Maine Island Trail (Portland, ME)
Maine gave us America's first water trail, so you'd be remiss not to experience it while in Portland. "One of my favorite islands on the trail is Jewell Island, a rugged and wild place that's just eight miles from the Portland waterfront," says Zack Anchors, owner at Portland Paddle. "In just a few hours you can paddle from a bustling harbor filled with cargo ships and lobster boats to a quiet and remote beach on Jewell that's surrounded by cliffs, with a campsite facing the open ocean." If you're gung-ho for an overnight, Anchors says there are trails all over the island worth exploring (and two climbable observation towers that were used during WWII to spot German subs).