Schooner J. & E. Riggin Music & Dance Cruise

The Schooner J. & E. Riggin Music & Dance Cruise gives you a front-row view of Maine’s coast from the deck of a historic windjammer. Over four nights, you depart Rockland and sail Penobscot Bay, gliding past spruce-lined islands and classic lighthouses, then settling into quiet anchorages chosen by wind and tide. The 2026 departure runs May 22 to May 26, a polished long weekend for couples and friends who want the waterfront without the crowds.

On board, you travel to the sound of the Gawler Family Band, with John and Ellen Gawler and their daughters leading live sets and contra dancing. Expect fiddles, banjos, and cello, plus a social rhythm that’s easy to join whether you dance every set or watch from the rail. Your fare includes cozy cabin lodging and meals by Chef Jocelyn Schmidt, with evenings that often finish under the stars and may include a traditional lobster bake on a remote island beach.

Late May stays cool on the Midcoast, so pack smart layers, including a light jacket or sweater for night breezes. Bring comfortable, non-slip shoes for deck time and dancing, plus a reusable water bottle for shore stops (potable water is available on board). The schooner sails rain or shine, and if weather turns, we shift the gathering into the warm galley for music and conversation.

Boarding typically runs 5:00 PM to 6:00 PM at Windjammer Wharf in Rockland, and you return before noon on the final day. Book early, these specialty sailings often sell out well ahead, and 2026 fares start at $1,375 per person (double occupancy). Consider ride-share or local transit since holiday-weekend parking can be tight, and if you arrive a night early, Rockland has upscale inns and boutique hotels near the harbor, with additional rentals in the Midcoast and Camden area.