Every sailing day trip in Maine we offer is fully customizable and built around your group’s vision of a perfect day on the water. Whether we’re exploring the islands, sailing past lighthouses, or anchoring at a secluded cove for a swim, the goal is simple: give you a day that feels easy, personal, and genuinely fun.
Example Itinerary:
Each trip is tailored to your group and the wind conditions that day, but a frequently requested, guest favorite sailing route begins in downtown Portland before heading out into Casco Bay. From there, we'll pass Portland Head Light for a close-up view from the water and weave through the classic rocky islands that make this stretch of coast so unique. When the timing feels right, we’ll drop anchor so you can swim, relax, or just soak it all in, refreshments in hand, before a peaceful sail back toward the harbor.
Guests should park in the Cutter Street Parking Lot at East End Beach. The captain will meet you at the designated pickup point and transfer you to the boat aboard our private tender.
Guests should park in the Cutter Street Parking Lot at East End Beach. The captain will meet you at the designated pickup point and transfer you to the boat aboard our private tender.
