Did Our Charter Gambit Work? | Mid Season Update

• August 22, 2026 by BoatFools Sailing |
• Language: EN
• Play Time: 00:09:18
• SAILING YOUTUBERS

@boatfools #sailboatcharter #bareboatcharter #morgan382 #morgan384 #sailingmaine

Did Our Charter Gambit Work? | Mid Season Update

Was putting our own sailboats into charter a brilliant idea—or a terrible mistake?

We're halfway through our first charter season, and it's time for an honest update.

CHAPTERS:
00:00 Intro
00:36 Did Our Sailboat Charter Gambit Work?
09:08 Outro

This year, BoatFools Sailing took a gamble: instead of simply owning and sailing our boats, we decided to put two classic Morgan sailboats into a limited charter program here in Maine.

The boats are Va Bene, our 1980 Morgan 382, and Panache, our Morgan 384. They're closely related Ted Brewer-designed cruising boats, but getting two older sailboats ready for charter—and then handing the keys over to other sailors—has been an education.

So… did our charter gambit work?

At the halfway point, the answer is: the jury is still out.

In this mid-season update, we talk about what's gone right, what's gone wrong, some of the surprises we've encountered, and what we're learning about the realities of putting privately owned sailboats into charter.

There have been some great experiences.

There have also been a few moments that made us question exactly what we'd gotten ourselves into.

We're not naming names or throwing anyone under the bus. This isn't about individual charterers. It's about the bigger experiment: Can a limited charter program help offset the substantial cost of owning and maintaining a cruising sailboat without taking all the fun out of owning it?

And perhaps the bigger question for other boat owners:

Does chartering your sailboat actually make financial and practical sense?

We're only halfway through the season, so we're not ready to declare this experiment a success—or a failure. But we've already learned plenty.

Come aboard Va Bene and Panache as we take stock of our first season in the sailboat charter business and ask the question we've been wondering ourselves:

Was this a mistake?

If you're considering buying a sailboat, putting your own boat into charter, joining a bareboat charter program, or simply wondering what happens when you hand your boat over to someone else for a week, this one's for you.

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• Language: en

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Did Our Charter Gambit Work? | Mid Season Update Locations

• Maine (45.253783,-69.4454689)