(Chart with track courtesy of the Lees, via sondrawinter.wixsite.com/in-the-lee)
Okay, here’s today’s How Not To Sail Minute (a shout out to the Lees)…
…and look just slightly below for HNTS full episode 34, Not Always Utopia, and for the link to the Lees’ blog.
So I’m tempted to feel like a proud papa…but the fact is, although Jimmy and Sondra started later than I did, they are now totally lapping me in our respective cruising adventures.
You may be familiar with the our friends (and patrons!) the Lees from How Not To Sail episode 34, Not Always Utopia?…in which they describe the purchase, refit, and maiden voyage of their Caliber 40 LRC, s/v Utopia. (If you’re not familiar, I’d urge you to check it out…I think it turned out to be one of my best episodes! You’ll see it just below here.)

They managed to pack a large number of “learning opportunities” into just a few weeks, and it really comes alive “on tape.” So if you’ve been curious to hear what the cruising life is like, I highly recommend checking out this episode.
Hanging Out with The Lees
I managed to visit Jimmy and Sondra at my very own marina while they were in the midst of their first adventure post-refit. And not long thereafter, we convened aboard Jacie Sails for me to record their travailsโer, adventuresโfor the Not Always Utopia episode. (Of course, I apparently forgot to get a photo during this recording session…which seems to be a recurring theme with me.)
JOIN THE PATREON CREW: SUPPORT HOW NOT TO SAIL FOR AS LITTLE AS $3 A MONTH
(I suspect this may have been around the time of the 2022 St. Pete Boat Show and How Not To Sail Patrons-Only meetup…)

Clearly I saw the Lees at the 2022 Annapolis Boat Show as well, as the photographic evidence suggests…

As you can clearly see from this excellent sketch, Jimmy and Sondra were also at the 2025 Annapolis How Not To Sail meetup. (And clearly I had a large time, since I forgot to take any photos!)

Fortunately, Sondra is clearly better at this stuff than I, and was kind enough to send a actual photo:

Damn, they’re showing me up!
ANYwho… I thought I was a big cheese sailing to Cuba with “The Admiral” in January 2017…and “circumnavigating” South Florida to launch Season One of the How Not To Sail podcast.
But it turns out, I am but a small cheese, and the Lees are having a grand time.
Since Ep. 34: Not Always Utopia was released, the Lees have:
- Sold their house
- Cruised South Florida and The Bahamas
- Hiked the Appalachian Trail
- Headed to the Western Caribbean, where they are now…
…and so much more!
Living the Dream in the Tropics…and Blogging
And now they’re in Belize, having come from Ft. Myers via the Dry Tortugas on a six-day passage. They got to experience some larger waves than usual, as well as their farthest west and farthest south marks…and bioluminescence! (If I spelled that right.)
But instead of me blathering on about the passage, I encourage you to follow our friends in their own words, on their blog, which is in fact quite well done, and gives a very thorough look at what cruising is like. (Plenty of great photos, too…which Sondra seems much better at remembering to take than I am when I’m out on the water.)
You can even go back and have a look at Sondra and Jimmy’s 5-year Plan, and all the preparation that went into making this dream come true.
(Fun fact: While updating me on their most recent doings via Signal, Sondra mentioned that she’d see the post about my stay in Grand Rivers, Kentucky…and that they had been there alsoโI believe while selling their previous boat. What are the odds?!??)
Be sure and check out Sondra and Jimmy’s blog In The Lee for the latest in their Caribbean adventure…

…and here’s wishing the crew of Utopia fair winds…and whatever kind of seas you prefer!
โB








