse yourself in the culture, don’t be expecting like a five-star service.”
Cultural Immersion & Responsible Tourism
-
Journey Through Contrasts: Shayla brings travelers to both historic, restored areas and struggling local neighborhoods to show Cuba’s rich contrasts.
- Quote (Shayla, 11:19): “I always take people through the heart of Havana...then I take them to a place that is called Muraliando, that is a community art place...You can have lunch with the locals.”
-
Travel Beyond Havana: Adventures include rural experiences, like trips to Vinales, revealing daily realities for Cubans.
Safety, Logistics, and Trust
- Client Security: Emphasizes researching destinations, using the State Department warning system, vetted tour operators, and controlled local logistics.
- Quote (Shayla, 13:40): “Cuba is a very secure place...I always put [safety info] on my clients' itinerary...Transportation [is] provided for my clients...to stay safe.”
Business Wisdom: Retention, Referrals, and Reputation
-
Client Nurturing: Strong focus on post-trip follow-ups, addressing any issues, and inviting travelers to their next adventure.
- Quote (Shayla, 14:59): “Follow up, follow up, follow up, follow up, follow up.”
-
Reviews and Certifications: Positive testimonials on Google and “Very Very Vacation” endorsed her business growth and credibility as a certified travel advisor.
- Quote (Shayla, 16:14): “That is the number one source that I get...Also as a NAFTA verified travel advisor...people know that I've been vetted...certified.”
Mindset for Success: Resilience & Vision
-
Persistent Mindset: Shayla emphasizes the importance of resilience for entrepreneurs—staying focused on goals and repeating affirmation through vision boards and journals.
- Quote (Shayla, 17:02): “Resilience sometimes is a tool that you can use to move forward and not giving up too soon...stay persistent, stay focused, create a vision board.”
-
Vision Boards & Goal Setting: Encourages clients and aspiring travel professionals to map out ambitions step by step, visualizing their north star.
- Quote (Shayla, 17:38): “When you do a vision board, you’re visualizing what you want to accomplish...I have it on my wall in my office. So I see it constantly.”
Breaking into the Travel Industry
- How to Start: Shayla shares her unconventional path into travel entrepreneurship and recommends formal travel schooling for newcomers, underscoring the importance of industry knowledge and legal compliance.
- Quote (Shayla, 18:33): “You have to start by going to travel school.”
- Quote (Shayla, 19:20): “You have a big responsibility when you're booking people...I didn’t know that I could be liable...So having learned that, I went on and immediately got into travel school.”
The Next Adventures
-
Upcoming Projects:
- Organizing a 40-person Latin dance cruise, “Norwegian Jewel” (goal: first big group).
- Quote (Shayla, 19:51): “I am going to get 40 people on board of my Norwegian jewel for the adrenaline Latin dance cruise.”
- Leading a 16-person trip to Ireland; aiming for incentive thresholds and client intimacy.
- Quote (Shayla, 22:16): “And I get to go for free. So 16, it was the magic number.”
- Planning a new immersive tour to Italy.
- Organizing a 40-person Latin dance cruise, “Norwegian Jewel” (goal: first big group).
-
Vision for Growth: Dreams of eventually chartering a cruise for hundreds, while steadily growing.
- Motivational Moment (21:03):
- Ray Gutierrez: “You're going to launch a cruise with 500 guests. Done.”
- Shayla Paz: “Yeah. Some people bark more than they can chew. So you have to start small, but you have to be ambitious when you start small.”
- Motivational Moment (21:03):
Notable Quotes & Memorable Moments
- On Falling in Love with Travel’s Surprises:
“The first time I got on a plane was for knee surgery. I didn’t know anybody in Havana...and the kindness of a stranger started everything.” — Shayla Paz (04:04) - On Mindful, Purposeful Travel:
“Don’t go on a trip with expectations...go open-minded.” — Shayla Paz (09:17) - On Building A Legacy:
“Resilience...is a tool that you can use to move forward and not giving up too soon.” — Shayla Paz (17:02) - On Being a Connector:
“I want [my clients] to see, to experience what the real Cuba is like.” — Shayla Paz (12:46) - Motivational Push:
“You have to start small, but you have to be ambitious when you start small.” — Shayla Paz (21:38)
Timestamps for Key Segments
- Shayla’s Why / Family Story: 00:00–03:19
- Philosophy of Adventure: 03:19–04:52
- Three Times You Travel: 05:45–06:37
- Client Motivations & Mythbusting Cuba: 06:43–08:55
- Expectations & Immersion: 09:17–12:46
- Safety Abroad: 13:08–14:33
- Client Engagement / Business Best Practices: 14:33–16:14
- Resilience, Vision, Mindset: 17:02–18:25
- Breaking Into Travel Business: 18:33–19:49
- Upcoming Group Trips & Growth: 19:51–23:05
- Passion Projects / Legacy: 23:37–24:03
Closing Thoughts
This episode offers a warm, insightful exploration of what it means to design travel experiences that are not just bucket-list destinations, but opportunities for true transformation and connection. Shayla Paz’s story underlines the power of resilience, purposeful entrepreneurship, and embracing one’s cultural roots to create a business that brings people—and families—closer, one adventure at a time. Whether aspiring travel professionals or would-be adventurers, listeners will find both practical advice and heartfelt inspiration.