Windjammer Days has been a Boothbay Harbor tradition for 64 years, but what does it actually take to keep one of Maine's most recognizable waterfront festivals going?

In this episode of the Maine Famous Podcast, April sits down with Bruce White, longtime volunteer, board member, and Boothbay local, to go behind the scenes of Windjammer Days. Together, they discuss how a simple idea involving a handful of schooners grew into a week-long celebration featuring tall ships, fireworks, tug-of-war across the harbor, codfish relay races, live music, and thousands of visitors each summer.

The conversation is also about something bigger: the volunteers, traditions, and sense of community that have allowed Windjammer Days to endure for generations.

In this episode of the Maine Famous Podcast, April sits down with Matt Partridge and Ryan Edwards, the new owners of Five Gables Inn in East Boothbay, Maine.

The two longtime friends talk about what it’s actually like to step into ownership of a beloved coastal Maine inn with decades of returning guests and a reputation already firmly in place.

Over the course of the conversation, they discuss the pressure of preserving tradition while modernizing the guest experience, the realities of staffing and housing in Maine’s tourism economy, and the unexpected lessons they learned after arriving in Boothbay.

They also share stories about proposal weekends, repeat guests who’ve been visiting for 30 years, lobster dinners at the inn’s cottage, and the kinds of porch conversations that turn into lasting memories.

“One minute you’re serving breakfast,” Ryan says. “The next, someone’s yelling that there’s a leak upstairs and you need a wrench.”

Greg Soutiea didn’t set out to become an innkeeper. After years working in corporate property management in Boston, he and his wife Lauren were burned out by the constant cycle of “putting out fires.” Then a stay at a small inn on the coast of Ireland changed the trajectory of their lives.

In this episode, Greg shares how the couple took a leap of faith and purchased Craignair Inn, a nearly 100-year-old property perched beside the ocean on the St. George Peninsula. Today, the inn has quietly become one of Midcoast Maine’s most distinctive destinations, with a celebrated brunch program, a 250-bottle whiskey collection, rotating local art exhibitions, chef dinners, and direct access to the trails of Clark Island Preserve.

But this conversation goes beyond hospitality. Greg opens up about workforce housing, building community, creating meaningful guest experiences, and why he believes the best inns should feel less like luxury resorts and more like home.

We also talk about sunsets that turn the granite causeway gold, the surprising number of artists living on the peninsula, and why some guests come for the whiskey while others come for the peace and quiet.