This is a three-day and two-night guided expedition across the breadth of Casco Bay. Along the way, you’ll camp on the islands of the Maine Island Trail and experience the diverse environments found in the bay — from the exposed ocean-like conditions along the outer islands to the calm and peaceful estuaries of the inner waters.

You’ll start out kayaking alongside the busy working waterfront of Portland harbor and quickly pass into calmer waters and past tiny island hamlets, hidden beaches, and rugged, rocky headlands. The group will often spend the first night on Jewell Island, a large, wild island with gorgeous trails to explore, or on Bangs Island, a less visited gem with panoramic views of the bay. From there, the group will often island-hop west towards Harpswell, either returning to Jewell for a second night or camping on Whaleboat Island, Rasperry Island, or another nearby site on the Maine Island Trail.

Duration: 3 days, 2 nights