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.”
The 2025 Annapolis Sailboat Show marked a turning point in modern sailing. With record-breaking attendance, dozens of new boat premieres, and a strong focus on hybrid propulsion and sustainable design, this event showcased the future of cruising — comfortable, connected, and environmentally conscious. This online course brings the docks to your screen, exploring the innovations and trends that are reshaping the sailing world.
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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 Instructors
JEFF & JEAN
Jeff and Jean assist couples in realizing their sailing dreams with their company Two Can Sail. As Licensed Yacht Brokers they work with one couple at a time to provide cruising lifestyle training including; boat shopping/purchase and personal training aboard the couple’s boat. Jeff has been actively boating over 50 years, sailing as Captain since the age of 15. Jean has been sailing since she was 12 years old on vessels ranging from sunfish to 80’ schooners. Jean was an Accredited Marine Surveyor (AMS) and was a member of the Society of Accredited Marine Surveyors (SAMS) and ABYC Standards Certified. Jeff holds an Electrical/Computer Engineering degree and has worked with almost all forms of electronic navigation. Both Jeff and Jean are 100GT Masters, ASA Certified Sailing Instructors and together have sailed over 260 different models of sailboats including 61 models of cruising catamarans.
