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A bigger boat will generally sail faster, have a more sea-kindly motion, and more storage at the expense of higher maintenance, dockage, and operating costs. Duh! Being able to sail out of bad weather, carry more provisions/fuel/guests in better comfort can make an unpleasant or prolonged passage less so. In many more remote places you may have problems with dockage and anchoring.
So why aren't there more big boats out there? I think it's because there's a point where the cost outweighs the benefits. Most of the boats cruising today are in the 40-45' range. This doesn't make that size perfect but it does make one think. Having sailed and worked aboard large sailing yachts I can attest to the comfort level, benefits of crew, and dryness. I can also discuss to the costs of repair and maintenance. Finding a lift for larger and heavier boats can be a real task in the less traveled parts of the world.
Many folks have commented on docking and while that can be more difficult with larger boats (especially single screw without a bow thruster) I would also bring up navigating narrow openings into anchorages and maneuvering around boats in crowded mooring/anchoring fields.
I also think that most cruising boats are manned by couples and while powered winches are nice, taking in large sails with a crew of 2 can be a tough act. Yes, I know the mantra "reef early, and often" but manhandling an 800 square foot main is a lot more work and dangerous than a 400 square foot one, powered winch or not.
If you're coastal cruising, sailing marina to marina, or popular spot to popular spot, a large boat is a real benefit. If you're gunkholing, sailing into narrow reef channels, careening to put on some bottom paint or do repairs, trying to find a lift or railway to get hauled, or dodging coral heads getting to the small anchorage, then small is the way to go.
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