Goal Digger Retreats

Our annual Goal Digger Retreats are “dream vacation” meets “business building” infused with high octane growth strategies.  We share with you the latest need-to-know developments in the industry, the latest innovative marketing techniques, and a big dose of mindset mastery to carry you to the next level of your business.  These amazing events are our biggest events of the year, and not to be missed. They are offered at different amazing destinations annually, and will be the highlight of your year to get you motivated, inspired, and back in action with your travel business. 

The Goal Digger weekend is about getting the clarity that your travel business needs to grow, and scale to the next level. This is also your chance to connect with Cyndi, a seven-figure travel entrepreneur who runs an award-winning agency, has been featured in the media, hosts a TV show featured around the world, who travels and works from all over the world…

…It’s a weekend of collaboration, connection, community with like-minded all-stars, fun, and an emphasis on scaling your business beyond your dreams. 

Each event features accommodations, some meals, unique experiences, and a mini-photo shoot so you get new headshots to use in future marketing.

2020 Goal Digger in Disney World: January 15 – 17, 2020

2021 Goal Digger in Jamaica: April 21 – 24, 2021

Want to see what it’s like to attend one of our retreats?

Watch this fun video, and see what all the buzz is about.

Do You Have a Calling to Travel?

If you’re feeling the call to travel and turn your wanderlust into a viable, portable, profitable, abundant travel business there is a reason you found your way to this page.  I have helped hundreds of people successfully transition into making travel their new way of life. I’ve been honored to support the launch of over 100+ unique travel brands, and I specialize in helping clients map their businesses to 6+ figures and beyond.  No longer tied to stressful, structured jobs my clients enjoy the freedom of traveling as much as they want while running their travel businesses from anywhere in the world. I invite you to start your journey by taking my free masterclass today.


Learn the simple systems our clients use to create wildly successful, portable, profitable, travel businesses in record time. In our new masterclass you’ll discover:


  • Simple and effective ways to launch your travel brand
  • How to attract your first clients
  • Avoid common pitfalls new travel agents make that cost them thousands of dollars
  • The keys to monetizing your travel business
  • How to position yourself as an expert in hot travel niches that sell
  • Take advantage of top travel perks and discounts while you travel the world on vacation