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Smile and Wave Sailing

Home In-Your-Yacht Sailing Lessons
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Learn to operate your own boat today!

Congratulations of your new (or new to you) boat! Buying your own boat is massive commitment to the sailing lifestyle!  I am happy to become your personal sailing or powerboating coach so that you can start taking your family and friends on those dreamy cruises capably and safely.

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It Easy and Fun

All POW children have opportuntity learn the art and science of sailing from our world-class coaches and top rated instructors in our summer camp sessions starting at just 7 y/o. But there is no reason for adults and staff to miss out! Private lessons are available right here.

Our Private Lesson Sessions are 1.5 hours long and they are a combination of on-shore theory and on-the-water practice taught by our master instructors. Lesson plans have been crafted to make learning sailing easy, rewarding and fun.

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Learn on brand new RS Quest

Lessons are by appointment only and generally taught in the afternoon on Smile and Wave’s brand new 2019 model RS Quest Performance training boat. This boat is very comfortable for up to 3 adults, easy to maneuver, responsive, unsinkable, and very safe in all types of conditions up to 25 knots of wind.

Advanced students will enjoy having the choice of symmetric or assymmetric spinnaker and the option of using a trapeze for the crew.

Lessons may also be taught in student’s own boat if they so desire.

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Affordable Lesson Packages

We offer a lesson package that works for you. Custom clinics, advanced racing lesson or our Zero to Hero program, whether is just 1 lesson or 6, we will do what it takes to take to the sailing level you want to be. Check out our pricing below and remember:  Lessons must be pre-booked with a deposit by cash, check, credit card or house charge. For more info or reservations text Jaime @ (787) 640-0849 or book online by clicking below.

1 Single Lesson

1.5 Hours Total

Try this if you are not sure sailing is for you but want to find out. It can be anything you want. A quick lesson, and advanced coaching clinic or a refresher for sailors that have not gone sailing for while.


  • One Person: $150
  • Two People: $250

2-Lesson Package

3 Hours Total

This 2-Lesson pack lower the price per hour considerably and its perfect for those that know how to sail and want to take their sailing to new level by trying the trapeze for the first time or learning to fly the assymetrical spinnaker.


  • One Person: $275
  • Two People: $415

4-Lesson Package

6 Hours Total

This 6-hour course can get the very coachable from ready to sail on their own if they have some sailing experience. It offers great value for the dollar and its one of our most popular lesson packs.


  • One Person: $475
  • Two People: $715

6-Lesson Package

9 Hours Total

This is our Zero to Hero package and will get most non-sailors ready to solo sail with safety and performance. You will learn from rigging to docking and everything in between and get you qualified to sail any of our sailboats by yourself. If you have never sailed and you are ready to become a sailor, this your lesson pack!


  • One Person: $650
  • Two People: $975