Have I ever told you about my good friend, “Chatty” George P. Tooley?

A lot of people know him as ChatGPT, but that’s only because they ain’t as close to him as I am.

Ol’ “Chatty” George, I call him.

Being at the beach on vacation, I had an interesting conversation with Chatty George this morning that I thought you all would enjoy. I think it highlights well where my admiration - and my disdain - lies when it comes to people, and skill with the natural world.

My disdain lies with thrill seekers, fame seekers, those looking to set records, who simply use the natural world as a way to make a name for themselves or draw attention to themselves. I don’t have a lot of respect for such individuals, nor do I find much use for their type of knowledge about the world.

My admiration, on the other hand, is readily dedicated to common men and women whose knowledge of the natural world comes from intimacy with the natural world from sheer love, and is applied in practical ways, for practical purposes. It’s the sort of knowledge and experience I greatly value and respect when it comes to the woods - which is the realm I am intimate and familiar with - as well as to that of the sea - one I am almost completely ignorant about, but fascinated by.

Here is the conversation I had this morning with my buddy “Chatty” George P. Tooley. Enjoy!

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ME: Who is considered the most skilled sailor in the world?

CHATTY GEORGE: Identifying the most skilled sailor in the world is subjective, as sailing involves various disciplines, such as racing, solo circumnavigation, long-distance cruising, and technical innovation. However, some sailors stand out as legends in their respective fields due to their extraordinary achievements, skill, and influence. Here are some widely regarded as among the best… (Goes on to list a bunch of fame seekers)

ME: Omit all competitive sailors from consideration.

CHATTY GEORGE: Excluding competitive sailors, the title of the “most skilled sailor in the world” often shifts to those known for their mastery of practical seamanship, long-distance cruising, and navigating challenging conditions. These sailors are celebrated for their endurance, ingenuity, and contributions to the art of sailing rather than racing… (Again goes on to list a bunch of fame seekers)

ME: Omit all competitive sailors. I’m not interested in people trying to do things first, circumnavigate the globe, or anything like that. I’m only interested in real sailors with real, practical accumulation of knowledge and intimacy of the sea for the sheer love of the sea

CHATTY GEORGE: If you’re looking for sailors who embody deep, practical knowledge of the sea and an intimate connection to it—not for fame, records, or competition, but purely for the love of sailing and the sea—here are some names and types of individuals that align with this spirit:

1. Lin and Larry Pardey

• Why They Fit: The Pardeys sailed for decades purely for the joy of exploring and living at sea. Their voyages were not about setting records or seeking attention but about embracing a minimalist, self-reliant lifestyle. They avoided engines and focused on traditional skills like celestial navigation and sail-only voyaging.

• Legacy: Their books and philosophy emphasize the joy and simplicity of living with the sea.

2. Eric and Susan Hiscock

• Why They Fit: This couple dedicated their lives to long-distance cruising for the love of adventure and the challenge of mastering the ocean. They avoided dramatics or record-setting and instead focused on practical seamanship and living a life closely tied to the rhythms of the sea.

3. James Wharram

• Why He Fits: Wharram wasn’t chasing fame but rather exploring a life of harmony with the ocean. He designed and built Polynesian-inspired catamarans, then lived aboard them, sailing around the world and proving their practicality. His approach was deeply rooted in respect for traditional maritime cultures and sustainable living.

4. Alain Bombard (For His Philosophy)

• Why He Fits: Bombard famously sailed across the Atlantic in a small, inflatable boat without provisions—but not for glory. His real focus was on understanding survival at sea and building a deep, personal relationship with the ocean. He sought to teach others to respect and understand the sea rather than fear it.

5. John Kretschmer

• Why He Fits: Kretschmer is a modern sailor who spends his life helping others build a love for the sea. He leads ocean passages to teach practical seamanship and the art of sailing for its own sake. His books, such as Sailing a Serious Ocean, reflect his deep connection to the water and his joy in passing knowledge to others.

6. Traditional Polynesian Navigators

• Why They Fit: These navigators, such as those trained through the Polynesian Voyaging Society, sail the vast Pacific using traditional methods, including celestial navigation and reading ocean swells, winds, and bird patterns. They don’t sail for fame or records but as part of a cultural and spiritual connection to the sea.

7. Lyn and Eric Kaufman (Everyday Cruisers)

• Why They Fit: Known as low-profile, dedicated sailors, they represent the countless cruisers who quietly live aboard their boats and sail not for achievement but for the profound peace and fulfillment it brings. Their approach is humble and steeped in real-world knowledge.

8. The Anonymous Everyday Sailors

• This group includes the unnamed coastal and bluewater sailors who:
• Spend decades mastering their local waters or exploring distant shores.
• Know their boats intimately, maintaining them with care.
• Live their lives at sea not as a challenge but as a harmonious existence.
• They might be solo sailors who anchor in quiet bays, liveaboards navigating Caribbean waters, or fisher-sailors blending work and love of the ocean.

Key Characteristics of “Real” Sailors:

• Practical Seamanship: Deep knowledge of navigation, weather patterns, and boat maintenance.

• Intimacy with the Ocean: An intuitive understanding of tides, currents, and marine life gained from years at sea.

• Philosophy of the Sea: A spiritual or philosophical connection that transcends mere adventure.

(Painting by Alexander Shenderov 1897 - 1967)