The Sailing Adventure

Join Captains Courageous for 7 days and nights of discovery, adventure, growth and connection in the US and British Virgin Islands - one of the world’s most acclaimed sailing venues. You and your fellow adventurers will explore and experience the islands’ crystal clear waters, gentle trade breezes, white sand beaches, dramatic peaks, stunning coral reefs and friendly people.  As you navigate, crew and captain your sailboat, you’ll find your heart and mind opening to deeper relationships, clearer communication, greater trust, and higher levels of collaboration and leadership. You'll be challenged and supported.  You’ll relax and grow.  You’ll have the time of your life.


What We Do and Why We Do It

Everything we do - including how and where we sail the boat - is designed to help you discover more about what makes you happy, what makes you successful, and how to create more of both the inner and outer experiences you want in your life. Personal growth experiences are woven seamlessly into vacation-like activities, sometimes through structured exercises, sometimes through facilitated conversations and coaching, and always through mindful attunement to individual and group dynamics.

Throughout the adventure, you will have the opportunity to hone your sailing skills—or learn the basics of sailing. You’ll be coming aboard as crew, sharing in every aspect of running a sailboat: navigating, steering, sail handling, engineering, and anchoring.  You’ll participate in the care and feeding of the crew on all levels – physically, mentally, emotionally, spiritually. You’ll have opportunities for hiking, snorkeling, beachcombing, and perhaps scuba diving. You'll also have time ashore to experience the natural beauty, the people and the culture of the Virgin Islands. You’ll be invited to bring a deeper level of awareness and engagement to each of your experiences.

 You'll leave the islands relaxed, expanded and energized.  Back home, you'll find that your memories, awareness and skills as a Courageous Captain will serve you well in your professional life, your home life, and your own interior life.  And if that weren't enough, you'll have had an outrageously great time with a great group of people!


Where? When? How?

We begin and end at Red Hook on the US Virgin Island of St. Thomas.  Sailing through the crystal clear waters of both British and US territories, we will visit islands that dreams are made of:  St. John, the tall and natural island which is mostly national park; Jost van Dyke, home of the bubbly waters pool; Norman Island, rumored to be the site of Robert Louis Stevenson’s “Treasure Island”; the Baths, the dramatic grotto playground on Virgin Gorda; the famous Bitter End Yacht Club on North Sound; Cane Garden Bay, one of the most picturesque anchorages you’ll find anywhere.

The dates for the next Sailing Adventure are not yet set.  The cost will be determined based on seasonal rates and group size, and will be all-inclusive except transportation to and from Red Hook and related travel expenses.  There are nonstop flights to St. Thomas from several US cities, and connecting flights from other locations.



An open heart and mind are required, along with a willingness to participate fully, using every experience to learn and grow.

Space is limited, and an application must be submitted. 

If you’ve never participated in personal growth work in a group setting (or even if you have), we strongly suggest that you first participate in our online workshop Navigating By Heart. A small amount of advance reading is required.