Your Dinghy Might Be the Most Important Boat You Own

Your Dinghy Might Be the Most Important Boat You Own

The Small Boat That Makes Cruising Possible
Picture of Jeff and Jean
Jeff and Jean

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By Jeff & Jean Grossman

It’s easy to think of a dinghy as just a way to get from your boat to shore.

But ask experienced cruisers Jeff and Jean Grossman, and they’ll tell you it’s much more than that.

Your dinghy is your transportation, your grocery getter, your emergency backup, and often your connection to every adventure beyond the anchorage. Knowing how to choose it, maintain it, and operate it safely can make cruising easier, safer, and a whole lot more enjoyable.

A quiet dinghy ride at sunrise shows how this small boat connects cruisers to the places beyond the anchorage.

In Master Your Dinghy, Jeff and Jean draw on decades of offshore sailing, yacht brokerage, and cruising experience to share the practical lessons they’ve learned from thousands of miles on the water. Rather than focusing on theory, they dive into the real-world decisions sailors face every day, from selecting the right dinghy and outboard to storing, towing, maintaining, and safely operating it in a variety of conditions.

One of the biggest takeaways from the course is that a dinghy deserves the same care and attention as the mothership. The little details matter, and overlooking them can quickly turn a routine trip ashore into an unnecessary challenge.

A dinghy carries the crew across calm water as the sun sets, turning a simple ride back into part of the adventure.


Along the way, Jeff and Jean share memorable stories, hard-earned lessons, and simple safety practices that every sailor should know, whether you’re planning your first cruising adventure or have years of experience behind the helm.

If you’ve ever wondered whether you’re making the most of your dinghy, or if you want to cruise with greater confidence, this course is for you.

Watch the Replay On Demand


Whether you’re outfitting your first cruising boat or refining your current setup, Master Your Dinghy is packed with practical advice you’ll use every time you leave the dock. Watch the on-demand replay and learn why mastering your dinghy might be one of the best investments you can make in your sailing future.

About the Authors

Jeff Grossman and Jean Levine took a sabbatical to sail their Skye 51 ketch, Polyphonic, from Florida to Grenada and back. Both are 100GT Masters and ASA Certified Sailing Instructors. Jean is also a retired SAMS Marine Surveyor. Together, they run Two Can Sail, an education-focused company that helps couples prepare for cruising life.

Learn more at www.TwoCanSail.com


Join The Discussion

  • Master Your Dinghy Online Course

    Posted by Diona on July 14, 2026 at 11:11 am

    Your dinghy is more than just transportation to and from shore. It’s one of the most important tools you’ll use while cruising, and mastering it can make every adventure safer, easier, and more enjoyable.

    In this on-demand course, Jeff and Jean Grossman share practical, real-world advice on choosing the right dinghy, launching and retrieving it, towing, docking, loading passengers and gear, and handling the situations every cruiser eventually encounters. Their decades of sailing and cruising experience shine through with tips you can apply on your very next outing.

    The replay is now available on demand!

    👉 Watch the full course here: https://americansailing.com/learn-to-sail/online-class/master-your-dinghy

    Let’s hear from you: What’s the best dinghy tip you’ve learned, or what’s one challenge you’re still trying to master?

    • This discussion was modified 2 months ago by  Diona.
    Diona replied 2 months ago 1 Member · 0 Replies
  • 0 Replies

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