Sail Smarter - Online Class

4:30 PM PT / 7:30 PM ET

Sail Smarter

with 

Jeff & Jean

 | 

Two Can Sail
Learn the real-world systems, habits, teamwork, and lessons that help sailors cruise with more confidence, less stress, and far fewer “learning experiences.”
90-Minute Live Session
On Demand Replay Available
Live Q&A
Every sailor dreams about the freedom of cruising, but life aboard comes with far more than trimming sails and plotting courses. Successful cruisers learn how to manage systems, stay organized, solve problems, work together as a team, and adapt when things don’t go according to plan. In this fun and highly practical online class, Captains Jeff Grossman and Jean Levine of Two Can Sail share the real-world lessons, hard-earned wisdom, and unforgettable stories that help sailors cruise smarter, safer, and happier.
FREE
39
Sail Smarter

Online class overview

This lively and experience-packed online class combines practical cruising knowledge with the honest realities of life aboard. Through storytelling, humor, and decades of offshore experience, Jeff and Jean share the lessons sailors usually learn the hard way. From provisioning strategies and docking techniques to boat organization, cruising systems, maintenance expectations, weather realities, and teamwork aboard, this online class focuses on the habits and mindset that make cruising more enjoyable and less stressful. Attendees will also hear the famous “Unwritten Laws of Sailing,” including reminders that “the most dangerous thing on a boat is a schedule,” that “boats will find ways to humble you, independent of experience,” and that “if everything on your boat is working at the same time, you’ve missed something.” These timeless sayings reflect the humor, realities, and lessons that come with life on the water. Whether you’re dreaming about coastal cruising, planning Bahamas adventures, or preparing for extended cruising, this online class delivers practical advice you can immediately apply aboard your own boat.

Who is this online class for?

This online class is designed for cruising couples, newer boat owners, sailors preparing for extended cruising, and anyone transitioning from day sailing or chartering into real-world cruising life. It’s especially valuable for sailors who want to become more confident managing the everyday realities of cruising, including onboard systems, docking, provisioning, maintenance, and teamwork aboard.

What will I learn?

In this online class sailors will learn how experienced cruisers prepare their boats, organize onboard systems, prioritize upgrades, and avoid many of the common mistakes that create unnecessary stress and expense. You’ll also gain practical insight into docking and maneuvering cruising boats, weather awareness, provisioning strategies, cruising technology, maintenance expectations, and the teamwork required to successfully cruise together. Most importantly, you’ll leave with realistic expectations, practical systems, and the confidence to enjoy cruising more fully.

List of topics:

  • Organizing and inventorying your boat
  • Creating onboard manuals and system diagrams
  • Understanding cruising boat systems and maintenance
  • Prioritizing upgrades and safety equipment
  • Provisioning and galley organization strategies
  • Docking and maneuvering techniques for cruising boats
  • Dinghy and outboard handling tips
  • Cruising weather realities and passage planning
  • Managing boat projects and maintenance expectations
  • Teamwork and communication aboard as a couple
  • Practical cruising technology and navigation tools
  • Real-world cruising stories and lessons learned

Your Host
Jeff & Jean
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!

Get the class Bundle

Online Class Registration

@ 4:30 PM PT / 7:30 PM ET (90 min)

Regular Price

$

39

ASA Member Price

$

29

On-Demand Access

All registrations include unlimited on-demand access to the recordings of the live online class. So if you are unable to attend live you can still register and watch at your leisure.

ASA MEMBER DISCOUNT

American Sailing Members can claim their discount in the Member Portal. If you’re not a current member then for only $59/year you can join or renew today!