5 Step Plan to Cruising

with

Jeff & Jean

Two Can Sail

Dreaming of sailing off into the sunset with your partner? Make it a reality with a proven step-by-step guide designed for couples.

90-Minute Live Session

On Demand Replay Available

Live Q&A

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.

FREE

5 Step Plan to Cruising

Online class 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 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!

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Online Class Registration

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

Regular Price

ASA Member Price

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!