Never done it but what about going to the edge of your world and having your boat fall down fully loaded with stuff possibly your player character too...

Also if you don't like the swamp use the hoe to build a road around the islands so you can move a cart between your outpost and the crypt. Roads will remove many of the hazards such as leeches and stamina loss from wanting to jump over the water, if you dislike a biome build a base in it until you're more comfortable with it and you'll quickly learn how to deal with the problems.

Also imagine the very situation you had in the swamp happening in the plains, it can be way worse.