Couples Sailing

Unlock the secrets to successful cruising for couples! Discover essential skills and strategies to ensure harmonious and enjoyable voyages together.

1x 90 Min Session English Unlimited Access

Dreaming of setting sail with your partner? Join us as Jeff & Jean, of Two Can Sail, cover the unique dynamics of cruising together as a couple. In this online class we'll explore essential aspects such as building trust, enhancing communication, and mastering seamless coordination.

American Sailing Members - Save $10



Designed specifically for couples who share a passion for sailing, this online class is perfect for both beginners and experienced sailors alike. Whether you envision long-term voyages or prefer shorter day or weekend trips, gain the confidence to embark on unforgettable sailing adventures together - with the knowledge and skills needed to make your sailing experiences both safe and enjoyable.


Discover the secrets of cruising with just two onboard in this comprehensive online class. From docking and anchoring to handling Man Overboard (MOB) situations single-handedly. Learn unique techniques that Jeff and Jean have developed, specifically designed for couples. Suitable for sailors of all levels, unlock the skills needed to master the art of sailing as a couple.


  • Couples Communication
  • MOB Single-Handed
    A quick and safe way that even inexperienced sailors can execute.
  • Docking
    How to set up lines for exit and return so one deck hand can easily handle it - with NO jumping to/from the boat.
  • Mooring Ball Pick Up
    Made easy for two.
  • Dividing Up Jobs
    Pink, Blue, and Purple Jobs (not tied to a gender)
  • How to Shop for a Boat Together
    If you don’t own yet, learn how to make the compromises needed to find a new home you both will love.


JEFF & JEAN | Two Can Sail

Jeff has been actively sailing for over 45 years and Jean has been sailing since she was 12 years old. Both Jeff and Jean have extensively cruised the Caribbean, Bahamas and Florida on their Skye 51. Jeff holds an Electrical Engineering degree and has worked with almost all forms of electronic navigation from B-52 Inertial Navigation systems to modern integrated Nav Suites. Jean is a retired Accredited Marine Surveyor, and was a member of the Society of Accredited Marine Surveyors and ABYC Standards Certified. Both Jeff and Jean are 100GT Masters and ASA Certified Sailing Instructors.

Over 15 years ago, Jeff and Jean founded Two Can Sail to address the unique needs of couples cruising and to assist in couples realizing their sailing dreams. Together they help couples gain the perspectives and tools needed to safely pursue the cruising lifestyle while having fun and staying together!