Nathanael Herreshoff’s crowning achievement was Reliance, a sailboat of awe-inspiring size and power. Yet his influence on sailing flows to this day from a simple boat less than one-fifth the length of Reliance.

The 144-foot Reliance was a stunning feat of design and engineering by the man who was known as Captain Nat. He was a taciturn New Englander until he imagined Reliance, and then he became a bold swashbuckler. 

Herreshoff shocked the sailing world when he went off-the-rails radical with his concept of a U.S. defender in the 1903 America’s Cup. Some critics said the boat was too dangerous to sail. Thomas Flemming Day, the editor of the influential Rudder magazine, described it as an “ugly brute.” 

Day was a respected yachting journalist, but his characterization of Reliance was laughable. The low-freeboard hull with its gently curving sheerline and long overhangs was a study in classic sailing beauty. The boat was no brute, but she was a giant, a graceful one in appearance, if not in her handling.

It took a professional crew of 64 to manage 16,160 square feet of sail that weighed four tons and was spread over a rig featuring a 108-foot boom and a bowsprit that increased the boat’s length to 201 feet. The mainsail was said to be the largest sail ever made. The loads were so great that sheets had to be made of four-inch diameter manila rope. 

Reliance was built by the Herreshoff Manufacturing Co. in Bristol, Rhode Island, with the designer as the supervising engineer, using steel and bronze for the hull and mast and aluminum for the deck. It weighed 189 tons, light for its size. The hull was shallow—critics likened it to a skimming dish—and its lead ballast deep with a draft of 19 feet.

The project would be remarkable today. That it was accomplished with the technology available more than 120 years ago tells us why they called Herreshoff the Wizard of Bristol.

Reliance won the Cup, and then was relegated to a status as a colorful footnote in yacht racing history. Nothing like her was ever built again. But nine years later, at 64 years old, Herreshoff would create the small boat that may be his most enduring legacy.

Herreshoff designed and built the 26-foot mahogany-planked sloop for his own sailing pleasure. He made it simple and easy to rig so he could step aboard and sail away whenever he felt like it. According to his grandson Halsey Herreshoff, he sailed almost every day in Bristol harbor near his office or at Bermuda where he spent winter months.

Captain Nat named the boat Alerion. The word means eagle, but it has become almost synonymous with the term daysailer. With the invention of fiberglass boatbuilding, near replicas of Alerion, which by then was enshrined at Mystic Seaport, were produced by several builders. They were as handsome as the original, and just as plain and simple. 

In 1988, at the Annapolis Sailboat Show, a lanky East Coast sailor named Ralph Schactner invited me aboard a gorgeous little vessel he had conceived and was putting into production.

It was a stunning new iteration of Alerion that wedded hull lines like those drawn by Herreshoff with a high-performance underbody designed by Carl Schumacher. Unlike other designs in the daysailer genre of the time, this one, sold as the Alerion Express 28, was lavishly finished, with a flag blue hull, teak decks and a low, graceful, cream-colored cuddy cabin with oval portlights and varnished teak accents. The fast, elegant daysailer was born.

The boat’s commercial success inspired a new niche of sailboat design that has stressed aesthetics over practicality. These redefined daysailers aren’t meant for cruising or racing—they don’t have lifelines, some don’t even have self-bailing cockpits.

Luxury daysailers, as they have come to be known, have admirable sailing qualities, but many are bought just for the pride of owning one and showing it off. They are status symbols, toys for adults, which on a per-foot basis are some of the most expensive production boats you can buy. But more than anything, they are simply beautiful sailboats.

This column isn’t meant to be a daysailer shopping guide, but following are three distinct types to consider.

For the purist: The C.W. Hood 32 looks a lot longer than its 32.5 feet thanks to its long overhangs and low freeboard in the manner of, yes, Reliance. The deck is perfectly flush and there is no attempt at below-deck accommodations. This boat is purely about sailing, and with its modern underbody it does that with alacrity while flaunting its retro look.

For the sports car enthusiast: Saffier daysailers appeal to sailors who might admire cars like Aston Martins or Corvettes. They look and sail like miniaturized versions of contemporary offshore racing boats. The Saffier 24, with its inverted bow and straight sheerline, resembles, on a tiny scale and minus the foils, some of the today’s racing foilers that sail at highway speeds. Its big sister, the Saffier 33, looks in profile like a first generation TP52. Both have state-of-the-art rigs and sail-trimming systems just like real racing boats.

For anyone who can afford it: The Wallynano 37 is the créme de la créme of daysailers. Just looking at the boat can stir the soul of a sailor. The lines inspired by 19th century pilot cutters and drawn by André Hoek flow aft from a sharp plumb bow to a shapely, long overhanging transom. Bulwarks, cockpit coamings and a sleek cabinhouse add to a traditional look that belies the 21st century speeds the Nano’s tall carbon rig, long sprit and slim bulb keel (with a draft of 8.5 feet) produce. All of this for about $400,000.

What would the father of the daysailer think of the luxury daysailer boom if he were around to see it? Nathanael Herreshoff would love it. He’d go into swashbuckling mode and design the most innovative, radical and beautiful daysailers around. Then, at the end of the day, he’d walk from his office to take a sail around the harbor in a true daysailer, Alerion.