Cakewalk: A 281-Foot Superyacht Built in Connecticut by Derecktor Shipyard
The 281-foot Cakewalk, launched this summer from Derecktor Shipyard in Bridgeport, Connecticut, is more than an impressive yacht: it is a clear example of high-end American shipbuilding. With a steel hull, aluminum superstructure and richly finished interiors in wood, stone and wrought iron, Cakewalk was conceived and executed to meet the demanding standards of northern European design and construction while proudly wearing an American stamp.

Derecktor has a long history as a versatile shipyard, having built America’s Cup defenders and a diverse portfolio of commercial and military vessels as well as pleasure craft. That blend of commercial structural skill and yacht-level finishing made Derecktor an attractive choice for the owner of Cakewalk V, an American industrialist who wanted to prove that a U.S. yard could deliver a superyacht of world-class quality.
Project manager Captain Bill Zinser, who has worked closely with the owner for 15 years and supervised construction of previous Cakewalk yachts, says the owner set out to demonstrate that an American yard could compete with the best European builders. Cakewalk V was designed to follow a northern European aesthetic and craftsmanship standard — specifically German and Dutch levels of finish — and Zinser believes Derecktor achieved and in some respects exceeded that brief.
Derecktor’s Bridgeport facility had not previously built a private yacht on this scale. Cakewalk’s 2,998 gross tons across six decks makes her the largest private yacht by volume launched from a U.S. yard since the early 20th century. At well over $100 million to build, she represents a rarefied class of yachts, with costs and attention to detail far above ordinary megayacht construction.

Design and styling
British designer Tim Heywood was charged with producing a yacht that felt timeless rather than aggressively modern. The result is a “modern classic” with strong, sculptural lines and graceful curves. Heywood emphasizes unity of design and an elegant, understated profile; on Cakewalk those curves and the deep-blue steel hull create an appearance he describes as sculptural.
Interior layout and guest amenities
The main saloon is arranged like a refined library, complete with a fireplace, a grand piano and rich cherry finishes. Forward from the saloon is a formal dining area centered beneath a chandelier and a custom table that seats the yacht’s full complement of 12 guests. A spiral staircase amidships connects four of the six decks.
Six guest suites are located on the main deck to maximize oversized windows and water views; each suite includes a private head and spa tub. The owner’s private deck occupies the entire deck above the main deck and includes a panoramic master suite with semicircular forward windows, separate his-and-her baths with jacuzzis, multiple lounges, a gymnasium and dedicated spa and recreation spaces. The owner’s aft deck includes outdoor dining for 14.
The bridge deck offers a game room, an aft lounge and ample forward sunpads. Above that, the sun deck features observation chairs, a whirlpool spa, bar and multiple lounge areas. The lower deck houses The Boathouse, a 47-by-40-foot tender bay capable of storing Cakewalk’s tender fleet and water toys.
Tenders and water toys
Cakewalk carries a curated tender and toy inventory for both private use and charter. Highlights include a 32-foot limited-edition AquaRiva Cento, a 35-foot custom Intrepid for watersports and diving, and a 37-foot Vikal custom limousine tender. The yacht also carries four personal watercraft, two SeaBob underwater scooters, diving and snorkeling gear, water skis, wakeboards and assorted inflatables.
Engineering and performance
Powered by twin 3,300-hp MTU diesel engines, Cakewalk cruises on her displacement hull at about 15 knots and can reach a top speed of roughly 17 knots. Her range is approximately 5,000 nautical miles, enabling long passages and transoceanic cruising.
One notable engineering feature is the large tender bay with 40-foot-wide electric-hydraulic doors and two overhead sliding crane beams for launching and recovering tenders. Because the bay opens directly to the sea, the yard reinforced framing and bulwarks to meet classification standards so the structure can withstand flooding and heavy seas if the doors are opened underway. Sound and vibration specifications were also set very tight so the main-deck guest accommodations remain quiet and comfortable.
Shipyard choice and the building process
Derecktor operates three facilities: a headquarters yard in Mamaroneck, New York; a repair yard in Dania, Florida; and the Bridgeport, Connecticut, big-boat yard where Cakewalk was built. The owner and project team valued Derecktor’s commercial shipbuilding expertise and its pool of finish craftsmen who specialize in high-end yacht work. The construction was international in scope: European subcontractors and specialists were brought in for selected systems and Heywood provided styling while a Dutch naval architecture firm contributed architectural work.
With a complement of approximately 25 crew members, Cakewalk was built both for the owner’s private use and for charter. Although capable of voyaging nearly anywhere on her steel hull, her initial chartering plan emphasizes the Caribbean and Mediterranean cruising seasons.
Cakewalk blends rugged passagemaking capability with elegant styling and luxurious accommodations. As Captain Zinser puts it, she is “a seaworthy boat that looks beautiful” and a demonstration that American yards can deliver superyachts of the highest quality.
See related story: Need a superyacht? Try U.S.
This article originally appeared in the December 2010 issue.