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Why not get in touch … If you’re after a low-priced boat that needs some work on it, buying at the start of the off-season could be a good idea as you can get it ready for the sailing season next year. With a sloop, there is less standing and running rigging with one mast, which means there is less to manage and maintain overall. Trade In And Trade Up. Buy a sailing boat from private vendors and boat dealers. If you will use your boat for water sports, a water ski or wake board boat is best. Editor's Note: Thinking about buying a boat? Search and buy your used boat on the big international boat market boat24.com! These experienced monohull cruisers made the jump to a 46-foot cruising cat, and they're never going back. A sloop is generally faster and sails closer to the wind. What to Know When You’re Buying a Boat . General Information. Reasons To Buy USED Boats: The biggest advantage of purchasing a used boat is the price. 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