Contessa Sailboats

Explore Contessa sailboats and the details behind each model. If you are shopping for a Contessa sailboat, we keep an eye out for Used Contessa Sailboats.

Model Listings Year Built LOA (ft) Beam (ft) Draft (ft) Disp. (lbs) Hull Designer Rig Keel
Contessa 3250 for sale197132 ft9.5 ft5.5 ft9,500 lbsMonohullDavid SadlerMasthead SloopFin
Contessa 2821 for sale197727.67 ft9.42 ft4.83 ft6,970 lbsMonohullDoug PetersonMasthead SloopFin
Contessa 2611 for sale196525.5 ft7.5 ft4 ft5,400 lbsMonohullDavid SadlerMasthead SloopLong
Contessa Ood 347 for sale197833.67 ft11.08 ft6.33 ft8,050 lbsMonohullDoug PetersonMasthead SloopFin
Contessa 251 for sale198025 ft7.2 ft4.1 ft4,750 lbsMonohullPeter ColeMasthead SloopFin
Contessa 271 for sale198127.5 ft10 ft5.42 ft5,750 lbsMonohullRob HumphreysFractional SloopFin
Contessa 331 for sale198432.67 ft11.08 ft5.82 ft8,988 lbsMonohullRob HumphreysFractional SloopFin
Contessa 351 for sale197435.5 ft11.42 ft6.33 ft13,500 lbsMonohullDoug PetersonMasthead SloopFin
Contessa 391 for sale197938.67 ft12.25 ft7.25 ft14,250 lbsMonohullDoug PetersonMasthead SloopFin
Contessa 431 for sale197742.75 ft12.5 ft7.25 ft21,000 lbsMonohullDoug PetersonMasthead SloopFin
Contessa 38197338.5 ft11.5 ft6.25 ft15,500 lbsMonohullSparkman & StephensMasthead SloopFin

Contessa sailboats: a small Lymington yard's boats, proven by an ocean race

Jeremy Rogers began building boats in wood in Lymington, but it was a modified Folkboat — engineer David Sadler's own Contessa of Parkstone, raced successfully and named for his wife, Tessa — that gave the marque its name and its direction. When the Folkboat Association objected to Rogers' modifications, he and Sadler tooled up to build in fibreglass instead, launching the Contessa 26 in 1966. Five years later the same partnership produced the Contessa 32, the boat that would define the brand: it won Boat of the Year honors at the 1972 London Boat Show, trained sailors for Britain's armed forces, and was the only yacht in its class to finish the 1979 Fastnet Race. The company that built it went through receivership, an interim builder, and a mid-1990s buyback before returning to boatbuilding on a small, made-to-order scale — a shift the yard has held to ever since.

Origins and ownership

Rogers opened his own boatyard in Lymington in 1961, aged 23, after a five-year apprenticeship with wooden-boat builder Jack Chippendale. Grocer Vernon Sainsbury backed the move into fibreglass production, paying in full up front for the sixth hull to be sure of getting a boat with the early teething problems ironed out. The first Contessa, Contessa of Lymington, was followed by nearly 350 sisterships over the next eleven years, and the design later spawned the Contessa 32, which Rogers began building with Sadler in 1971. At its peak the company employed about 200 people and turned out two boats a week across five factories around Lymington. Alongside the Lymington-built boats, around 400 Contessa 26s were built under licence in Canada by J.J. Taylor and Sons.

The early-1980s recession put Jeremy Rogers Ltd into receivership, and the Contessa 26 and 32 moulds were sold off; Rogers kept the business going by building Etchells keelboats and one-off racing and cruising yachts from 1988. Mike Slack acquired the Contessa 32 moulds during this period and built about twenty-five more 32s in Lowestoft, including a boat named Dart Dash, before Rogers bought the tooling back in 1995. Production resumed the following year, in 1996, this time on a more modest, made-to-order scale — a business Classic Boat has described as effectively custom-building each boat. In 2009 the company moved from a landlocked site in Milford-on-Sea to Lymington Yacht Haven. Jeremy Rogers retired in 2012, handing the business to his son Kit, who ran it with his wife Jessie while his father stayed on as a mentor; Kit's brother Simon became managing director in October 2025. Jeremy Rogers died in October 2022, survived by his wife Fiona and their three sons, Simon, Kit and David. Alongside its Contessa boatbuilding, the yard also builds Atlas davits for superyachts and manufactures parts for Royal Navy Type 45 and Type 26 destroyers and minesweeping systems.

