“Start low to the ground,” says Andrew Joslin, who first slept in a tree 10 years ago, when he was a tech worker who regularly slept in a hammock in his Boston backyard. Now 60, Joslin lives in rural Massachusetts, where he works as an arborist. If you intend to sleep 15 feet off the ground or higher, first learn to climb safely. You’ll need 150 feet of arborist rope, a harness, a helmet, carabiners and a special tree-sleeping hammock, or a lightweight platform called a portaledge. Before you ascend, check the weather. You don’t want to be dozens of feet off the ground in the dark during high winds or lightning.
Assess the tree’s health. Note dead limbs. “Take a stick and bang the trunk,” Joslin says. “Does it sound hollow or solid?” As you climb, remain alert. Listen for wildlife, particularly the telltale buzz indicating a bee swarm or wasp hive.