Educators Retreat: Florida Keys Sailing

This Educators Retreat is an exclusive course designed for educators or campus influencers only. We hope you can join this special crew! 

You're invited to join a voyage - among an inspired, committed and impassioned crew of educators - on a collective exploration of Whole Child Education. Experience firsthand Outward Bound’s effective learn by doing philosophy.  

We’d love to have you join this crew as we unpack the Outward Bound experiential framework and tactics of progression-based learning and transference back to students in academic settings.

No sailing experience is required.

Course Details

Dates: January 31-February 4, 2020 
Arrive 3:00 PM January 31. Depart 1:00 PM February 4. *
Start/End:  Big Pine Key, FL
Cost: $500. 

* Shuttles between Miami airport and the Outward Bound Big Pine Key base are available on arrival and departure day.


In a phased teaching progression, instructors introduce beginning, intermediate and advanced skills in chart and compass navigation, small boat seamanship, weather observation, and anchoring.

You will build technical skills, explore the backcountry of the Keys, swim in the warm water, and have awe-inspiring wildlife moments, all while traveling and living on the pulling boat.  Formal and informal discussions with peers will offer you an opportunity to engage and reflect on your experience and identify practical applications for transference back at your school.

Course Area

The backcountry of Florida Bay offers challenging shoal draft navigation and the opportunity to explore mangrove keys, tidal flats and coral patch reefs. These warm, shallow waters provide an exciting cruising area for Outward Bound’s sailing boats and some of the best training ground for developing advanced sailing skills. The Atlantic side offers excellent open water sailing and snorkeling at the outer reefs. The course area extends to the Everglades, with beautiful sand beaches and a maze of rivers and bays to explore. 


The Educators Florida Keys Sailing Retreat is designed for campus influencers to connect, learn from and inspire one another in our collective effort to advance whole child learning and expand the Outward Bound progression model to the traditional classroom. Come prepared to see things differently, discover deeper insights, and offer your own educator experience with peers. Let’s be transparent about our personal challenges and successes. 


If you would like to speak with a specialist about details of this expedition, please contact Brett Wagenheim at 207-466-4701.

How to Enroll

1. Register your interest by completing and submitting the form below...

2. You will receive an automatic email confirming that we have received your registration.

3. We will send you an enrollment email (with links to complete a full application and pay the tuition) in the next few days! Enrollment will be complete once you complete step 3.

Sign up to attend the Educators Retreat in the Florida Keys
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