Getting there is part of the adventure. For Tess and Chris it meant a drive to Port Clyde, then about an hour by ferry across open water, since Monhegan sits roughly 12 miles off the coast of Maine and can only be reached by boat or helicopter . The island covers barely a square mile, has no cars and no paved roads, and is home to only about 65 year round residents, mostly lobstering families who work the waters around it.

What Monhegan lacks in size it makes up for in character. Roughly 17 miles of trails wind through spruce forests and out to some of the tallest cliffs on the Maine coast, past the island lighthouse, which has stood on Lighthouse Hill since the 1800s. Since the 1890s it has also been a beloved artists colony, drawing painters like Edward Hopper, George Bellows, Rockwell Kent, and generations of Wyeths, all chasing the same rugged light and quiet that Chris fell for. Down at Lobster Cove, the rusting wreck of the tugboat D.T. Sheridan still sits on the rocks where it ran aground in 1948, which is where a certain drone flight turned into a proposal.