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Catching Up with Out The Gate Sailing and the Commodore

“I’ve gotten into some trouble by likening landfalls to orgasms, and I think that’s a very apt comparison in the sense that it’s fulfilling and it’s temporal and it comes and it goes quickly. It’s very [much] like that in that you’ve done all of these things to get there, and it worked — and it’s great.”

Nobody puts things quite like Warwick ‘Commodore’ Tompkins Jr. puts things.

The inimitable Commodore Tompkins.
© 2019 Latitude 38 Media LLC / The Tompkins Archives

The preceding was from a conversation with Benjamin Shaw, host of the Out The Gate Sailing podcast. Among the most memorable of his landfalls, the Commodore explained, was arriving in Tahiti at the conclusion of a race, and spotting Mont Orohena. “The offshore breezes and the smell of vanilla came to us off the shore. Sunlight began to illuminate the top of the mountain,” Tompkins recalled. He said his second-most memorable landfall was sailing under the Gate into San Francisco.

The August conversation explored the roots of the Commodore’s life at sea, beginning, of course, with his childhood aboard Wander Bird (a historic schooner that’s been in the news lately for all the wrong reasons). Shaw asked the Commodore if his father, Captain Warwick M. Tompkins Sr., passed on a love for sailing to him. The Commodore revealed what he truly loves about our lifestyle and sport.

“It’s not just a love of sailing,” Tompkins said.”I describe my father as masterful, and that is correct. But he was very good at it.”

“If it’s more than a love of sailing,” Shaw asked, “what is it that has kept you on the water racing and enjoying sailing throughout your life?”

“Responsiveness, I think, is the real key. If you dance with someone, and they’re very good at it, then the experience is gratifying. Sailing is like that. You get on a boat, you hoist the sails, and everyone is pretty much on the same boat up to that point; and you trim the sails and you steer the boat. And if you do this correctly, the boat is like a good dance partner   . . . you’re constantly making small adjustments and trying to make the boat perform to the maximum capability. You’re judging all the things that make it perform properly. So it’s constantly using your head and making judgments. And if you do it all right, you come out.”

The conversation climaxed with the Commodore’s philosophy. “There’s a recurrent theme in any of my answers to your questions; there is a philosophy, and the philosophy is important, and the rest is details.”

The Commodore and Nancy Tompkins aboard the Wylie 38+ Flash Girl.
© 2019 The Tompkins Archives

“Share with us your philosophy,” Shaw asked.

“When you get into hard weather, the boat should be secure and safe. You don’t worry about the boat, you worry about yourself — that’s part of the philosophy. You need to have a boat that goes upwind, so you can take the boat to windward if you have to. You need to carry small sails, you need to carry a sea anchor . . .

“Part of the philosophy is the details. However good they are, in a good construction, they vanish into the mix. It’s just a pleasure to use. All the details come together.”

This is just one of many conversations on Out The Gate. Shaw has also spoken with Allison Payne, known by many as ‘WhaleGirl’; cruisers Bruce and April Winship, who are authors of Set Sail And Live Your DreamsPaul Exner, a sailing coach and mentor to adventurers; and captain Captain Kira Maixner of Modern Sailing.

We hope you enjoy Out The Gate as much as we have.



  1. Ken Brinkley 5 years ago

    Yes I have ? The commodores philosophy is worth its weight in gold !

  2. Jonathan Livingston 5 years ago

    Cheers to Commodore! many a watch I have shared with this great man. I will leave all of his shore side philosophical musings for another time, However, his contributions to anyone that sails with him at Sea and are mentored by him ( if so willing) are a gift from the sea gods. Seamanship skills and the decorum of oceanic sanctity thereof are part and parcel of this great man’s legacy. Helm balanced, reef tucked in, all gear sorted, not a drop of water below, warm and dry, with cup of hot chocolate, wind at 90 Apparent, vang eased, 12 Knotts and ripping, discussing relationship nuances and or a Patrick O’Brian book where Lucky Jack box-hauls the brig….I remember Commodore driving along at high speed, kite up, rooster tail erupting and a happy owner was below practicing his conducting for La Traviata after arrival at the Finish…
    I watched him build his boat…it took years….every detail was treated like tasting fine wine…I asked , When are you going to be done? He said..” I does not matter…I get great satisfaction out of doing the job right…”
    That sort of summs it up! Balance the helm, pay attention, be prepared, know how to manage your self or your boat in any weather and what ever it is you do…………… proud of your work and do it like Myron Spaulding would do it….. hahahaha oh, and no duct tape or Styrofoam cups on any of his voyages or vessels under his command.


  3. Helen Cuming 4 years ago

    We have a photo signed Warwick M Tompkins when he was a crew member M.Y Eleanor 24th October 1924 Sandakan Borneo
    Helen [email protected]

  4. Sarah Wheeler Cobb 3 years ago

    Greetings, my father, Willard W. Wheeler, as a young boy of 18 years, sailed on the Wanderbird, July-September, 1938. We have a substantial photo album of photos that include life at sea, including articles on little Commodore Tompkins and sister. We are hoping to make contact with someone who might direct us to a place or someone who we could archive this lovely book of photos to. If we could be directed to someone who could help us find a worthy home of such a tremendous chronicle of this boat and this journey, we would be most grateful.

    • Elaine Gilbert 3 years ago

      Have you considered the San Francisco Maritime National Historical park? They have a research center which collects and preserves photographs and documents related to west coast sailing.

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