What is Reddit's opinion of Twenty Affordable Sailboats To Take You Anywhere?

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Nice. If that's the (possible) plan and you're looking for traditionally-defined "bluewater" boats, then be absolutely sure to browse http://bluewaterboats.org/ It's a great resource with a lot of good info on some of the classics. You could also look at 20 Affordable Boats to Take You Anywhere. I'd say that both are just starting points.

If the old boat/fixer route is where you're headed, definitely pick up This Old Boat and Don Casey's Complete Illustrated Sailboat Maintenance Manual. I'd say both are essential and excellent references for the purchase and restoration work required for older boats (or just boats in general, really).