I bought a new Santana 27 in 1970 and sailed it on Lake Michigan for 37 years. Last year when we got a new boat, I shipped it to my son to use on the Chesapeake. We have loved the boat and don't think we could have made a better choice in this size range.
It was solidly built, sails and handles well. and is comfortable. It is also fairly fast for its era and it is stiff. In 1996, we took first in fleet in the annual Chicago to Waukegan race mostly on a reach in 30 m.p.h. winds with full main and 155% genoa. Most of the other boats were newer and bigger but could not carry full sail in those conditions.
It has also been a comfortable cruiser for its size able to handle some pretty rough conditions.
If you are buying a boat this old you do have to be prepared to put time and effort into repair and maintenance regularly. Decks delaminate, water leaks will cause rot in the bulkheads and even the bunks and cabinetry. check under the chain plates for soft spots in the bulkheads and for signs of leakage around
hatches and windows. After 22 years I had to replace all the interior bulk heads and cabinets in my 27. Delamination in parts of the deck have been repaired from time to time and the hull and deck have been painted a couple of times. The boat still looks good and sails like new. If you buy a newer boat, there will probably be a lot less work but then you can't find one for a few thousand dollars either. Besides working on a boat is almost as much fun as sailing it, isn't it? After 38 years, I'm still happy with the Santana 27 and don't think we could have made a better choice in this size range.
