Boat for a USA Mid Atlantic to Bermuda trip?

What are some of the more affordable sail boats capable of making a trip like this? Anything sub $20,000. Thanks!

Lucky you- it’s a buyer’s market! The number of different boats/brands available are numerous. Personally I think you should look for something with a strong sea-going hull and rig. After those most necessary items, look for comfort and safety items such as a reliable diesel, good strong stanchions and lifelines, water storage, a good layout- someplace you can sleep under way (central and snug- lee cloths or boards), and a stove you can cook on when heeled over. Make sure the cockpit is not so large that it would compromise the boat if it filled with water, and make sure the drains are substantial and direct. There should be plenty for sale this time of year big enough for your needs in your price range( I’ve done that trip on a 28 foot wooden cutter and a crew of 3) . Watch out for spongy decks (rot) especially around fittings, masts stepped on deck that have compressed the step ( look beneath the step- is there a compression post? Is there a head door? Can you close the door?). Masts stepped on the keel are usually stronger. Brands? I’m partial to full keeled boats like Cape Dory, I don’t like spade rudders for cruising as they are more vulnerable to damage and catching lines etc. Make sure you have abundant and strong cleats for your anchor rodes (at least 2) and some good anchors too. It doesn’t hurt to have your halliards run to the cockpit. A self steering device would be a nice purchase if you have any money left!

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