We  offer the widest selection of team building sailing events and retreats in Southern California.  Since 2000, our sails have taken senior executive teams from Fortune 500 companies, law firms, medical practices,  and smaller corporate teams of all sizes.  Our clients regularly say how their sails were the most enjoyable and effective team building experience they ever had.  Follow up interviews reveal that their lessons learned at sea directly improved their teamwork, trust and cooperation back in the workplace.  

Each of our sails are custom designed to your team's needs and goals.  Choose from sailboat races on yachts, tall ship sails and races on brigantines, America's Cup sails or sailing retreats to Catalina Island.  Our clients rave about our customer service and how we exceed their expectations! 

A waypoint is a GPS navigational point of every single location on earth, the vector of latitude and longitude.  The location under your feet has a waypoint.  Your home has a waypoint. A departing dock has a waypoint. Hawaii has a waypoint.  The island or finish line ahead of you have a waypoint. Your destination waypoint determines your course and guides your way.

Without a waypoint to aim toward, a boat will drift off course and even shipwreck on the rocks.  People do it all the time in their lives and marriages.  Businesses can too.  Fixing your course with a destination waypoint makes all the difference.  It reduces wasted time and troubles of getting off course. It helps to mark progress along the way. It even shapes behavior.  If you are aiming for a happy marriage, ship mates or business team, then good seamanship and character is required—not optional.  

These three waypoints will help keep your team on course to success:



 The one constant in sailing is change.  Conditions change.  Winds change, from steady to howling to dead calm and back again.  Currents change.  Crew members and skippers change, come and go, and so do the boats.  Every sail has unexpected surprises.  Don’t be surprised—expect it before leaving the dock.  Your standing rigging may snap, a sail may rip, and the mainsheet breaks. Worst of all, someone could forget to bring the snacks!  

Adjust your expectations and your attitude.  The currents in business change all the time.  Anticipate change and be ready to adjust when it happens.  Flexible teams will beat rigid teams every time. 


Whether you are married or single, everyone on a boat is a mate.  You may have ten or twenty other mates on board. Be a good mate.  Mates that are self-centered, lazy, complaining, demanding, critical or moody will ruin happy crews or happy marriages. 

 Good seamanship offers help, cooperates, communicates clearly, and leaves bad moods at the dock.  Encouragement, positive feedback, flexibility and enthusiasm contribute to everyone’s performance. 


 If you ever fall behind in a race—join the club. Every sailor knows the view from behind.  When this happens, keep hope alive.  Keep sailing on.  You never know if the boat ahead of you will snag their spinnaker or hit a whale.  You never know if your course turns out to be faster than theirs.  And If you are ever in the doldrums (the wind stops), and your boat isn’t moving, remember that everyone else is in the doldrums too.  Try to squeeze out any advantage whatsoever. Even an extra ¼ mile per hour can make the difference to a win.  And if you ever lose a race, sign up for the next and try again.  As two-time America’s Cup winner Dennis Conner once told me, he never loses even when he loses.  “We don’t think of it as losing, because we just gained more experience and knowledge that will help us in the next race.  We never lose.  We only learn.  Even our losses are wins.”  


MEET Rick Rupp, CEO, Chief enthusiasm officer

 I love the ocean and I love taking others out there with me --especially those who have never sailed before.  Every sail is exciting and unique.  A kind of magic happens when people get together on the same boat in the wide blue sea. I also learn personal life lessons on every sail, and I teach these lessons to my guests.  I started WayPoint Sailing in 2000 as the perfect combination of my love for sailing and my skills as a life coach (, licensed Marriage and Family Therapist, and speaker on building successful relationships and teams. Read more about my story in my interview as one of LA's Most Inspiring Stories  with Voyage LA   

Sailing at sea has meant adventure, beauty and romance throughout the ages.    Make your life and business a similar adventure.  Like any good mate, contribute your gifts and talents to your team, marriage and family.  Have good seamanship.  Be flexible.  Never give up.  Stay fixed on your waypoint.  

Call us to put new wind in your team's sails.  Don't just go off site for your next retreat...go off shore!

Fair Winds to you and your team,


Rick Rupp, CEO, WayPoint Sailing