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I paddled about a quarter mile down and across the harbor in a 5' plastic toy pool boat when I must have been about 10. I wanted to see if the hamburgers at the Country Club (across the harbor) were better than the ones at the Yacht Club. I didn't drown or have need of my life jacket. Decided that the burgers weren't worth the trip. The background of my avatar photo shows the Country Club's golf course. The boat in the middleground shows the influence of a hamburger forty years later.
 

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Robert Manry crossed the Atlantic in a 13ft boat in the mid-1960s.

In the end, I'm not sure these anecdotes translate to anyone else. One's success on any passage is influenced by a combination of one's specific boat and her condition, the skipper, the crew, the weather and luck.
 

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I personally haven't traveled very far on a very small boat as I really enjoy my creature comforts. I do know of a young Japanese man who sailed a 19 footer from Japan to San Francisco. There is also a Mini Transat race for 21 footers.
So I'd say it wasn't a matter of how big the boat was, but the sailor's er xxxxs.
 

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I stay for weeks at a time on my 20 foot Mirage 5.5m. Sail all over Pamlico Sound, NC. I could easily go to Florida if I had the time off work long enough for such a trip. I stay on weekends in my 16 foot Chrysler on an inland lake (Kerr). It is really cramped but can be done. It is warm and dry at night.
It is more about what kind of a trooper you are than what kind of a boat you have. But I would not go smaller than 20 feet for any kind of long distance sailing.
 

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In a 9'6" sailboat, I've circumnavigated,...

So here is my question:what is the the longest distance you've sailed in the smallest boat you owned!?
The Curious Sailor


... Cuttyhunk Pond. :) We've sailed many, many, harbors on the NE coast in this boat. In fact, in two small sailboats(under 10'), we've sailed hundreds of miles, many of those miles with 4 of us onboard.

But to your question, so far, we've sailed a Cape Dory 28 the farthest from our home waters. In our case, distance sailed from home - so far - had more to with our age at the time, than the boat.

These days I'm more engaged in the quality of the miles we sail, than the quantity.
 

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Sailed my 24 foot Bristol from Long Island out to Block Island, Cuttyhunk, Marthas Vineyard and Nantucket and all around Narragansett Bay. Even stopped off at Bristol Rhode Island to pick up a part at the factory. Sailed it to New York and Sandy Hook several times when going west.
 

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I wandered from St. Simons Is., Ga. through the keys to Tarpon Springs, Fl. in my 26' double ended gaff rigger. That was primarily harbor hopping, longest trip I recall was probably Marathon to Ft. Myers. Fun days.
 

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Robert Manry crossed the Atlantic in a 13ft boat in the mid-1960s.

In the end, I'm not sure these anecdotes translate to anyone else. One's success on any passage is influenced by a combination of one's specific boat and her condition, the skipper, the crew, the weather and luck.
Got a copy of his book Tinkerbelle on my boats bookshelf. Great read about a man and his dream. Unfortunately, his life was cut short but, he did get to fulfill his dream.
 

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Jaguar 22 which is the UK version of a Catalina 22. She started me off in this cruising thing.

One summer did Troon to Stornoway and back rounding the Mull of Kintyre on the way out and transiting the Crinan canal on the return.

Next summer I trailed it down to the Adriatic and did Pula down to Albania and back.
 

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Re: In a 9'6" sailboat, I've circumnavigated,...



... Cuttyhunk Pond. :) We've sailed many, many, harbors on the NE coast in this boat. In fact, in two small sailboats(under 10'), we've sailed hundreds of miles, many of those miles with 4 of us onboard.

But to your question, so far, we've sailed a Cape Dory 28 the farthest from our home waters. In our case, distance sailed from home - so far - had more to with our age at the time, than the boat.

These days I'm more engaged in the quality of the miles we sail, than the quantity.

I plan on doing some miles in my sailing tender with no centre plate or rudder

just the steering oar


 
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