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Optimal Size for Coastal Cruising
I heard a saying once, don''t remember where, that I like to paraphrase: "Get the smallest boat that will do what you need it to do." Usually, smaller boats get used more often. Depending on how many people you plan to take with you, particularly overnight, something 28 to 32 feet should do. I have a 28'' Sabre that I''ve sailed in New England waters for the past 5 years, with two adults and 3 small kids. It''s cramped with all three kids aboard, fabulous for a couple or singlehanded.
You''ll need a boat that''s good in light air, particularly in Long Island Sound. Sabres are great in light air, and I have always felt completely at ease with her in heavier stuff too. She''s shrugged off nasty weather in Block Island Sound with confidence, and she is faster than just about anything else her size that I''ve ever encountered.
8000 lbs. 4.5'' draft, 9''2" beam. Very easy to singlehand.
Some other boats that I like for New England coastal cruising are: C&C, newer Tartans, Pearson 30, Ericcson, Cal. I''m not crazy about any of the "Big Three".