Thu June 18th, 2026
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.
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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
The Unwritten Lessons of Cruising
REAL-WORLD HABITS THAT MAKE CRUISING EASIER
Cruising is about far more than sailing from one destination to another. Life aboard requires planning, organization, communication, maintenance awareness, and the ability to stay flexible when things don’t go according to plan. In this seminar, Captains Jeff Grossman and Jean Levine share the practical systems, habits, and mindset that help sailors cruise more confidently, avoid unnecessary stress, and enjoy life aboard more fully.
LESSONS FROM LIFE AFLOAT
From docking mishaps and maintenance surprises to provisioning challenges and changing weather, cruising has a way of teaching lessons quickly. Jeff Grossman and Jean Levine share real-world experiences, practical advice, and honest insights that help sailors avoid many of the common mistakes cruisers often learn the hard way. Through storytelling and highly applicable guidance, you’ll gain valuable strategies you can immediately apply aboard your own boat.
CRUISE WITH MORE CONFIDENCE
Whether you’re preparing for your first cruising adventure or planning extended time aboard, confidence comes from understanding what to realistically expect. This online class provides practical insight into the mindset, preparation, and decision-making that help cruisers operate more efficiently and enjoy the experience more fully. You’ll leave with greater clarity, realistic expectations, and tools to cruise with more confidence and less stress.
Your Hosts
Jeff & Jean
Jeff Grossman and Jean Levine of Two Can Sail have sailed together for more than 20 years and cruised extensively throughout the Caribbean aboard their Skye 51.
Both are 100-ton Masters, ASA Certified Sailing Instructors, and experienced yacht consultants and buyer brokers. Jean is also an Accredited Marine Surveyor (SAMS AMS). Together, they have operated and instructed aboard more than 200 sail and power vessels.
Known for blending deep technical knowledge with humor and relatable storytelling, Jeff and Jean help sailors better prepare for the realities of cruising life while keeping the experience fun, approachable, and practical.
Online Class Registration
Thursday, june 18th
@ 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!