The Contessa 26 is actually a masthead rigged version of a Folkboat (although Contessa also produced a version that was a Folkboat complete with its original fractional
rig.) I owned a Folkboat back in the 1970''s and really loved this little boat. These are super boats in many ways. But while I know that quite a few Folkboats and Contessa 26''s that have done circumnavigations and long distance passages, these are very small 26 footers that really lack the kind of weight bearing capacities and storage abilities that make them a reasonable choice for a globe trotter. While I lived on my Folkboat as a 23 year old and had no problem getting around without and engine, the 4''6 head room (Contessa''s have a little more than that) and low freeboard when added to the marginally the lack of self-bailing cockpits (they are below the waterline if loaded to go voyaging) when combined with the downflooding exposuer of their sail lockers make them a dubious choice at best.
While the Contessa 32 has gotten good press as seaworthy example of a late RORC/ early IOR race boat, that press has to be viewed in the context in which it was generated. The Contessa 32''s reputation comes from the almost 25 year old study that was performed post Fastnet Disaster. The conclusion was that the Contessa 32 was seaworthy for a "Raceboat" of that era. We now understand a lot more about seaworthiness and proper engineering and while the Contessa 32 was certainly a good boat for its day with reasonably comfortable motion and a comparatively low center of gravity for that era, compared for example to boats designed for offshore cruising in the wake of the Fastnet research, I am not really sure that the Contessa 32 is all that great an offshore boat, especially when loaded heavily with stores and gear which would tend to raise the VCG.
Respectfully,
Jeff