Upwind with the Uncategorizable Dee Caffari

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

Augie Diaz: Lucky AND Good

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

Life Lessons from Dave Perry

Vince Brun Profile in Seahorse

Only One Jud (Smith)

4 Replies to “Upwind with the Uncategorizable Dee Caffari”

  1. 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?

  2. 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!

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