Dreaming of sailing off into the sunset with your partner? Make it a reality with a proven step-by-step guide designed for couples.
Sailing away on your own boat is a romantic dream shared by many couples—but making it a reality takes more than just buying a boat. This course introduces the essential knowledge, mindset, and preparation needed to transition from land life to live aboard cruising. Whether you're curious or committed, learn what it takes to sail together successfully.
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ONLINE COURSE OVERVIEW
This course is based on the Two Can Sail Five Step Plan, developed by experienced cruising instructors Jeff Grossman and Jean Levine. The plan is designed to guide couples through the entire process of learning, buying and living on a sailboat—from sampling the lifestyle and building skills to choosing the right boat and preparing for life aboard. Filled with real-life stories, expert advice, and practical checklists, this course supports couples with different skill levels and goals. You’ll discover what it really takes to sail safely and happily as a team.
Who is this online class for?
This course is ideal for couples dreaming of buying a sailboat and going cruising, especially those new to the lifestyle. Whether you’re a beginner with zero sea time or seasoned sailors looking to share the adventure with your partner, this course helps you build a strong foundation for a safe, enjoyable, and enduring cruising life together.
What Will I Learn?
You’ll learn how to test the cruising lifestyle, gain essential sailing skills, navigate relationship dynamics aboard, and choose the right boat. You'll also learn how to plan for equipment, budgeting, safety, and long-term cruising success—all tailored for couples. Through real stories and step-by-step checklists, you’ll prepare for a smooth transition from dreamers to doers.
List of Topics:
- Sampling the cruising lifestyle through chartering and classes
- Communication and decision-making for couples aboard
- Selecting and testing different boat types (monohull, catamaran, etc.)
- Essential sailing and seamanship skills for both partners
- Choosing a sailing school and setting realistic goals
- Provisioning, living aboard, and handling systems
- Safety procedures, equipment, and emergency readiness
- Understanding boat ownership, budgeting, and buying process
Why Sailing as a Couple Deserves a Game Plan
Shared dreams, stronger partnership
Sailing away with your partner is a beautiful vision, but it takes more than romance and wanderlust to make it work. Buying a boat, preparing for life aboard, and navigating the realities of cruising as a couple can be overwhelming without a plan. This course gives you the structure, insight, and confidence to turn your shared dream into a successful reality step by step, side by side.
Communication, Planning, and Partnership
From sampling the lifestyle to making the final purchase, you’ll learn how to approach each stage of the cruising journey with clarity and purpose. Communication strategies, decision-making tools, boat comparisons, and budgeting tips are all designed with couples in mind so you can build a strong foundation for sailing and living together at sea.
Proven advice from Jeff and Jean of Two Can Sail
With decades of cruising, yacht sales, and training experience, Jeff Grossman and Jean Levine have helped hundreds of couples prepare for life on the water. Their step-by-step plan is rooted in practical know-how and real-world success. From evaluating boats to navigating relationship dynamics, their instruction combines technical skill with emotional readiness so you’re not just buying a boat, you’re building a life together.
YOUR HOST
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 Yacht shopping/purchase and personal training aboard the couple’s Yacht. Jeff has been actively Yachting 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 is a retired Accredited Marine Surveyor and was a member of the Society of Accredited Marine Surveyors and ABYC Standards Certified. Jeff holds an Electrical/Computer Engineering degree and has worked with almost all forms of electronic navigation. Jeff and Jean are 100GT Masters, American Sailing Certified Instructors, and together have sailed over 260 different models of Yachts including 61 models of cruising catamarans. Between Surveying and being Yacht Brokers, Jeff & Jean have been personally involved in hundreds of Purchase & Sale transactions.
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!
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