The Island Adventure

Join Captains Courageous for a week of discovery, adventure, growth and connection on the island of St. Croix in the U.S. Virgin Islands.

You and your fellow adventurers will explore and experience the islands’ natural and cultural riches and activities, coupled with guided opportunities for reflection, interaction and challenge. You’ll find your heart and mind opening to deeper knowing, greater trust and confidence, stronger relationships, clearer communication,  and authentic collaboration. You'll be challenged and supported. You’ll relax and grow. 

You’ll lead your life with heart.


What We Do and Why We Do It

Captains Courageous draws from the best of Caribbean culture and activities and weaves them seamlessly into a joyous and profound experience of personal awareness and growth.  Combining vacation-like excursions with structured exercises and facilitated conversation, and seasoned with a generous dose of free time, the Island Adventure challenges you and nurtures you like nothing you’ve ever experienced.

You’ll discover the richness of the rain forest, the never-ending flow of trade winds and waves, the healing warmth of tropical sun and water, the playful majesty of coral reefs, the lingering remains and lessons of a time and culture gone by, the special tastes of tropical foods and drinks, the rhythms and sounds that will move your body and soul.

As you participate, The Island Adventure invites you to deeper levels of awareness and engagement in every activity, every conversation, everything you do.  It’s all 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.

When all is said and done, you’ll return home with much more than a good tan and a great story.  You’ll be relaxed, expanded and energized.  You’ll see through new eyes. You'll know your heart even more. Back home, you'll find that your memories, awareness and skills as a Courageous Captain will serve you well in your home life, your professional 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?

St. Croix, in the U.S. Virgin Islands, is an island of wild and peaceful beauty, with wide-open spaces surrounded by crystal clear waters. The trade breezes blow, the sun shines, the beaches beckon. The people are warm and friendly, the atmosphere laid-back and welcoming. Read more about St. Croix.

Currently, the Island Adventure is not on the calendar. But please read on to learn about future adventures!

The Island Adventure begins on a Saturday morning and ends the following Friday night.  You should plan to travel on the day before and the day after (or later if you choose to extend your time in the Caribbean).  From the US mainland, there are nonstop flights from Miami, Atlanta and Charlotte.  From Denmark there’s a weekly nonstop.  From other locations, you can connect through one of those gateways, or through St. Thomas or San Juan, Puerto Rico. If you’re a US citizen or lawful permanent resident, no passport is necessary.

You’ll be residing in a casual beachside resort, and your accommodations and meals are included in your price, as are all activity fees that are part of the Adventure. Gratuities, souvenirs, and any activities or purchases on your own are not included, nor is travel to and from the island.

The price per person is $3450, based on double occupancy.  A $500 deposit confirms your space, subject to paying in full no later than 60 days prior. Discounts are available for same-household couples and for early registration and payment. Because participation is limited to 12 people, payments are refundable only if your space can be filled. Read the Fine Print.

Photo by ALotOfPeople/iStock / Getty Images


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 recommend you first participate in our online workshop Navigating By Heart