The designers

Contessa's design story runs through several names beyond the founding Sadler partnership. Sparkman & Stephens supplied the pedigree for the Contessa 38, campaigned at the 1973 One Ton Cup in Sardinia, though production was limited to just six boats. A fast Contessa 38 named Thunder, built for that same regatta, inspired Rogers' next and longest partnership, with the American designer Doug Peterson. Peterson drew the Contessa 35, Gumboots, in which Rogers won the 1974 One Ton Cup — a race he interrupted mid-event to help rescue a family from a sinking boat — and later the OOD34, the boat on which Rogers brought injection moulding to yacht building for the first time, in 1978. Robin Knox-Johnston was among the OOD34's first buyers; more than 50 were built, plus a further eight of its 1982 successor, the Contessa 34. In the early 1980s Rogers also built a handful of specialist one-off Peterson racers, including Smerelda Prima for the Aga Khan and Apollo V for Alan Bond's 1981 Admiral's Cup campaign. Rob Humphreys closed out the badge with the final two boats to carry the Contessa name, the Contessa 33 and Contessa 27.

Construction through the eras

Rogers was one of the first British builders to embrace fibreglass, in the 1960s, according to Yachting Monthly, and stayed at the front of the field: the 1978 OOD34 brought injection moulding into yacht construction for the first time, an innovation Yachting World credited as ahead of its time. Manufacturing method also tracked geography as the brand crossed the Atlantic. English-built Contessa 32s used solid fibreglass decks throughout, while the Canadian-licensed boats built by J.J. Taylor moved to balsa-cored decks later in that production run; the Canadian hulls were also built to Lloyd's specifications and, if anything, ran slightly heavier than their English counterparts. Assent, the Contessa 32 that alone finished the 1979 Fastnet Race, carried nothing more exotic than that standard lay-up — contrary to popular belief, she was never specially strengthened for extreme sailing.

Lines and generations

The Contessa 26 opened the line in 1966: a fibreglass reworking of Sadler's Folkboat that Rogers built almost 350 times in Lymington, with around 400 more built under licence in Canada. The Contessa 32 became the flagship, and its total production numbers vary by source: SAILING Magazine counted more than 700 built in England before production stopped in 1983, while Classic Boat's more recent count puts Jeremy Rogers Ltd's cumulative total at about 650. The two don't reconcile, but several hundred Contessa 32s left Lymington across five decades on any reading. The rare Contessa 38 sits at one extreme of the range, with just six boats built for the 1973 One Ton Cup; Peterson's racing designs — the 35, 28, 43, OOD34 and 39 — filled out the 1970s; and the quarter-tonner Hobnail, launched in 1975, became the first of 23 Contessa 25 hulls. Humphreys' Contessa 33 and 27 closed out the badge in the 1980s.

Who Contessa is for

Contessa built pocket cruiser-racers meant to go to sea and be raced hard, not admired at the dock — a reputation earned through service with Britain's armed forces and a Fastnet Race that sank boats built to look tougher. That makes the range a natural fit for sailors who want a small, proven offshore boat over a roomy modern cruiser, and for owners drawn to one-off racing pedigree, from Aga Khan and Admiral's Cup commissions to the six-boat Contessa 38. It also suits buyers comfortable with a marque that changed hands, moulds, and scale more than once, and that rebuilt itself around bespoke, one-at-a-time construction rather than volume production.

Frequently asked questions

01What is the Contessa 32 known for?+
The Contessa 32 was the first Contessa model used by Britain's armed forces for training, and Assent, a 32 sailed by Willy Ker, was the only yacht in Class 5 to finish the 1979 Fastnet Race. Ker went on to sail her 100,000 miles, largely single-handed, into extreme high latitudes — and, contrary to popular belief, she carried nothing more than the standard Contessa lay-up rather than any special strengthening.
02Who designed the Contessa 32?+
David Sadler designed the Contessa 32 in collaboration with builder Jeremy Rogers. Rogers began building it in 1971, and it was named Boat of the Year at the following year's London Boat Show.
03Did Contessa 32 production ever restart after the company's 1980s receivership?+
Yes. Jeremy Rogers bought back the Contessa 32 moulds in 1995, and production resumed the following year on a small, made-to-order basis — a change from the volume manufacturing of the original run.
04What's the difference between English-built and Canadian-built Contessa 32s?+
English-built Contessa 32s used solid fibreglass decks throughout their run. Canadian-built 32s, produced under licence by J.J. Taylor and Sons, moved to balsa-cored decks later in the production run and were built to Lloyd's specifications, ending up, if anything, slightly heavier than their English counterparts.
05Where does the Contessa name come from?+
It traces back to a modified Folkboat, Contessa of Parkstone, built and raced successfully by engineer David Sadler and named for his wife, Tessa. When the Folkboat Association objected to Sadler's modifications, he and Jeremy Rogers moved away from the class identity and tooled up to build in fibreglass instead, launching the Contessa 26 in 1966.