Our Story


Captains Courageous began as a dream.

What if we did a heart-centered personal development experience ...

... on a sailboat in the Caribbean?!


In 1990 Martha Boston did it, and Captains Courageous was born.  She gathered up a crew of adventurous souls to spend some time sailing in the Caribbean, each with the express intention of using the experience to learn, grow and transform.  It was powerful, adventurous and fun; and she decided to do more.  She named the adventures and the company “Captains Courageous” – not after the famous book and movie of the same name, but because the words, derived from old French, mean “Leaders of Heart.”  That is what she saw emerging in each of the participants, and that is the transformation she wanted to continue to experience and inspire in others.

Since then, Captains Courageous has sailed all around the eastern Caribbean, the Bahamas and Florida - with business executives honing their leadership skills, with business developers on teambuilding missions, with teenagers, with families, and with mixed groups of friends who had come aboard as strangers.  In all their variety, Captains Courageous participants share one thing in common:  a desire to expand their experience of heart in daily life, using an awesome tropical adventure as the catalyst.

In 2006 an avid sailor and life coach from Florida heard about Captains Courageous, and called to see how he could get involved.  Peter Branning began coaching on sailing adventures and quickly became director of marine activities.  He and Martha sailed together so much that in 2011 they married. Later that year, Martha broke her spine, and it looked like sailing would be a thing of the past.  But after a year of surgeries and physical therapy, she was back, and she and Peter were ready to being the next phase of Captains Courageous – from a permanent home in the Virgin Islands. 

Today Captains Courageous has its headquarters on a hillside on the island of St. Croix, overlooking the Caribbean Sea. Inspired by the island’s richness of culture, heritage, and natural beauty and resources, Captains Courageous has expanded to offer island-based adventures as well as sailing adventures.  In addition, business teams can have their own adventure on land or sea or both, custom-designed to address their specific goals and challenges. Individuals and families can tuck into a beachside resort or onto a sailboat for a few days of intensive coaching and extensive fun.  Non-travelers can participate in online coaching or in live interactive online workshops.