Contessa at 60
A proper regatta celebrating a significant milestone in sailing history...
Think Contessa and immediately the word ‘class’ springs to mind, alongside ultimate seaworthiness, handling and some of the most graceful lines ever to come off a naval architect’s board. To celebrate the first sixty years, this weekend saw a remarkable gathering of Contessa yachts in Yarmouth at the western end of the Isle of Wight, where the current custodians of the business, the descendants of the legendary Jeremy Rogers, put on a regatta that will live long in the memory. It was how regattas should be - Corinthian and friendly with lovely touches like a bespoke bottle of Contessa gin for every boat entered, whilst being ultimately competitive and enjoyable. Solent sailing at its very best.
Shoreside it was relaxed and friendly with the peerless Royal Solent Yacht Club hosting an international crowd who had come from far and wide to celebrate and enjoy each others’ company. It was standing-room only and how the club catered for so many hungry and thirsty sailors was a credit to their incredible staff and volunteers.
An opening dinner on the Friday night saw the club packed to the rafters with crews chatting intently on refit programmes, tuning tips, and the imparting of techniques to make their Contessas go faster. It was like a giant family of enthusiasts. A rally of extraordinary proportions and one of the highlights of my year if I’m honest, followed by the official regatta dinner on Saturday night that again was simply exemplary and exquisite.
What you can’t avoid taking away from regattas like these is the enthusiasm. Genuinely these sailors just love their boats and it matters not a jot whether it’s a 26, a 32, a 34 or whatever, it’s the Contessa marque that they have bought into and adore.
For those that don’t know the history of this legendary boat-building affair, you have to go back to 1966 when Jeremy Rogers started building stripped-plank Folkboats but then decided to make them in glassfibre in collaboration with David Sadler who was both a client and a designer. Rogers tweaked the sheerline and the transom to make what was a traditional boat, faster and more comfortable. It was genius.
Soon after the Folkboat, Rogers began on the Contessa 26, a design that even today is a winner. Jeremy’s son, and current MD of Contessa Yachts, Simon Rogers has won no less than three Gold Roman Bowls in the Round the Island races in the Contessa 26 and some of the sums being spent today on tricking these gorgeous little boats up are eye-watering - six figures easily with carbon rudders, 3DL sails, carbon masts etc etc…
The big breakthrough for Contessa yachts was the 32. Launched at the 1971 boat show in Earl’s Court, London, almost immediately it had a two-year waiting list and was quite rightly named as ‘Boat of the Show’ that year.
The legend though was made in the 1979 Fastnet Race where the Contessa 32 showed its incredibly seaworthiness in surviving the storm that saw 21 people perish (15 sailors and six others). From that moment on, the Contessa 32 was revered and even today new yachts are commissioned on a bespoke basis. In essence, it’s the perfect boat, and interestingly in Yarmouth last weekend, the 1979 survivor ‘Assent’ was raced by the Rogers family. Incredible to see her up close.
Rogers and Sadler went on to design 12 variations of the Contessa starting with the Contessa 25, and on to the 26, 27, 28, 32, 33, 34/OOD34, 35, 36, 38, 39 and even a 43 that sailed in the Admiral’s Cup. This was boat-building of the highest quality and I was lucky enough to know Jeremy back in the day and fondly remember going to the yard and seeing the production line in progress with my late father who knew him well. Today the family are dear friends and the way they are giving back into the community of Contessa owners is remarkable.
In picking Yarmouth as the spot for an unrivalled weekend of fun and camaraderie, they struck gold. On Saturday, despite the wind not playing ball, it was a sight to behold on a perfect Solent with the sun shining where T-shirts and shorts, and the odd swim dip of the transom, was the order of the day.
Come Sunday, the Solent bit back with wind against tide and some terrific rollers down the Island side making it a challenge for even the very best. Consistency was key for overall victory but race wins were shared down the fleets. Everyone could have a good race. It was wonderful to watch.
If you had to design a perfect regatta, you would end up with the Jeremy Rogers 60th. From beginning to end it was a pinch yourself to believe it moment in sailing. It’s how regattas should be. It was a wonderful spectacle conducted in the most gentlemanly of spirits with happy faces everywhere from the front of the fleet to the back. Literally it made me want one just to join the party next year from the 11-13 June - it’s worth flying back from Naples for. Honestly it was that good.
Memories made. The Contessa at 60 is alive and well. They’ll be celebrating the 100th and there will still be committed owners and eager crews sailing these boats. Thank you for an absolute classic. And Happy Birthday.
Magnus Wheatley












It was a fabulous occasion! The team at the Royal Solent are so professional and welcoming, it’s always a pleasure to attend any event there. So many beautiful yachts, obviously cherished by their owners and crew, it was a struggle to know where to look next. A wonderful regatta!
Thanks so much for a fabulous post about the Contessa Regatta. Just a heads up: only the Contessa 26 and 32 were designed in collaboration with David Sadler. The others were mostly Doug Peterson designs. I know this without a shadow of doubt, being Jeremy’s widow!