A Grand History

From the drawing board of America's greatest yacht designer, Nathanael G. Herreshoff, the world's most successful and powerful racing yachts took form.  Their venue was the peak of international yacht racing, the America's Cup.  Their time the "Gilded Age" of the late 1800s.   Pictured above is "Captain Nat's" magnificent creation Reliance - considered the the most powerful single masted vessel ever built. 

Ventura's documented status among America's landmarks is attributed to her Herreshoff pedigree and longevity.  She is a rarity among rarities, as one of the very few large Herreshoff yachts left in the world. Records of her history and that of "Captain Nat" are found in many great institutions including Harvard, M.I.T., the venerable Mariner's Museum, and the Smithsonian.  Modern media over the past several years have also featured Ventura on CNN, the BBC, Good Morning America and as far as the Tokyo broadcasting company NRK. 

A true wooden ship, Ventura's hull is solid mahogany, decks are Indian teak, and her hollow wooden mast is made of American spruce. She is 62.5 feet long, weighs 28 tons and very comfortably carries up to 28 passengers and crew.  Records indicate she was commissioned in 1919, launched in late 1920 or early 1921, and saw her first full season at a private mooring on Long Island's "Gold Coast" of Oyster Bay in 1922.   She was originally owned by philanthropist George Baker (founder of today's Citibank) and sailed primarily as Mr. Bakers' private duck hunting yacht!


 Ventura's graceful bow slices through the water.

Ventura's graceful bow slices through the water.

Ventura has sailed passengers from all walks of life and has even seen combat duty in WWII.  On 9/11, she was among the very first vessels to ferry New Yorkers from the World Trade Center to safety.  (For which she was awarded highest honors from the Federal government and the United States Maritime Community.) 

Fun stories abound:  Ventura is the unofficial, official "Great Gatsby Yacht" of NYC.  That's because Gatsby author F. Scott Fitzgerald sailed aboard Ventura with Mr. Baker and his daughter Daisy. Both Ventura and Daisy are referred to in the story. Come aboard and take yourself back to the roaring 20's!  FYI Daisy was the babe playing tennis!

Ventura’s history is so much the experiences of people who have sailed aboard. Some are famous with their accomplishments ashore putting them on a world stage. Some are “just plain folks.” 

Two of our favorite stories have come from a previous owner, Ted Baker (no relation to the original owner) back when Ventura was sailing the Caribbean about a half-century ago. Ted and Captain Pat rendezvous’d in the Caribbean some years back and spent an afternoon “yarning” (and drinking rum) and swapping Ventura stories. Baker spoke of one guest, the actress Maureen O’Hara, and a gal pal mixing martinis on a balcony overlooking Ventura’s dock in St. Thomas, USVI. The sunset, the famous stunning red head and friend perched above the harbor with one playing “Taps” – the positioning of the trumpet being critical and herein saved for another story at another time.

Ted also told of Ventura’s centerboard box being problematic with marine growth. His innovative solution: sail to the Old Mr Boston distillery on nearby St Croix, fill the box from a large barrel of rot gut gin, and shake, via the motion of the ocean. The process took a while, according to Ted, with the crew dutifully involved with the mixology.

 Captain Nathanael Herreshoff, in a formal portrait taken for his wedding. 

Captain Nathanael Herreshoff, in a formal portrait taken for his wedding. 

Nathanael Greene Herreshoff, or "Captain Nat" as he was often referred to, was an American Naval Architect. He revolutionized yacht design and produced a succession of undefeated America's Cup yachts between 1893 - 1920. The longest winning streak in sports history!

Herreshoff is credited with being perhaps the most innovative sailboat designer of all time.

His designs were notably graceful, scientifically engineered, and speedy.  His work included meticulous innovations in cutting sailcloth, and innovative use of rolled sheets of bronze for hull materials.  Because of his many accomplishments, Herreshoff was among the few people ever made an honorary member of the New York Yacht Club, his name being listed immediately before those of England's King George V and the Prince of Wales. His fame spread around the world and the period of his greatest activity from 1890 to 1920 became known as the "Herreshoff Era" so greatly did his personality and the yachts he designed dominate the sport.

Today, the yachts designed by the "Wizard of Bristol" are highly sought after and prized by connoisseurs the world over.

We're proud to pay homage to the great Captain Nat and take passengers sailing around New York City in a true classic sailing yacht!


Port – North Cove Marina, New York City
Capacity – Up to 28
Crew – 3 including Captain, 4 with Galley Slave
Rig - Sloop
Length – 62.5'
Year Commissioned –1919