In early July, I sat down for a coffee with Dee Caffari on one of her rare days between adventures—and then just hit record, sat back, and spent the next hour marveling at how much she’s accomplished. Twenty years ago, Dee became the first woman to sail solo around the world nonstop (and, oh by the way, in the “wrong” direction, against the world’s prevailing winds and currents). Two years after that, she finished seventh out of 30 in the Vendée Globe Race, a non-stop lap of the planet, this time in the “easy” direction.

She’s been around the world six times total (so far), and she’s also had to work around lots of pre-conceived expectations. Taking on such a wide variety of challenges has led to her being almost written off by potential teams as “just” a solo sailor—”and yet when I go back to the shorthanded stuff, I’m considered a team sailor because I’ve been on the Volvo [Ocean Race].” To everyone, she insists, “I’m just me; I can be quite adaptable and flexible.”
We spoke just a few days after she finished the Transatlantic Race on a heavy monohull; the next day, she was flying to France to get ready for a nonstop, unassisted, race around the world on a 100-foot trimaran with The Famous Project. Learning to sail a multihull has been like learning to sail all over again, she says; “such an alien environment, everything’s on edge the whole time.” If successful, her seventh lap of the planet will help set a world record for the fastest circumnavigation with an all-female crew.
No matter what kind of sailing she’s talking about, Dee’s enthusiasm is infectious; it’s easy to see why she’s also a popular motivational speaker. I tried to capture that passion in her Seahorse profile, which is out now in the November issue and available below. Thanks to Seahorse for the excuse to chat with such an impressive (and fun) sailor!
And thanks to you all for being here. See you next Thursday.
Read Upwind with Dee
Previous Seahorse Profiles
Listening to the Legendary Butch Ulmer
Steve Clark Just Can’t Sit Still
Seahorse Profile: Sharing a Brain
Paul Callahan: Maximizing His Unique Potential
Giving Paul Bieker Some Seahorse Love
Betsy Alison: Using All the Tools
Jerry Kirby: All the Stories are True
Peter Harken: What an Amazing Guy
Buddy Melges: He Really Was a Wizard
Toppa Talks: One Job, One (Big) Dream
Circus Minimus: The Rich Life of Bill Mattison
Mark Reynolds: Hard Chines and Unasked Questions
Dawn Riley: Setting the Standard
Clicks of Chance: Onne van der Wal
Just Say Yes: Stan and Sally Honey
Rod Davis: Why You Need His Wisdom in 2021
Rod Johnstone: An Amazing Legacy of Yacht Designs
A Final Conversation with Harry Anderson
Great article, Carol! I can hear Dee’s laugh and see her smile with every word!
Thanks Liz!
Carol, my only sailing experience was (hard-) earned as a kid while playing with plastic toy boats in the bathtub, where a circumnavigation was likely far less challenging than what Dee Caffari achieves today. Yet, I much enjoy your writings in general…whether on boats or books….and wonder whether Seahorse employs staff writers? And, would that interest you, or take too much time away from making your own sailing memories in Rhode Island and elsewhere?
Larry,
As I understand it, Seahorse only has a few staff. Our current freelance arrangement works well for all parties; for me, as you suggest, because I can put time into articles like this one when not making my own sailing memories. Thanks for reading and following, and congrats on those bathtub circumnavigations!