PODCAST | From Charter Dreamers to Catamaran Owners
It started with a charter. One trip to the British Virgin Islands was all it took to shift Mike and Cyndi Crosby’s perspective—from vacationers along for the ride to aspiring sailors with a dream of doing it themselves. That first week aboard sparked a transformation that would unfold over nearly two decades, one sea mile and sailing course at a time.
In this episode of Ahoy!, the Cruising World podcast, Editor-in-Chief Andrew Parkinson talks with the Crosbys about their journey from the guest cabin to the helm. With no prior sailing experience, they built their seamanship through YouTube tutorials, ASA classes, lake sailing wipeouts, and hands-on charter experience—eventually leading them to purchase their first cruising catamaran: a Fountaine Pajot Isla 40, now part of a BVI-based charter fleet.
Mike shares how buying a 28-foot monohull to sail on a local lake gave him the feel and feedback that big cats couldn’t. Cyndi reflects on how the learning curve evolved into confidence, and how they’ve found deep personal connections among the anchorages and communities of the BVI. Together, they offer a candid look at what it really takes to go from curious to capable.
Along the way, they didn’t just embrace sailing—they built a lifestyle. From charting their course as charter guests to managing their own vessel in a charter program, the Crosbys offer practical insight for anyone eyeing a similar path. And with a brand-new Fountaine Pajot 44 on the way, their story is still unfolding.
“If you’ve ever stepped off a charter cat thinking, What if we did this for real?—this episode is for you,” Parkinson says.
Tune in to hear how Mike and Cyndi Crosby turned a spark of inspiration into a cruising life of their own design—proving you don’t need to grow up sailing to fall in love with the sea. You just need the right spark—and the willingness to follow where it leads.
See more from their story here.
Listen now on Spotify or wherever you get your podcasts.
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